Morning Brew Newsletter Tech Stack

You know i just had like a mentally transformative experience where a week before junior year of college at michigan my dad passed away suddenly he passed away from a stroke he was 49 years old he was perfectly healthy and after that experience everything just became clearer around one how most things that we worry about on a daily basis in life are wildly unimportant and two how your time on your uh life countdown clock you have no idea when it’s gonna hit zero and basically i said to myself if if i knew my countdown clock was hitting zero tomorrow what would i rather be doing with my time and it was like a no-brainer it was like i knew that i would hey friends and welcome back to deep dive the ongoing podcast where every week i sit down with authors entrepreneurs creators and other inspiring people and we talk about how they got to where they are and the strategies and tools that we can learn that can help us apply to try and hopefully live our best lives what you’re about to hear is a conversation between me and alex lieberman the co-founder and executive chairman of a company called morning brew and morning brews is like huge media company now but it started off as an email newsletter and we kind of dig into the story behind that and interestingly alex sold morning brew to business insider for around 75 million dollars a couple years ago at the age of 28. so he made like tens of millions of dollars at the age of 28 which is absolutely absurd and like super inspiring and ridiculously interesting because it’s like hey how the hell did you do that and b what the hell do you do beyond that point when you feel like you’ve made it in life and so we talk a lot about kind of lessons that we can learn from his journey of building this business from day one and so if you’re if you’ve been thinking of starting a business or growing a business or kick starting a business or anything like that you’ll find a lot of valuable stuff in there but then we also talk about like kind of what it means to find purpose in life and live life beyond such a windfall and how alex is kind of navigating some of these challenges i got a bunch of value out of this conversation i always loved talking to alex and i’ve had a few zoom calls over the years um and i’m very excited for you guys to hear the conversation as well so without further ado i hope you enjoy this conversation between me and alex lieberman alex thank you so much for being on the deep dive how are you doing today good man thanks so much for having me it’s gonna be it’s gonna be fun um i’d love to get started so you’ve got a a super interesting back story and i would just like i i would love to start with a question of how how did we get here what was the backstory of alex lieberman yeah so i am originally from new jersey uh and i grew up in a finance family so everyone in my family no matter where you looked on my family tree worked on wall street my dad worked in sales and trading my mom worked in sales and trading my grandpa worked in sales and trading and so growing up uh you know and having the value of you know family is the most important thing there was only one possible career in my mind which was to work on wall street like i really didn’t think about anything else uh and so i went to a small private school in new jersey it was great for for some things wasn’t great for other things i loved it for the academics and the athletics didn’t love it for uh the social part of the experience and so i wanted a very different experience in my college experience and so i ended up going to the university of michigan which was very non-traditional from my high school basically my high school i had 120 people in my graduating class a third of the class went to ivy leagues a third of the class went to what are called nez cac schools like northeastern schools like colgate middlebury uh and then there was a third that were kind of like the the degenerates in the class that would go somewhere else and i was one of those people i went to the university of michigan um loved my experience there i was in the business program and i was kind of on the path uh up to that point i was on the path to work on wall street because that was my goal and so i did internships after each year in college i was in the business program and i got into my senior year at michigan and the way it works uh you know in the states with internships is you have a uh your internship after your junior year in finance and if you do well in that internship you get an offer and so then in your senior year in your last year of college you don’t have to recruit for jobs you already have that job for when you leave school and so that that’s what happened for me i had my internship at morgan stanley working in sales and trading junior year i got an offer back and so i accepted that offer i got into my senior year at michigan i didn’t have to recruit for a job i only had to take three classes my entire senior year because i had completed my credits and so i got into the year and i was basically like okay this is gonna be fun i’ll play a lot of video games but i should probably do something else in order to keep my brain sharp for when i graduate and go you know work in finance and so i i started helping students prepare for job interviews and one of the ways that i would help them is i would do my a mock interview with them that was something my dad always did with me when i was prepping for interviews is he would mock interview me as as if we he was an interviewer and one question i would always ask students is how do you keep up with the business world to me this was like the layup question just to get them comfortable not be nervous and every student basically said the same thing which was i read the wall street journal uh it’s what my parents told me to do but it’s a bit dense it’s a bit dry and that just really resonated with me because i was like this is crazy these students are about to spend 50 percent of their life of their waking hours between the ages of 21 and let’s call it 70 working in business and they read business news because they feel like they have to because their parents told them to like it sounded crazy it started so i started writing a daily business roundup about the business world that in the beginning was really shitty like it was a really bad product uh but it was good enough to really catch people’s eye and get their interest and sending out that first newsletter in i believe it was october of 2014 so my first semester senior year was the start of what would be a seven year journey of building morning brew amazing okay i i that that was the point where i wanted to zoom in on so there’s a lot of people that would that would notice something that huh it’s it’s kind of weird that all of these people applying to all these jobs are like reading business news but seeming to not enjoy it what was it that made you take that leap to therefore i’m going to write my own email newsletter because that’s not a normal thing to think like what was going on there yeah i mean it’s interesting because i was not thinking about it as a business at all the the interesting thing is like i’ve never thought about myself as like an entrepreneur or that i have to build a business but i’ve always been a tinkerer like i’ve always just like tried doing random things and i i started writing that newsletter which by the way at the time wasn’t called morning brew it was called market corner uh and i’ll describe what that product looked like in the beginning because again it was pretty mediocre but basically i wrote it because one selfishly i wanted to keep up to date with what was happening in the business world so that when i left college and i went into my job in finance i felt like my brain was on top of things and so the process of reading what was going on in business and distilling it into these bite-sized chunks was almost like a forced function for me staying on top of my game then the second part i would say was more selfless which was i just wanted to help these students keep up to date with the business world and to me the way to do it was just to start writing this thing and i had an abundance of time how did you have an abundance of time yeah so as you know as i had mentioned basically i got into my senior year i had already gotten my job so i had that junior year internship and i got an offer to work full-time at so now you’re it’s like you’re coasting the rest of the year yeah exactly basically my fourth year of college my senior year i was coasting i didn’t have to recruit for a job i only had to take three classes and so i only really had to spend two hours any given day throughout senior year of college actually spent on academics in college and i spent i had to spend zero amount of time on jobs and so that left you know however many waking hours uh 14 waking hours a day to do something with my time and this was one of the things that i decided to do with my time uh did you try and do anything else with your time i’m curious to stay here any other experiments running in the background uh nothing that was uh as i would say productive as this i probably spent three or four hours a day working on uh market corner market corner which would then turn into morning brew i did spen i spent a lot of time playing video games such as i played a lot of fifa nhl uh and call of duty i also in my senior year tried to experience a lot of just extracurriculars at michigan so i went to like sports events that i never thought of going to like i went to uh the university of michigan gymnastics meet i went to the soccer games just because i kind of thought to myself this is the last year that i’m really going to be able to experience this amazing university as a student i might as well just like make the most of it and then i was a teaching assistant my senior year i uh was a ta for a real estate class which was actually my favorite class it was um it was a interdisciplinary grad level real estate class where basically the class was not lectures it was you were tasked with picking an actual physical location in the us where you thought there was an opportunity to buy the location like buy the real estate develop a property and turn it into a residential retail commercial like a multi-use property and it was an interdisciplinary group so where it was a business student it was an architecture student it was a legal student and it was an urban planning student and so the four of us literally spent a semester where we went to parts of michigan and we drew up our plan for developing like a full-blown you know 250 000 square foot property the architect literally drew out the exact specs of the property the urban planner wrote up the documents that you would use to apply to the city i worked on the financials and the legal uh student uh basically shared what the pipeline was of contracts that we would have to figure out for the property so that was one other thing i did senior year so you said that sounds super cool uh and you said this class was your favorite i wonder like what did you learn from this class that maybe you’ve applied applied later in life yeah i mean this is the interesting thing i loved my experience at michigan but if you were to ask me why i loved it i would not say it was for the academics because i would say there’s maybe two classes in the entirety of my education at michigan that i feel like i’ve actually applied in my career and i think this just speaks to where a lot of academia is broken and i think it’s broken for a lot of reasons i think uh it’s broken because it teaches you what to think versus how to think i think it’s broken because a lot of people are lifelong academics and that’s not inherently bad but i wish there was more attraction to entrepreneurs and practitioners going back to universities because i think it would make what you learn far more applicable because it’s being taught by people that actually did the thing i loved this class because it was one of the two classes where i actually felt like this is simulating what i’m going to be dealing with in real life it is a real life project that i could see myself doing this in the future if i wanted to you know invest in real estate this is something i would go through and it was interdisciplinary in nature which is inherently all of your experience in your career and life is working with people that have diversity of thought and experience from you nice so this real estate was class number one what was class number two that actually taught you something my excel class it was the class yeah yeah okay it was my class that uh basically taught us how to uh do pivot tables uh visual basic shortcuts in excel and for me like excel is a program that i probably will use my entire life with different levels of kind of intensity or frequency when i was working in finance before i went full-time on morning brew i used excel a lot like i was doing a lot of just modeling and calculations in excel today i would say i use it maybe once or twice a week but having that proficiency in excel it’s kind of like i would consider it kind of the the timeless skill in the same way that i would say actually the most valuable class i’ve ever taken my life was my fourth grade typing class like i i’ve used this skill more than any other skill in life and i’ve talked to people who didn’t take typing and i can see the impact that it’s had on them and so yeah i just view excel as a timeless skill just like i have you typing on my computer as a timeless skill interesting so a few thoughts on this yeah firstly so um my brother is working on a startup to try and um compete with excel really yeah it’s called causal um they’re trying to basically be the new xl but for um number crunching because excellent has all these different excellent has all these different use cases and it’s it’s a very general tool but you’ll you’ll get like ridiculous you know trillion dollar companies using excel to manage their forecasting and you’ll also get people using it to figure out the scores in their five-a-side football league and yeah their kids kids football practice and their sort of uh their thesis is that uncertainty calculations and modeling and stuff is really hard to do in excel where you have like loads of uncertainty with all these different numbers plugging in it’s really hard when you when an excel sheet gets really big for anyone other than the person who made it to understand what’s going on and even then that person probably doesn’t understand what’s going on and so it’s really hard to kind of change your assumptions and all this all this stuff so they’re building building uh i see it right now i looked it up causal app causal replaces your spreadsheets with a better way to build models connect to data and share dashboards with your team your brother sounds very smart um oh they they they raised 4.2 million in 2021. uh this is awesome uh yeah i can also read more about it recently oh really you should look into that start using um i was gonna say now now you have to get ultimately that if they get big enough you have to get them to work with uh universities so universities teach causal courses oh my goodness that’s a great idea yeah yeah good for you know any kind of number crunching and modeling and stuff yeah um i also very much agree on on the typing front so you know i’ve put in large amounts of time and effort into actually just practicing my typing once in a while through typing tests and stuff oh i’ve seen the video yeah whatever the speed was it was is absolutely ridiculous i remember watching that video and then doing a typing test and just feeling horrible about myself after doing that test what was the speed again i think it was one 156 words per minute that’s my record i need to try and bump that up but it’s it’s it’s kind of weird so these last few days i’ve been on this team retreat in wales currently overlooking the hills it’s very nice um but i sort of set myself the challenge that every day i was going to write a whole first draft chapter of my book each day each day it’s sort of been like sort of five six there’s seven thousand words and it’s just kind of i think have you done it yeah so every time the last few days i’ve been banging out one chapter and i need to do another one today but i’ve already done four thousand words in about a one and a half hour slot this morning and it’s like amazing that i i think previously when my typing speed was half or a third what it currently is it’s like it would be a bit of a bottleneck like my brain would think faster than i’d be able to type yeah but the faster my typing speed is gone it’s like i can type at the speed of thought almost and so it’s almost so easy or so easy to if i’ve got something in my head to translate it into words on a page and it’s it’s you know it’s really bad obviously but like you know the first draft of anything is really crap so that’s what my editor keeps on saying just like spew out all the stuff you’ve got in your head onto the page like and then we’ll we’ll clean it up in post so so honestly that was something i’m very interested about because if i remember correctly like i remember the general um you know the general gist of the book that you’re writing and when i’ve thought about writing books the thing that’s always kind of been like the bottleneck in my head is will i be able to just write chapters from my head or am i going to have to like be referencing uh resources online or references but if i do that is that going to distract me because now i’m plugged into technology so when you’re writing these chapters a day are you fully disconnected from the internet and you’re just writing five thousand to seven thousand words of whatever comes to your mind um great question yeah so i was i was worried about this as well um uh i i’m connected to the internet because i use it go to a lot of google docs which is annoying for offline stuff but if i ever get to a place where i need research or something like that i’ll just do a little apparently all writers do this tk um you just write tk need research about xyz over here um you know yesterday i was working on a chapter where i was talking about kind of feelings of anxiety and self-doubt when it comes to procrastination and i knew i wanted a line that sort of described the feeling of anxiety but i couldn’t be bothered to sit down and figure out oh crap how to describe the feeling of anxiety so i just wrote uh anxiety is that feeling of tk xyz and then me or the editor will come back to it later and it just sort of keeps me in the flow yeah so you just give yourself the permission to like leave space and revisit the things that you do need to do more research later on which by the way we should talk about this at some point in the conversation about uh the feelings of anxiety related to procrastination because i would actually argue that is one of the biggest things in my life that creates self-doubt lack of self-belief it stems from feeling like i’m a chronic procrastinator in life and i have been since freshman year of college okay that’s okay we’ll do we’ll we’ll put a bookmark on that and definitely come back to it because i imagine people would find that surprising given kind of your your story um yeah so definitely bookmark in there i was going to ask as well so other than typing and excel have you ever have you found any other sort of meta skills that are generally useful for life yes but they weren’t taught in university uh so one is storytelling and selling like i think the number one skill that helped me be a strong founder especially in the early days of building our business is the ability to sell and i think i’m blessed in the sense that that’s just one of my intuitive superpowers it’s something my dad worked on with me as i was growing up he was really focused on my ability to articulate uh he thought that was really important i ended up taking a business communications class at michigan but to be totally honest i didn’t find it very valuable half the time was spent doing kind of public speaking half the time was spent literally like digital communication like how to write an email and i found that to to be tough tough as in like not helpful but yeah i mean sales i would say is that if you are trying to elevate yourself as a professional in any way not just as an entrepreneur just in your career you find yourself selling yourself far more times than you realize so like just even talking about a business when we were starting morning brew we’re talking about a startup that was a media company media companies are generally not venture backable so you can’t raise from institutions uh we had a newsletter that’s all we had we had 30 000 subscribers at the time we weren’t making any money but we had to raise money in order to possibly get to a place of making money and so selling investors on why a 21 year old and a 19 year old who have a media company where media companies are generally not profitable businesses and we weren’t making money yet and by the way it’s not really a media company it’s a newsletter we had to sell them on why they should put their hard-earned money in our business we had to sell our initial employees on why they should leave their steady jobs to join a business that’s making zero dollars and we had to sell advertisers because that was the first way we made money as a business we had to sell advertisers like discover card large financial institutions on why they should even bother wasting their time on a company that reaches 30 000 people versus allocating that time to thinking about say a television commercial that reads reaches millions of people and so i’d say that is the number one meta skill i’d actually argue it’s a meta skill even like in personal life not just professional life i’ve i’ve heard a lot of people say that that you know the the skill of selling is kind of yeah is well one of the one of the most useful skills you can have but i’ve always kind of wondered and i never quite followed this thought of like what does what does that actually mean like i wouldn’t say i’m good at selling but i’ve i guess i have sold stuff in the past and i just don’t really think of selling as like a thing you sell yourself on youtube every time you post a video like and this is actually an interesting thing of and i’ve thought a lot about this is what’s the difference between sales and or selling and storytelling and my view is just if something comes off as selling it’s just shitty storytelling uh and and and so my view is like why do people watch your videos for a long time why did you just hit three million subscribers on youtube when there’s a bunch an abundance of content because you’re not the first person to talk about topics related to productivity to bettering yourself right you have found a way to storytell in a way that captivates people and keeps them engaged so you are innately good at storytelling i just don’t think i think it is quite natural and intuitive to you it doesn’t feel like work to script and then uh deliver that in front of a camera you couldn’t be where you are today without being exceptional at storytelling how do people get better at this it’s a great question um my answer would be it’s a combination of practice of shadowing and feedback and of understanding the fundamentals of what it means to story tell well so going in reverse order i think that there there are tried and true there’s the science to it there’s like tried and true formulas for what is a captivating story for people uh and so like for example i’m reading uh the book creativity inc right now which is the story of pixar like are there are story arcs which is like there is a hero the hero is on a journey the hero on the journey experiences a challenge uh in experiencing the the challenge they go through adversity they overcome the challenge and they reach their goal like that is one story arc i think there are a number of formulas this way so at base level i think studying the best storytellers of all time uh and studying the formulas that they use to tell stories is the first step the second step is what i would say is the combination of practice and shadowing and so the example i’ll use for you is in the early days of morning brew when we had to pitch advertisers on advertising in our newsletter i had never sold in a professional setting anything before but i had to do it there was no option we had to make money and so i you know got reps pitching probably in our first year 250 advertisers on 30-minute calls about who morning brew was what we stood for and why spending your money with us was worth your time and your money based on what your goals were and the first pitch i did probably the second pitch probably the 20th pitch i did was really bad but every time i would take five to ten minutes after a pitch and i’d have a reflection period where i would write down what are the things that i think i did well and what is one thing i would change for the next pitch i do and i would record every pitch i did as well so then thinking about shadowing and feedback right i was delivering feedback for myself but a big thing that i did with our junior sales people when they joined morning brew was when they would do a pitch in the early days i would join them on those calls so that first of all like i would do the sales pitch they would listen to me so they would sponge up that information we would do that for a few weeks and then gradually i would hand off the reigns to them where they would start doing the pitch we would record it we would listen back to it together after which by the way for anyone who hasn’t listened to their voice before and hasn’t listened to themselves do a sales pitch it is going to be excruciating for you to do the first time but it is so valuable i would give them feedback and then they would use that feedback the next time and you know you look at a company like gong gong is a multi-billion dollar sales software company there’s a reason it’s such a valuable business so what gog basically allows you to do is allow sales orgs to record every sales call they have and then in in a database holds all of the sales calls organized by who the seller was the type of client that it was and it also will do things as sophisticated as say what percentage of the time on the call were you talking versus what percentage of the time was the person talking and it will categorize what were you talking about almost like you know on youtube how you can kind of set the chapters of an episode it does that automatically in your sales call and so then any seller can go on to gong and study what are quote unquote the best calls that have led to the conversations that convert their clients the end of the day there is the there is this art and science to understanding what works for you to storytell in a way that leverages your strengths um but also understanding the science of what works well and what are kind of like the the the natural story arcs that people over the course of time are always attracted to nice that’s a that’s a great answer was that off the cuff or have you have you ever thought about this before that that was off the cuff yeah yeah that was good that was like framework i love it it was like very meta we were using a storytelling framework and talking about storytelling framework 100 alrighty little interlude to tell you a little bit about this book the e-myth revisited which is a book that both me and alex absolutely swear by in terms of it just being super helpful in building businesses it’s about why most small businesses don’t work and what to do about it by michael gerber now this is a book that i usually recommend for basically anyone who wants to scale up their business but if you don’t have time to read the book and i do recommend you do actually read it you can check out a summary of the book over a short form who are very kindly sponsoring this episode of the podcast if you haven’t heard by now short form is the absolute best service that summarizes books they just have sick book summaries and they’re way more than just book summaries they’re like include one page summaries of the book just in a single page but they also include chapter by chapter summaries of each of the chapters and they also include these like interactive exercises in between some of the sections so you can really engage with the points and even better they also kind of regard books as being you know with a little bit more critical appraisal kind of vibes than a lot of other book summary services do so if for example in the book michael gerber makes a point which is particularly controversial or which another author might disagree with then they’ll add a little short form note that says hey this point was a bit controversial like maybe you should check out this other book that argues for the exact opposite and that’s just really good in terms of just getting a balanced viewpoint on the stuff that we read there’s two main ways that i personally use short form the first one is when if i get a new book recommendation and i don’t necessarily want to read the book directly or i’m not 100 sold on reading the book then i’ll often go on short form on my phone or my laptop and be like hey has short form got a summary of the book usually they do if it’s the sort of nonfiction that i enjoy reading and then i’ll often read the book summary first and if i like the book summary then i may or may not decide to read the book itself and secondly i use short form as a way of revisiting my highlights from books so for example i’ve only read the e myth revisited once but i’ve actually read the short form summary of it about three times uh once in preparation for my part-time creatorpreneur course but also twice just randomly because i was like this has been a really good book i first read it in 2019 changed my life i don’t want to reread it because it’s like i’ve got most of the value but let me just revisit the points so something like short form is super helpful for that if any of that sounds up your straight then head over to short form dot com forward slash deep dive and with that url you will get 20 off the annual premium subscription and you’ll get access to the best service that summarizes books in the world okay so it’s march 2015 you launch morning brew as a proper newsletter with a proper website that people can actually sign up for what happens next we become obsessed with two things how do we make this newsletter as good as humanly possible and how do we grow it as quickly as possible and so i would say we did kind of some pretty creative things to make the newsletter really good in the early days i’d say the first thing was austin and i said to ourselves like we can help write this thing but we need more support and so we had reached out in our newsletter to students who are reading our newsletter and we said hey if you’re interested in writing about business and you want to get your words in front of hundreds or thousands of people we’d love you to come right for the brew and so we ended up having a rotation of probably eight writers at any given time from different universities who were writing call two stories a week in our newsletter so that was kind of like our our uh newsroom of sorts and these writers were not paid they were just doing it because they wanted to get their brand and their words into the world and they they were excited about what morning brew was and what it represented then we found an editor and that editor was someone who was in the business school with us at michigan so he’s very into markets and he still works in finance today but he also wrote for michigan’s newspaper so he had really strong editing chops so he was the guy who basically set the content schedule for those six to eight college students and then he would edit their first drafts then this the third thing we did is kind of the i would say the the least traditional from the beginning austin and i said our content needs to read like you’re having a conversation with your smart and sociable best friend it can’t read like traditional business news where it feels like a robot is throwing up words on you yeah and so we’re like what is gonna give our our uh content that x factor that’s gonna feel quick-witted and smart and funny and so we’re like we need to find a funny person and so we we put out we put it out a uh you know a job post for a funny person and we found our funny person and our funny person was this guy grant he was in a program called organizational studies at michigan which was quasi business schools like similar to the business school less focused on finance and more focused on like uh organizational organization building culture et cetera so he was in that program but he was also in the improv troupe at michigan and so he was hilarious and he was a good writer and understood business and so we brought him on as that literally the the the job we called it was he was our voice editor so we had our writers we had our uh editor and we had our voice editor and that was the process that we got to of putting out our newsletter every day and that gave austin and i more time to grow the thing and so the way that we thought about growing our thing was the the visual i have is like a bicycle so you have a bicycle and you have a hub in the middle the metal hub and then you have spokes that go out to the the the wheel like the outside of the wheel of the bicycle right so you have a hub and you have spokes and our view was spokes are all of the people that we think should read morning brew so those are college business students hubs are the people that are basically the people or the channels that have access to all of these spokes how do we get the attention of hubs so we don’t have to go to every spoke and convince them to read our newsletter and so at michigan what that looked like was teachers and club presidents if we could get in front of teachers classes we could get in front of 75 to 500 students and if we could get in front of club presidents we could get into in front of say 50 to 250 students and so basically for all of our second semester senior year at michigan austin and i spent going back to the the importance of storytelling and selling we spent our whole second semester in about 150 club meetings or or classes pitching club uh students on why they should read morning brew and so we’d go into a class we would give our two-minute uh appeal about what boarding brew was why this was the best business newsletter in the world how it was free so there was no downside you could sign up and if you didn’t like it you could unsubscribe no hard feelings and then what we would do is we’d pass around a sheet of paper with a pen and we would ask students to write down their email address we would take that notepad after the class and we would type in manually all of their email addresses and the reason we passed around a pad and a paper is because the conversion rate of people writing down their email on a pad was significantly higher than us getting in front of the class and saying pull out your laptop go to morningbrew.com and put in your email address because there were far more steps it was pulling out laptop opening laptop going to safari or chrome putting in morning brew putting an email address whatever that is five or six steps whereas the new pad and paper it was two steps it was grab the grab the pen and write down your email and we basically just pushed the rest of the steps on austin and myself to actually input it and so that was how we got say our first 2 500 to 5 000 subscribers and then the next process became okay we’ve saturated the michigan market now what and then now what became how do we find austin and alex at every other college in america so how do we find the the two people that are gonna basically get in front of all the hubs at other schools that aren’t us and so that’s what led to our college ambassador program and our college ambassador program you know it still exists to this day we learned so much with it and i think it was unique at the time because i never heard of a media company doing a college ambassador program when i think of college ambassador programs i think of like red bull uh college ambassador or ambassador program where people park the red bull car in front of a university they have people with backpacks that hand out red bulls but never for a media company and we ended up going through many iterations where the first ambassador program we went for the quality approach we were where we were like let’s get the best ambassadors across the country to represent morning brew so we had this super uh rigorous application process it was like harder to get into our ambassador program than to get into harvard uh or oxford it was like we put out an application people applied they dropped their resume we ended up accepting i think 15 ambassadors who were like they were the influencers in their business programs at their schools they were in all of the clubs they were the class president you know they sat in the front of their class and it absolutely bummed our first ambassador program did not work well it didn’t work well because what we didn’t account for is that while all of these students that we accepted were really impressive people don’t have a good sense of time management when they’re in college like they really haven’t figured that out yet and so these students were the people who are already so involved on things in campus that they had they actually were the people the least amount of time and they had spread themselves so thin that they could never commit to our program so the second time we did it we went exact opposite approach we went with the quantity approach where we fully automated the process so we sent out an application but everyone was accepted we just wanted wanted it to have an error of exclusivity so you’d fill out an application you’d get an automated email from us that you were one of a few people accepted to this program and then you’d get automated emails from us about how to start sharing morning brew so you’d get a google drive that included marketing collateral a script for what to say in classes sign up sheets that you could print out to pass around classes only when you got to say i think it was 25 sign ups did you actually get put into a group with austin and i where we talked to you and so we had this vetting system for big top of funnel uh but only have human interaction with students when they’ve kind of proven that they can do well as an ambassador and when we did that second program we had 250 ambassadors across 200 schools and so that was our focus uh kind of for the rest of college was growth and getting the content down that really reminds me of the whole you know do things that don’t scale yep because you know if i imagine like we we’ve just launched a new a new newsletter for our creatorpreneur brand you know trying to help creators think more like entrepreneurs the last thing on my mind would be let me go out manually recruit some ambassadors and get them to spread the word for my email list it’s just it’s so rogue it’s so it’s so analog in the world that we live in today i gotta be honest if i’m you i’m thinking about how do i every time colin and samir post a video how am i commenting with my newsletter on their videos because because the people watching their videos are all creators yeah so you’re growing this newsletter basically door-to-door uh but like at scale um yeah what what did the numbers look like in that first year like 2015 when you were yeah so when i graduated from michigan uh i want to say we were at 10 000 subscribers oh so we got to 10 000 by the end of senior year but i had a decision to make because i graduated from college and i had this job to work in finance so i basically had to make the decision am i going to do this job that again was my dream for my entire life like this was the peak this was the pinnacle or was i going to quit my job tell my overprotective jewish mom that i was gonna go do this newsletter thing that makes no money uh that has ten thousand people on it rather than doing the thing that i dreamed of uh i did not do the second uh i went and i worked at morgan stanley sales and training generally you start early in the day so i would wake up at five a.m every day i would i would go to the office i would work out i’d be at the desk by 6 30 i’d trade from 6 30 until 7 pm 7 pm i’d go back to my apartment and basically from 8 p.m to when i fell asleep with my laptop on my lap i would work on morning brew and that was effectively my entire experience at morgan stanley until i quit my job how long did you do this before you quit the job so i i started at i graduate june of 2015 i go to new york my job starts july of 2015 at morgan stanley i quit my job september of 2016. so just over a year it was right after uh labor day of of 2016 and the reason i quit was basically austin as i mentioned he’s two years younger and he had had his junior year internship he got an offer to work in investment banking and he now had to make a decision basically two years after me was he going to go full time into investment baking or do morning brew and i vividly remember austin came to new york uh for a weekend we got beers at this like really old bar one of the oldest bars in new york city we basically talked about like what are we gonna do like there’s a clear fork in the road it was a fork in the road of we’re either gonna go full time on this thing or we’re not and if we don’t go full time on this thing like this is it’s either gonna stop or it’s gonna just be kind of like a shell of itself because i was working a lot austin investment banking i remember during his internship he had pulled like four all-nighters in his summer of his internship and so it was very much like this was an inflection point and we decided to go full time on it and i i think we had different reasons for going full time on it and for me the reason i went full time was a few fold i thought about things in terms of regret what would i regret more would i more regret staying at morgan stanley and seeing someone create effectively their version of morning brew and it succeeding or would i more regret leaving morgan stanley doing morning brew and morning brew fails and i have to find a new job and to me the answer was obviously when i answered that question which is i would far more regret staying at morgan stanley and seeing someone succeed with their version of morning brew just because they risked their time when when i wouldn’t that was the first way i thought about it the second way i thought about it was what is the worst case scenario so i thought i always use things as like the worst case scenario framework in a decision and can you live with the worst case scenario so the what what’s the worst case scenario if i quit my job and went full-time on morning brew and the worst case scenario was i quit my job i work on morning brew and then say six months later it fails because the vast majority of businesses fail and then i was like then what what would have happened in that worst case scenario and i said first maybe morgan stanley would take me back because i had this entrepreneurial experience that made me maybe maybe unique in my experience and uh they would value that and i would say i said no let’s say that’s the worst case scenario and i burned my bridges and they wouldn’t take me back then what it was like maybe this makes a good business school story where i could apply to business school and i said you know what maybe uh this is a common story and it would get me into business school and i said maybe um i met other people while i was doing this startup in the startup scene and i could go start another company or join an early stage company and i basically got like four or five layers deep of options and i was like if none of these are options after morning brew fails then this isn’t actually like a morning brew problem this is an alex problem of not keeping his options open as a professional and so that was the second way i looked at it and the third way i looked at it was simply about how do i want to live my life it sounds cliche but i very much you know i just had like a mentally transformative experience where a week before junior year of college at michigan uh my dad passed away suddenly uh he passed away uh from a stroke he was 49 years old he was perfectly healthy like literally built the same as me similar uh physical health and after that experience everything just became clearer around one how most things that we worry about on a daily basis in life are wildly unimportant and two how really like you know your your time on your uh life countdown clock you have no idea when it’s gonna hit zero you look at the statistics and you hope that it’s gonna hit zero around you know 80 years old or later but you really have no idea and basically i said to myself if if i knew my countdown clock was hitting zero tomorrow what would i rather be doing with my time and it was like a no-brainer it was like i knew that i was so more so far more enjoying the experience of building my own thing and tinkering like i was tinkering in kindergarten than sitting in front of a computer screen and trading mortgages wow yeah i’m sorry to hear about your dad that that must have been really tough for you at the time yeah it was uh it was really tough for a few reasons obviously it was it was shocking it was one of those things like he he was my best friend and it was like you know he was the guy that when i would uh be walking from class uh back to home or vice versa like he was the person i was texting or calling and it was uh it was a surreal thing like there was a period of time after he passed away where i would just be walking in new york city and i would call his number just to relive that experience and it registers it’s pretty funny thing now for a while i’d call his number and it would just you know go to like this number is not in service because after he passed away we didn’t you know he didn’t keep his phone obviously and then at probably six months to a year later they reinstate phone numbers get recycled and so i still do this to this day probably i do probably like once a year now where i call his number and there’s a family who has his phone number now and it’s just interesting to hear it’s been the same family for the last like seven years and uh they’re probably like who is this random 973 number that calls us once a year says nothing and hangs up um but yeah i mean so there was apps there was a there was a huge void that i felt because it really was my best friend and then i think the final thing is it um it made me think a lot about just like my emotions and how i process emotions because i think as a function of growing up in a wall street family as a function of you know being a man and there being certain gender norms with being a man i think as a function of my own coping mechanisms i found like my my best trick my best trick and my worst trick was to take emotionally provoking things and push them into my body and not feel them and i’m really good at that trick and i think that trick paid dividends in my career as an entrepreneur because i think as was hitting the fan at different times like i was cool as a cucumber i really did not feel like scared at any moment in our journey even if it was completely rational to feel scared but the reason i say that is you know after my dad passed away i only cried once and it was such an interesting thing to me and that i felt guilty about for a long time because i was like this is probably the worst thing that’s gonna happen to me in my life is a tragedy like this and i only cried once like how do i only cry once about losing my best friend suddenly and so this is something i still work on to this day and think about to this day which is how do i better have access to my emotions because they’re absolutely there my body has just buried them how do i have better access to my emotions so i can experience things fully and emotions give you amazing data in life to know what you love what you don’t love what you want to do and what you don’t want to do wow i think thank you for being so open about this yeah of course this is this is something that i have been thinking about as well in the sense of yeah being an uh sort of entrepreneur bro um you know growing up in a asian family meets kind of an old boys school meets you know talking about and feeling emotions and stuff very much frowned upon yep uh and then i discovered stoicism and i was like yeah stoicism kool-aid like yeah you know this is how i’ve been living anyway i’m a stoic sage etc cetera i don’t feel i don’t feel negative emotions if i don’t want to i i’m also right now trying to figure out how basically it’s going to sound kind of weird but like how to feel more oh no this is what i’m working on constantly yeah how how are you doing it uh well one this is like the focus i would say there’s two topics that i generally focus all of my time with my therapist on one is how do i feel more but i’ve changed the wording over time to be like intentional with not how do i feel more because i think that uh implies like that i am feeling less right now and i’m not feeling enough and there’s something wrong with me and i and so what i’ve changed it to me is how can i fully feel my feelings so whatever my feelings are whatever my emotions are how can i get to a place where i am fully feeling them and nice and so you know what we spend a lot of time doing is she will help me visualize like moments in my life to try to because what she’s realized about me is like i i’m a very visual person and so like i get images whenever i think of something and so for example you know i shared with her in probably our second or third session together that i was uh bullied in school probably from fifth grade to the end of high school like i i was bullied i never felt like i was a part of a group like i always aspired to be part of like the cool group in high school i never felt a part of that group i felt like i was always trying to seek their approval but never received that approval and so a lot of times she’ll actually have me visualize that she’ll be like what is a moment that you felt really lonely and felt really sad for yourself because you didn’t feel like you were belonging in high school and i would describe a moment i’d be like you know it was down to the couches the senior couches in the high school at the school i went to i was sitting at the couches there were like eight people there i would say something people would dismiss it and people literally like turn their bodies to not include me in that discussion and she would tell me to like close my eyes and like sit with envisioning those people talking and closing their bodies to be me being on the outskirts and she would say what comes up for you you know what would your older self right now if you were sitting next to your 17 year old self what would you say to him as he’s feeling really upset for himself that he doesn’t feel belonging and so i think she’s trying to leverage what she knows that is intuitive and natural to me which is visuals and put me back in kind of this time machine of life the other thing she tells me to do is like to sit with emotions when i feel them meaning like any type of emotions like when i’m laughing hysterically at something she’s like before you go on to the next thing because your best trick is distraction distraction through intellectualization or doing something before you do either of those before you intellectualize or you distract if you’re laughing hysterically or if you’re annoyed with something that a family member said or you’re pissed with your co-founder just spend 30 seconds and just sit in it like just sit in it don’t have any expectations of it but just sit in that feeling because you’re retraining yourself to realize that you are in fact feeling something and over time it will become natural where you don’t have to get yourself for 30 seconds to sit in that feeling have you found working with a therapist useful extremely useful extremely useful i find it useful because one i think in a force it forces for me the accountability to reflect which i think in the busyness of life i will get out of the habit of doing and i think it’s really important i also think again at the end of the day a therapist is someone who has tools that they’ve been taught in their career so like if i wanted to figure out for myself how can i feel my feelings fully right i could go one way i could do it is go read many books on it and maybe get to that answer or i could have an hour-long session with someone who has read probably all of those books also and just can almost be like the summary of those books but what i will say is i think a therapist is kind of like anything else in life where the they’re serving a purpose to help you tackle challenges that are preventing you from being fully filled up in life and different therapists have different specialties and so what i mean by that is there was a therapist who i worked for work so i worked with for probably this first seven years that i was doing therapy that was my first therapist and she was amazing but i would say there was a natural kind of like uh deceleration of the learning curve or the benefit curve where in the beginning she gave me all of these tools for my anxiety for my ocd and then it kind of plateaued because i had those tools and i found that we were talking about the same thing over and over and what i realized is for a long time i kind of was just going through the motions of doing therapy with this person because i was like oh but this is therapy this is what i do and i think what i only ended up doing later which was important to reflect on is like okay but it serves a purpose is it still serving that purpose and what i realized for myself is this therapist had a specific set of skills skills that helped uh with the things i was working on at the time but as i improved in those areas and i had new challenges i want to work on maybe my current therapist isn’t the one who’s going to be most helpful in these new challenges and so i ended up changing a therapist to someone who i thought who was for uh could be more helpful with things like feeling my emotions or like self-love and self-belief because it was a therapist who her modality was things like uh hokomi therapy which is about feeling the body like it’s very body focused therapy and so that’s a big learning i had is like how easy our brains can get into autopilot and just assume what we’re doing is the thing to do if we don’t question it do you do these sessions of zoom or in real life or i do it over zoom so my therapist is based in colorado and we do yeah we do these zoom meetings uh usually every week or other week which by the way this gets into another topic like for the for a long long time i felt very guilty about doing therapy a lot because i’m very much like a money hoarder and so i could i would get into like i’d get anxious about spending money on therapy i’d be like oh my god this is a lot like you know my therapist is uh 300 an hour i’m like this is a ton of money like what do i really need to spend on this and at some point i got to the point where i was like if if i am not willing to spend my money on someone who is helping me see the world more clearly and live a more fulfilled life i do not deserve to have money that i have because that is crazy to not spend on something that is quite literally making my life better um and uh yeah so i talk to her every week or other week um and it’s it’s really good i will say as someone who has a very creative and distracted brain it is very easy for me even as we’re talking now for me to get distracted with things on my computer and so what i did now and i do with my therapist is i literally close everything the only application i have open with her is zoom uh zoom and notes because i’m i’m constantly writing down notes as we’re talking so i can reflect on tools she’s given me and also hold myself accountable and her accountable to like am i still getting value out of this and so that’s a big thing that i’ve had to change with zoom because when i was in person with my therapist like it was harder to get distracted i tried a therapist for like three or four weeks a few months ago actually like last year now that was ages ago and i found that like i wasn’t really a fan like the first two or three sessions was sort of helpful but then i did find session four and five and six we were sort of just sort of talking about the same stuff and part of me was thinking oh i don’t know if that’s just the modality of zoom just not being great for connecting with someone in that way but it’s it sounds like you’re getting a lot of value out of this therapist through the zoom sessions yeah and what i would say is like i think therapy is in a lot of ways like speed dating where i think it is very reasonable to see like eight therapists as a hypothetical number before landing on one therapist because it’s almost like what are the odds that you go on a first date with someone and that person ends up being uh your partner your life partner it’s like the odds are literally it’s like de minimis and so in the same way like every therapist has a different personality has different sets of tools and you have very specific needs uh that requires very specific tools and personality in a way that lands with you it’s like to think the first person you talk to is gonna be the right person is like you’re you know you’re betting that you’re gonna win the lottery yeah okay you’re right i’m sold um i will ask you for your therapist to email the rest afterwards because that seems good a good first option cool um yeah i guess i guess in my mind i was thinking of therapists as kind of like being doctors in that they are fungible in that one doctor at least here where we follow guidelines is practically identical to another doctor at the junior levels anyway but i guess therapist yes i i would argue that yeah therapists are very non-fungible excellent that’s your nft the non-fundable therapist so you’re at morgan stanley for like a year and a bit where you’re working ridiculous hours and you’re kind of hustling to get this morning briefing off the ground this is a very common story amongst basically all of the entrepreneurs you and i know where in the early days of the thing especially there is a level of you know to use the that terminology hustle and grind and maybe losing a bit of sleep and maybe not take fully fully taking care of your health and really not prioritizing things like self-care and a balanced work life and these days it seems like that sort of stuff is a bit like you know there is a sort of anti-hustle movement of like no life should always be balanced at all times and like self-care is really important and stuff and no one would say that that’s not true but if you ask a lot of entrepreneurs who’ve built something from the ground up especially in the early days they would have said that no hang on in the early days i needed to de-prioritize self-care and stuff for the sake of getting this thing off the ground yeah so i wonder with the benefit of hindsight um do you think if you had had more of a balanced life you and austin had more of a balanced life you would have more than that that morning brew could have been as successful as it now is or how do you think about that i think the answer is no i don’t think morning brew would have been as successful if we were more balanced in our life as in spent less time on morning brew but there’s a big caveat here that goes back to the idea of uh guilt around procrastination i think that it would have been possible to have more balance and been a successful morning brew if i was more efficient and smarter in my work and not a procrastinator and i have not proven to myself in life yet that i am capable of that but if i can prove to myself that i am capable of that i think it opens up a lot more time for non-work things can you tell me more about this procrastination stuff like how yeah how in particular i’m interested in the early days where you’ve got a job and you’re doing this thing on the side and now i you know we’ll come to this but i can imagine you’re chilling because you’ve got like because you’re stupidly rich and et cetera et cetera but like you know in the in the early days when you were you were hustling what did the procrastination look like i’d say there’s two types of procrastination it’s doing non-work to avoid work and it’s doing the wrong work to avoid work oh that’s nice and so doing non-work to avoid work is where i would spend a lot of time on social media and i would spend that time on social media instead of doing work and i would say actually that’s gotten worse over time as i’ve created started creating content on twitter and other platforms the addiction to the dopamine hits of likes and validation has gotten really bad bad to the point where like i’m literally thinking about do i want to create a like an aaa for phone addiction the the second type is work to avoid work and what i mean by that is this goes back to like how we’re taught from a young age uh and in school what it means to do work and i think it means you’re given an assignment you do the assignment uh you’re given a test you take the test you create checklists you do the things on the checklist and there’s a feeling of that felt really good to do those things on those checklists i feel like i’ve achieved what i wanted to achieve but the issue is is that as a startup grows and it evolves the things that you should be spending your time on change and they look different than the things that you were spending your time on perhaps six months ago and also the things that you felt really good about doing and so here’s an example i mean there was a period of time where i would spend hours a day reaching out on linkedin to potential uh advertisers of morning brew and i’d do all this linkedin outreach to hundreds of them then i would schedule calls with them uh and i would do all of this busy work related to outreach for selling advertisers and it felt productive because on my to-do list was reach out to morning brew advertisers schedule calls and morning brew advertisers felt very productive and it felt productive because the justification in my head was hey we need to make money as a business through advertising this is time well spent but as we were growing something that became more important or became i’d say a more important job of me as the ceo of the business was planning was thinking okay where do we want the business to be three months from now six months from now 12 months from now and this was at a time when we didn’t have traction uh so we didn’t we didn’t have the bible for running a business and so what would happen would would be what i just described to you of like setting a strategy in the future so that i know how i should be planning my time today who we should be hiring today like really important things i would never spend time on it i would just never do those things luckily i had a partner in austin where he was starting to think about those things and he picked up the slack there but it was i was doing work that felt good that i could justify was value adding to the business to avoid the work that really needed to be done to push the business forward and so i would say those are two types of procrastination and for me what would end up happening is i’ve used this term before of like the procrastination hangover and basically it’s the feeling of after a long day feeling shitty like feeling this like yucky feeling of like damn i just wasted a day i wasted a day because i wasted time doing things that don’t grow me for things that if i did them they would grow me and i wasted time on things that are easy tasks for me to do because i didn’t have the courage or the focus to do those hard tasks and every time that happens and i have a procrastination hangover i think i lose a little bit of trust and self-belief in myself because i haven’t kept my word to myself of doing the things that are most important to do and growing myself yeah that makes so much sense i think a big part of i think the emotional barriers to procrastination i i find it it tends to be two things it’s either self-doubt or it’s fear i i think it’s self-doubt on two levels on one level it’s self-doubt of i don’t think i’m good enough to do this thing but on a deeper level it’s i’m i’m not the sort of person who does things i am i am the sort of person who is a procrastinator and you’ve got so these these two levels of self-doubt and then you’ve got the fear aspect of it which is fear of not living up to certain expectations for yourself or for others or like fear of what people will think and you know that’s why singing in public is way harder than singing in the shower because you know you’ve got you’ve got the fear component michael my question for you is does that kind of framing make sense with your experience yeah it totally does yeah i think it it makes me because i have felt because i’ve identified as a procrastinator for so long it’s left me with kind of two conflicting thoughts or feelings on one side it has made me lose self-belief in myself because it has made me feel like whereas i want to believe that i am capable of anything it has made me lose belief that that is possible because i haven’t proven to myself that i can work really hard and smart to make anything happen it’s also made me lose kind of like belief and and respect for myself because i feel like to what you just said before i’m not gonna realize my potential because procrastination is keeping me from doing it and while i know it’s quite simple what needs to be done to not procrastinate which is to not procrastinate i have not shown an ability to do that and so i don’t know what is going to change that and then on the flip side of this so that is kind of like the the negative kind of like self-loathing version of this i’ve tried to have a more productive thought about this to say procrastination is part of my way it is part of my way of working where as someone who is very creative who has ideas all over the place who’s easily distracted i can’t i can’t you know uh i can’t take one but not have the other if i want to be someone who has an abundance of ideas uh and who has all these positive attributes from thinking in the way i think i can’t just expect that i’m going to be someone who does not procrastinate at all and is super linear and focused and basically i’ve that narrative is alex you have to own the fact that procrastination is part of your process and it’s okay and actually like to say you won’t reach your potential uh is to say that you believe that if you write yourself a procrastination you wouldn’t rid yourself of all the other things that make you great that make you possible of your potential i don’t know if i totally buy that argument i think that’s why it’s tough for me is i i try to as i’m experiencing this turn it into a positive where i’m not so down to myself because i don’t want to keep harming my self-belief but i also don’t buy that it has to be a part of me i guess it sort of in a way is can can kind of be a coping mechanism for dealing with the negative feeling it’s like oh the negative feeling is actually positive so it’s all good kind of stuff yeah and i think it’s um it’s one of those thoughts like it’s like that negative feeling isn’t doing anything for me anyway it’s only holding me back it’s making me believe in myself less so how do i get to myself where i believe in myself more so at least that you know it puts it puts me on a more solid foundation to push forward in life what what’s your take on this i i was doing a lot of it on the book and it was after having a session with rachel who’s our editor and also kind of book writing coach having had loads of experience with it where we basically diagnosed that it was self-doubt that was the main cause there where my standards were just too high i was trying to produce stuff you know i was comparing my shitty first draft to james clare or mark manson or tim ferriss’s or dan pink’s final draft yeah and i was like oh you know this every the the stuff i’m writing is just and realizing that like loads of people have this thought as well when starting youtube channels like they see themselves on camera and they’re like oh my god like i can’t i can’t string sentences together without making mistakes etc etc but they’re comparing it to someone else’s final draft because you never see a non-edited version of someone’s video and within our youtuber academy there are some you know sometimes i would just upload a completely unedited version of one of my videos for people to see just unlisted and they’d be like oh my god this makes me feel so much better because i realize that even a pro like ali still has takes an hour to film a 20 minute video because of all the stumbling and stuff that happens along the way and now when it when it comes to youtube the conversion from a shitty first draft into a decent looking output is something i’m very familiar with having done it 500 times whereas in writing the conversion of a crappy first draft into a decent looking book is something i’m not at all familiar with having done it zero times yeah so it’s like i don’t have that data or that conviction to know that actually the thing that i’m doing is good enough whereas in youtube i know that we can always fix it in post that’s fine we’ll we’ll we’ll deal with it this podcast i know i can just take a break turn the air conditioning on get a coffee we’ll you know we’ll fix it in post yeah i didn’t have that for writing after diagnosing that it was self-doubt that was the problem and basically you know the solution to that is just lower your bar lower the standards embrace embrace the crap a little bit more now i’ve actually found it pretty easy to not procrastinate on on book stuff i still procrastinate in the sense i’ll go and make a cup of tea i’ll go and kind of wander around a little bit but i kind of know that okay my job for these next few days is to bang out 6 000 words a day for each first draft of the chapter and it’s and it’s being done so in that sense i don’t procrastinate but in but it was it was only that little that mental flip of self-doubt is the cause here that made it work for me i have a question how did you and maybe this is just how you’re wired or oriented like as you gained uh subscribers on the youtube channel which by the way congrats on three million uh as you were along this journey how did you not feel the pull to ultimately get sucked into checking views on your videos in a way that ultimately is procrastination from doing work that would allow you to make better videos did you ever go through periods in kind of your youtube career of checking views subscriber count watch time obsessively or was that just never really in your dna um yeah i’ve had phases where i go through it and it normally makes me feel quite bad to go through it if the numbers are going up then it’s like ah crap the numbers are going up we’re gonna we’re gonna get into a down slump soon and the numbers are going down like they are right now it’s like oh crap we’re in a down slump oh i don’t know i i think this might be the beginning of the end what i’ve found is that the the best way for me to overcome this is to just and and everyone says that it sounds so cliche but just to dissociate my own self-worth from the things that i cannot control as much as possible so now i i think i’ve gotten better at this over time just uploading a video and looking at the views and the numbers but like really trying not to let them affect anything because my bar is now an internal thing that i control which is i will upload a video if i think it’s good or if i if i think it’s a message where it’s worth sharing that would be helpful to at least one person and when i have that sort of zen attitude towards it that’s when a i feel i make better content because now i’m not concerned about oh my god what’s the audience gonna think a b i feel a lot better about it that’s what we’re all trying to achieve and again it sounds so simple like oh you know don’t don’t watch your v don’t look your views don’t like your subscribers don’t look at you know how your channel is trending over time just enjoy just feel good about that you’ve gone through the process of putting content you feel proud about it into the world it sounds so simple it’s just uh it can be very hard at times yeah i i think this is where kind of intrinsic and extrinsic motivation comes in where when when for me the youtube channel was purely a side hustle it’s like oh i’ll make whatever videos i want because i want to help people and it’s all good and maybe two or three people if they sign up to my course it becomes profitable whatever i don’t really care but now that the youtube channel is the foundation of the whole business now it’s like oh like you know the stakes are so much higher at least in my mind what if this just crumbles around me and everything dies and end up broken homeless and alone and i’m not worthy of love and all that all of those geez that’s a lot going back to the therapist this is probably good stuff with them all of that all of that kind of stuff just comes comes to the forefront yeah well i mean that’s an interesting thing you bring up right which is like your youtube work has kind of moved from play to job because it is yeah it’s it’s your job in the sense that it is the source of your livelihood and not not to create obligation for you but livelihood of other people also yes and so it’s like how do you feel the benefit of that play when it is quite literally a job yeah and honestly that’s the thing oh one one thing that um so i’ve i’ve got a coach his name’s corey he might have seen on on twitter uh he and i basically kind of brainstormed solutions to this problem about two weeks ago and actually i started using affirmations and this is surprisingly helpful um i’m just going to read you out my affirmations and yeah like just like i don’t i don’t do this every day i still need to make it part of my morning routine but oh well one thing i have found helpful is for the last month or so i’ve been doing journaling in the form of morning pages every day and often i will think to myself you know am i am i feeling bad about some performance of a video or something and then i’ll sort of reverse engineer okay why am i feeling bad i’m feeling bad because xyz yeah and it will often come back to these affirmations so these are yeah i want to hear the affirmations yeah um so number one i already have enough i don’t need more money or success i am playing my infinite game to learn and teach cool stuff on my own terms number two my life experience is interesting and worthwhile people would love to hear what i have to say about it three i don’t care about numbers i just do my thing and my amazing team will take care of the rest four if i lost everything i’d be able to build back up again to this infinite game over time and it would be even more fun five creative energy surges through me and leads to new and brilliant ideas six today i am brimming with energy and overflowing with joy and then finally i have been given endless talents which i can use whenever i feel like it to create value in the world and all of these affirmations are just sort of tackling a negative thought process or a negative belief about myself that no one cares what i have to say i lucked into this position and now it’s going to come crumbling around me at any time i really have to try very very very hard to make content that peop to make sure people care about the content because me just speaking from the heart is not going to be interesting and it’s like all these so someone from the outside would say no you can make a video about whatever you want you’ve got three million goddamn subscribers just like don’t worry about it but like from the inside it feels like oh no but like oh we it was so lucky to get here right now it’s just gonna come crumbling down so i find that affirmations genuinely i love that can can you read the uh the fourth one again that one really resonated with me i wanted to read and i just want to react to it because that one stood out to me the fourth one if i lost everything i’d be able to build back up to this infinite game over time and it would probably be even more fun both so that’s that’s the most provoking one for me and the reason is is and i think this loops back into procrastination i i actually think at its core procrastination is the source of me feeling so provoked by this and i think it’s why i have kind of like this money hoarding mentality because it almost feels like you know with this business i did this was my one shot and my one luck at making money because after this because i’m a procrastinator i’m not going to be able to achieve success and so i need to hold on to whatever the hell i have because for the remainder of my you know however many years on planet earth uh i’m not going to be able to reaccumulate right and so it’s like such a sad thing right that’s like such a sad perspective that basically like i i’ve quote-unquote peaked and i’m not gonna do anything of worth or value in life moving forward because i procrastinate and so i’ve proven to myself that i can’t be a good diligent worker that can push through any challenge and i think that’s why the fourth one stands out to me so much and i think it’s why i’m so focused on things like not spending on a therapist nice yeah that’s good so you quit the job a year down a year down the line you at austin went on it full time i want to kind of fast forward to when when the sale happened because i’m curious about like money and that kind of stuff and i know we’re skipping up a lot of a lot of the ground midway through but i imagine people can find the story on the internet if they want to learn more well what was the story behind selling morning brew we we sold the business in october of 2020 to um business insider’s parent company which is axel springer large media company based out of berlin germany and that was a conversation that had basically been a year in the making in november of 2019 we had been approached by uh this guy who uh now works at one of the uh at one of axel springer’s um european media businesses but at the time he was a senior person at uh business insider and we had become friendly the the reason we reached out is we we’d become friendly so basically to give context on why we had become friendly as i would you know i was just hustling to grow morning brew one of the growth tactics that i thought about is let me reach out to big business publications who are always looking for more content to drive website uh traffic and let me see if they would syndicate our newsletters on their website uh and so i reached out to one of the editors at business insider saying hey would you syndicate all of morningbird’s newsletters so every day you basically have an extra article that you can put out that you didn’t have to write you didn’t have to pay to have it written and can you just have a call to action at the end to sign up for morningbrew and so for us the benefit is hypothetically a lot of traffic to drive subscribers and i’d asked him a ton of times it clearly wasn’t a priority i reached out to him probably like the 10th time and he was like i don’t want to deal with you anymore let me introduce you to this guy so he introduced me to the guy that i was referring to before who ultimately kind of became the champion of this deal and uh this guy and myself we became uh friends we got beers on stone street in new york city which is this street it’s kind of like this alleyway with a bunch of bars in the financial district of new york city it’s a great spot to go to next time you visit new york um we would go back and forth playing ping pong at our different offices so i’d go to business insider’s offices play ping-pong there he would come to our we work space which we were in at the time play pong he reaches out in in uh november of 2019 and is basically like hey business insider is looking to do more kind of the the phrase to get people into acquisitions if you want to test it is not hey would you be interested being acquired it’s like we’re interested in deep partnerships would you be interested in a deep partnership and and i was like uh do you mean acquiring morning brew and he’s like yeah it’s something we’d be interested in viewer and up to that point austin and i had not thought at all about selling the business uh we had been approached a few times uh but we really weren’t interested what i always said is everything that i wanted at the time is what i had we got to be in charge of our own destiny i was learning and growing a lot was surrounded by amazing team didn’t have to worry about money i was putting like creating something valuable in the world if those five things weren’t being messed up why would i change it ultimately he was like well what’s a price at which you would be interested in having a conversation and i’d said uh 50 million dollars and so you know this person was like well that’s something that would be in you know the the sphere of what we would be open to so let’s have a conversation and so we started having a conversation basically deal terms were put in front of us in february of 2020. okay just a question on that front when you throw out 50 million and he’s like yeah we can work with that like don’t you just like crap your pants like what’s going on in your mind i i if i remember correctly at that time austin and i were like holy that’s a lot of money we should probably have this conversation like that’s that’s enough money but basically we were always like what’s a stupid amount of money that it’d be worth having a conversation about a stupid amount of money that was our thing so like austin we’re like yeah we should probably have this conversation so then we’re having our conversation typically the way that a deal goes down is we had a banker so we had a banker who he hired this banker was the person who interfaced with insider uh an axel springer because normally what you the reason one of the reasons you are banker is like if you have austin and i interfacing with them and a deal like it gets to be a very like tough negotiation and an emotional negotiation kind of ends up awkward when you end up closing the deal and you’re like yeah all those things that we yelled at each other about let’s just forget about those so baker kind of acts as like the intermediary so the relationship doesn’t get hurt in any way the banker also was the person who managed our data room so all of our financials and information about the business that’s what insider an actual springer would look like to come up with what they thought the terms of the deal should be and that this is kind of how any acquisition process happens and so ultimately they put terms in front of us in february of 2020. the terms we thought looked good and reasonable at the at the time like we’re like okay this is a really good deal the reason the deal ended up getting extended is march of 2020 is when the pandemic started and so when the pandemic started our business for a period of kind of like three weeks got absolutely crushed so there was a period of three weeks where we thought our advertising was going to be going was going to go down by 50 percent we were getting call after call from brand saying hey we don’t know what’s happening in the world we are pulling back all of our marketing and so during that time period it was really going back to the early days of morning brew where it was just straight up survival mode finally in you know called april our business normalized things were back they were strong and uh at that then at that point like you know uh our insider like i think uh they were had things going on they were working on things so really it took a year to do this deal we ended up closing the deal finally in october of 2020 and you know i’ll always remember exactly where i was uh i was in my mom’s place in new jersey i was with my mom i was with my girlfriend at the time now fiance they had bought uh champagne they had bought balloons and we have basically there’s a final call where like the deal has already been finalized all the documents have been signed and in a deal process like this the number the number of pages of documentation it like the the final kind of like document book the deal book was probably i can’t remember the exact number i think it was 400 pages um the documents were signed and we all get on a zoom austin myself and all the parties from uh axel springer and insider that were very involved in the process and then basically on the call is when someone from axel springer is like okay we’re starting the wiring process yeah and they’re like that’s basically them saying we’re hitting up uh axel springer’s bank right now to wire you austin and any other equity holders in the business their money for what we’re paying for the business and what i remember in that moment going back to talking about feelings is i felt nothing nice i felt i felt nothing my fiance my mom were super happy for me you know they they wanted me to pop champagne like they were they were they understandably and rationally they were so happy for me but it was like i don’t know i didn’t feel anything and i think i didn’t feel anything because one nothing in that moment changed about what i was doing on the business the thing that did change like the objective thing that changed was that we now had a new partner who thankfully was you know saying that like we could run the business as we wanted to which is what they’ve allowed us to do and the only other thing that changed was obviously you know a few more zeros in the bank account and i didn’t feel anything about that because uh something i had just known about myself i wasn’t really going to change my habits and to this point that really has been the case like if you were to ask me what have i spent on since being acquired and coming into more money than i could have imagined there’s nothing in my life that i’ve spent on that i wouldn’t have spent on prior um you know you know maybe i’m spending a few more dollars to a trip that i’m taking this summer with my fiance than i would have we bought a dog i would have bought a dog otherwise and also i think the other part of it is going up to that point we knew the business was valuable we knew that our equity was valuable and so we knew kind of as long as we didn’t things up we would make money at some point but yeah that was the kind of interesting thing is i didn’t feel anything and you know just to kind of kind of complete the feeling around the money here you know as we’re talking a year and a half now after the acquisition i would say i am no more happy in life today than i was before we did the deal and i had less money i would actually argue that i probably met the same happiness today and for a while i was less happy because i was less happy for a few reasons one is because i knew money could no longer be a motivator it could no longer be a crutch for doing things and so i think in a lot of ways i had to refine like what is go what is going to motivate me moving forward in april of 2021 i moved out of the ceo role into the executive chairman rollup morning brew so that’s five months after the deal and i think for the first six months of being in that new role my happiness absolutely went down because i was like wow this whole business has been my identity for my entire professional life like people know me quote-unquote know me as alex from morning brew i as the executive chairman now who now is spending say 30 hours on the business out of 80 hours i’m getting one step further from the business to start tasting what it’s like to not be a part of this business at some point and what i realized in that moment is no amount of money can help me in that feeling of feeling a loss of identity of not knowing what motivates me and trying to figure out what is it going to be that’s my north star pushing me forward it sounds like in well since you started morning brew and kind of grew it to the point that i got acquired you’re in a way you don’t need to answer the question of what am i doing here what is my purpose because you have a very nicely packaged purpose in morningbrew.com and watching numbers go up and employees being kept happy and advertisers being kept happy and the product being made better and better is in a way such an all-consuming thing that you really it really doesn’t give you much space to sit down and think huh wha what do i really want to do here i think like i was chatting to my brother about this so he’s in you know they’re in early early stage startup mode series a where he’s spending all day on sales calls because they haven’t yet figured out the sales yep you know i was asking him like how how do you feel about this this was uh maybe about six months ago he was like yeah you know it doesn’t feel great but it’s like my baby and like once you have a baby like you’ve just gotta you know feed the baby like yeah it’s it’s not even a choice it’s it’s not even a thought that would cross his mind and he was asking me you know why do you still do the youtube channel where because where some of the time it feels like a slog totally like honestly it’s it wouldn’t it would never cross my mind to not be doing the youtube channel but if suddenly someone offered me 100 million to sell my youtube channel then it would be like okay would you do it i don’t know i probably i probably would um as long as there was and and and the reason i would is because i think over over time i’ve tried to basically create this almost meditation for myself guided meditation where it’s like close your eyes visualize yourself in like the nicest apartment you can imagine like hanging out with the girl and like you know chilling your friends are around you’ve got 100 million in the bank you don’t need to worry about money mate like what are you gonna do tomorrow like how are you actually spending your time yep and i kind of realized that basically the stuff that i’m doing right now i.e making videos writing a book and recording podcasts once in a while is broadly the stuff i would be doing i probably won’t bother making more courses like that’s the only bit of the business that we do for the extrinsic reason of that well it helps fund the business but if for example someone were to come around along and say hey you guys never need to worry about money ever again we will fund you forever we would just put all of our courses completely free online yeah everyone to access so that’s the only real difference there and then that made me feel good because it helped me realize that for me my north star thing is like i just want to learn have the freedom to learn stuff and teach stuff on my own terms and whenever i feel uh the number anxiety around oh numbers aren’t going up as much as i’d like i come back to that thing of like no but even if i had 100 million in the bank i would still be doing this thing so why don’t i just act as if that’s true right now why don’t i just act as if i don’t need to worry about money and just make them make the content that i want because i think it’s interesting and valuable and also the money will take care of itself coming back to affirmation number two which is which is basically that um yeah how was that for you i i think that was good um and i think it’s a beautiful thing again that this stuff you’re spending your time on is the stuff that you would spend your time on even if you never had to worry about a dollar again you know other than uh the course and monetizing the course one thing i’m wondering and i don’t know if you’ve thought about this and maybe it’s just like such a basic emotion that you feel that’s hard to describe how do you know you’re enjoying writing a book or how do you know that you’re enjoying that you enjoy writing scripts and recording youtube videos like how do you know that it’s something that fills you up uh one is looking through my calendar at previous weeks and asking myself did this thing energize me or did this thing drain me and generally for writing and for talking to a camera and for doing podcasts those are the things that energize me and kind of working with a team to brainstorm ideas most other things generally admin related generally operations related generally spread of cell to advertisers related completely drained me so i don’t bother doing them anymore so that’s nice another thing is that i often think you know what would i want written on my gravestone what i want people to say at my funeral and other than kind of good father good husband kind of vibes the third thing that i really value is being an inspirational teacher to other people um to kind of to sort of help them basically help people live their best life which sounds super cliche but i think that is a thing that i can imagine that if i could do that and i’m kind of doing doing that at the moment so if i could just continue doing that that that to me feels like a life well lived and then i’ve tried this exercise called the ideal ordinary week which is you fast forward in your google calendar like five years get rid of all the recurring events that are still there and then you basically block out what are um what do you wanna be doing and for me it’s like oh you know i’d like to play squash twice a week i’d like to do board games and i host friends etc etc and i’d like to have this sort of four hour block of deep work or whatever each day where i can read and write and learn cool things and share share ideas almost almost broadly the schedule that ryan holliday has where he just you know from 9am till 1pm he’ll just go to his little room live with books all around him and just read and write and then he’ll hang out with the family for the rest of the day so i really like that model of like this four hour work day where the work that i’m doing is basically around teaching other people cool stuff and learning new things myself so that is my kind of rough first draft hypothesis of this is the life i think i would enjoy and i’m kind of close enough to it that i get that real-time feedback of after a session of book writing like this morning i did like two hours of just non-stop typing on the book and at the end of it i was like yeah that was good that felt fun uh similarly this podcast right now i’m feeling like yeah this is sick and afterwards i’m gonna think oh i had an amazing conversation with alex that was so fun so it’s like i’m i’m looking up for those sorts of feelings that i get yeah so it’s an interesting thing because as much as you say you’re like trying to feel more you do have an awareness of after you spend your time on certain things just like generally like sitting in that moment like how do you how does that feel to you like do you feel like even like do you feel more tired do you feel lethargic or do you feel like you’re you’ve been woken up or like do you feel like your body’s opened or closed like it seems like you actually have a sense of that and you do that without kind of like you know labeling it as like a tool or an exercise yeah i think so i think i have a pretty strong idea of that and i i think also another thing that i i just always ask myself just this question of like would i do this for free and when it comes to things like playing squash or badminton or tennis that doesn’t even cross my mind because obviously the answer is yes but it’s when money becomes the extrinsic factor that it crowds out intrinsic motivation right because it becomes blurred and you don’t know how much each one is contributing to it yes yeah exactly and so when i when i was dabbling for a few months and being a part-time doctor doing kind of shift in the emergency department here and there the thing i was finding myself doing is every half an hour as i was typing stuff on the computer and just feeling a bit like i’m on the phone to radiology and they’re not replying and i have to sit here for the next five minutes waiting for someone to take my call would i do this would i really do this if i won the lottery and i didn’t have to worry about money the answer was like probably not like i would much rather be in the studio with my team thinking what cool youtube video we can make to share a concept from psychology being here on the phone to radiology so it was i i think that question is a thing i often think about i think that makes sense and and to make it a little bit harder what i found to be difficult was how did i know when something didn’t give me energy versus when something was hard and i was making an excuse for not being good at the hard thing or wanting to work on the hard thing and so the example i’ll use here is like the op like the the parts of the business that you know are austin super powers uh for when we were you know working hand in hand together so things like planning things like uh hiring road map things like uh even running like the traction process like those were things that i didn’t feel like i loved doing but i was trying to distinguish do i not love doing these things because they’re harder to me and things that come harder to me because it’s harder i don’t love doing it because it’s harder and so that’s actually an excuse and that’s a good reason to do the thing to prove that i can do something hard or is it because i just really don’t love the thing because i like doing something that’s like more creative in nature or interactive in nature or something that’s earlier in the process of building something from scratch and so for me i would say that added another kind of like access or variable it was like i’m always thinking in my head on this spectrum from 100 intrinsically motivated to 100 extrinsically validated or extrinsically motivated where am i living on this and do i feel like it is at a place on the scale that feels like it’s in check and it’s a good reason to do the thing and then the second one was outside of the the money versus intrinsic thing am i do i is something that i’m not doing because i don’t feel quote unquote good energy from it is it because i actually don’t like it or is it because it’s hard and this is a good excuse to not do the hard thing nice so you’ve got your intrinsic extrinsic access and you have your hard easy access exactly nice and you can use that in the book if you want nice thank you and and i guess your concern is that am i like let’s say you’re doing something that’s 100 intrinsic but also 100 easy you’d be like oh wait a minute is this really intrinsic or is it just because it’s easy that i’m enjoying this exact exactly you know when you’re at this point where you’ve got extra zeros in your bank account and you don’t know what to do with them and you’re like what do i what do i do with my life yeah how did you go about finding that north star is yeah how did you think about that well if i’m being honest i’m still in the process i still don’t really know what i want to be when i grow up i know there are some options uh like one option is to build more businesses like to go back to kind of the earliest stage and put cool into the world the second is to help others become great entrepreneurs because i do think i love the energy of early stage entrepreneurs uh you know i’ve seen the impact that entrepreneurship can have on a country on an economy on a group of people and to me that’s really profound so that’s one thing a third thing that i’ve considered which is totally out of left field is to become a therapist myself is like literally to go get a psychology degree become a therapist the the kind of like business or startup variant of that is to become an executive coach to coach entrepreneurs uh and so what am i doing today well one it’s like the time i spend on morning brew is like creating content finding creators to launch shows at morning brew and dealing with the biggest hairiest problems with austin and the le the the lens that i look through this is like how do i just learn as much as possible in this experience at morning brew right now because i’m in a really privileged point in the business where we have 275 people i have access to all these people we’re building something really cool how do i just soak this all up for learning uh that can selfishly help me in building businesses in the future and then outside of that right now i’m basically spending time angel investing and seeing kind of how it lands with me to angel invest versus coach people so i’ve started to coach a few people uh and and for me again it’s not really for money it’s just like do am i enjoying coaching and also part of it it’s like can i prove to myself that i actually can add value to entrepreneurs and like push back on this imposter syndrome and then the third thing that i candidly want to spend more time on is like really focusing on on not optimizing health because i sometimes i feel like optimizing is actually a bad word like i feel like it creates actually a lot a lack of balance uh and to me everything is good in not everything but most things are good in moderation and optimization sometimes doesn’t allow for moderation but there are things like working on my food intake my sleep like things that generally just give me the best energy in life and those are things that i want to spend time on uh that i haven’t yet spent nearly enough time on and so to answer your question i am very scared about not knowing at the age of 28 what i want to do for the for many years but i’m optimistic that if i’m patient and if i’m both patient and inpatient patient macro impatient and like feeling like i’m not moving fast enough to answer this question then i’ll get to a play like that i am where i’m supposed to be and that uh things will work themselves out alex thank you so much this has been absolutely wonderful uh where can people find out more about you and we’ll have links to all of the stuff obviously in the video description of the show notes as well yeah first of all thank you so much for having me i’m very excited for when you finish your book and i can add it to uh my reading list and my bookshelf as well you can follow me uh at business barista on twitter uh and you can check out my two podcasts founders journal which is my startup show about lessons from the entrepreneurial journey and imposters where i talk to world-class performers from ray dalio to jay shetty about their careers and how they were able to excel in their career careers even in the face of really deep challenges and uh the mental health journey that went along with those challenges amazing stuff alex thank you so much for coming on everyone thanks so much for having me you next time all right so that’s it for this week’s episode of deep dive thank you so much for watching or listening all the links and resources that we mentioned in the podcast are going to be linked down in the video description or in the show notes depending on where you’re watching or listening to this if you’re listening to this on a podcast platform then do please leave us a review on the itunes store it really helps other people discover the podcast or if you’re watching this in full hd or 4k on youtube then you can leave a comment down below and ask any questions or any insights or any thoughts about the episode that would be awesome and if you enjoyed this episode you might like to check out this episode here as well which links in with some of the stuff that we talked about in the episode so thanks for watching do hit the subscribe button if you aren’t already and i’ll see you next time bye you know i just had like a mentally transformative experience where a week before junior year of college at michigan my dad passed away suddenly he passed away from a stroke he was 49 years old he was perfectly healthy and after that experience everything just became clearer around one how most things that we worry about on a daily basis in life are wildly unimportant and two how your time on your uh life countdown clock you have no idea when it’s gonna hit zero and basically i said to myself if if i knew my countdown clock was hitting zero tomorrow what would i rather be doing with my time and it was like a no-brainer it was like i knew that i would hey friends and welcome back to deep dive the ongoing podcast where every week i sit down with authors entrepreneurs creators and other inspiring people and we talk about how they got to where they are and the strategies and tools that we can learn that can help us apply to try and hopefully live our best lives what you’re about to hear is a conversation between me and alex lieberman the co-founder and executive chairman of a company called morning brew and morning brews is like huge media company now but it started off as an email newsletter and we kind of dig into the story behind that and interestingly alex sold morning brew to business insider for around 75 million dollars a couple years ago at the age of 28. so he made like tens of millions of dollars at the age of 28 which is absolutely absurd and like super inspiring and ridiculously interesting because it’s like hey how the hell did you do that and b what the hell do you do beyond that point when you feel like you’ve made it in life and so we talk a lot about kind of lessons that we can learn from his journey of building this business from day one and so if you’re if you’ve been thinking of starting a business or growing a business or kick starting a business or anything like that you’ll find a lot of valuable stuff in there but then we also talk about like kind of what it means to find purpose in life and live life beyond such a windfall and how alex is kind of navigating some of these challenges i got a bunch of value out of this conversation i always loved talking to alex and i’ve had a few zoom calls over the years um and i’m very excited for you guys to hear the conversation as well so without further ado i hope you enjoy this conversation between me and alex lieberman alex thank you so much for being on the deep dive how are you doing today good man thanks so much for having me it’s gonna be it’s gonna be fun um i’d love to get started so you’ve got a a super interesting back story and i would just like i i would love to start with a question of how how did we get here what was the backstory of alex lieberman yeah so i am originally from new jersey uh and i grew up in a finance family so everyone in my family no matter where you looked on my family tree worked on wall street my dad worked in sales and trading my mom worked in sales and trading my grandpa worked in sales and trading and so growing up uh you know and having the value of you know family is the most important thing there was only one possible career in my mind which was to work on wall street like i really didn’t think about anything else uh and so i went to a small private school in new jersey it was great for for some things wasn’t great for other things i loved it for the academics and the athletics didn’t love it for uh the social part of the experience and so i wanted a very different experience in my college experience and so i ended up going to the university of michigan which was very non-traditional from my high school basically my high school i had 120 people in my graduating class a third of the class went to ivy leagues a third of the class went to what are called nez cac schools like northeastern schools like colgate middlebury uh and then there was a third that were kind of like the the degenerates in the class that would go somewhere else and i was one of those people i went to the university of michigan um loved my experience there i was in the business program and i was kind of on the path uh up to that point i was on the path to work on wall street because that was my goal and so i did internships after each year in college i was in the business program and i got into my senior year at michigan and the way it works uh you know in the states with internships is you have a uh your internship after your junior year in finance and if you do well in that internship you get an offer and so then in your senior year in your last year of college you don’t have to recruit for jobs you already have that job for when you leave school and so that that’s what happened for me i had my internship at morgan stanley working in sales and trading junior year i got an offer back and so i accepted that offer i got into my senior year at michigan i didn’t have to recruit for a job i only had to take three classes my entire senior year because i had completed my credits and so i got into the year and i was basically like okay this is gonna be fun i’ll play a lot of video games but i should probably do something else in order to keep my brain sharp for when i graduate and go you know work in finance and so i i started helping students prepare for job interviews and one of the ways that i would help them is i would do my a mock interview with them that was something my dad always did with me when i was prepping for interviews is he would mock interview me as as if we he was an interviewer and one question i would always ask students is how do you keep up with the business world to me this was like the layup question just to get them comfortable not be nervous and every student basically said the same thing which was i read the wall street journal uh it’s what my parents told me to do but it’s a bit dense it’s a bit dry and that just really resonated with me because i was like this is crazy these students are about to spend 50 percent of their life of their waking hours between the ages of 21 and let’s call it 70 working in business and they read business news because they feel like they have to because their parents told them to like it sounded crazy it started so i started writing a daily business roundup about the business world that in the beginning was really shitty like it was a really bad product uh but it was good enough to really catch people’s eye and get their interest and sending out that first newsletter in i believe it was october of 2014 so my first semester senior year was the start of what would be a seven year journey of building morning brew amazing okay i i that that was the point where i wanted to zoom in on so there’s a lot of people that would that would notice something that huh it’s it’s kind of weird that all of these people applying to all these jobs are like reading business news but seeming to not enjoy it what was it that made you take that leap to therefore i’m going to write my own email newsletter because that’s not a normal thing to think like what was going on there yeah i mean it’s interesting because i was not thinking about it as a business at all the the interesting thing is like i’ve never thought about myself as like an entrepreneur or that i have to build a business but i’ve always been a tinkerer like i’ve always just like tried doing random things and i i started writing that newsletter which by the way at the time wasn’t called morning brew it was called market corner uh and i’ll describe what that product looked like in the beginning because again it was pretty mediocre but basically i wrote it because one selfishly i wanted to keep up to date with what was happening in the business world so that when i left college and i went into my job in finance i felt like my brain was on top of things and so the process of reading what was going on in business and distilling it into these bite-sized chunks was almost like a forced function for me staying on top of my game then the second part i would say was more selfless which was i just wanted to help these students keep up to date with the business world and to me the way to do it was just to start writing this thing and i had an abundance of time how did you have an abundance of time yeah so as you know as i had mentioned basically i got into my senior year i had already gotten my job so i had that junior year internship and i got an offer to work full-time at so now you’re it’s like you’re coasting the rest of the year yeah exactly basically my fourth year of college my senior year i was coasting i didn’t have to recruit for a job i only had to take three classes and so i only really had to spend two hours any given day throughout senior year of college actually spent on academics in college and i spent i had to spend zero amount of time on jobs and so that left you know however many waking hours uh 14 waking hours a day to do something with my time and this was one of the things that i decided to do with my time uh did you try and do anything else with your time i’m curious to stay here any other experiments running in the background uh nothing that was uh as i would say productive as this i probably spent three or four hours a day working on uh market corner market corner which would then turn into morning brew i did spen i spent a lot of time playing video games such as i played a lot of fifa nhl uh and call of duty i also in my senior year tried to experience a lot of just extracurriculars at michigan so i went to like sports events that i never thought of going to like i went to uh the university of michigan gymnastics meet i went to the soccer games just because i kind of thought to myself this is the last year that i’m really going to be able to experience this amazing university as a student i might as well just like make the most of it and then i was a teaching assistant my senior year i uh was a ta for a real estate class which was actually my favorite class it was um it was a interdisciplinary grad level real estate class where basically the class was not lectures it was you were tasked with picking an actual physical location in the us where you thought there was an opportunity to buy the location like buy the real estate develop a property and turn it into a residential retail commercial like a multi-use property and it was an interdisciplinary group so where it was a business student it was an architecture student it was a legal student and it was an urban planning student and so the four of us literally spent a semester where we went to parts of michigan and we drew up our plan for developing like a full-blown you know 250 000 square foot property the architect literally drew out the exact specs of the property the urban planner wrote up the documents that you would use to apply to the city i worked on the financials and the legal uh student uh basically shared what the pipeline was of contracts that we would have to figure out for the property so that was one other thing i did senior year so you said that sounds super cool uh and you said this class was your favorite i wonder like what did you learn from this class that maybe you’ve applied applied later in life yeah i mean this is the interesting thing i loved my experience at michigan but if you were to ask me why i loved it i would not say it was for the academics because i would say there’s maybe two classes in the entirety of my education at michigan that i feel like i’ve actually applied in my career and i think this just speaks to where a lot of academia is broken and i think it’s broken for a lot of reasons i think uh it’s broken because it teaches you what to think versus how to think i think it’s broken because a lot of people are lifelong academics and that’s not inherently bad but i wish there was more attraction to entrepreneurs and practitioners going back to universities because i think it would make what you learn far more applicable because it’s being taught by people that actually did the thing i loved this class because it was one of the two classes where i actually felt like this is simulating what i’m going to be dealing with in real life it is a real life project that i could see myself doing this in the future if i wanted to you know invest in real estate this is something i would go through and it was interdisciplinary in nature which is inherently all of your experience in your career and life is working with people that have diversity of thought and experience from you nice so this real estate was class number one what was class number two that actually taught you something my excel class it was the class yeah yeah okay it was my class that uh basically taught us how to uh do pivot tables uh visual basic shortcuts in excel and for me like excel is a program that i probably will use my entire life with different levels of kind of intensity or frequency when i was working in finance before i went full-time on morning brew i used excel a lot like i was doing a lot of just modeling and calculations in excel today i would say i use it maybe once or twice a week but having that proficiency in excel it’s kind of like i would consider it kind of the the timeless skill in the same way that i would say actually the most valuable class i’ve ever taken my life was my fourth grade typing class like i i’ve used this skill more than any other skill in life and i’ve talked to people who didn’t take typing and i can see the impact that it’s had on them and so yeah i just view excel as a timeless skill just like i have you typing on my computer as a timeless skill interesting so a few thoughts on this yeah firstly so um my brother is working on a startup to try and um compete with excel really yeah it’s called causal um they’re trying to basically be the new xl but for um number crunching because excellent has all these different excellent has all these different use cases and it’s it’s a very general tool but you’ll you’ll get like ridiculous you know trillion dollar companies using excel to manage their forecasting and you’ll also get people using it to figure out the scores in their five-a-side football league and yeah their kids kids football practice and their sort of uh their thesis is that uncertainty calculations and modeling and stuff is really hard to do in excel where you have like loads of uncertainty with all these different numbers plugging in it’s really hard when you when an excel sheet gets really big for anyone other than the person who made it to understand what’s going on and even then that person probably doesn’t understand what’s going on and so it’s really hard to kind of change your assumptions and all this all this stuff so they’re building building uh i see it right now i looked it up causal app causal replaces your spreadsheets with a better way to build models connect to data and share dashboards with your team your brother sounds very smart um oh they they they raised 4.2 million in 2021. uh this is awesome uh yeah i can also read more about it recently oh really you should look into that start using um i was gonna say now now you have to get ultimately that if they get big enough you have to get them to work with uh universities so universities teach causal courses oh my goodness that’s a great idea yeah yeah good for you know any kind of number crunching and modeling and stuff yeah um i also very much agree on on the typing front so you know i’ve put in large amounts of time and effort into actually just practicing my typing once in a while through typing tests and stuff oh i’ve seen the video yeah whatever the speed was it was is absolutely ridiculous i remember watching that video and then doing a typing test and just feeling horrible about myself after doing that test what was the speed again i think it was one 156 words per minute that’s my record i need to try and bump that up but it’s it’s it’s kind of weird so these last few days i’ve been on this team retreat in wales currently overlooking the hills it’s very nice um but i sort of set myself the challenge that every day i was going to write a whole first draft chapter of my book each day each day it’s sort of been like sort of five six there’s seven thousand words and it’s just kind of i think have you done it yeah so every time the last few days i’ve been banging out one chapter and i need to do another one today but i’ve already done four thousand words in about a one and a half hour slot this morning and it’s like amazing that i i think previously when my typing speed was half or a third what it currently is it’s like it would be a bit of a bottleneck like my brain would think faster than i’d be able to type yeah but the faster my typing speed is gone it’s like i can type at the speed of thought almost and so it’s almost so easy or so easy to if i’ve got something in my head to translate it into words on a page and it’s it’s you know it’s really bad obviously but like you know the first draft of anything is really crap so that’s what my editor keeps on saying just like spew out all the stuff you’ve got in your head onto the page like and then we’ll we’ll clean it up in post so so honestly that was something i’m very interested about because if i remember correctly like i remember the general um you know the general gist of the book that you’re writing and when i’ve thought about writing books the thing that’s always kind of been like the bottleneck in my head is will i be able to just write chapters from my head or am i going to have to like be referencing uh resources online or references but if i do that is that going to distract me because now i’m plugged into technology so when you’re writing these chapters a day are you fully disconnected from the internet and you’re just writing five thousand to seven thousand words of whatever comes to your mind um great question yeah so i was i was worried about this as well um uh i i’m connected to the internet because i use it go to a lot of google docs which is annoying for offline stuff but if i ever get to a place where i need research or something like that i’ll just do a little apparently all writers do this tk um you just write tk need research about xyz over here um you know yesterday i was working on a chapter where i was talking about kind of feelings of anxiety and self-doubt when it comes to procrastination and i knew i wanted a line that sort of described the feeling of anxiety but i couldn’t be bothered to sit down and figure out oh crap how to describe the feeling of anxiety so i just wrote uh anxiety is that feeling of tk xyz and then me or the editor will come back to it later and it just sort of keeps me in the flow yeah so you just give yourself the permission to like leave space and revisit the things that you do need to do more research later on which by the way we should talk about this at some point in the conversation about uh the feelings of anxiety related to procrastination because i would actually argue that is one of the biggest things in my life that creates self-doubt lack of self-belief it stems from feeling like i’m a chronic procrastinator in life and i have been since freshman year of college okay that’s okay we’ll do we’ll we’ll put a bookmark on that and definitely come back to it because i imagine people would find that surprising given kind of your your story um yeah so definitely bookmark in there i was going to ask as well so other than typing and excel have you ever have you found any other sort of meta skills that are generally useful for life yes but they weren’t taught in university uh so one is storytelling and selling like i think the number one skill that helped me be a strong founder especially in the early days of building our business is the ability to sell and i think i’m blessed in the sense that that’s just one of my intuitive superpowers it’s something my dad worked on with me as i was growing up he was really focused on my ability to articulate uh he thought that was really important i ended up taking a business communications class at michigan but to be totally honest i didn’t find it very valuable half the time was spent doing kind of public speaking half the time was spent literally like digital communication like how to write an email and i found that to to be tough tough as in like not helpful but yeah i mean sales i would say is that if you are trying to elevate yourself as a professional in any way not just as an entrepreneur just in your career you find yourself selling yourself far more times than you realize so like just even talking about a business when we were starting morning brew we’re talking about a startup that was a media company media companies are generally not venture backable so you can’t raise from institutions uh we had a newsletter that’s all we had we had 30 000 subscribers at the time we weren’t making any money but we had to raise money in order to possibly get to a place of making money and so selling investors on why a 21 year old and a 19 year old who have a media company where media companies are generally not profitable businesses and we weren’t making money yet and by the way it’s not really a media company it’s a newsletter we had to sell them on why they should put their hard-earned money in our business we had to sell our initial employees on why they should leave their steady jobs to join a business that’s making zero dollars and we had to sell advertisers because that was the first way we made money as a business we had to sell advertisers like discover card large financial institutions on why they should even bother wasting their time on a company that reaches 30 000 people versus allocating that time to thinking about say a television commercial that reads reaches millions of people and so i’d say that is the number one meta skill i’d actually argue it’s a meta skill even like in personal life not just professional life i’ve i’ve heard a lot of people say that that you know the the skill of selling is kind of yeah is well one of the one of the most useful skills you can have but i’ve always kind of wondered and i never quite followed this thought of like what does what does that actually mean like i wouldn’t say i’m good at selling but i’ve i guess i have sold stuff in the past and i just don’t really think of selling as like a thing you sell yourself on youtube every time you post a video like and this is actually an interesting thing of and i’ve thought a lot about this is what’s the difference between sales and or selling and storytelling and my view is just if something comes off as selling it’s just shitty storytelling uh and and and so my view is like why do people watch your videos for a long time why did you just hit three million subscribers on youtube when there’s a bunch an abundance of content because you’re not the first person to talk about topics related to productivity to bettering yourself right you have found a way to storytell in a way that captivates people and keeps them engaged so you are innately good at storytelling i just don’t think i think it is quite natural and intuitive to you it doesn’t feel like work to script and then uh deliver that in front of a camera you couldn’t be where you are today without being exceptional at storytelling how do people get better at this it’s a great question um my answer would be it’s a combination of practice of shadowing and feedback and of understanding the fundamentals of what it means to story tell well so going in reverse order i think that there there are tried and true there’s the science to it there’s like tried and true formulas for what is a captivating story for people uh and so like for example i’m reading uh the book creativity inc right now which is the story of pixar like are there are story arcs which is like there is a hero the hero is on a journey the hero on the journey experiences a challenge uh in experiencing the the challenge they go through adversity they overcome the challenge and they reach their goal like that is one story arc i think there are a number of formulas this way so at base level i think studying the best storytellers of all time uh and studying the formulas that they use to tell stories is the first step the second step is what i would say is the combination of practice and shadowing and so the example i’ll use for you is in the early days of morning brew when we had to pitch advertisers on advertising in our newsletter i had never sold in a professional setting anything before but i had to do it there was no option we had to make money and so i you know got reps pitching probably in our first year 250 advertisers on 30-minute calls about who morning brew was what we stood for and why spending your money with us was worth your time and your money based on what your goals were and the first pitch i did probably the second pitch probably the 20th pitch i did was really bad but every time i would take five to ten minutes after a pitch and i’d have a reflection period where i would write down what are the things that i think i did well and what is one thing i would change for the next pitch i do and i would record every pitch i did as well so then thinking about shadowing and feedback right i was delivering feedback for myself but a big thing that i did with our junior sales people when they joined morning brew was when they would do a pitch in the early days i would join them on those calls so that first of all like i would do the sales pitch they would listen to me so they would sponge up that information we would do that for a few weeks and then gradually i would hand off the reigns to them where they would start doing the pitch we would record it we would listen back to it together after which by the way for anyone who hasn’t listened to their voice before and hasn’t listened to themselves do a sales pitch it is going to be excruciating for you to do the first time but it is so valuable i would give them feedback and then they would use that feedback the next time and you know you look at a company like gong gong is a multi-billion dollar sales software company there’s a reason it’s such a valuable business so what gog basically allows you to do is allow sales orgs to record every sales call they have and then in in a database holds all of the sales calls organized by who the seller was the type of client that it was and it also will do things as sophisticated as say what percentage of the time on the call were you talking versus what percentage of the time was the person talking and it will categorize what were you talking about almost like you know on youtube how you can kind of set the chapters of an episode it does that automatically in your sales call and so then any seller can go on to gong and study what are quote unquote the best calls that have led to the conversations that convert their clients the end of the day there is the there is this art and science to understanding what works for you to storytell in a way that leverages your strengths um but also understanding the science of what works well and what are kind of like the the the natural story arcs that people over the course of time are always attracted to nice that’s a that’s a great answer was that off the cuff or have you have you ever thought about this before that that was off the cuff yeah yeah that was good that was like framework i love it it was like very meta we were using a storytelling framework and talking about storytelling framework 100 alrighty little interlude to tell you a little bit about this book the e-myth revisited which is a book that both me and alex absolutely swear by in terms of it just being super helpful in building businesses it’s about why most small businesses don’t work and what to do about it by michael gerber now this is a book that i usually recommend for basically anyone who wants to scale up their business but if you don’t have time to read the book and i do recommend you do actually read it you can check out a summary of the book over a short form who are very kindly sponsoring this episode of the podcast if you haven’t heard by now short form is the absolute best service that summarizes books they just have sick book summaries and they’re way more than just book summaries they’re like include one page summaries of the book just in a single page but they also include chapter by chapter summaries of each of the chapters and they also include these like interactive exercises in between some of the sections so you can really engage with the points and even better they also kind of regard books as being you know with a little bit more critical appraisal kind of vibes than a lot of other book summary services do so if for example in the book michael gerber makes a point which is particularly controversial or which another author might disagree with then they’ll add a little short form note that says hey this point was a bit controversial like maybe you should check out this other book that argues for the exact opposite and that’s just really good in terms of just getting a balanced viewpoint on the stuff that we read there’s two main ways that i personally use short form the first one is when if i get a new book recommendation and i don’t necessarily want to read the book directly or i’m not 100 sold on reading the book then i’ll often go on short form on my phone or my laptop and be like hey has short form got a summary of the book usually they do if it’s the sort of nonfiction that i enjoy reading and then i’ll often read the book summary first and if i like the book summary then i may or may not decide to read the book itself and secondly i use short form as a way of revisiting my highlights from books so for example i’ve only read the e myth revisited once but i’ve actually read the short form summary of it about three times uh once in preparation for my part-time creatorpreneur course but also twice just randomly because i was like this has been a really good book i first read it in 2019 changed my life i don’t want to reread it because it’s like i’ve got most of the value but let me just revisit the points so something like short form is super helpful for that if any of that sounds up your straight then head over to short form dot com forward slash deep dive and with that url you will get 20 off the annual premium subscription and you’ll get access to the best service that summarizes books in the world okay so it’s march 2015 you launch morning brew as a proper newsletter with a proper website that people can actually sign up for what happens next we become obsessed with two things how do we make this newsletter as good as humanly possible and how do we grow it as quickly as possible and so i would say we did kind of some pretty creative things to make the newsletter really good in the early days i’d say the first thing was austin and i said to ourselves like we can help write this thing but we need more support and so we had reached out in our newsletter to students who are reading our newsletter and we said hey if you’re interested in writing about business and you want to get your words in front of hundreds or thousands of people we’d love you to come right for the brew and so we ended up having a rotation of probably eight writers at any given time from different universities who were writing call two stories a week in our newsletter so that was kind of like our our uh newsroom of sorts and these writers were not paid they were just doing it because they wanted to get their brand and their words into the world and they they were excited about what morning brew was and what it represented then we found an editor and that editor was someone who was in the business school with us at michigan so he’s very into markets and he still works in finance today but he also wrote for michigan’s newspaper so he had really strong editing chops so he was the guy who basically set the content schedule for those six to eight college students and then he would edit their first drafts then this the third thing we did is kind of the i would say the the least traditional from the beginning austin and i said our content needs to read like you’re having a conversation with your smart and sociable best friend it can’t read like traditional business news where it feels like a robot is throwing up words on you yeah and so we’re like what is gonna give our our uh content that x factor that’s gonna feel quick-witted and smart and funny and so we’re like we need to find a funny person and so we we put out we put it out a uh you know a job post for a funny person and we found our funny person and our funny person was this guy grant he was in a program called organizational studies at michigan which was quasi business schools like similar to the business school less focused on finance and more focused on like uh organizational organization building culture et cetera so he was in that program but he was also in the improv troupe at michigan and so he was hilarious and he was a good writer and understood business and so we brought him on as that literally the the the job we called it was he was our voice editor so we had our writers we had our uh editor and we had our voice editor and that was the process that we got to of putting out our newsletter every day and that gave austin and i more time to grow the thing and so the way that we thought about growing our thing was the the visual i have is like a bicycle so you have a bicycle and you have a hub in the middle the metal hub and then you have spokes that go out to the the the wheel like the outside of the wheel of the bicycle right so you have a hub and you have spokes and our view was spokes are all of the people that we think should read morning brew so those are college business students hubs are the people that are basically the people or the channels that have access to all of these spokes how do we get the attention of hubs so we don’t have to go to every spoke and convince them to read our newsletter and so at michigan what that looked like was teachers and club presidents if we could get in front of teachers classes we could get in front of 75 to 500 students and if we could get in front of club presidents we could get into in front of say 50 to 250 students and so basically for all of our second semester senior year at michigan austin and i spent going back to the the importance of storytelling and selling we spent our whole second semester in about 150 club meetings or or classes pitching club uh students on why they should read morning brew and so we’d go into a class we would give our two-minute uh appeal about what boarding brew was why this was the best business newsletter in the world how it was free so there was no downside you could sign up and if you didn’t like it you could unsubscribe no hard feelings and then what we would do is we’d pass around a sheet of paper with a pen and we would ask students to write down their email address we would take that notepad after the class and we would type in manually all of their email addresses and the reason we passed around a pad and a paper is because the conversion rate of people writing down their email on a pad was significantly higher than us getting in front of the class and saying pull out your laptop go to morningbrew.com and put in your email address because there were far more steps it was pulling out laptop opening laptop going to safari or chrome putting in morning brew putting an email address whatever that is five or six steps whereas the new pad and paper it was two steps it was grab the grab the pen and write down your email and we basically just pushed the rest of the steps on austin and myself to actually input it and so that was how we got say our first 2 500 to 5 000 subscribers and then the next process became okay we’ve saturated the michigan market now what and then now what became how do we find austin and alex at every other college in america so how do we find the the two people that are gonna basically get in front of all the hubs at other schools that aren’t us and so that’s what led to our college ambassador program and our college ambassador program you know it still exists to this day we learned so much with it and i think it was unique at the time because i never heard of a media company doing a college ambassador program when i think of college ambassador programs i think of like red bull uh college ambassador or ambassador program where people park the red bull car in front of a university they have people with backpacks that hand out red bulls but never for a media company and we ended up going through many iterations where the first ambassador program we went for the quality approach we were where we were like let’s get the best ambassadors across the country to represent morning brew so we had this super uh rigorous application process it was like harder to get into our ambassador program than to get into harvard uh or oxford it was like we put out an application people applied they dropped their resume we ended up accepting i think 15 ambassadors who were like they were the influencers in their business programs at their schools they were in all of the clubs they were the class president you know they sat in the front of their class and it absolutely bummed our first ambassador program did not work well it didn’t work well because what we didn’t account for is that while all of these students that we accepted were really impressive people don’t have a good sense of time management when they’re in college like they really haven’t figured that out yet and so these students were the people who are already so involved on things in campus that they had they actually were the people the least amount of time and they had spread themselves so thin that they could never commit to our program so the second time we did it we went exact opposite approach we went with the quantity approach where we fully automated the process so we sent out an application but everyone was accepted we just wanted wanted it to have an error of exclusivity so you’d fill out an application you’d get an automated email from us that you were one of a few people accepted to this program and then you’d get automated emails from us about how to start sharing morning brew so you’d get a google drive that included marketing collateral a script for what to say in classes sign up sheets that you could print out to pass around classes only when you got to say i think it was 25 sign ups did you actually get put into a group with austin and i where we talked to you and so we had this vetting system for big top of funnel uh but only have human interaction with students when they’ve kind of proven that they can do well as an ambassador and when we did that second program we had 250 ambassadors across 200 schools and so that was our focus uh kind of for the rest of college was growth and getting the content down that really reminds me of the whole you know do things that don’t scale yep because you know if i imagine like we we’ve just launched a new a new newsletter for our creatorpreneur brand you know trying to help creators think more like entrepreneurs the last thing on my mind would be let me go out manually recruit some ambassadors and get them to spread the word for my email list it’s just it’s so rogue it’s so it’s so analog in the world that we live in today i gotta be honest if i’m you i’m thinking about how do i every time colin and samir post a video how am i commenting with my newsletter on their videos because because the people watching their videos are all creators yeah so you’re growing this newsletter basically door-to-door uh but like at scale um yeah what what did the numbers look like in that first year like 2015 when you were yeah so when i graduated from michigan uh i want to say we were at 10 000 subscribers oh so we got to 10 000 by the end of senior year but i had a decision to make because i graduated from college and i had this job to work in finance so i basically had to make the decision am i going to do this job that again was my dream for my entire life like this was the peak this was the pinnacle or was i going to quit my job tell my overprotective jewish mom that i was gonna go do this newsletter thing that makes no money uh that has ten thousand people on it rather than doing the thing that i dreamed of uh i did not do the second uh i went and i worked at morgan stanley sales and training generally you start early in the day so i would wake up at five a.m every day i would i would go to the office i would work out i’d be at the desk by 6 30 i’d trade from 6 30 until 7 pm 7 pm i’d go back to my apartment and basically from 8 p.m to when i fell asleep with my laptop on my lap i would work on morning brew and that was effectively my entire experience at morgan stanley until i quit my job how long did you do this before you quit the job so i i started at i graduate june of 2015 i go to new york my job starts july of 2015 at morgan stanley i quit my job september of 2016. so just over a year it was right after uh labor day of of 2016 and the reason i quit was basically austin as i mentioned he’s two years younger and he had had his junior year internship he got an offer to work in investment banking and he now had to make a decision basically two years after me was he going to go full time into investment baking or do morning brew and i vividly remember austin came to new york uh for a weekend we got beers at this like really old bar one of the oldest bars in new york city we basically talked about like what are we gonna do like there’s a clear fork in the road it was a fork in the road of we’re either gonna go full time on this thing or we’re not and if we don’t go full time on this thing like this is it’s either gonna stop or it’s gonna just be kind of like a shell of itself because i was working a lot austin investment banking i remember during his internship he had pulled like four all-nighters in his summer of his internship and so it was very much like this was an inflection point and we decided to go full time on it and i i think we had different reasons for going full time on it and for me the reason i went full time was a few fold i thought about things in terms of regret what would i regret more would i more regret staying at morgan stanley and seeing someone create effectively their version of morning brew and it succeeding or would i more regret leaving morgan stanley doing morning brew and morning brew fails and i have to find a new job and to me the answer was obviously when i answered that question which is i would far more regret staying at morgan stanley and seeing someone succeed with their version of morning brew just because they risked their time when when i wouldn’t that was the first way i thought about it the second way i thought about it was what is the worst case scenario so i thought i always use things as like the worst case scenario framework in a decision and can you live with the worst case scenario so the what what’s the worst case scenario if i quit my job and went full-time on morning brew and the worst case scenario was i quit my job i work on morning brew and then say six months later it fails because the vast majority of businesses fail and then i was like then what what would have happened in that worst case scenario and i said first maybe morgan stanley would take me back because i had this entrepreneurial experience that made me maybe maybe unique in my experience and uh they would value that and i would say i said no let’s say that’s the worst case scenario and i burned my bridges and they wouldn’t take me back then what it was like maybe this makes a good business school story where i could apply to business school and i said you know what maybe uh this is a common story and it would get me into business school and i said maybe um i met other people while i was doing this startup in the startup scene and i could go start another company or join an early stage company and i basically got like four or five layers deep of options and i was like if none of these are options after morning brew fails then this isn’t actually like a morning brew problem this is an alex problem of not keeping his options open as a professional and so that was the second way i looked at it and the third way i looked at it was simply about how do i want to live my life it sounds cliche but i very much you know i just had like a mentally transformative experience where a week before junior year of college at michigan uh my dad passed away suddenly uh he passed away uh from a stroke he was 49 years old he was perfectly healthy like literally built the same as me similar uh physical health and after that experience everything just became clearer around one how most things that we worry about on a daily basis in life are wildly unimportant and two how really like you know your your time on your uh life countdown clock you have no idea when it’s gonna hit zero you look at the statistics and you hope that it’s gonna hit zero around you know 80 years old or later but you really have no idea and basically i said to myself if if i knew my countdown clock was hitting zero tomorrow what would i rather be doing with my time and it was like a no-brainer it was like i knew that i was so more so far more enjoying the experience of building my own thing and tinkering like i was tinkering in kindergarten than sitting in front of a computer screen and trading mortgages wow yeah i’m sorry to hear about your dad that that must have been really tough for you at the time yeah it was uh it was really tough for a few reasons obviously it was it was shocking it was one of those things like he he was my best friend and it was like you know he was the guy that when i would uh be walking from class uh back to home or vice versa like he was the person i was texting or calling and it was uh it was a surreal thing like there was a period of time after he passed away where i would just be walking in new york city and i would call his number just to relive that experience and it registers it’s pretty funny thing now for a while i’d call his number and it would just you know go to like this number is not in service because after he passed away we didn’t you know he didn’t keep his phone obviously and then at probably six months to a year later they reinstate phone numbers get recycled and so i still do this to this day probably i do probably like once a year now where i call his number and there’s a family who has his phone number now and it’s just interesting to hear it’s been the same family for the last like seven years and uh they’re probably like who is this random 973 number that calls us once a year says nothing and hangs up um but yeah i mean so there was apps there was a there was a huge void that i felt because it really was my best friend and then i think the final thing is it um it made me think a lot about just like my emotions and how i process emotions because i think as a function of growing up in a wall street family as a function of you know being a man and there being certain gender norms with being a man i think as a function of my own coping mechanisms i found like my my best trick my best trick and my worst trick was to take emotionally provoking things and push them into my body and not feel them and i’m really good at that trick and i think that trick paid dividends in my career as an entrepreneur because i think as was hitting the fan at different times like i was cool as a cucumber i really did not feel like scared at any moment in our journey even if it was completely rational to feel scared but the reason i say that is you know after my dad passed away i only cried once and it was such an interesting thing to me and that i felt guilty about for a long time because i was like this is probably the worst thing that’s gonna happen to me in my life is a tragedy like this and i only cried once like how do i only cry once about losing my best friend suddenly and so this is something i still work on to this day and think about to this day which is how do i better have access to my emotions because they’re absolutely there my body has just buried them how do i have better access to my emotions so i can experience things fully and emotions give you amazing data in life to know what you love what you don’t love what you want to do and what you don’t want to do wow i think thank you for being so open about this yeah of course this is this is something that i have been thinking about as well in the sense of yeah being an uh sort of entrepreneur bro um you know growing up in a asian family meets kind of an old boys school meets you know talking about and feeling emotions and stuff very much frowned upon yep uh and then i discovered stoicism and i was like yeah stoicism kool-aid like yeah you know this is how i’ve been living anyway i’m a stoic sage etc cetera i don’t feel i don’t feel negative emotions if i don’t want to i i’m also right now trying to figure out how basically it’s going to sound kind of weird but like how to feel more oh no this is what i’m working on constantly yeah how how are you doing it uh well one this is like the focus i would say there’s two topics that i generally focus all of my time with my therapist on one is how do i feel more but i’ve changed the wording over time to be like intentional with not how do i feel more because i think that uh implies like that i am feeling less right now and i’m not feeling enough and there’s something wrong with me and i and so what i’ve changed it to me is how can i fully feel my feelings so whatever my feelings are whatever my emotions are how can i get to a place where i am fully feeling them and nice and so you know what we spend a lot of time doing is she will help me visualize like moments in my life to try to because what she’s realized about me is like i i’m a very visual person and so like i get images whenever i think of something and so for example you know i shared with her in probably our second or third session together that i was uh bullied in school probably from fifth grade to the end of high school like i i was bullied i never felt like i was a part of a group like i always aspired to be part of like the cool group in high school i never felt a part of that group i felt like i was always trying to seek their approval but never received that approval and so a lot of times she’ll actually have me visualize that she’ll be like what is a moment that you felt really lonely and felt really sad for yourself because you didn’t feel like you were belonging in high school and i would describe a moment i’d be like you know it was down to the couches the senior couches in the high school at the school i went to i was sitting at the couches there were like eight people there i would say something people would dismiss it and people literally like turn their bodies to not include me in that discussion and she would tell me to like close my eyes and like sit with envisioning those people talking and closing their bodies to be me being on the outskirts and she would say what comes up for you you know what would your older self right now if you were sitting next to your 17 year old self what would you say to him as he’s feeling really upset for himself that he doesn’t feel belonging and so i think she’s trying to leverage what she knows that is intuitive and natural to me which is visuals and put me back in kind of this time machine of life the other thing she tells me to do is like to sit with emotions when i feel them meaning like any type of emotions like when i’m laughing hysterically at something she’s like before you go on to the next thing because your best trick is distraction distraction through intellectualization or doing something before you do either of those before you intellectualize or you distract if you’re laughing hysterically or if you’re annoyed with something that a family member said or you’re pissed with your co-founder just spend 30 seconds and just sit in it like just sit in it don’t have any expectations of it but just sit in that feeling because you’re retraining yourself to realize that you are in fact feeling something and over time it will become natural where you don’t have to get yourself for 30 seconds to sit in that feeling have you found working with a therapist useful extremely useful extremely useful i find it useful because one i think in a force it forces for me the accountability to reflect which i think in the busyness of life i will get out of the habit of doing and i think it’s really important i also think again at the end of the day a therapist is someone who has tools that they’ve been taught in their career so like if i wanted to figure out for myself how can i feel my feelings fully right i could go one way i could do it is go read many books on it and maybe get to that answer or i could have an hour-long session with someone who has read probably all of those books also and just can almost be like the summary of those books but what i will say is i think a therapist is kind of like anything else in life where the they’re serving a purpose to help you tackle challenges that are preventing you from being fully filled up in life and different therapists have different specialties and so what i mean by that is there was a therapist who i worked for work so i worked with for probably this first seven years that i was doing therapy that was my first therapist and she was amazing but i would say there was a natural kind of like uh deceleration of the learning curve or the benefit curve where in the beginning she gave me all of these tools for my anxiety for my ocd and then it kind of plateaued because i had those tools and i found that we were talking about the same thing over and over and what i realized is for a long time i kind of was just going through the motions of doing therapy with this person because i was like oh but this is therapy this is what i do and i think what i only ended up doing later which was important to reflect on is like okay but it serves a purpose is it still serving that purpose and what i realized for myself is this therapist had a specific set of skills skills that helped uh with the things i was working on at the time but as i improved in those areas and i had new challenges i want to work on maybe my current therapist isn’t the one who’s going to be most helpful in these new challenges and so i ended up changing a therapist to someone who i thought who was for uh could be more helpful with things like feeling my emotions or like self-love and self-belief because it was a therapist who her modality was things like uh hokomi therapy which is about feeling the body like it’s very body focused therapy and so that’s a big learning i had is like how easy our brains can get into autopilot and just assume what we’re doing is the thing to do if we don’t question it do you do these sessions of zoom or in real life or i do it over zoom so my therapist is based in colorado and we do yeah we do these zoom meetings uh usually every week or other week which by the way this gets into another topic like for the for a long long time i felt very guilty about doing therapy a lot because i’m very much like a money hoarder and so i could i would get into like i’d get anxious about spending money on therapy i’d be like oh my god this is a lot like you know my therapist is uh 300 an hour i’m like this is a ton of money like what do i really need to spend on this and at some point i got to the point where i was like if if i am not willing to spend my money on someone who is helping me see the world more clearly and live a more fulfilled life i do not deserve to have money that i have because that is crazy to not spend on something that is quite literally making my life better um and uh yeah so i talk to her every week or other week um and it’s it’s really good i will say as someone who has a very creative and distracted brain it is very easy for me even as we’re talking now for me to get distracted with things on my computer and so what i did now and i do with my therapist is i literally close everything the only application i have open with her is zoom uh zoom and notes because i’m i’m constantly writing down notes as we’re talking so i can reflect on tools she’s given me and also hold myself accountable and her accountable to like am i still getting value out of this and so that’s a big thing that i’ve had to change with zoom because when i was in person with my therapist like it was harder to get distracted i tried a therapist for like three or four weeks a few months ago actually like last year now that was ages ago and i found that like i wasn’t really a fan like the first two or three sessions was sort of helpful but then i did find session four and five and six we were sort of just sort of talking about the same stuff and part of me was thinking oh i don’t know if that’s just the modality of zoom just not being great for connecting with someone in that way but it’s it sounds like you’re getting a lot of value out of this therapist through the zoom sessions yeah and what i would say is like i think therapy is in a lot of ways like speed dating where i think it is very reasonable to see like eight therapists as a hypothetical number before landing on one therapist because it’s almost like what are the odds that you go on a first date with someone and that person ends up being uh your partner your life partner it’s like the odds are literally it’s like de minimis and so in the same way like every therapist has a different personality has different sets of tools and you have very specific needs uh that requires very specific tools and personality in a way that lands with you it’s like to think the first person you talk to is gonna be the right person is like you’re you know you’re betting that you’re gonna win the lottery yeah okay you’re right i’m sold um i will ask you for your therapist to email the rest afterwards because that seems good a good first option cool um yeah i guess i guess in my mind i was thinking of therapists as kind of like being doctors in that they are fungible in that one doctor at least here where we follow guidelines is practically identical to another doctor at the junior levels anyway but i guess therapist yes i i would argue that yeah therapists are very non-fungible excellent that’s your nft the non-fundable therapist so you’re at morgan stanley for like a year and a bit where you’re working ridiculous hours and you’re kind of hustling to get this morning briefing off the ground this is a very common story amongst basically all of the entrepreneurs you and i know where in the early days of the thing especially there is a level of you know to use the that terminology hustle and grind and maybe losing a bit of sleep and maybe not take fully fully taking care of your health and really not prioritizing things like self-care and a balanced work life and these days it seems like that sort of stuff is a bit like you know there is a sort of anti-hustle movement of like no life should always be balanced at all times and like self-care is really important and stuff and no one would say that that’s not true but if you ask a lot of entrepreneurs who’ve built something from the ground up especially in the early days they would have said that no hang on in the early days i needed to de-prioritize self-care and stuff for the sake of getting this thing off the ground yeah so i wonder with the benefit of hindsight um do you think if you had had more of a balanced life you and austin had more of a balanced life you would have more than that that morning brew could have been as successful as it now is or how do you think about that i think the answer is no i don’t think morning brew would have been as successful if we were more balanced in our life as in spent less time on morning brew but there’s a big caveat here that goes back to the idea of uh guilt around procrastination i think that it would have been possible to have more balance and been a successful morning brew if i was more efficient and smarter in my work and not a procrastinator and i have not proven to myself in life yet that i am capable of that but if i can prove to myself that i am capable of that i think it opens up a lot more time for non-work things can you tell me more about this procrastination stuff like how yeah how in particular i’m interested in the early days where you’ve got a job and you’re doing this thing on the side and now i you know we’ll come to this but i can imagine you’re chilling because you’ve got like because you’re stupidly rich and et cetera et cetera but like you know in the in the early days when you were you were hustling what did the procrastination look like i’d say there’s two types of procrastination it’s doing non-work to avoid work and it’s doing the wrong work to avoid work oh that’s nice and so doing non-work to avoid work is where i would spend a lot of time on social media and i would spend that time on social media instead of doing work and i would say actually that’s gotten worse over time as i’ve created started creating content on twitter and other platforms the addiction to the dopamine hits of likes and validation has gotten really bad bad to the point where like i’m literally thinking about do i want to create a like an aaa for phone addiction the the second type is work to avoid work and what i mean by that is this goes back to like how we’re taught from a young age uh and in school what it means to do work and i think it means you’re given an assignment you do the assignment uh you’re given a test you take the test you create checklists you do the things on the checklist and there’s a feeling of that felt really good to do those things on those checklists i feel like i’ve achieved what i wanted to achieve but the issue is is that as a startup grows and it evolves the things that you should be spending your time on change and they look different than the things that you were spending your time on perhaps six months ago and also the things that you felt really good about doing and so here’s an example i mean there was a period of time where i would spend hours a day reaching out on linkedin to potential uh advertisers of morning brew and i’d do all this linkedin outreach to hundreds of them then i would schedule calls with them uh and i would do all of this busy work related to outreach for selling advertisers and it felt productive because on my to-do list was reach out to morning brew advertisers schedule calls and morning brew advertisers felt very productive and it felt productive because the justification in my head was hey we need to make money as a business through advertising this is time well spent but as we were growing something that became more important or became i’d say a more important job of me as the ceo of the business was planning was thinking okay where do we want the business to be three months from now six months from now 12 months from now and this was at a time when we didn’t have traction uh so we didn’t we didn’t have the bible for running a business and so what would happen would would be what i just described to you of like setting a strategy in the future so that i know how i should be planning my time today who we should be hiring today like really important things i would never spend time on it i would just never do those things luckily i had a partner in austin where he was starting to think about those things and he picked up the slack there but it was i was doing work that felt good that i could justify was value adding to the business to avoid the work that really needed to be done to push the business forward and so i would say those are two types of procrastination and for me what would end up happening is i’ve used this term before of like the procrastination hangover and basically it’s the feeling of after a long day feeling shitty like feeling this like yucky feeling of like damn i just wasted a day i wasted a day because i wasted time doing things that don’t grow me for things that if i did them they would grow me and i wasted time on things that are easy tasks for me to do because i didn’t have the courage or the focus to do those hard tasks and every time that happens and i have a procrastination hangover i think i lose a little bit of trust and self-belief in myself because i haven’t kept my word to myself of doing the things that are most important to do and growing myself yeah that makes so much sense i think a big part of i think the emotional barriers to procrastination i i find it it tends to be two things it’s either self-doubt or it’s fear i i think it’s self-doubt on two levels on one level it’s self-doubt of i don’t think i’m good enough to do this thing but on a deeper level it’s i’m i’m not the sort of person who does things i am i am the sort of person who is a procrastinator and you’ve got so these these two levels of self-doubt and then you’ve got the fear aspect of it which is fear of not living up to certain expectations for yourself or for others or like fear of what people will think and you know that’s why singing in public is way harder than singing in the shower because you know you’ve got you’ve got the fear component michael my question for you is does that kind of framing make sense with your experience yeah it totally does yeah i think it it makes me because i have felt because i’ve identified as a procrastinator for so long it’s left me with kind of two conflicting thoughts or feelings on one side it has made me lose self-belief in myself because it has made me feel like whereas i want to believe that i am capable of anything it has made me lose belief that that is possible because i haven’t proven to myself that i can work really hard and smart to make anything happen it’s also made me lose kind of like belief and and respect for myself because i feel like to what you just said before i’m not gonna realize my potential because procrastination is keeping me from doing it and while i know it’s quite simple what needs to be done to not procrastinate which is to not procrastinate i have not shown an ability to do that and so i don’t know what is going to change that and then on the flip side of this so that is kind of like the the negative kind of like self-loathing version of this i’ve tried to have a more productive thought about this to say procrastination is part of my way it is part of my way of working where as someone who is very creative who has ideas all over the place who’s easily distracted i can’t i can’t you know uh i can’t take one but not have the other if i want to be someone who has an abundance of ideas uh and who has all these positive attributes from thinking in the way i think i can’t just expect that i’m going to be someone who does not procrastinate at all and is super linear and focused and basically i’ve that narrative is alex you have to own the fact that procrastination is part of your process and it’s okay and actually like to say you won’t reach your potential uh is to say that you believe that if you write yourself a procrastination you wouldn’t rid yourself of all the other things that make you great that make you possible of your potential i don’t know if i totally buy that argument i think that’s why it’s tough for me is i i try to as i’m experiencing this turn it into a positive where i’m not so down to myself because i don’t want to keep harming my self-belief but i also don’t buy that it has to be a part of me i guess it sort of in a way is can can kind of be a coping mechanism for dealing with the negative feeling it’s like oh the negative feeling is actually positive so it’s all good kind of stuff yeah and i think it’s um it’s one of those thoughts like it’s like that negative feeling isn’t doing anything for me anyway it’s only holding me back it’s making me believe in myself less so how do i get to myself where i believe in myself more so at least that you know it puts it puts me on a more solid foundation to push forward in life what what’s your take on this i i was doing a lot of it on the book and it was after having a session with rachel who’s our editor and also kind of book writing coach having had loads of experience with it where we basically diagnosed that it was self-doubt that was the main cause there where my standards were just too high i was trying to produce stuff you know i was comparing my shitty first draft to james clare or mark manson or tim ferriss’s or dan pink’s final draft yeah and i was like oh you know this every the the stuff i’m writing is just and realizing that like loads of people have this thought as well when starting youtube channels like they see themselves on camera and they’re like oh my god like i can’t i can’t string sentences together without making mistakes etc etc but they’re comparing it to someone else’s final draft because you never see a non-edited version of someone’s video and within our youtuber academy there are some you know sometimes i would just upload a completely unedited version of one of my videos for people to see just unlisted and they’d be like oh my god this makes me feel so much better because i realize that even a pro like ali still has takes an hour to film a 20 minute video because of all the stumbling and stuff that happens along the way and now when it when it comes to youtube the conversion from a shitty first draft into a decent looking output is something i’m very familiar with having done it 500 times whereas in writing the conversion of a crappy first draft into a decent looking book is something i’m not at all familiar with having done it zero times yeah so it’s like i don’t have that data or that conviction to know that actually the thing that i’m doing is good enough whereas in youtube i know that we can always fix it in post that’s fine we’ll we’ll we’ll deal with it this podcast i know i can just take a break turn the air conditioning on get a coffee we’ll you know we’ll fix it in post yeah i didn’t have that for writing after diagnosing that it was self-doubt that was the problem and basically you know the solution to that is just lower your bar lower the standards embrace embrace the crap a little bit more now i’ve actually found it pretty easy to not procrastinate on on book stuff i still procrastinate in the sense i’ll go and make a cup of tea i’ll go and kind of wander around a little bit but i kind of know that okay my job for these next few days is to bang out 6 000 words a day for each first draft of the chapter and it’s and it’s being done so in that sense i don’t procrastinate but in but it was it was only that little that mental flip of self-doubt is the cause here that made it work for me i have a question how did you and maybe this is just how you’re wired or oriented like as you gained uh subscribers on the youtube channel which by the way congrats on three million uh as you were along this journey how did you not feel the pull to ultimately get sucked into checking views on your videos in a way that ultimately is procrastination from doing work that would allow you to make better videos did you ever go through periods in kind of your youtube career of checking views subscriber count watch time obsessively or was that just never really in your dna um yeah i’ve had phases where i go through it and it normally makes me feel quite bad to go through it if the numbers are going up then it’s like ah crap the numbers are going up we’re gonna we’re gonna get into a down slump soon and the numbers are going down like they are right now it’s like oh crap we’re in a down slump oh i don’t know i i think this might be the beginning of the end what i’ve found is that the the best way for me to overcome this is to just and and everyone says that it sounds so cliche but just to dissociate my own self-worth from the things that i cannot control as much as possible so now i i think i’ve gotten better at this over time just uploading a video and looking at the views and the numbers but like really trying not to let them affect anything because my bar is now an internal thing that i control which is i will upload a video if i think it’s good or if i if i think it’s a message where it’s worth sharing that would be helpful to at least one person and when i have that sort of zen attitude towards it that’s when a i feel i make better content because now i’m not concerned about oh my god what’s the audience gonna think a b i feel a lot better about it that’s what we’re all trying to achieve and again it sounds so simple like oh you know don’t don’t watch your v don’t look your views don’t like your subscribers don’t look at you know how your channel is trending over time just enjoy just feel good about that you’ve gone through the process of putting content you feel proud about it into the world it sounds so simple it’s just uh it can be very hard at times yeah i i think this is where kind of intrinsic and extrinsic motivation comes in where when when for me the youtube channel was purely a side hustle it’s like oh i’ll make whatever videos i want because i want to help people and it’s all good and maybe two or three people if they sign up to my course it becomes profitable whatever i don’t really care but now that the youtube channel is the foundation of the whole business now it’s like oh like you know the stakes are so much higher at least in my mind what if this just crumbles around me and everything dies and end up broken homeless and alone and i’m not worthy of love and all that all of those geez that’s a lot going back to the therapist this is probably good stuff with them all of that all of that kind of stuff just comes comes to the forefront yeah well i mean that’s an interesting thing you bring up right which is like your youtube work has kind of moved from play to job because it is yeah it’s it’s your job in the sense that it is the source of your livelihood and not not to create obligation for you but livelihood of other people also yes and so it’s like how do you feel the benefit of that play when it is quite literally a job yeah and honestly that’s the thing oh one one thing that um so i’ve i’ve got a coach his name’s corey he might have seen on on twitter uh he and i basically kind of brainstormed solutions to this problem about two weeks ago and actually i started using affirmations and this is surprisingly helpful um i’m just going to read you out my affirmations and yeah like just like i don’t i don’t do this every day i still need to make it part of my morning routine but oh well one thing i have found helpful is for the last month or so i’ve been doing journaling in the form of morning pages every day and often i will think to myself you know am i am i feeling bad about some performance of a video or something and then i’ll sort of reverse engineer okay why am i feeling bad i’m feeling bad because xyz yeah and it will often come back to these affirmations so these are yeah i want to hear the affirmations yeah um so number one i already have enough i don’t need more money or success i am playing my infinite game to learn and teach cool stuff on my own terms number two my life experience is interesting and worthwhile people would love to hear what i have to say about it three i don’t care about numbers i just do my thing and my amazing team will take care of the rest four if i lost everything i’d be able to build back up again to this infinite game over time and it would be even more fun five creative energy surges through me and leads to new and brilliant ideas six today i am brimming with energy and overflowing with joy and then finally i have been given endless talents which i can use whenever i feel like it to create value in the world and all of these affirmations are just sort of tackling a negative thought process or a negative belief about myself that no one cares what i have to say i lucked into this position and now it’s going to come crumbling around me at any time i really have to try very very very hard to make content that peop to make sure people care about the content because me just speaking from the heart is not going to be interesting and it’s like all these so someone from the outside would say no you can make a video about whatever you want you’ve got three million goddamn subscribers just like don’t worry about it but like from the inside it feels like oh no but like oh we it was so lucky to get here right now it’s just gonna come crumbling down so i find that affirmations genuinely i love that can can you read the uh the fourth one again that one really resonated with me i wanted to read and i just want to react to it because that one stood out to me the fourth one if i lost everything i’d be able to build back up to this infinite game over time and it would probably be even more fun both so that’s that’s the most provoking one for me and the reason is is and i think this loops back into procrastination i i actually think at its core procrastination is the source of me feeling so provoked by this and i think it’s why i have kind of like this money hoarding mentality because it almost feels like you know with this business i did this was my one shot and my one luck at making money because after this because i’m a procrastinator i’m not going to be able to achieve success and so i need to hold on to whatever the hell i have because for the remainder of my you know however many years on planet earth uh i’m not going to be able to reaccumulate right and so it’s like such a sad thing right that’s like such a sad perspective that basically like i i’ve quote-unquote peaked and i’m not gonna do anything of worth or value in life moving forward because i procrastinate and so i’ve proven to myself that i can’t be a good diligent worker that can push through any challenge and i think that’s why the fourth one stands out to me so much and i think it’s why i’m so focused on things like not spending on a therapist nice yeah that’s good so you quit the job a year down a year down the line you at austin went on it full time i want to kind of fast forward to when when the sale happened because i’m curious about like money and that kind of stuff and i know we’re skipping up a lot of a lot of the ground midway through but i imagine people can find the story on the internet if they want to learn more well what was the story behind selling morning brew we we sold the business in october of 2020 to um business insider’s parent company which is axel springer large media company based out of berlin germany and that was a conversation that had basically been a year in the making in november of 2019 we had been approached by uh this guy who uh now works at one of the uh at one of axel springer’s um european media businesses but at the time he was a senior person at uh business insider and we had become friendly the the reason we reached out is we we’d become friendly so basically to give context on why we had become friendly as i would you know i was just hustling to grow morning brew one of the growth tactics that i thought about is let me reach out to big business publications who are always looking for more content to drive website uh traffic and let me see if they would syndicate our newsletters on their website uh and so i reached out to one of the editors at business insider saying hey would you syndicate all of morningbird’s newsletters so every day you basically have an extra article that you can put out that you didn’t have to write you didn’t have to pay to have it written and can you just have a call to action at the end to sign up for morningbrew and so for us the benefit is hypothetically a lot of traffic to drive subscribers and i’d asked him a ton of times it clearly wasn’t a priority i reached out to him probably like the 10th time and he was like i don’t want to deal with you anymore let me introduce you to this guy so he introduced me to the guy that i was referring to before who ultimately kind of became the champion of this deal and uh this guy and myself we became uh friends we got beers on stone street in new york city which is this street it’s kind of like this alleyway with a bunch of bars in the financial district of new york city it’s a great spot to go to next time you visit new york um we would go back and forth playing ping pong at our different offices so i’d go to business insider’s offices play ping-pong there he would come to our we work space which we were in at the time play pong he reaches out in in uh november of 2019 and is basically like hey business insider is looking to do more kind of the the phrase to get people into acquisitions if you want to test it is not hey would you be interested being acquired it’s like we’re interested in deep partnerships would you be interested in a deep partnership and and i was like uh do you mean acquiring morning brew and he’s like yeah it’s something we’d be interested in viewer and up to that point austin and i had not thought at all about selling the business uh we had been approached a few times uh but we really weren’t interested what i always said is everything that i wanted at the time is what i had we got to be in charge of our own destiny i was learning and growing a lot was surrounded by amazing team didn’t have to worry about money i was putting like creating something valuable in the world if those five things weren’t being messed up why would i change it ultimately he was like well what’s a price at which you would be interested in having a conversation and i’d said uh 50 million dollars and so you know this person was like well that’s something that would be in you know the the sphere of what we would be open to so let’s have a conversation and so we started having a conversation basically deal terms were put in front of us in february of 2020. okay just a question on that front when you throw out 50 million and he’s like yeah we can work with that like don’t you just like crap your pants like what’s going on in your mind i i if i remember correctly at that time austin and i were like holy that’s a lot of money we should probably have this conversation like that’s that’s enough money but basically we were always like what’s a stupid amount of money that it’d be worth having a conversation about a stupid amount of money that was our thing so like austin we’re like yeah we should probably have this conversation so then we’re having our conversation typically the way that a deal goes down is we had a banker so we had a banker who he hired this banker was the person who interfaced with insider uh an axel springer because normally what you the reason one of the reasons you are banker is like if you have austin and i interfacing with them and a deal like it gets to be a very like tough negotiation and an emotional negotiation kind of ends up awkward when you end up closing the deal and you’re like yeah all those things that we yelled at each other about let’s just forget about those so baker kind of acts as like the intermediary so the relationship doesn’t get hurt in any way the banker also was the person who managed our data room so all of our financials and information about the business that’s what insider an actual springer would look like to come up with what they thought the terms of the deal should be and that this is kind of how any acquisition process happens and so ultimately they put terms in front of us in february of 2020. the terms we thought looked good and reasonable at the at the time like we’re like okay this is a really good deal the reason the deal ended up getting extended is march of 2020 is when the pandemic started and so when the pandemic started our business for a period of kind of like three weeks got absolutely crushed so there was a period of three weeks where we thought our advertising was going to be going was going to go down by 50 percent we were getting call after call from brand saying hey we don’t know what’s happening in the world we are pulling back all of our marketing and so during that time period it was really going back to the early days of morning brew where it was just straight up survival mode finally in you know called april our business normalized things were back they were strong and uh at that then at that point like you know uh our insider like i think uh they were had things going on they were working on things so really it took a year to do this deal we ended up closing the deal finally in october of 2020 and you know i’ll always remember exactly where i was uh i was in my mom’s place in new jersey i was with my mom i was with my girlfriend at the time now fiance they had bought uh champagne they had bought balloons and we have basically there’s a final call where like the deal has already been finalized all the documents have been signed and in a deal process like this the number the number of pages of documentation it like the the final kind of like document book the deal book was probably i can’t remember the exact number i think it was 400 pages um the documents were signed and we all get on a zoom austin myself and all the parties from uh axel springer and insider that were very involved in the process and then basically on the call is when someone from axel springer is like okay we’re starting the wiring process yeah and they’re like that’s basically them saying we’re hitting up uh axel springer’s bank right now to wire you austin and any other equity holders in the business their money for what we’re paying for the business and what i remember in that moment going back to talking about feelings is i felt nothing nice i felt i felt nothing my fiance my mom were super happy for me you know they they wanted me to pop champagne like they were they were they understandably and rationally they were so happy for me but it was like i don’t know i didn’t feel anything and i think i didn’t feel anything because one nothing in that moment changed about what i was doing on the business the thing that did change like the objective thing that changed was that we now had a new partner who thankfully was you know saying that like we could run the business as we wanted to which is what they’ve allowed us to do and the only other thing that changed was obviously you know a few more zeros in the bank account and i didn’t feel anything about that because uh something i had just known about myself i wasn’t really going to change my habits and to this point that really has been the case like if you were to ask me what have i spent on since being acquired and coming into more money than i could have imagined there’s nothing in my life that i’ve spent on that i wouldn’t have spent on prior um you know you know maybe i’m spending a few more dollars to a trip that i’m taking this summer with my fiance than i would have we bought a dog i would have bought a dog otherwise and also i think the other part of it is going up to that point we knew the business was valuable we knew that our equity was valuable and so we knew kind of as long as we didn’t things up we would make money at some point but yeah that was the kind of interesting thing is i didn’t feel anything and you know just to kind of kind of complete the feeling around the money here you know as we’re talking a year and a half now after the acquisition i would say i am no more happy in life today than i was before we did the deal and i had less money i would actually argue that i probably met the same happiness today and for a while i was less happy because i was less happy for a few reasons one is because i knew money could no longer be a motivator it could no longer be a crutch for doing things and so i think in a lot of ways i had to refine like what is go what is going to motivate me moving forward in april of 2021 i moved out of the ceo role into the executive chairman rollup morning brew so that’s five months after the deal and i think for the first six months of being in that new role my happiness absolutely went down because i was like wow this whole business has been my identity for my entire professional life like people know me quote-unquote know me as alex from morning brew i as the executive chairman now who now is spending say 30 hours on the business out of 80 hours i’m getting one step further from the business to start tasting what it’s like to not be a part of this business at some point and what i realized in that moment is no amount of money can help me in that feeling of feeling a loss of identity of not knowing what motivates me and trying to figure out what is it going to be that’s my north star pushing me forward it sounds like in well since you started morning brew and kind of grew it to the point that i got acquired you’re in a way you don’t need to answer the question of what am i doing here what is my purpose because you have a very nicely packaged purpose in morningbrew.com and watching numbers go up and employees being kept happy and advertisers being kept happy and the product being made better and better is in a way such an all-consuming thing that you really it really doesn’t give you much space to sit down and think huh wha what do i really want to do here i think like i was chatting to my brother about this so he’s in you know they’re in early early stage startup mode series a where he’s spending all day on sales calls because they haven’t yet figured out the sales yep you know i was asking him like how how do you feel about this this was uh maybe about six months ago he was like yeah you know it doesn’t feel great but it’s like my baby and like once you have a baby like you’ve just gotta you know feed the baby like yeah it’s it’s not even a choice it’s it’s not even a thought that would cross his mind and he was asking me you know why do you still do the youtube channel where because where some of the time it feels like a slog totally like honestly it’s it wouldn’t it would never cross my mind to not be doing the youtube channel but if suddenly someone offered me 100 million to sell my youtube channel then it would be like okay would you do it i don’t know i probably i probably would um as long as there was and and and the reason i would is because i think over over time i’ve tried to basically create this almost meditation for myself guided meditation where it’s like close your eyes visualize yourself in like the nicest apartment you can imagine like hanging out with the girl and like you know chilling your friends are around you’ve got 100 million in the bank you don’t need to worry about money mate like what are you gonna do tomorrow like how are you actually spending your time yep and i kind of realized that basically the stuff that i’m doing right now i.e making videos writing a book and recording podcasts once in a while is broadly the stuff i would be doing i probably won’t bother making more courses like that’s the only bit of the business that we do for the extrinsic reason of that well it helps fund the business but if for example someone were to come around along and say hey you guys never need to worry about money ever again we will fund you forever we would just put all of our courses completely free online yeah everyone to access so that’s the only real difference there and then that made me feel good because it helped me realize that for me my north star thing is like i just want to learn have the freedom to learn stuff and teach stuff on my own terms and whenever i feel uh the number anxiety around oh numbers aren’t going up as much as i’d like i come back to that thing of like no but even if i had 100 million in the bank i would still be doing this thing so why don’t i just act as if that’s true right now why don’t i just act as if i don’t need to worry about money and just make them make the content that i want because i think it’s interesting and valuable and also the money will take care of itself coming back to affirmation number two which is which is basically that um yeah how was that for you i i think that was good um and i think it’s a beautiful thing again that this stuff you’re spending your time on is the stuff that you would spend your time on even if you never had to worry about a dollar again you know other than uh the course and monetizing the course one thing i’m wondering and i don’t know if you’ve thought about this and maybe it’s just like such a basic emotion that you feel that’s hard to describe how do you know you’re enjoying writing a book or how do you know that you’re enjoying that you enjoy writing scripts and recording youtube videos like how do you know that it’s something that fills you up uh one is looking through my calendar at previous weeks and asking myself did this thing energize me or did this thing drain me and generally for writing and for talking to a camera and for doing podcasts those are the things that energize me and kind of working with a team to brainstorm ideas most other things generally admin related generally operations related generally spread of cell to advertisers related completely drained me so i don’t bother doing them anymore so that’s nice another thing is that i often think you know what would i want written on my gravestone what i want people to say at my funeral and other than kind of good father good husband kind of vibes the third thing that i really value is being an inspirational teacher to other people um to kind of to sort of help them basically help people live their best life which sounds super cliche but i think that is a thing that i can imagine that if i could do that and i’m kind of doing doing that at the moment so if i could just continue doing that that that to me feels like a life well lived and then i’ve tried this exercise called the ideal ordinary week which is you fast forward in your google calendar like five years get rid of all the recurring events that are still there and then you basically block out what are um what do you wanna be doing and for me it’s like oh you know i’d like to play squash twice a week i’d like to do board games and i host friends etc etc and i’d like to have this sort of four hour block of deep work or whatever each day where i can read and write and learn cool things and share share ideas almost almost broadly the schedule that ryan holliday has where he just you know from 9am till 1pm he’ll just go to his little room live with books all around him and just read and write and then he’ll hang out with the family for the rest of the day so i really like that model of like this four hour work day where the work that i’m doing is basically around teaching other people cool stuff and learning new things myself so that is my kind of rough first draft hypothesis of this is the life i think i would enjoy and i’m kind of close enough to it that i get that real-time feedback of after a session of book writing like this morning i did like two hours of just non-stop typing on the book and at the end of it i was like yeah that was good that felt fun uh similarly this podcast right now i’m feeling like yeah this is sick and afterwards i’m gonna think oh i had an amazing conversation with alex that was so fun so it’s like i’m i’m looking up for those sorts of feelings that i get yeah so it’s an interesting thing because as much as you say you’re like trying to feel more you do have an awareness of after you spend your time on certain things just like generally like sitting in that moment like how do you how does that feel to you like do you feel like even like do you feel more tired do you feel lethargic or do you feel like you’re you’ve been woken up or like do you feel like your body’s opened or closed like it seems like you actually have a sense of that and you do that without kind of like you know labeling it as like a tool or an exercise yeah i think so i think i have a pretty strong idea of that and i i think also another thing that i i just always ask myself just this question of like would i do this for free and when it comes to things like playing squash or badminton or tennis that doesn’t even cross my mind because obviously the answer is yes but it’s when money becomes the extrinsic factor that it crowds out intrinsic motivation right because it becomes blurred and you don’t know how much each one is contributing to it yes yeah exactly and so when i when i was dabbling for a few months and being a part-time doctor doing kind of shift in the emergency department here and there the thing i was finding myself doing is every half an hour as i was typing stuff on the computer and just feeling a bit like i’m on the phone to radiology and they’re not replying and i have to sit here for the next five minutes waiting for someone to take my call would i do this would i really do this if i won the lottery and i didn’t have to worry about money the answer was like probably not like i would much rather be in the studio with my team thinking what cool youtube video we can make to share a concept from psychology being here on the phone to radiology so it was i i think that question is a thing i often think about i think that makes sense and and to make it a little bit harder what i found to be difficult was how did i know when something didn’t give me energy versus when something was hard and i was making an excuse for not being good at the hard thing or wanting to work on the hard thing and so the example i’ll use here is like the op like the the parts of the business that you know are austin super powers uh for when we were you know working hand in hand together so things like planning things like uh hiring road map things like uh even running like the traction process like those were things that i didn’t feel like i loved doing but i was trying to distinguish do i not love doing these things because they’re harder to me and things that come harder to me because it’s harder i don’t love doing it because it’s harder and so that’s actually an excuse and that’s a good reason to do the thing to prove that i can do something hard or is it because i just really don’t love the thing because i like doing something that’s like more creative in nature or interactive in nature or something that’s earlier in the process of building something from scratch and so for me i would say that added another kind of like access or variable it was like i’m always thinking in my head on this spectrum from 100 intrinsically motivated to 100 extrinsically validated or extrinsically motivated where am i living on this and do i feel like it is at a place on the scale that feels like it’s in check and it’s a good reason to do the thing and then the second one was outside of the the money versus intrinsic thing am i do i is something that i’m not doing because i don’t feel quote unquote good energy from it is it because i actually don’t like it or is it because it’s hard and this is a good excuse to not do the hard thing nice so you’ve got your intrinsic extrinsic access and you have your hard easy access exactly nice and you can use that in the book if you want nice thank you and and i guess your concern is that am i like let’s say you’re doing something that’s 100 intrinsic but also 100 easy you’d be like oh wait a minute is this really intrinsic or is it just because it’s easy that i’m enjoying this exact exactly you know when you’re at this point where you’ve got extra zeros in your bank account and you don’t know what to do with them and you’re like what do i what do i do with my life yeah how did you go about finding that north star is yeah how did you think about that well if i’m being honest i’m still in the process i still don’t really know what i want to be when i grow up i know there are some options uh like one option is to build more businesses like to go back to kind of the earliest stage and put cool into the world the second is to help others become great entrepreneurs because i do think i love the energy of early stage entrepreneurs uh you know i’ve seen the impact that entrepreneurship can have on a country on an economy on a group of people and to me that’s really profound so that’s one thing a third thing that i’ve considered which is totally out of left field is to become a therapist myself is like literally to go get a psychology degree become a therapist the the kind of like business or startup variant of that is to become an executive coach to coach entrepreneurs uh and so what am i doing today well one it’s like the time i spend on morning brew is like creating content finding creators to launch shows at morning brew and dealing with the biggest hairiest problems with austin and the le the the lens that i look through this is like how do i just learn as much as possible in this experience at morning brew right now because i’m in a really privileged point in the business where we have 275 people i have access to all these people we’re building something really cool how do i just soak this all up for learning uh that can selfishly help me in building businesses in the future and then outside of that right now i’m basically spending time angel investing and seeing kind of how it lands with me to angel invest versus coach people so i’ve started to coach a few people uh and and for me again it’s not really for money it’s just like do am i enjoying coaching and also part of it it’s like can i prove to myself that i actually can add value to entrepreneurs and like push back on this imposter syndrome and then the third thing that i candidly want to spend more time on is like really focusing on on not optimizing health because i sometimes i feel like optimizing is actually a bad word like i feel like it creates actually a lot a lack of balance uh and to me everything is good in not everything but most things are good in moderation and optimization sometimes doesn’t allow for moderation but there are things like working on my food intake my sleep like things that generally just give me the best energy in life and those are things that i want to spend time on uh that i haven’t yet spent nearly enough time on and so to answer your question i am very scared about not knowing at the age of 28 what i want to do for the for many years but i’m optimistic that if i’m patient and if i’m both patient and inpatient patient macro impatient and like feeling like i’m not moving fast enough to answer this question then i’ll get to a play like that i am where i’m supposed to be and that uh things will work themselves out alex thank you so much this has been absolutely wonderful uh where can people find out more about you and we’ll have links to all of the stuff obviously in the video description of the show notes as well yeah first of all thank you so much for having me i’m very excited for when you finish your book and i can add it to uh my reading list and my bookshelf as well you can follow me uh at business barista on twitter uh and you can check out my two podcasts founders journal which is my startup show about lessons from the entrepreneurial journey and imposters where i talk to world-class performers from ray dalio to jay shetty about their careers and how they were able to excel in their career careers even in the face of really deep challenges and uh the mental health journey that went along with those challenges amazing stuff alex thank you so much for coming on everyone thanks so much for having me you next time all right so that’s it for this week’s episode of deep dive thank you so much for watching or listening all the links and resources that we mentioned in the podcast are going to be linked down in the video description or in the show notes depending on where you’re watching or listening to this if you’re listening to this on a podcast platform then do please leave us a review on the itunes store it really helps other people discover the podcast or if you’re watching this in full hd or 4k on youtube then you can leave a comment down below and ask any questions or any insights or any thoughts about the episode that would be awesome and if you enjoyed this episode you might like to check out this episode here as well which links in with some of the stuff that we talked about in the episode so thanks for watching do hit the subscribe button if you aren’t already and i’ll see you next time bye