Lessons From Selling Morning Brew For $75 Million At 28 - Alex Lieberman
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Oh, by the way, before we get into this episode, I would love to tell you a little bit about Life Notes. Now, Life Notes is a weekly-ish email that I send completely for free to my subscribers, and it contains my notes from life. So notes from books that I've read, podcasts I'm listening to, conversations I'm having, and experiences I'm having in work and in life. And around once a week, I write these up and share them in an email with my subscribers. So if you would like to get an email from me that contains the stuff that I'm learning, almost in real time as I'm learning it, you might like to subscribe. There is a link down in the show notes or in the video description.

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 life countdown clock, you have no idea when it's going to hit zero. And basically I said to myself, 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...

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 Brew is this 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 a couple of 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, A, 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've been thinking of starting a business or growing a business or kickstarting 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 love talking to Alex. He and I have had a few Zoom calls over the years, and I'm very excited for you guys to hear this 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 going to be fun. I'd love to get started. So you've got a super interesting backstory. And I would just like, I would love to start with a question of how did we get here? What was the backstory of Alex Lieberman?

Yeah, so I am originally from New Jersey 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 and having the value of 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.

And so I went to a small private school in New Jersey. It was great for some things, wasn't great for other things. I loved it for the academics and the athletics, didn't love it for 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 different.

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. Uh, a third of the class went to what are called NESCAC 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. 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

And the way it works in the States with internships is you have 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'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 work in finance. And so I started helping students

prepare for job interviews. And one of the ways that I would help them is I would do 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 if 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. 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% 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. 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. 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.

Okay, 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 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 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 started writing that newsletter, which by the way, at the time wasn't called Morning Brew, it was called Market Corner.

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 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. Oh, so now 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 as to any other experiments running in the background. Uh, yeah.

Nothing that was, as I would say, productive as this. I probably spent three or four hours a day working on Market Corner, which would then turn into Morning Brew. I did spend a lot of time playing video games. I played a lot of FIFA, NHL, 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 the University of Michigan gymnastics meet. I went to the soccer games just because I,

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 was a TA for a real estate class, which was actually my favorite class. It was an interdisciplinary grad level real estate class where basically you

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 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 student 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. And you said this class was your favorite. I wonder, like, what did you learn from this class that maybe you've 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 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 love this class because it was one of the two classes where I actually felt like this is simulating what I'm gonna 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 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 basically taught us how to do pivot tables, 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

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 timeless skill in the same way that I would say actually the most valuable class I've ever taken in 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 view typing on my computer as a timeless skill. - Ooh, interesting. So a few thoughts on this. - Yeah. - Firstly, so my brother is working on a startup to try and compete with Excel. - Really?

Yeah, it's called Causal. They're trying to basically be the new Excel, but for number crunching. Because Excel has all these different use cases and it's a very general tool. But 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 for their kids' football practice. And...

Their thesis is that uncertainty calculations and modeling and stuff is really hard to do in Excel where you have loads of uncertainty with all these different numbers plugging in. It's really hard 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 a product. 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, and they raised 4.2 million in 2021. This is awesome. Yeah, I'm going to read more about it. - Recently. - Oh, really? - So you should look into that. Start using causal. - I was going to say, now you have to get, ultimately, if they get big enough, you have to get them to work with universities, so universities teach causal courses. - Oh my goodness, that's a great idea. Yeah, it'll be good for any kind of number crunching and modeling and stuff. I also very much agree on the typing front.

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 absolutely ridiculous. I remember watching that video and then doing a typing test and feeling horrible about myself after doing that test. What was the speed again? I think it was one, one, five, six words per minute is my record. I need to try and bump that up.

But 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. 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, seven thousand words. And it's just kind of, I think, normally when it comes to...

Yeah. So every day for the last few days, I've been banging out one chapter and I need to do another one today. But I've already done 4,000 words in about a one and a half hour slot this morning. And it's like amazing that 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 has 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, 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

And then we'll clean it up in post. So honestly, that was something I'm very interested about because if I remember correctly, like I remember the general, 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 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 5,000 to 7,000 words of whatever comes to your mind?

Great question. Yeah, so I was worried about this as well. I'm connected to the internet because I use 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. You just write TK, need research about XYZ over here. 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, anxiety is that feeling of TKXYZ. 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 gave 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 in some point of the conversation about

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 put a bookmark on that and definitely come back to it because I imagine people would find that surprising given kind of your story. Yeah. So definitely bookmark in there. I was going to ask as well. So other than typing and Excel, have you ever found any other sort of meta skills that are generally useful for life? Yes, but they weren't taught in university. So one is storytelling and selling. Like I think the number one skill is

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. 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 digital communication, like how to write an email. And I found that to be tough, tough as in like not helpful. But yeah, I mean, sales, I was...

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.

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 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 heard a lot of people say that, that, you know, the skill of selling is kind of, yeah, is 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 that actually mean? Like, I wouldn't say I'm good at selling, but I guess I have sold stuff in the past and I just don't really think of

Selling is like a thing. You sell yourself on YouTube every time you post a video. And this is actually an interesting thing. And I've thought a lot about this is what's the difference between sales or selling and storytelling? And my view is just if something comes off as selling, it's just shitty storytelling. And so my view is like, why do people...

watch your videos for a long time? Why did you just hit 3 million subscribers on YouTube when there's 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

to script and then 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. My answer would be it's a combination of practice, of shadowing and feedback, and of understanding the fundamentals of what it means to storytell well. So going in reverse order,

I think that 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. And so like, for example, I'm reading the book Creativity Inc right now, which is the story of Pixar. Like 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.

In experiencing 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 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 got reps and

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 10 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 salespeople 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 reins to them where they would start doing the pitch and

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 Gong basically allows you to do is allow sales orgs to record every sales call they have. And then in a database or...

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 onto Gong and study what are quote unquote the best calls that have led to the conversations that convert their clients. At the end of the day, there is this art and science to understanding what works for you to storytell in a way that leverages your strengths

But also understanding the science of what works well and what are kind of like the natural story arcs that people over the course of time are always attracted to. Nice. That's a great answer. Was that off the cuff or have you thought about it before? That was off the cuff. Bloody hell, that was good. That was a three-part framework. I love it. I'm just like, bloody hell. Yeah.

It was like very meta. We were using a storytelling framework and talking about storytelling framework. 100%. Alrighty, a 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 at Shortform, who are very kindly sponsoring this episode of the podcast. If you haven't heard by now, Shortform 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 elite 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, 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 Shortform is super helpful for that. If any of that sounds up your street, then head over to shortform.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 and,

to students who are reading our newsletter. And we said, "Hey, if you're interested in writing about business and you wanna get your words in front of hundreds or thousands of people, we'd love you to come write 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 it two stories a week in our newsletter.

So that was kind of like our 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 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 we 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, um,

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. And so we were like, what is going to give our content that X factor that's going to feel quick-witted and smart and funny? And so we were like, we need to find a funny person.

And so we put out 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

organizational organization, building culture, et cetera. So he was in that program, but he was also in the improv troop at Michigan. And so he was hilarious and he was a good writer and understood business. And so we brought him on as the, literally the, the, the job we called it was he was our voice editor. So we had our writers, we had our 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 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 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 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 importance of storytelling and selling, we spent our whole second semester in about 150 club meetings or classes

pitching 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 Morning 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 students

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 pad and paper, it was two steps. It was 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 thought 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 two people that are going to 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 had never heard of a media company doing a college ambassador program. When I think of college ambassador programs, I think of like Red Bull 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 where we were like, let's get the best ambassadors across the country to represent Morning Brew. So we had this super rigorous application process. It was like harder to get into our ambassador program than to get into Harvard 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 bombed. 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 actually were the people with 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 and

But everyone was accepted. We just wanted it to have an air 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. Yeah.

only when you got to say, I think it was 25 signups, 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,

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 kind of for the rest of college was growth and getting the content out. That really reminds me of the whole, you know, do things that don't scale. Yep. Because, you know, if I imagine, like we've just launched a new newsletter for our creative 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 so rogue. It's so analog in the world that we live in today. I got to 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 the people watching their videos are all creators. Yeah. So you're growing this newsletter online.

door to door, but like at scale. What did the numbers look like in that first year, like 2015 when you were in college? So when I graduated from Michigan, I want to say we were at 10,000 subscribers. 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 going to go do this newsletter thing that makes no money, that has 10,000 people on it, rather than doing the thing that I dreamed of. I did not do the second. I went and I worked at Morgan Stanley. Sales and training,

Generally, you start early in the day. So I would wake up at 5 a.m. every day. 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 p.m. 7 p.m., 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 a labor day of, of 2016. And the reason I quit was because,

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 banking or do Morning Brew? And I vividly remember Austin came to New York 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 going to do? Like there's a clear fork in the road. It was a fork in the road of, we're either going to 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 going to stop or it's going to 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 think we had different reasons for going full-time on it. And for me,

The reason I went full-time was a fewfold. 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 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 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,

maybe Morgan Stanley would take me back because I had this entrepreneurial experience that made me unique in my experience and they would value that. And 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, no, maybe this is a common story and it wouldn't get me into business school. And I said, maybe...

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 I'm not going

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, you

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, like literally built the same as me, similar 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 time on your life countdown clock, you have no idea when it's going to hit zero.

You look at the statistics and you hope that it's going to hit zero around, you know, 80 years old or later, but you really have no idea. And basically I said to myself, 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 at the time yeah it was um it was really tough for a few reasons obviously it was it was shocking

It was one of those things like he was my best friend and it was like, you know, he was the guy that when I would be walking from class back to home or vice versa, like he was the person I was texting or calling. And 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...

in retrospect, it's pretty funny thing now for a while I would call his number and it would just, you know, it'd 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

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 they're probably like, who is this random 973 number that calls us once a year, says nothing and hangs up? But yeah, I mean, so there was a huge void that I felt because it really was my best friend. And then I think the final thing is,

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 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 shit 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 going to 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, what you don't want to do. Wow. Yeah.

Wow. Thank you for being so open about this. Yeah, of course. This is something that I have been thinking about as well in the sense of, you know, being a sort of entrepreneur bro, um,

you know, growing up in an Asian family meets kind of an all boys school meets, you know, talking about and feeling emotions and stuff very much frowned upon. Yep. 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, et cetera, et cetera. I don't feel, I don't feel negative emotions if I don't want to. 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 are you doing it? 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?

I've changed the wording over time to be like intentional with not how do I feel more? Because I think that implies like that I am feeling less right now and I'm not feeling enough and there's something wrong with me. And so what I've changed it to be 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, 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'd share with her in probably our second or third session together that,

I was bullied in school probably from fifth grade to the end of high school. Like 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, when is a moment that you felt really lonely and frustrated?

And

And she would tell me to like close my eyes and like sit with envisioning those people talking and closing their bodies to me, 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 ex,

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 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 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, sorry, worked with for probably the 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 a,

deceleration of the learning curve or the benefit curve where 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 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, Hakomi 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 you do these sessions of zoom or in real life? 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 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 would get anxious about spending money on therapy.

I'd be like, oh my God, this is a lot. Like, you know, my therapist is $300 an hour. I'm like, this is a shit ton of money. Like, do I really need to spend on this? And at some point I got to the point where I was like, 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. And yeah, so I talked to her every week or other week and 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 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, it was ages ago.

And I found that like, I wasn't really fan, like the first two or three sessions were 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 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

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, uh, 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 going to be the right person is like, you're, you know, you're betting that you're going to win the lottery.

Yeah. Okay. You're right. I'm sold. I will ask you for your therapist's email address afterwards because that seems like a good first option. Cool. Yeah. 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 therapists... Yes. I would argue that, yeah, therapists are very non-fungible.

Excellent. That's your NFT, the non-fungible therapist. So you were 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 terminology hustle and grind and maybe losing a bit of sleep and maybe not taking 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 deprioritize self-care and stuff for the sake of getting this thing off the ground. So I wonder, with the benefit of hindsight, 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 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 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 procrastinating

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'm 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, so like 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 early days when 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 AA for phone addiction? 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 and in school what it means to do work.

And I think it means you're given an assignment, you do the assignment. 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 made. There was a period of time where I would spend hours a day reaching out on LinkedIn to potential

advertisers of Morning Brew. And I do all this LinkedIn outreach to hundreds of them. Then I would schedule calls with them. 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 with 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. So we didn't have the Bible for running a business. And so what would happen 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 ended 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,

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 find it tends to be two things. It's either self-doubt or it's fear. 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 am not the sort of person who does things. I am the sort of person who is a procrastinator. And you've got 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 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 the, you've got the fear component. My question for you is, does that kind of framing make sense with your experience? Yeah, it totally does. I think it, it makes me because I have felt because I have 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 respect for myself because I feel like to what you just said before, I am 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 negative kind of like self-loathing version of this. I've tried to have a more productive thought about this to say,

But 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, 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 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. Basically, that narrative is, Alex, you have to own the fact that

that procrastination is part of your process and it's okay. And actually, like to say you won't reach your potential is to say that you believe that if you rid yourself of 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 try to, as I'm experiencing this, turn it into a positive where I'm not so down on 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, 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 one of those thoughts. 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 it puts me on a more solid foundation to push forward in life. What's your take on this? 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 Clear or Mark Manson or Tim Ferriss' or Dan Pink's final draft. And I was like, oh, you know, the stuff I'm writing is just shit. 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, I can't string sentences together without making a mistake, et cetera, et cetera. 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 realized 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 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 take a break, turn the air conditioning on, get a coffee. 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 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 being done. So in that sense, I don't procrastinate. But 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 subscribers on the YouTube channel, which, by the way, congrats on 3 million. 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? 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, oh crap, the numbers are going up.

We're going to get into a downslump soon. And if the numbers are going down like they are right now, it's like, oh crap, we're in a downslump. Oh, I don't know. I think this might be the beginning of the end. What I've found is that the best way for me to overcome this is to just, and everyone says this and 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 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 think it's a message 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 going to think? 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 look at your views, don't look at your subscribers, don't look at, you know, how your channel's trending over time. 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 just it can be very hard at times. Yeah, 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. What if I don't really care? But now that the YouTube channel is the foundation of the whole business now, it's like, oh, shit.

The stakes are so much higher, at least in my mind. What if this just crumbles around me and everything dies and I end up broken, homeless and alone and I'm not worthy of love and all that? - Jeez, that's a lot. Go back to the therapist. This is probably good stuff to unpack with him. - All of that kind of stuff just 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, it's your job in the sense that it is the source of your livelihood and 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, honestly, that's the thing. Oh, one thing that, so I've got a coach, his name's Corey, you might've seen him on Twitter. He,

And I basically kind of brainstormed solutions to this problem about two weeks ago. And actually, I started using affirmations. And they're surprisingly helpful. I'm just going to read you out my affirmations. Yeah. Just like...

I don't do this every day. I still need to make it part of my morning routine. But, oh, 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 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 X, Y, Z. And it will often come back to these affirmations. So these are the affirmations. Yeah, I want to hear the affirmations. Yeah. 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 I have 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 people... To make sure people will care about the content because me just speaking from the heart is not going to be interesting. And it's like all of these...

so someone from the outside would say, no, you can make a video about whatever you want. You've got 3 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 and now it's just going to come crumbling down. So I, I find the 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 it. 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 a backup to this infinite game over time. And it would probably be even more fun. Well,

So that's the most provoking one for me. And the reason is, and I think this loops back into procrastination. 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. Yeah.

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, I'm not going to be able to reaccumulate.

And so it's like such a sad thing, right? That's like such a sad perspective to have basically. Like 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.

Yeah. That's good. So...

you quit the job a year down, a year down the line, you and Austin went on it full time. I want to kind of fast forward to when, when the sale happened. Cause 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, if they want to learn more. 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 this guy who now works at one of Axel Springer's European media businesses. But at the time, he was a senior person at

Business Insider, and we had become friendly. The reason he reached out is we had become friendly. So basically, to give context on why we had become friendly, as 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 traffic, and let me see if they would syndicate our newsletters on their website. And so I reached out to one of the editors at Business Insider saying, hey, would you syndicate

all of Morning Brew'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 Morning Brew? 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 now,

This guy and myself, we became 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. 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 WeWork space, which we were in at the time, play ping pong there.

He reaches out in November of 2019 and is basically like, hey, Business Insider is looking to do more kind of... The phrase to get people into acquisitions, if you want to test it, is not, hey, would you be interested in being acquired? It's like, we're interested in deep partnerships. Would you be interested in a deep partnership? And I was like...

"Do you mean acquiring Morning Brew?" And he's like, "Yeah, it's something we'd be interested in if you were." And up to that point, Austin and I had not thought at all about selling the business. We had been approached a few times, 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 said, $50 million. And so, you know, this person was like, well, that's something that would be in, you know, 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, hang on. Just a question on that front. When you throw out 50 million, 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? If I remember correctly, at that time, Austin and I were like,

"Holy shit, that's a lot of money. "We should probably have this conversation." Like that's enough money. 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 we hired. This banker was the person who interfaced

with insider and Axel Springer. Cause normally what you, the reason, one of the reasons you hire a 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 banker 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 and Axel Springer would look like to come up with what they thought the terms of the deal should be. And 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 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

where we thought our advertising was going to go down by 50%. We were getting call after call from brands 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 end of 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 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 of pages of documentation, like 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. The documents were signed and we all get on a Zoom, Austin, myself, and all of the parties from 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. And they're like, that's basically them saying we're hitting up 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. Mm-hmm.

- Nice. - I felt nothing. My fiance, my mom were super happy for me. They wanted me to pop champagne. 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 something I had just known about myself, I wasn't really gonna change my habits. And to this point, that really has been the case.

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. 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 fuck 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 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 going to motivate me moving forward. In April of 2021, I moved out of the CEO role into the executive chairman role at 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 instead 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

It really doesn't give you much space to sit down and think, huh, what do I really want to do here? I was chatting to my brother about this. So he's in, you know, they're in early stage startup mode, series A, where he's spending all day on sales calls because they haven't yet figured out the sales. And I was asking him, like, how do you feel about this? This was a...

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 got to 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, that would be like, hmm, okay. Would you do it? I don't know. I probably would. And the reason I would is because I think 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 going to do tomorrow? Like, how are you actually spending your time? 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 wouldn'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 for 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 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 the content that I want because I think it's interesting and valuable. And just trust that the money will take care of itself coming back to affirmation number two, which is basically that. Yeah, how was that for you? I think that was good. 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 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 it'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?

Writing scripts and recording YouTube videos. Like how do you know that is something that fills you up? One is looking through my calendar at previous weeks and asking myself did this thing energize me or did this thing grade 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 trying to sell to advertisers related and

completely drain 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 would 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 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 that at the moment. So if I could just continue doing 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--

What do you want me 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, et cetera, et cetera. 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 ideas. Almost broadly the schedule that Ryan Holiday has where he just, you know, from 9 a.m. till 1 p.m., he'll just go to his little room 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 workday

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 nonstop typing on the book. And at the end of it, I was like, yeah, that was good. That felt fun.

Similarly, this podcast right now, I'm feeling like, yeah, this is sick. And afterwards, I'm going to think, oh, I had an amazing conversation with Alex. That was so fun. So it's like I'm looking at 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 more? 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 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. Yeah, totally. But it's when money becomes an 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 was dabbling for a few months and being a part-time doctor doing kind of shifts 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, oh, 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 than being here on the phone to radiology. So it was, I think that question is a thing I often think about. I think that makes sense. 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 to

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 opera, like the,

the parts of the business that, you know, are Austin superpowers for when we were, you know, working hand in hand together. So things like planning, things like hiring roadmap, things like 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 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 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 so I can use that in the book if you want. Nice. Thank you. 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, shit, wait a minute.

Is this really intrinsic or is it just because it's easy that I'm enjoying this? 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, shit, what do I do with my life? Yeah. How did you go about finding that North Star? 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.

Like one option is to build more businesses, like to go back to kind of the earliest stage and put cool shit into the world. The second is to help others become great entrepreneurs because I do think –

I love the energy of early stage entrepreneurs. 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 kind of like business or startup variant of that is to become an executive coach, to coach entrepreneurs. Yeah.

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 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 position.

point in the business where we have 275 people, I have access to all of these people, we're building something really cool. How do I just soak this all up for learning 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. 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 sometimes I feel like optimizing is actually a bad word. Like I feel like it creates actually a lack of balance. And to me, everything is good in – not everything, but most things are good in moderation and optimization sometimes doesn't allow for moderation. Right.

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 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 many years.

But I'm optimistic that if I'm patient, if I'm both patient and impatient, patient, macro, impatient, and like feeling like I'm not moving fast enough to answer this question, that I'll get to a place like that I am where I'm supposed to be and that things will work themselves out.

Alex, thank you so much. This has been absolutely wonderful. Where can people find out more about you? And we'll have links to all of this stuff, obviously, in the video description and 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 my reading list and my bookshelf as well. You can follow me at Business Barista on Twitter. And yeah,

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 careers even in the face of really deep challenges and the mental health journey that went along with those challenges amazing stuff alex thank you so much for coming on thanks so much for having me see 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.

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