Lessons From Selling Morning Brew For $75 Million At 28 - Alex Lieberman

Alex Lieberman 0:00 You know, I just had like a, a mentally transformative experience where a week before junior year of college at Michigan, my dad passed away suddenly. He passed away, uh, 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 i- on a daily basis in life are wildly unimportant, and two, how your time on your, uh, life countdown clock, you have no idea when it's gonna hit zero. And basically I said to myself, "If, if I knew my countdown clock was hitting zero tomorrow, what would I rather be doing with my time?" And it, it was like a no-brainer. It was like I knew that I would-

Ali Abdaal 0:44 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 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 do 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 kinda lessons that we can learn from his journey, uh, of building this business from day one. And so if you're been-- 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 kinda 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, a few Zoom calls over the years. Um, 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?

Alex Lieberman 2:08 Good, man. Thanks so much for having me.

Ali Abdaal 2:10 It's gonna be, it's gonna be fun. Um, I'd love to get started. So you've got a, a s- a super interesting backstory, and I would just, like,

Ali Abdaal 2:17 I, I would love to start with a question of how, how did we get here? What was the backstory of Alex Lieberman?

Alex Lieberman 2:24 Yeah. So I am originally from New Jersey. Uh, and I grew up in a finance family. So everyone in my family, no matter where you looked on my family tree, worked i- on Wall Street. Uh, my dad worked in sales and trading. My mom worked in sales and trading. My grandpa worked in sales and trading. And so growing up, uh, you know, h- and having the value of, you know, family as 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.

Ali Abdaal 2:58 [laughs]

Alex Lieberman 2:59 Uh, and so I went to a small private school in New Jersey. It was great for, for some things, wasn't great for other things. I loved it for the academics and the athletics, didn't love it for, uh, the social part of the experience. And so I wanted a very different experience in my college, uh, experience. And so I ended up going to the University of Michigan, which was very nontraditional 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. Uh, up to that point, I was on the path to work on Wall Street because that was my goal, and so I did internships after each year in college. I was in the business program. And I got into my senior year at Michigan and the way it works, uh, you know, in the States with internships is you have a, uh, your internship after your junior year in finance, and if you do well in that internship you get an offer. And so then in your senior year, in your last year of college, you don't have to recruit for jobs. You already have that job for when you leave school. And so that, that's what happened for me. I had my internship at Morgan Stanley working in sales and trading junior year. I got an offer back. And so I accepted that offer. I got into my senior year at Michigan. I didn't have to recruit for a job. I only had to take three classes my entire senior year because I k- had completed my credits. And so I got into the year and I was basically like, "Okay, this is gonna be fun. I'll play a lot of video games, but I should probably do something else in order to keep my brain sharp for when I graduate and go, you know, work in finance." And so I st- I started helping students prepare for job interviews, and one of the ways that I would help them is I would do mo- 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, as if we-- he was an interviewer. And one question I would always ask students is, "How do you keep up with the business world?" To me, this was like the layup question, just to get them comfortable, not be nervous. And every student basically said the same thing, which was, "I read The Wall Street Journal. Uh, it's what my parents told me to do, but it's a bit dense. It's a bit dry." And that just really resonated with me because I was like, "This is crazy." These students are about to spend 50% 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.

Ali Abdaal 5:57 Hmm.

Alex Lieberman 5:58 It sto- so I started writing a daily business roundup about the business world that in the beginning was really shitty, like it was a really bad product. Uh, but it was good enough to really catch people's eye and, 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, a seven-year journey of building Morning Brew.

Ali Abdaal 6:26 Amazing. Okay. I, I... That, that was the point where I wanted to zoom in on. So there's a lot of people that would s- that would notice something that, huh, it's, it's kind of weird that all of these people applying to all these jobs are, like, reading business news but seeming to not enjoy it. What was it that made you take that leap to, therefore I'm gonna write

Ali Abdaal 6:44 my own email newsletter? 'Cause that's not a normal thing to think. Like, what, what was going on there?

Alex Lieberman 6:48 Yeah. I mean, it's interesting because I was not thinking about it as a business at all. The, the interesting thing is, like, I've never thought about myself as, like, an entrepreneur or that I have to build a business, but I've always been a tinkerer. Like, I've always just, like, tried doing random things. And I, I started writing that newsletter, which by the way at the time wasn't called Morning Brew, it was called Market Corner. Uh, and I'll describe what that product looked like in the beginning because again it was pretty mediocre. But basically I wrote it because one, selfishly I wanted to keep up to date with what was happening in the business world so that when I left college and I went into my job in finance I felt like my brain was on top of things. And so the process of reading what was going on in business and distilling it into these bite-sized chunks was almost like a forced function for me staying on top of my game. Then the second part I would say was more selfless, which was I just wanted to help these students keep up to date with the business world. And to me, the way to do it was just to start writing this thing, and I had an abundance of time.

Ali Abdaal 7:50 How did you have an abundance of time?

Alex Lieberman 7:52 Yeah. So as I, you know, as I had mentioned, basically I got into my senior year. I had already gotten my job, so I had that junior year internship. And I got an offer to work full-time-

Ali Abdaal 8:05 Oh

Alex Lieberman 8:05 ... at-

Ali Abdaal 8:06 So now you're, it's like you're coasting the rest of the year.

Alex Lieberman 8:07 Yeah, exactly. Basically my fourth year of college, my senior year, I was coasting. I didn't have to recruit for a job.

Ali Abdaal 8:13 Yeah.

Alex Lieberman 8:14 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.

Ali Abdaal 8:41 Uh, did you try and do anything else with your time? I'm curious as to-

Alex Lieberman 8:43 Um

Ali Abdaal 8:43 ... if you had any other experiments running in the background.

Alex Lieberman 8:45 [laughs] Uh, nothing that was, uh, as I would say, productive as this. I probably spent three or four hours a day working on m- uh, Market Corner, Market Corner which would then turn into Morning Brew. I did spe- spend a lot of time playing video games. Such as I played a lot of FIFA, NHL, uh, and Call of Duty. Um, 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 had never thought of going to. Like, I went to, uh, the University of Michigan gymnastics meet. I went to the soccer, uh, games. Just 'cause I kind of thought to myself, "This is the last year that I'm really gonna be able to experience this u- amazing university as a student. I might as well just, like, make the most of it."

Ali Abdaal 9:35 Mm.

Alex Lieberman 9:35 And then I was a, a teaching assistant my senior year. I, uh, was a TA for a real estate class, which was actually my favorite class. It was, um, it was a interdisciplinary grad level real estate class where basically the class was not lectures, it was you were tasked with picking an actual physical location in the US where you thought there was an opportunity to buy the location, like buy the real estate, develop a property, and turn it into a residential, retail, commercial, like a multi-use property. And it was an interdisciplinary group. So where it was a business student, it was an architecture student, it was a legal student, and it was an urban planning student. And so the four of us literally spent a semester where we went to parts of Michigan and we drew up our plan for developing, like, a full-blown, you know, 250,000 square foot property. The architect literally drew out the exact specs of the property. The urban planner wrote up the documents that you would use to apply to the city. I worked on the financials. And the legal, uh, student, uh, basically shared what the pipeline was of contracts that we would have to figure out for the property. So that was one other thing I did senior year.

Ali Abdaal 10:52 So you said... That sounds su- super cool. Uh,

Ali Abdaal 10:55 and you said this class was your favorite. I wonder, like, what did you learn from this class that maybe you've applied, applied later in life?

Alex Lieberman 11:01 Yeah. I mean, this is the interesting thing. I loved my experience at Michigan, but if you were to ask me why I loved it, I would not say it was for the academics because I would say there's maybe two classes in the entirety of my education at Michigan that I feel like I've actually applied in my career. And I think this just speaks to where a lot of academia is broken, and I think it's broken for a lot of reasons. I think, uh, it's broken because it teaches you what to think versus how to think. I think it's broken because a lot of people are lifelong academics. And that's not inherently bad, but I wish there was more attraction to entrepreneurs and practitioners going back to universities because I think it would make what you learn far more applicable because it's being taught by people that actually did the thing. I loved this class because it was one of the two classes where I actually felt like this is simulating what I'm 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, you know, invest in real estate. This is something I would go through. And it was interdisciplinary in nature, which is inherently all of your experience in your career and life is working with people that have diversity of thought and experience from you.

Ali Abdaal 12:16 Mm. Nice. So this real estate was class number one. What was class number two that actually taught you something?

Alex Lieberman 12:22 My, my Excel class. It was the class-

Ali Abdaal 12:25 An Excel class?

Alex Lieberman 12:25 Yeah, yeah.

Ali Abdaal 12:25 Okay.

Alex Lieberman 12:26 It, it was my class that, uh, basically taught us how to, uh, do pivot tables, uh, visual basic, shortcuts in Excel. And for me, like Excel is a program that I probably will use my entire life with different levels of kind of intensity or frequency. When I was working in finance, uh, before I went full-time on Morning Brew, I used Excel a lot. Like, I was doing a lot of just modeling and calculations in Excel. Today I would say I use it maybe once or twice a week, but having that proficiency in Excel, it's kind of like, I would consider it kind of the, the timeless skill in the same way that I would say actually the most valuable class I've ever taken in my life was my fourth grade typing class. Like, I, I've used this skill-

Ali Abdaal 13:18 Nice [laughs]

Alex Lieberman 13:18 ... 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.

Ali Abdaal 13:28 Ooh, interesting. So a, a, a few thoughts on this.

Alex Lieberman 13:32 Yeah.

Ali Abdaal 13:32 Um, firstly, so, um, my brother is, is working on a startup to try and, um, compete with Excel.

Alex Lieberman 13:39 Really?

Ali Abdaal 13:40 Uh, yeah. It's called Causal. Um, and they're trying to basically be the new Excel, but for, um, number crunching. Because Excel has-

Alex Lieberman 13:48 That's pretty cool

Ali Abdaal 13:48 ... all these different p- Excel has all these different use cases, and it's, it's, it's a very general tool. But you'll, you'll get like ridiculous, you know, trillion dollar companies using Excel to manage their forecasting, and you'll also get people using it to figure out the scores in their five-a-side football league and-

Alex Lieberman 14:03 Yeah

Ali Abdaal 14:03 ... for their kids, kids football practice. And their sort of, uh, their thesis is that uncertainty calculations and modeling and stuff is really hard to do in Excel where you have like loads of uncertainty with all these different numbers plugging in. It's really hard when you- when an Excel sheet gets really big for anyone other than the person who made it to understand-

Alex Lieberman 14:21 Totally

Ali Abdaal 14:21 ... 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-

Alex Lieberman 14:28 I, I see it right now. I looked it up

Ali Abdaal 14:30 Yeah

Alex Lieberman 14:30 ... Causal app. Causal replaces your spreadsheets with a better way to build models, connect to data-

Ali Abdaal 14:34 That's the one

Alex Lieberman 14:34 ... and share dashboards with your team. Your brother sounds very smart. Um, oh, they, they, they raised 4.2 million in 2021. Uh, this is awesome. I, yeah.

Ali Abdaal 14:44 Yeah. They raised another series-

Alex Lieberman 14:44 I gotta, I gotta read more about it

Ali Abdaal 14:45 ... I think just recently.

Alex Lieberman 14:46 Oh, really?

Ali Abdaal 14:47 So you should look into that. [laughs] Start using Causal. Um, the other thing-

Alex Lieberman 14:49 I, I was gonna say now, now you have to get, ultimately they, if they get big enough, you have to get them to work with, uh, universities so universities teach Causal courses.

Ali Abdaal 14:57 Oh my goodness, that's a great idea. Yeah.

Alex Lieberman 14:58 Yeah.

Ali Abdaal 14:58 It'd be good for, you know, any kind of number crunching and modeling and stuff.

Alex Lieberman 15:01 Yeah.

Ali Abdaal 15:01 Um, I also very much agree on the, on, on the typing front. So, you know, I've, 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.

Alex Lieberman 15:11 Oh, oh, I've seen-

Ali Abdaal 15:12 And-

Alex Lieberman 15:12 ... the video. Yeah.

Ali Abdaal 15:13 Yeah. [laughs]

Alex Lieberman 15:13 Whatever the speed was, it was, it was absolutely ridiculous. I remember watching that video and then doing a typing test [laughs]

Ali Abdaal 15:19 Yeah

Alex Lieberman 15:19 ... and feeling horrible about myself after doing that test.

Ali Abdaal 15:23 But typing is one of these-

Alex Lieberman 15:23 What was your speed again?

Ali Abdaal 15:24 I think it was 1-156 words per minute is my record.

Alex Lieberman 15:27 [laughs]

Ali Abdaal 15:27 I need to try and, and bump that up. But it's, it's, it's kind of weird. So these last few days I've been on this team retreat in Wales, currently overlooking the hills. It's very nice. Um, but I sort of set myself the challenge that every day I was gonna write a whole first draft chapter of my book each day. Each day it's sort of been like sort of 5,000, 6,000, 7,000 words. And it's just kind of, I think normally-

Alex Lieberman 15:49 Have you done it?

Ali Abdaal 15:49 ... when it comes to... Yeah. I say every day-

Alex Lieberman 15:52 Wow

Ali Abdaal 15:52 ... for the last few days I've been banging out one chapter and I, 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, I, I think previously when my typing speed was half or a third what it currently is, it's like it would be a bit of a bottleneck. Like, my brain would think faster than I'd be able to type.

Alex Lieberman 16:09 Yeah.

Ali Abdaal 16:09 But the faster my typing speed has gone, it's like I can type at the speed of thought almost. And so it's, it's almost so easy t- or so easy to, if I've got something in my head, to translate it into words on a page. And it's, it, you know, it's really bad obviously, but like, you know, the first draft of any- anything is really crap. So that's what my editor keeps on saying. Just like spew out all the stuff you've got in your head onto the page, like and then we'll, we'll clean it up in post.

Alex Lieberman 16:32 So, so honestly, that was something I'm very interested about because i- if I remember correctly, like I remember the general, um,

Alex Lieberman 16:40 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 gonna have to like be referencing, uh, resources online or references? But if I do that, is that gonna distract me-

Ali Abdaal 17:00 Mm

Alex Lieberman 17:00 ... because now I'm plugged into technology?

Ali Abdaal 17:02 Yeah.

Alex Lieberman 17:02 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?

Ali Abdaal 17:11 Um, great question. Yeah. So I was, I was worried about this as well. Um, uh, as, uh, I'm connected to the internet because I use a... go to a lot of Google Docs.

Alex Lieberman 17:17 Yeah.

Ali Abdaal 17:17 Which is an- 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.

Alex Lieberman 17:27 Yeah.

Ali Abdaal 17:27 Um, you just write TK need research about XYZ over here. Um, you know, yesterday I was working on a chapter where I was talking about kind of feelings of anxiety and self-doubt when it comes to procrastination. And I knew I wanted a line that sort of described the feeling of anxiety, but I couldn't be bothered to sit down and figure out, oh crap, how to describe the feeling of, of anxiety. So I just wrote, uh, anxiety is that feeling of TK XYZ. [laughs] And then me or the editor will come back to it later, and it just sort of keeps me in the flow.

Alex Lieberman 17:56 Yeah.

Ali Abdaal 17:56 Um.

Alex Lieberman 17:56 So you just give yourself the permission-

Ali Abdaal 17:58 Yeah

Alex Lieberman 17:58 ... to like leave space and revisit the things that you do need to do more research later on.

Ali Abdaal 18:01 Yeah.

Alex Lieberman 18:02 Which by the way, we should talk about this at some point in the conversation about c- uh, the feelings of anxiety related to-

Ali Abdaal 18:09 Mm

Alex Lieberman 18:09 ... procrastination. 'Cause 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.

Ali Abdaal 18:24 Okay. That's... Okay, we'll then, uh, we'll, we'll put a bookmark on that-

Alex Lieberman 18:27 Yeah

Ali Abdaal 18:27 ... and definitely come back

Ali Abdaal 18:28 to it, because I imagine people would find that surprising given [laughs] kind of your, your story. Um-

Alex Lieberman 18:33 Yeah

Ali Abdaal 18:33 ... so definitely bookmarking there. Uh, I was gonna ask aswell, so other than typing and Excel, have you ever, have you found any other sort of meta skills that are generally useful for life?

Alex Lieberman 18:42 Yes, but they weren't taught in university. Uh, so one is storytelling and selling. Like, I think the number one skill that helped me be a strong founder, especially in the early days of building our business, is the ability to sell, and I think I'm blessed in the sense that that's just one of my intuitive superpowers. It's something my dad worked on with me as I was growing up. He, he was really focused on my ability to articulate. Uh, he thought that was really important. I ended up taking a, uh, 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 le- digital communication, like how to write an email, and I found that to, to, to be tough. Tough as in, like, not helpful. But yeah, I mean, sales, I would say is the... If you are trying to elevate yourself as a professional in any way, not just as an entrepreneur, just in your career, you find yourself selling yourself far more times than you realize. So, like, just even talking about a business, when we were starting Morning Brew, we're talking about a startup that was a media company. Media companies are generally not venture backable, so you can't raise from institutions. Uh, we had a newsletter. That's all we had. We had 30,000 subscribers at the time. We weren't making any money, but we had to raise money in order to possibly get to a place of making money. And so selling investors on why a 21-year-old and a 19-year-old who have a media company, where media companies are generally not profitable businesses, and we weren't making y- money yet. And by the way, it's r- 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 $0. And we had to sell advertisers, because that was the first way we made money as a business. We had to sell advertisers like Discover Card, large financial institutions, on why they should even bother wasting their time on a company that reaches 30,000 people versus allocating that time to thinking about, say, a television commercial that reads mil- 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.

Ali Abdaal 21:08 I've, I've, I've heard a lot of people say that, that, you know, the, the skill of selling is kind of, yeah, is w- one of the, one of the most useful skills you can have. But I've always kind of wondered, and I never quite followed this thought of, like, what does, what does that actually mean? Like, I wouldn't say I'm good at selling, but I've, I guess I have sold stuff in the past, and I just don't really think of selling as, like, a thing. Um-

Alex Lieberman 21:31 You, you sell yourself-

Ali Abdaal 21:32 Yeah

Alex Lieberman 21:32 ... on YouTube every time you post a video. Like, a- and this is actually an interesting thing of, and I've thought a lot about this, is what's the difference between sales at, or selling and storytelling? And my view is just if something ca- comes off as selling, it's just shitty storytelling. Uh-

Ali Abdaal 21:50 Ooh. Okay

Alex Lieberman 21:50 ... a- and, a- a- 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 a bunch o- a, 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 d- just don't think... I think it is quite natural and intuitive to you. It doesn't feel like work to script-

Ali Abdaal 22:21 Mm

Alex Lieberman 22:21 ... and then, uh, deliver that in front of a camera. You couldn't be where you are today without being exceptional at storytelling.

Ali Abdaal 22:28 How do, how do people get better at this?

Alex Lieberman 22:30 It's a great question. Um, my answer would be it's a combination of practice, of shadowing and feedback, and of understanding the fundamentals of what it means to storytell well. So going in reverse order, I think that there, there are tried and true... There, there's the science to it. There's, like, tried and true formulas for what is a captivating story for people. Uh, and so, like, for example, I'm reading, uh, the book Creativity Inc right now, which is-

Ali Abdaal 23:04 Mm

Alex Lieberman 23:04 ... the story of Pixar. Like, there, there are story arcs, which is like there is a hero. The hero is on a journey. The hero on the journey experiences a challenge. Uh, in experiencing the ch- 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, are a number of formulas this way. So at base level, I think studying the best storytellers of all time, uh, and studying the formulas that they use to tell stories is the first step. The second step is what I would say is the combination of practice and shadowing. And so the-

Ali Abdaal 23:42 Mm

Alex Lieberman 23:42 ... example I'll use for you is in the early days of Morning Brew, when we had to pitch advertisers on advertising in our newsletter, I had never sold in a professional setting anything before, but I had to do it. There was no option. We had to make money. And so I, you know, got reps pitching probably in our first year 250 advertisers on 30-minute calls about who Morning Brew was, what we stood for, and why spending your money with us was worth y- 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.

Ali Abdaal 24:36 Hmm.

Alex Lieberman 24:37 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. 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 gonna 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, uh, 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, in a database holds all of the sales calls organized by who the seller was, the type of client that it was, and it, it also will do things as sophisticated as say, what percentage of the time on the call were you talking versus what percentage-

Ali Abdaal 25:53 Hmm

Alex Lieberman 25:53 ... 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, the chapters of an episode. It does that automatically in your sales call. And so then any seller can go on to Gong and study what are, quote-unquote, "the best calls" that have led to the conversations that convert their clients. The end of the day, there is the... There is this art and science to understanding what works for you to story tell in a way that leverages your strengths. Um, but also understanding the science of what works well and what are kind of like the, the, the natural story arcs that people over the course of time are always attracted to.

Ali Abdaal 26:36 Nice. That's a, that's a great answer. [laughs] I... W- was that off the cuff or have you, have you-

Alex Lieberman 26:41 No, that-

Ali Abdaal 26:42 ... thought about this before?

Alex Lieberman 26:42 That, that was off the cuff.

Ali Abdaal 26:44 Bloody hell. That was good. That was like-

Alex Lieberman 26:44 [laughs]

Ali Abdaal 26:44 ... a three-part framework. I love it.

Alex Lieberman 26:46 [laughs]

Ali Abdaal 26:46 I'm just like, "Bloody hell." [laughs] Um-

Alex Lieberman 26:48 It, it wa- it was like very meta. We were using a storytelling framework and talking about-

Ali Abdaal 26:51 Absolutely

Alex Lieberman 26:51 ... a storytelling framework.

Ali Abdaal 26:52 100%. All righty. 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, 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, appraisally kind of vibes than a lot of other book summary services do. So if, 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 Shortform 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 Shortform. The first one is when if I get a new book recommendation and I don't necessarily wanna read the book directly or I'm not 100% sold on reading the book, then I'll often go on Shortform on my phone or on my laptop and be like, "Hey, has Shortform 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 Shortform 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 Shortform summary of it about three times, uh, once in preparation for my part-time Creatorpreneur course, but also twice just randomly because I was like, "This has been a really good book. I first read it in 2019. Changed my life. I don't wanna 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/deepdive, 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.

Ali Abdaal 28:53 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. Uh, what happens next?

Alex Lieberman 29:03 We become obsessed with two things: how do we make this newsletter as good as humanly possible, and how do we grow it as quickly as possible? And so I would say we did kind of some pretty creative things to make the newsletter really good in the early days. I'd say the first thing was Austin and I said to ourselves, like, "We can help write this thing, but we need more support." And so we had reached out in our newsletter to students who were 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 kinda like our, our, uh, newsroom of sorts.

Ali Abdaal 29:56 Hmm.

Alex Lieberman 29:57 And these writers were not paid. They were just doing it because they wanted to get their brand and their words into the world, and they, they were excited about what Morning Brew was and what it represented. Then we found an editor, and that editor was somebody who was in the business school with us at Michigan, so he was very into markets, and he, he still works in finance today, but he also wrote for Michigan's newspaper, so he had really strong editing chops.

Ali Abdaal 30:22 Hmm.

Alex Lieberman 30:22 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, then, uh, the third thing we did is kind of the, I would say the, the least traditional From the beginning, Austin and I said our content needs to read like you're having a conversation with your smart and sociable best friend. It can't read like traditional business news where it feels like a robot is throwing up words onto you.

Speaker 30:48 Yeah.

Alex Lieberman 30:48 And so we're like, "What is gonna give our, our, uh, content that X factor that's gonna feel quick-witted, and smart, and funny?" And so we were like, "We need to find a funny person." And so we [laughs] we put out, we put it out a, uh, you know, a job post for f- 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 school. It was like similar to the business school, less focused on finance and more focused on like, uh, organizational- organization building, culture, et cetera. So he was in that program, but he was also in the improv troupe-

Speaker 31:31 Mm

Alex Lieberman 31:31 ... uh, 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.

Speaker 31:42 Nice.

Alex Lieberman 31:42 So we had our writers, we had our, uh, editor, and we had our voice editor, and that was the process that we got to of putting out our newsletter every day. And that gave Austin and I more time to grow the thing. And so the way that we tho- thought about growing our thing was the, the visual I have is like a bicycle. So you have a bicycle, and you have a hub in the middle, the metal hub, and then you have spokes that go out to the, the, the wheel, like the outside of the wheel of the bicycle, right? So you have a hub and you have spokes. And our view was spokes are all of the people that we think should read Morning Brew. So those are college business students. Hubs are the people that are basically, the people or the channels that have access to all of these spokes. How do we get the attention of hubs so we don't have to go to every spoke and convince them to read our newsletter? And so at Michigan, what that looked like was teachers and club presidents. If we could get in front of teachers' classes, we could get in front of 75 to 500 students, and if we could get in front of club presidents, we could get into, in front of, say, 50 to 250 students. And so basically for all of our s- second semester, senior year at Michigan, Austin and I spent, going back to the, the importance of storytelling and selling, we spent our whole second semester in about 150 club meetings or, or classes pitching clu- uh, students on why they should read Morning Brew. And so we'd go into a class, we would give our two-minute, uh, spiel 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 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-

Speaker 33:59 Mm

Alex Lieberman 33:59 ... pulling out laptop, opening laptop, going to Safari or Chrome, putting in Morning Brew, putting in email address, whatever that is, five or six steps, whereas the no- pad and paper, it was two steps. It was grab the, grab the pen and write down your email. And we basically just pushed the rest of the steps on Austin and myself to actually input it. And so th- that was how we got, say, our first 2,500 to 5,000 subscribers. And then the next thought process ba- became, "Okay, we've saturated the Michigan market, now what?" And the now what became, how do we find Austin and Alex at every other college in America?

Speaker 34:37 Mm.

Alex Lieberman 34:37 So how do we find the, the two people that are gonna basically get in front of all the hubs at other schools that aren't us? And so that's what led to our college ambassador program. And our college ambassador program, you know, it still exists to th- this day. We learned so much with it. And I think it was unique at the time because I'd never heard of a media company doing a college ambassador program. When I think of college ambassador programs, I think of like Red Bull, uh-

Speaker 35:02 Yeah

Alex Lieberman 35:02 ... 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, where we were like, "Let's get the best ambassadors across the country to represent Morning Brew." So we had this super, uh, rigorous application process. It was like harder to get into our ambassador program than to get into Harvard, uh, or Oxford. It was like we put out an application, people applied, they dropped their resume. We ended up accepting, I think, 15 ambassadors who were like, they were the influencers in their business programs at their schools. They were in all of the clubs. They were the class president. You know, they sat in the front of their class. And it, 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 were already so involved in c- on things in campus, that they ha- 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.

Speaker 36:21 Yeah.

Alex Lieberman 36:21 So the second time we did it, we went exact opposite approach. We went with the quantity approach, where we fully automated the process.

Speaker 36:27 Yeah.

Alex Lieberman 36:27 So we sent out an application, but everyone was accepted. We just wanted to, wanted it to have an air of exclusivity.

Speaker 36:34 Mm-hmm.

Alex Lieberman 36:34 So you'd fill out an application. You would get an automated email from us that you were one of a few people accepted to this program, and then you'd get automated emails from us about how to start sharing Morning Brew. So you'd get a Google Drive that included marketing collateral, a script for what to say in classes, sign-up sheets that you could print out to pass around classes. Only when you got to, say, I think it was 25 signups did you actually get put into a group with Austin and I where we talk to you.

Ali Abdaal 37:02 Yeah.

Alex Lieberman 37:02 And so we had this vetting system for big top of funnel, uh, but only have human interaction with students when they've kind of proven that they can do well as an ambassador. And when we did that second program, we had 250 ambassadors across 200 schools. And so that was our focus, uh, kind of for the rest of college, was growth and getting the content out.

Ali Abdaal 37:23 That really reminds me of the whole, you know, do things that don't scale.

Alex Lieberman 37:27 Yep.

Ali Abdaal 37:27 'Cause, you know, if I imagine... Like, we've, we've just launched a new, a new n- newsletter for our Creatorpreneur brand. You know, trying to help creators think more like entrepreneurs. The last thing on my mind would be, let me go out, manually recruit some ambassadors and get them to spread the word for my email list. [laughs] It's just, it's so rogue. It's so, it's so analog in the world that we live in today.

Alex Lieberman 37:46 [laughs] I, I gotta be honest.

Ali Abdaal 37:47 Yeah.

Alex Lieberman 37:47 If I'm you, I'm thinking about, how do I, every time Colin and Samir post a video-

Ali Abdaal 37:51 Yeah

Alex Lieberman 37:51 ... how am I commenting with my newsletter on their videos?

Ali Abdaal 37:54 [laughs] That's a good point.

Alex Lieberman 37:55 Because, because the people watching their videos-

Ali Abdaal 37:56 Yeah

Alex Lieberman 37:56 ... are all creators.

Ali Abdaal 37:58 Yeah. So [laughs] you're growing this newsletter basically door to door, uh, but like at scale.

Ali Abdaal 38:06 Um-

Alex Lieberman 38:06 Yep

Ali Abdaal 38:06 ... what, what do the numbers look like in, in that first year, like 2015 when you were still in college?

Alex Lieberman 38:11 Yeah. So when I graduated from Michigan, uh, I wanna say we were at 10,000 subscribers.

Ali Abdaal 38:15 Oh, okay.

Alex Lieberman 38:16 So we got to 10,000-

Ali Abdaal 38:17 Yeah

Alex Lieberman 38:17 ... by the end of senior year, but I had a decision to make because I graduated-

Ali Abdaal 38:21 Yeah

Alex Lieberman 38:21 ... 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.

Ali Abdaal 38:32 Yeah.

Alex Lieberman 38:33 Or was I going to quit my job, tell my overprotective Jewish mom that I was gonna go do this newsletter thing-

Ali Abdaal 38:42 [laughs]

Alex Lieberman 38:43 ... that makes no money, uh, that has 10,000 people on it, rather than doing the thing that I dreamed of?

Ali Abdaal 38:48 Mm.

Alex Lieberman 38:48 Uh, I did not do the second. [laughs] Uh, I went and I worked at Morgan Stanley. Sales and trading, generally you start early in the day. So I would wake up at 5:00 AM every day. I would, I would go to the office. I would work out. I'd be at the desk by 6:30. I'd trade from 6:30 until 7:00 PM. 7:00 PM I'd go back to my apartment, and basically from 8:00 PM to, uh, when I fell asleep with my laptop on my lap, I would work on Morning Brew. And that was effectively the, my entire experience at Morgan Stanley until I quit my job.

Ali Abdaal 39:23 Uh, how, how long did you do this before you quit the job?

Alex Lieberman 39:26 So I, I started at... I graduate June of 2015.

Ali Abdaal 39:31 Yeah.

Alex Lieberman 39:31 I go to New York. My job starts July of 2015 at Morgan Stanley. I quit my job September of 2016, so just over a year. It was right after, uh, Labor Day of, of 2016. And the reason I quit was basically Austin, as I'd 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.

Ali Abdaal 39:59 Yeah.

Alex Lieberman 39:59 Was he going to go full-time into investment banking or do Morning Brew? And I vividly remember Austin came to New York, uh, for a weekend. We got beers at this, like, really old bar, one of the oldest bars in New York City. We basically talked about, like, what are we gonna do? Like, there's a clear fork in the road. It was a fork in the road of we're either gonna go full-time on this thing or we're not, and if we don't go full-time on this thing, like, this is, it's either gonna stop or it's gonna just be kinda like a shell of itself.

Ali Abdaal 40:27 Yeah.

Alex Lieberman 40:27 Because I was working a lot. Austin, investment banking. I remember during his internship, he had pulled, like, four all-nighters in his summer of his internship. And so it was very much like this was an inflection point, and we decided to go full-time on it. And I, I think we had different reasons for going full-time on it. And for me, the reason I went full-time was a few-fold. I thought about things in terms of regret. What would I regret more? Would I more regret staying at Morgan Stanley and seeing someone create effectively their version of Morning Brew and it succeeding, or would I more regret leaving Morgan Stanley, doing Morning Brew, and Morning Brew fails and I have to find a new job? And to me, the answer was obviousl- when I answered that question, which is I would far more regret staying at Morgan Stanley and seeing someone succeed with their version of Morning Brew just because they risked their time when, when I wouldn't.

Ali Abdaal 41:25 Mm.

Alex Lieberman 41:25 That was the first way I thought about it. The second way I thought about it was what is the worst case scenario? So I thought, I always use things as, like, the worst case scenario framework in a decision, and can you live with the worst case scenario? So the wor- what, what's the worst case scenario if I quit my job and went full-time on Morning Brew? And the worst case scenario was I quit my job, I work on Morning Brew, and then, say, six months later it fails, because the vast majority of businesses fail. And then I was like, then what? What would happen in that worst case scenario? And I said, first, maybe Morgan Stanley would take me back because I have this entrepreneurial experience that made me maybe, maybe uni- unique in my experience and, uh, they would value that. And I was s- I said, nope, 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, nope, maybe, uh, this is a common story and it wouldn't get me into business school. And I said, maybe, um, I met other people while I was doing this startup in the startup scene and I could go start another company or join an early stage company. And I basically got like four or five layers deep of options. And I was like, if none of these are options after Morning Brew fails, then this isn't actually, like, a Morning Brew problem. This is an A- Alex problem of not keeping his options open as a professional. And so that was the second way I looked at it.

Ali Abdaal 42:50 Mm.

Alex Lieberman 42:50 And the third way I looked at it was simply about how do I wanna live my life? It sounds cliché, but- I very much, you know, I just had like a, a mentally transformative experience where a week before junior year of college at Michigan, uh, my dad passed away suddenly. Uh, he passed away-

Ali Abdaal 43:10 Oof

Alex Lieberman 43:10 ... uh, from a stroke. He was 49 years old. He was perfectly healthy. Like, literally built the same as me, uh, similar, uh, physical health. And after that experience, everything just became clearer around, one, how most things that we worry about on a daily basis in life are wildly unimportant. And two, how really, like, you know, your, your time on your, uh, life countdown clock, you have no idea when it's gonna hit zero. You look at the statistics and you hope that it's gonna hit zero around, you know, 80 years old or later, but you really have no idea. And basically I said to myself, "If, if I knew my countdown clock was hitting zero tomorrow, what would I rather be doing with my time?" And it, it was like a no-brainer. It was like

Alex Lieberman 43:58 I knew-

Ali Abdaal 43:58 Mm

Alex Lieberman 43:58 ... 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.

Ali Abdaal 44:11 Wow. Hey, I'm sorry to hear about your dad. That, that, that must've been really tough for you at the, at the time.

Alex Lieberman 44:17 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, he was my best friend, and it was like, you know, he was the guy that when I would, uh, be walking from class, uh, back to home or vice versa, like he was the person I was texting or calling. And it was, uh, it was a surreal thing. Like, there was a period of time after he passed away where I would just be walking in New York City and I would call his number just to relive that experience, and it [laughs] it registered like this 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 there's a family who has his phone number now, and it's just interesting to hear. It's been the same family for the last like seven years and, uh, they're probably like, "Who is this random 973 number that calls us once a year, says nothing, and hangs up?" Um, but yeah. I mean, uh, so there was abs- there was a h- there was a huge void that I felt because it really was my best friend. And then I think the final thing is it, um, it made me think a lot about just, like, my emotions and how I process emotions because I think as a function of growing up in a Wall Street family, as a function of, you know, being a man and there being certain gender norms with being a man, I think as a function of my own coping mechanisms, I found, like my, my best trick, my best trick and my worst trick was to take emotionally provoking things and push them into my body and not feel them. And I'm really good at that trick.

Ali Abdaal 46:09 Mm.

Alex Lieberman 46:09 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 a interesting thing to me and that I felt guilty about for a long time because I was like, "This is probably the worst thing that's gonna happen to me in my life, is a tragedy like this," and I only cried once. Like, how do I only cry once about losing my best friend suddenly? And so this is something I still work on to this day and think about to this day, which is how do I better have access to my emotions? 'Cause 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 wanna do, and what you don't wanna do.

Ali Abdaal 47:08 Wow. Thank, thank you for, for being so open about this. Um-

Alex Lieberman 47:11 Yeah, of course

Ali Abdaal 47:11 ... this is, this is something that I have been thinking about as well in the sense of, you know, being an, a sort of entrepreneur bro, um, you know, growing up in a Asian family meets kind of an all-boys school meets, you know, talking about and feeling emotions and stuff very much frowned upon.

Alex Lieberman 47:28 Yep.

Ali Abdaal 47:29 Uh, and then I discovered stoicism and I was like, "Yeah, stoicism Kool-Aid." Like, yeah, you know, this is how I've been living anyway. I'm a stoic sage, et cetera, et cetera. I don't feel emo- I don't feel negative emotions-

Alex Lieberman 47:39 [laughs]

Ali Abdaal 47:39 ... if I don't want to. I, I'm also right now trying to figure out how basic- [laughs] it's gonna sound kinda weird, but, like, how to feel more.

Alex Lieberman 47:48 Oh.

Ali Abdaal 47:48 Um.

Alex Lieberman 47:48 No, th- this is what-

Ali Abdaal 47:49 Yeah

Alex Lieberman 47:49 ... I'm working on constantly. Yeah.

Ali Abdaal 47:51 How, how, how are you doing it? [laughs]

Alex Lieberman 47:53 Uh, well, one, this is like the focus. Uh, I would say there's two topics that I generally focus all of my time with my therapist on. One is how do I feel more, but I, I've changed the wording over time-

Ali Abdaal 48:09 Tell me

Alex Lieberman 48:09 ... to be, like, intentional with not how do I feel more, because I think that, uh, implies, like, that I'm feeling less right now and I'm f- not feeling enough and there's something wrong with me. And I, and so w- 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?

Ali Abdaal 48:33 Oof.

Alex Lieberman 48:33 And-

Ali Abdaal 48:34 Nice

Alex Lieberman 48:34 ... a- and so, you know, what we spend a lot of time doing is she will help me visualize, like, moments in my life to try to... Because what she's realized about me is, like, I, I'm a very visual person, and so, like, I get images whenever I think of something. And so for example, you know, I shared with her in probably our second or third session together that I was, uh, bullied in school f- probably from... ... fifth grade to the end of high school. Like, I, I was bullied. I never felt like I was a part of a group. Like, I always aspired to be part of, like, the cool group in high school. I never felt-

Ali Abdaal 49:13 Yeah

Alex Lieberman 49:13 ... 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 felt really sad for yourself because you didn't feel like you were belonging in high school?" And I would describe a moment. I'd be like, "You know, it was down in the couches, the senior couches in the high school at the school I went to. I was sitting at the couches. There were, like, eight people there. I would say something. People would dismiss it, and people literally, like, turned their bodies to not include me in that discussion." And she would tell me to, like, close my eyes and, like, sit with envisioning those people talking and closing their bodies to me be- me being on the outskirts. And she would say, "What comes up for you? You know, what would your older self... Right now, if you were sitting next to your 17-year-old self, what would you say to him as he's feeling really upset for himself that he doesn't feel belonging?" And so I think she's trying to leverage what she knows that is intuitive and natural to me, which is visuals, and put me back in kind of this time machine of life. The other thing she tells me to do is, like, to sit with emotions when I feel them, meaning, like, a- 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, uh, a family member said or you're, uh, 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."

Ali Abdaal 51:08 Have you found working with a therapist useful?

Alex Lieberman 51:11 Extremely useful.

Ali Abdaal 51:11 [clears throat]

Alex Lieberman 51:12 Extremely useful. I find it useful because, one, I think it a force-- it forces, for me, the accountability to reflect, which I think in the busyness of life I will get out of the habit of doing, and I think it's really important. I also think a- 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 [chuckles] almost be, like, the summary of those books. But I, what I will say is I think a therapist is kinda like anything else in life, where th- 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, wo- sorry, worked with for probably the s- first seven years that I was doing therapy. That was my first therapist, and she was amazing. But I would say there was a natural kind of like, uh, deceleration of the learning curve or the benefit curve, where in the beginning she gave me-

Ali Abdaal 52:30 Yeah

Alex Lieberman 52:30 ... 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 wanna work on, maybe my current therapist isn't the one who's gonna be most helpful in these new challenges. And so I ended up changing a therapist to someone who I thought co- was for, uh, could be more helpful with things like feeling my emotions or, like, self-love and self-belief.

Ali Abdaal 53:22 Mm.

Alex Lieberman 53:22 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.

Ali Abdaal 53:37 Do, do you do these sessions over Zoom or in real life or-

Alex Lieberman 53:40 I do it over Zoom. So my therapist is based in Colorado, and we do, yeah, we do these Zoom meetings, uh, usually every week or other week. Which by the way, this gets into another topic. Like, for the f- for a w- a long, long time, I felt very guilty about doing therapy a lot because I'm very much, like, a money hoarder. And so I could-- I would get into-- Like, I 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, uh, $300 an hour, and like, "This is a shit ton of money. Like, what do I really need to spend on this?" And at some point I got to the point where I was like, "If, if I am not willing to spend my money on someone who is helping me see the world more clearly and live a more fulfilled life, I do not deserve to have money that I have, because that is crazy to not spend on something that is quite literally making my life better." Um-

Ali Abdaal 54:36 Yeah

Alex Lieberman 54:37 ... and, uh, yeah, so I talk to her every week or other week. Um, and it's, it's really good. I will say as someone who has a very creative and distracted brain, it is very easy for me, even as we're talking now, for me to get distracted with things on my computer. And so what I did now, and I do with my therapist, is I literally close everything. The only application I have open with her is Zoom, uh, Zoom and Notes 'cause I'm, I'm constantly-

Ali Abdaal 55:02 Mm

Alex Lieberman 55:02 ... 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. 'Cause when I was in person with my therapist, like, it was harder to get distracted.

Ali Abdaal 55:18 I tried a therapist, uh, for like three or four weeks a few months ago. Actually, like last year now. Damn, it was ages ago. And I found that, like, I wasn't really a fan. Like, the first two or three sessions were sort of helpful, but then I did find session four and five and six we sort of, we're 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, in that way." But it's, it sounds like you're getting a lot of value out, out of this therapist through the Zoom sessions.

Alex Lieberman 55:44 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 an, a-

Ali Abdaal 55:52 Yeah

Alex Lieberman 55:52 ... hypothetical number before landing on one therapist. Because-

Ali Abdaal 55:56 Okay

Alex Lieberman 55:56 ... it's almost like what are the odds that you go on a first date with someone and that person ends up-

Ali Abdaal 56:02 Mm

Alex Lieberman 56:02 ... being, uh, your partner, your life partner? It's like the odds are literally, uh, it's like de minimis. And so-

Ali Abdaal 56:08 Yeah

Alex Lieberman 56:08 ... 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-

Ali Abdaal 56:21 Mm

Alex Lieberman 56:21 ... the first person you talk to is gonna be the right person is like you're, y- you know, you're betting that you're gonna win the lottery.

Ali Abdaal 56:27 Yeah. Okay, you're right. I'm sold. Um, I will [laughs] ask you for your therapist's, uh, email address afterwards, uh, 'cause that seems like a-

Alex Lieberman 56:32 Sounds good

Ali Abdaal 56:33 ... a good first option.

Alex Lieberman 56:34 Cool.

Ali Abdaal 56:34 Um, yeah, I guess, I guess in my mind I was thinking of therapists as kinda like being doctors in that they are fungible, in that the [laughs] one, one doctor at l- at l- at least here where we follow guidelines, is practically identical to another doctor at the junior levels anyway. But I guess therapists-

Alex Lieberman 56:49 Yes

Ali Abdaal 56:49 ... if they work with you-

Alex Lieberman 56:50 I, I, I would argue that, yeah

Ali Abdaal 56:51 ... that's good.

Alex Lieberman 56:51 Therapists are very non-fungible.

Ali Abdaal 56:53 Excellent. [laughs] That's your NFT, the non-fungible therapist.

Alex Lieberman 56:56 [laughs]

Ali Abdaal 56:58 So you were at Morgan Stanley for like a year and a bit, where you're working ridiculous hours and you're kinda hustling to get this Morning Briefing off the ground. This is a very common story amongst basically all of the entrepreneurs you and I know, where in the early days of the thing especially, there is a level of, you know, to use the, that terminology, hustle and grind and maybe losing a bit of sleep and maybe-

Alex Lieberman 57:19 Yeah

Ali Abdaal 57:19 ... 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've 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."

Alex Lieberman 57:54 Yep.

Ali Abdaal 57:54 So I wonder g- with the benefit of hindsight-

Alex Lieberman 57:57 [laughs]

Ali Abdaal 57:57 ... um, do you think if you had had more of a balanced life-

Alex Lieberman 58:01 [laughs]

Ali Abdaal 58:01 ... if you and Austin had more of a balanced life, you would have, m- then that, that Morning Brew could've been as successful as it now is? Or how, how do you think about that?

Alex Lieberman 58:08 I think the answer is no. I don't think Morning Brew would've been as successful if we were more balanced in our life, as in spent less time on Morning Brew. But there's a big caveat here that goes back to the idea of, uh, guilt around procrastination. I think that it would have been possible to have more balance and been as successful Morning Brew if I was more efficient and smarter in my work and not a procrastinator. And I have not proven to myself in life yet that I am capable of that, but if I can prove to myself that I am capable of that, I think it opens up a lot more time for non-work things.

Ali Abdaal 58:46 Can you tell me more about this procrastination stuff? Like how-

Alex Lieberman 58:48 Yeah

Ali Abdaal 58:48 ... how's that, how... So l- like,

Ali Abdaal 58:50 um, in, in particular I'm interested in the early days where, where you've got a job and you're doing this thing on the side, and now I, you know, we'll, we'll come to this, but I can imagine you're chilling 'cause you've got like, 'cause you're stupidly rich and et cetera, et cetera. But like, you know, in, in the, in the early days when you were, you were hustling, what did the procrastination look like?

Alex Lieberman 59:06 I'd say there's two types of procrastination. It's doing non-work to avoid work, and it's-

Ali Abdaal 59:11 Mm

Alex Lieberman 59:11 ... doing the wrong work to avoid work.

Ali Abdaal 59:14 Ooh, that's nice.

Alex Lieberman 59:15 Uh-

Ali Abdaal 59:15 Okay. Type one. [laughs]

Alex Lieberman 59:17 A- 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 wanna create a, like an AA for phone addiction. The, the second type is work to avoid work. And what I mean by that is this goes back to, like, how we're taught from a young age, uh, and in school what it means to do work. And I think it means you're given an assignment, you do the assignment. Uh, you're given a test, you take the test. You create checklists, you do the things on the checklist. And there's a feeling of that felt really good to do those things on those checklists. I feel like I've achieved what I wanted to achieve. But the issue is, is that as a startup grows and it evolves, the things that you should be spending your time on change and they look different than the things that you were spending your time on perhaps six months ago, and also the things that you felt really good about doing.

Ali Abdaal 1:00:34 Right.

Alex Lieberman 1:00:34 And so here's an example I mean. There was a period of time where I would spend hours a day reaching out on LinkedIn to potential, uh, advertisers of Morning Brew, and I would do all this LinkedIn outreach to hundreds of them, then I would schedule calls with them, uh, and I would do all of this busy work related to outreach for selling advertisers. And it felt productive because on my to-do list was reach out to Morning Brew advertisers, schedule calls 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 are growing, something that became more important or became I'd say a more important job, uh, 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 t- time when we didn't have traction. Uh, so we didn't, we didn't have the bible for running a business. And so- What would happen would, would be what I just described to you of, like, setting a strategy in the future so that I know how I should be planning my time today, who we should be hiring today, like, really important things. I would never spend time on it. I would just never do those things. Luckily, I had a partner in Austin where he was starting to think about those things and he picked up the slack there. But it was... I was doing work that felt good that I could justify was value-adding to the business to avoid the work that really needed to be done to push the business forward. And so I would say those are two types of procrastination, and for me, what ended up happening is, uh, 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."

Ali Abdaal 1:02:29 Mm.

Alex Lieberman 1:02:29 "I wasted a day because I wasted time doing things that don't grow me for things that if I did them, they would grow me, and I wasted time on things that are easy tasks for me to do because I didn't have the courage or the focus to do those hard tasks." And every time that happens and I have a procrastination hangover, I think I lose a little bit of trust and self-belief in myself because I haven't kept my word to myself of doing the things that are most important to do and growing myself.

Ali Abdaal 1:03:02 Yeah, that makes so much sense. I think a big part of, I think, the emotional barriers to procrastination, I, I find it, it tends to be two things. It's either self-doubt or it's fear. I, I think it's self-doubt on two levels. On one level it's self-doubt of, "I don't think I'm good enough to do this thing," but on a deeper level it's, "I'm, I'm not the sort of person who does things. I am, I am the sort of person who is a procrastinator." And you've got, so these, these, 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-

Alex Lieberman 1:03:31 Yep

Ali Abdaal 1:03:31 ... or for others or, like, fear of what people will think and, you know, that's why singing in public is way harder than singing in the shower because y- you know, [laughs] you've got the, you've got the fear component. My que- my question for you is does that kind of framing make sense with your experience? And are there-

Alex Lieberman 1:03:44 Yeah, it totally does.

Ali Abdaal 1:03:46 Yeah.

Alex Lieberman 1:03:46 Yeah, I think it, it makes me... Because I have felt, uh, 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, and, uh, respect for myself because I feel like to the, 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.

Ali Abdaal 1:04:46 Mm.

Alex Lieberman 1:04:46 And then on the flip side of this... So that is kind of, like, the, the negative kind of, like, self-loathing version of this. I've tried to have a more productive thought about this to say procrastination is part of my way. It is part of my way of working, where as someone who is very creative, who has ideas all over the place, who's easily distracted, I ca- I can't, you know, I, I can't take one but not have the other. If I wanna be someone who has an abundance of ideas, uh, and who has all these positive attributes from thinking in the way I think, I can't just expect that I'm going to be someone who does not procrastinate at all and is super linear and focused. Basically I've... That narrative is, "Alex, you have to, uh, own the fact that procrastination is part of your process and it's okay." And actually, like, to say you won't reach your potential, uh, is to say that you believe that if you rid y- yourself of procrastination, you wouldn't rid yourself of all of the other things that make you great, that make you possible of your potential. I don't know if I totally buy that argument. I think that's why it's tough for me, is I, I try to as I'm experiencing this turn it into a positive where I'm not so down on myself because I don't wanna keep harming my self-belief. But I also don't buy that it has to be a part of me.

Ali Abdaal 1:06:07 I guess it sort of in a way is... can, can kind of be a coping mechanism for dealing with the negative feelings, like, "Oh, the negative feeling is actually positive, so i- it's all good," kind of stuff. [laughs]

Alex Lieberman 1:06:19 Yeah. And I think it's, um, it's one of those thoughts, like, it's like that negative feeling isn't doing anything for me anyway. It's only holding me back. It's making me believe-

Ali Abdaal 1:06:28 Yeah

Alex Lieberman 1:06:28 ... in myself less. So how do I get to myself where I believe in myself more? So at least it, you know, it c- puts, it cr- puts me on a more solid foundation to push forward in life. What, what's your take on this?

Ali Abdaal 1:06:39 I, I was doing a lot of it on the book, and it was after having a session with Rachel, who's our editor and also kind of book-writing coach, having had loads of experience with it, where we basically diagnosed that it was self-doubt that was the main cause there, where my standards were just too high. I was trying to produce stuff, you know. I was comparing my shitty first draft to James Clear or Mark Manson or Tim Ferriss' or Dan Pink's final drafts.

Alex Lieberman 1:07:03 Yeah.

Ali Abdaal 1:07:04 And I was like, "Oh, you know, this, every, uh, the, the, 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, like, I can't, 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 they realize that even a pro like Ali still has, takes-

Alex Lieberman 1:07:40 Yep

Ali Abdaal 1:07:40 ... an hour to film a 20-minute video because of all the stumbling and, and stuff that happens along the way. And now when it, when it comes to YouTube, the conversion from a shitty first draft into a decent-looking output is something I'm very familiar with, having done it 500 times. Whereas in writing, the conversion of a crappy first draft into a decent looking book is something I'm not at all familiar with, having done it zero times.

Alex Lieberman 1:08:01 Yeah.

Ali Abdaal 1:08:02 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- we can always fix it in post, and that's fine. We'll- we'll- we'll-

Alex Lieberman 1:08:13 Yeah

Ali Abdaal 1:08:13 ... we'll deal with it. This podcast, I know I can just take a break, turn the air conditioning on, get a coffee. We'll, you know, we'll fix it in post.

Alex Lieberman 1:08:18 Yeah.

Ali Abdaal 1:08:18 But I didn't have that for writing. After diagnosing that it was self-doubt that was the problem, and basically, you know, the s- the solution to that is just lower your bar, lower the standards, embrace- embrace the crap a little bit more. Now I've actually found it pretty easy to not procrastinate on, on book stuff. I still procrastinate in the sense I'll go and make a cup of tea, I'll go and kind of wander around a little bit, but I kinda know that, okay, my job for these next few days is to bang out 6,000 words a day for each first draft of the chapter, and it's, and it's being done. So in that sense, I don't procrastinate, but in... But it was, it was only that little, that mental flip of self-doubt is the cause here that made it work for me.

Alex Lieberman 1:08:53 I, I have a question.

Ali Abdaal 1:08:54 Mm.

Alex Lieberman 1:08:54 How did you... And maybe this is just how you're wired or oriented. Like, as you gained, uh, subscribers on the YouTube channel, which, by the way, congrats on three million.

Ali Abdaal 1:09:04 Oh, thank you.

Alex Lieberman 1:09:04 Uh, as you were along this journey, how did you not feel the pull to ultimately get sucked into checking views on your videos in a way that ultimately is procrastination from doing work that would allow you to make better videos? Did, did you ever go through periods in kind of your YouTube career of checking views, subscriber count-

Ali Abdaal 1:09:27 Yeah

Alex Lieberman 1:09:27 ... watch time obsessively, or was that just never really in your DNA?

Ali Abdaal 1:09:30 Um, yeah. I've, I've had phases where I go through it, and it normally makes me feel quite bad to go through it. If the numbers are going up, then it's like, "Ah, crap, the numbers are going up. We're gonna, we're gonna get into a down slump soon." And if the numbers are going down like they are right now, it's like, "Oh, crap, we're in a down slump. Oh, I dunno. I th- I think this might be the beginning of the end." What I've found is that the, the best way for me to overcome this is to just... And, and every- everyone says this and it sounds so cliche, but just to dissociate my own self-worth from the things that I cannot control-

Alex Lieberman 1:10:01 Yep

Ali Abdaal 1:10:01 ... as much as possible. So now, I, I think I've gotten better at this over time, just uploading a video and looking at the views and the numbers, but like really trying not to let them affect anything, because my bar is now an internal thing that I control, which is I will upload a video if I think it's good or if I, if I think-

Alex Lieberman 1:10:22 Yeah

Ali Abdaal 1:10:22 ... it's a message worth, worth sharing that would be helpful to at least one person. And when I have that sort of zen attitude towards it, that's when, A, I feel I make better content because now I'm not concerned about, "Oh my God, what's the audience gonna think?" But B, I feel a lot better about it.

Alex Lieberman 1:10:35 That's what we're all trying to achieve. And it, again, it sounds so simple. Like, oh, you know, don't, don't watch your v- 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 enjoy, just feel good about that you've gone through the process of putting content you feel proud about it into the world. It sounds so simple. It's just, uh, it can be very hard at times.

Ali Abdaal 1:10:56 Yeah. And I, and I think this is where kinda in- 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 'cause I wanna help people-"

Alex Lieberman 1:11:07 Yep

Ali Abdaal 1:11:07 ... and it's all good. And maybe two or three people, if they sign up to my course, it becomes profitable. Whatevs, I don't really care. But now that the YouTube channel is the foundation of the whole business, now it's like, "Oh, shit." Like [laughs] you know, 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 broke and homeless and alone, and I'm not worthy of s- of love and all that?

Alex Lieberman 1:11:25 Jeez.

Ali Abdaal 1:11:25 All, all of those sort of-

Alex Lieberman 1:11:25 Jeez, that's a lot.

Ali Abdaal 1:11:26 Yeah.

Alex Lieberman 1:11:26 Go back to the therapist. This is probably good stuff-

Ali Abdaal 1:11:28 Yeah

Alex Lieberman 1:11:28 ... to unpack with them. [laughs]

Ali Abdaal 1:11:30 [laughs] All of that, all of that kind of stuff just comes, comes to the forefront.

Alex Lieberman 1:11:34 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-

Ali Abdaal 1:11:41 Yeah

Alex Lieberman 1:11:41 ... it's, it's your job in the sense that it is the source of your livelihood and-

Ali Abdaal 1:11:45 Yes

Alex Lieberman 1:11:45 ... not, not to create obligation for you, but livelihood of other people also.

Ali Abdaal 1:11:48 Yes.

Alex Lieberman 1:11:49 And so it's like how do you-

Ali Abdaal 1:11:50 Exactly

Alex Lieberman 1:11:50 ... feel the benefit of that play when it is quite literally a job?

Ali Abdaal 1:11:54 Yeah. And, and honestly, that's the thing. Oh, one, one, one thing that, um... So I've, I've got a coach. His name is Corey. You might have seen him on, on, on Twitter. Uh, he and I basically kind of brainstormed solutions to this problem about two weeks ago. And actually, I started using affirmations, and they're surprisingly helpful. Um, I'm just gonna read you out my affirmations and-

Alex Lieberman 1:12:14 Yeah

Ali Abdaal 1:12:14 ... they j- just like w- I don't, I don't do this every day. I ne- I still need to make it part of my morning routine, but... Oh, one, one thing I have found helpful is for the last month or so, I've been doing journaling in the form of morning pages every day, and often I will think to myself, you know, "Am I, am I feeling bad about some performance of a video or something?" And then I'll sort of reverse engineer, "Okay, why am I feeling bad? I'm feeling bad because X, Y, Z."

Alex Lieberman 1:12:39 Yeah.

Ali Abdaal 1:12:39 And it will often come back to these affirmations. So these are the affirmations that-

Alex Lieberman 1:12:42 Yeah, I wanna hear the affirmations.

Ali Abdaal 1:12:43 Yeah. Um, so number one, "I already have enough. I don't need more money or success. I am playing my infinite game to learn and teach cool stuff on my own terms." Number two, "My life experience is interesting and worthwhile. People would love to hear what I have to say about it." Three, "I don't care about numbers. I just do my thing, and my amazing team will take care of the rest." Four, "If I lost everything, I'd be able to build back up again to this infinite game over time, and it would be even more fun." Five, "Creative energy surges through me and leads to new and brilliant ideas." Six, "Today I am brimming with energy and overflowing with joy." And then finally, "I have been given endless talents which I can use whenever I feel like it to create value in the world." And all of these affirmations are just sort of tackling a negative thought process or a negative-

Alex Lieberman 1:13:30 Yeah

Ali Abdaal 1:13:30 ... belief I have about myself that no one cares what I have to say. I lucked into this position, and now it's gonna come crumbling around me at any time. I really have to try very, very, very hard to make content that peop- that to, to make sure people will care about the content because me just speaking from the heart is not gonna be interesting. And it's like all these... So someone from the outside would say, "No, you can make a video about whatever you want. You've got three million goddamn subscribers. Just, like, don't worry about it."

Alex Lieberman 1:13:52 Yeah.

Ali Abdaal 1:13:52 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 gonna come crumbling down." So I, I find the affirmations genuinely helpful.

Alex Lieberman 1:13:59 I love that. Can, can you read the, uh, the fourth one again? That one really-

Ali Abdaal 1:14:03 Yes

Alex Lieberman 1:14:03 ... resonated with me. I want you to read it and I, I just wanna react to it 'cause that one stood out to me.

Ali Abdaal 1:14:08 The fourth one, if I lost everything, I'd be able to build back up to this infinite game over time, and it would probably be even more fun. Lol. [laughs]

Alex Lieberman 1:14:16 [laughs] So, so that's, that's the most provoking one for me. And the reason is, is... And I think this loops back into procrastination. I, I actually think at its core, procrastination is the source of me feeling so provoked by this. And I think it's why I have kinda like this money-hoarding mentality, because it almost feels like, you know, with this business I did, this was my one shot and my one luck at making money. Because after this, because I'm a procrastinator, I'm not going to be able to achieve success. And so I need to hold on to whatever the hell I have, because for the remainder of my, you know, however many years on planet Earth, uh, I'm not going to be able to reaccumulate, right? And so it's like such a sad thing, right? [laughs] That's like such a sad perspective to have.

Ali Abdaal 1:15:08 Mm-hmm.

Alex Lieberman 1:15:08 Basically, like I- I've quote-unquote "peaked" and I'm not gonna do anything of worth or value in life moving forward because I procrastinate. And so I've proven to myself that I can't be a good, diligent worker that can push through any challenge. And I think that's why the fourth one stands out to me so much, and I think it's why I'm so focused on things like not spending on a therapist.

Ali Abdaal 1:15:30 Nice.

Alex Lieberman 1:15:30 [laughs]

Ali Abdaal 1:15:31 Yeah. That's good.

Ali Abdaal 1:15:33 So you quit the job a year down, a year down the line.

Alex Lieberman 1:15:38 Yep.

Ali Abdaal 1:15:38 You and Austin went on it full time. I wanna kind of fa- fast-forward to when, when the sale happened.

Alex Lieberman 1:15:44 Yep.

Ali Abdaal 1:15:44 'Cause I'm curious about like money and that kind of stuff. And I, 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, on the internet if, if they wanna learn more.

Alex Lieberman 1:15:54 Yeah.

Ali Abdaal 1:15:54 What was the story behind selling Morning Brew?

Alex Lieberman 1:15:56 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, uh, Berlin, Germany. And that was a conversation that had basically been a year in the making. In November of 2019, we had been approached by, uh, this guy who, uh, wor- now works at one of the, uh, at one of Axel Springer's, um, European media businesses. But at the time, he was a senior person at, uh, Business Insider, and we had become friendly. The, the reason he reached out is we, we had become friendly. So basically, uh, to give context on why we had become friendly, as I wa- you know, I was just hustling to grow Morning Brew. One of the growth tactics that I had thought about is, let me reach out to big business publications who are always looking for more content to drive website, uh, traffic, and let me see if they would syndicate our newsletters on their website. Uh, and so I reached out to one of the editors at Business Insider saying, "Hey, would you syndicate all of 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, I don't wanna deal with you anymore. Let me introduce you to this guy." So he introduced me to the, the guy that I was referring to before, who ultimately kind of became the champion of this deal. And, m- uh, this guy a- and myself, we became, uh, friends. We got beers on Stone Street in New York City, which is this street. It's kinda like this alleyway with a bunch of bars in the financial district of New York City. It's a great spot to go to next time you visit New York. Um, we would go back and forth playing ping pong at our different offices. So I'd go to Business Insider's offices, play ping pong there. He would come to our WeWork space, which we were in at the time, play ping pong. He reaches out in, in, uh, November of 2019 and is basically like, "Hey, Business Insider is looking to do more kind of..." The, the, the phrase to get people into acquisitions, if you wanna test it, is not, "Hey, would, would you be interested in being acquired?" It's like, "We're interested in deep partnerships. Would you be interested in a deep partnership?" [laughs] And, and I was like, uh, "Do you mean acquiring Morning Brew?" And he's like, "Yeah, it's something. We'd be interested if you were." And up to that point, Austin and I had not thought at all about selling the business. Uh, we had been approached a few times, uh, but we really weren't interested. What I always said is, everything that I wanted at the time is what I had. We got to be in charge of our own destiny. I was learning and growing a lot, was surrounded by an amazing team, didn't have to worry about money. I was putting... Like, creating something valuable in the world. If those five things weren't being messed up, why would I change it? Ultimately, he was like, "Well, what's a price at which you would be interested in having a conversation?" And I'd said, uh, "$50 million." And so, you know, the, this person was like, "Well, that's something that would be in, you know, the, the sphere of what we would be open to, so let's have a conversation." And so we started having-

Ali Abdaal 1:19:15 That's-

Alex Lieberman 1:19:15 ... a conversation. Basically, deal terms were put in front of us in February of 2020.

Ali Abdaal 1:19:22 Okay, hang on. J- j- just a question on that front.

Alex Lieberman 1:19:24 Yeah?

Ali Abdaal 1:19:24 When you throw out $50 million and he's like, "Yeah, we can work with that," like, don't you just like crap your pants? Like, what, what's going on in, in your mind? [laughs]

Alex Lieberman 1:19:31 I, I, 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, that's enough money. Ba- basically, we were al- 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.

Ali Abdaal 1:19:48 Yeah.

Alex Lieberman 1:19:48 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, 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, uh, 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."

Ali Abdaal 1:20:24 Mm.

Alex Lieberman 1:20:24 So a 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.

Ali Abdaal 1:20:42 Mm.

Alex Lieberman 1:20:42 And that this is kind of how any acquisition process happens.

Ali Abdaal 1:20:45 Okay.

Alex Lieberman 1:20:45 And so ultimately they put terms in front of us in February of 2020. The terms we thought looked good and reasonable at the, at the time. Like, we're like, "Okay, this is a really good deal." The reason the deal ended up getting extended is, uh, March of 2020 is when the pandemic started. And so when the pandemic started, our business for a period of kind of like three weeks got absolutely crushed. So there was a period of three weeks where we thought our advertising was gonna be going d- 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 l- really going back to kind of the early days of Morning Brew where it was just straight up survival mode.

Ali Abdaal 1:21:30 Hmm.

Alex Lieberman 1:21:31 Finally in, you know, call it 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, it took a year to do this deal. We ended up closing the deal finally in October of 2020 and, you know, I'll always remember exactly where I was. Uh, I was in my mom's place in New Jersey. I was with my mom. I was with my girlfriend at the time, now fiance. They had bought, uh, champagne. They had bought balloons. And we have basically there's a final call where like the deal has already been finalized. All the documents have been signed. And in a deal process like this, the number, the number of pages of documentation, it, like the, the final kind of like document book, the deal book, was probably... I, I can't remember the exact number. I think it was 400 pages.

Ali Abdaal 1:22:28 Wow.

Alex Lieberman 1:22:28 Um, the documents were signed and we all get on a Zoom, Austin, myself, and all of the parties from, uh, Axel Springer and Insider that were very involved in the process. And then basically on the call is when someone from Axel Springer is like, "Okay, we're starting the wiring process."

Ali Abdaal 1:22:48 Yeah.

Alex Lieberman 1:22:49 And they're like, that's basically them saying, "We're hitting up, uh, Axel Springer's bank right now to wire you, Austin, and any other equity holders in the business their money for what we're paying for the business."

Ali Abdaal 1:23:01 Hmm.

Alex Lieberman 1:23:01 And what I remember in that moment, going back to talking about feelings, is I felt nothing.

Ali Abdaal 1:23:07 Hmm. Nice. [laughs] Okay.

Alex Lieberman 1:23:09 I felt, I felt nothing. My fiance, my mom were super happy for me. Uh, you know, they, they wanted me to pop champagne. Like, they were, they were, they understandably and rationally they were so happy for me.

Ali Abdaal 1:23:23 Hmm.

Alex Lieberman 1:23:23 But it was like, I don't know. I didn't feel a- 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.

Ali Abdaal 1:23:52 [laughs]

Alex Lieberman 1:23:55 And I didn't feel anything about that because, uh, 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. Like, if you were to ask me what have I spent on since being acquired and coming into more money than I could have imagined, there's nothing in my life that I have spent on that I wouldn't have spent on prior. Um, you know, you know, maybe I'm spending a f- 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. Um, 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, kind of complete the, 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'm probably about the same happiness today, and for a while I was less happy.

Ali Abdaal 1:25:12 Hmm.

Alex Lieberman 1:25:12 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.

Ali Abdaal 1:25:22 Yeah.

Alex Lieberman 1:25:22 And so I think in a lot of ways I had to refind like what is g- 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.

Ali Abdaal 1:25:57 Yep.

Alex Lieberman 1:25:57 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 gonna be that's my North Star pushing me forward.

Ali Abdaal 1:26:24 It sounds like in, well, since

Ali Abdaal 1:26:26 you started Morning Brew and kind of grew it to the point that it got acquired, your- In a way, you don't need to answer the question of what am I doing here, what is my purpose? Because you have a very nicely packaged purpose in morningbrew.com. And watching numbers go up and employees being kept happy, and advertisers being kept happy, and the product being made better and better is, in a way, such an all-consuming thing that you really... It really doesn't give you much space to sit down and think, "Huh, what, what, what do I really wanna do here?" I think, like, I wa- I was telling to my brother about this. So he's in... You know, they're in early, early-stage startup mode, Series A, where he's spending all day on sales calls 'cause they haven't yet figured out the sales thing.

Alex Lieberman 1:27:05 Yep.

Ali Abdaal 1:27:06 And I was asking him, like, "How, how do, how do you feel about this?" This was, uh, maybe about six months ago. And he was like, "Yeah, you know, it doesn't feel great, but it's like my baby. And, like, once you have a baby, like, you've just gotta, you know, feed the baby." Like [laughs]

Alex Lieberman 1:27:21 Yeah

Ali Abdaal 1:27:21 ... it's, it's, it's not even a choice. It's, it's not even a, a thought that would cross his mind. And he w- 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.

Alex Lieberman 1:27:30 Totally.

Ali Abdaal 1:27:30 And I'm 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 [laughs] then I would be like, "Hmm, okay." Um-

Alex Lieberman 1:27:42 Would you do it?

Ali Abdaal 1:27:44 I don't know. I-

Alex Lieberman 1:27:45 [laughs]

Ali Abdaal 1:27:45 ... I prob- I probably would, um, as long as there was... And, and, and the reason I would is because I think o- 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 could imagine, like, hanging out with a girl, and, like, you know, chilling. Your friends are around. You've got 100 million in the bank. You don't need to worry about money, mate. Like, what are you gonna do tomorrow? Like, how are you actually spending your time?

Alex Lieberman 1:28:15 Yep.

Ali Abdaal 1:28:16 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-

Alex Lieberman 1:28:41 Yeah

Ali Abdaal 1:28:42 ... 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 wanna learn... have the freedom to learn stuff and teach stuff on my own terms. And whenever I feel, uh, the number anxiety around, oh, numbers aren't going up as much as I'd like, I come back to that thing of like, no, but even if I had 100 million in the bank, I would still be doing this thing. So why don't I just act as if that's true right now? Why don't I just act as if I don't need to worry about money, and just make, make the content that I want because I think it's interesting and valuable?

Alex Lieberman 1:29:14 Totally.

Ali Abdaal 1:29:14 And just trust that the money will take care of itself, coming back to affirmation number two, which is, which is basically that.

Alex Lieberman 1:29:18 [laughs]

Ali Abdaal 1:29:19 Um, yeah. How was, how was that for you?

Alex Lieberman 1:29:21 Uh, I, I think that was good. Um, and I think it's a beautiful thing again that th- the stuff you're spending your time on is the stuff that you would spend your time on even if you never had to worry about a dollar again, you know, other than, uh, the course and monetizing the course. One thing I'm wondering, and I don't know if you've thought about this, and maybe it's just, like, such a basic emotion that you feel that 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 scripts and recording YouTube videos? Like, how do you know that is something that fills you up?

Ali Abdaal 1:29:56 Uh, one is looking through my calendar at previous weeks and asking myself, "Did this thing energize me or did this thing drain me?" And generally, for writing, and for talking to a camera, and for doing podcasts, those are the things that energize me. And kind of working with a team to brainstorm ideas. Most other things, generally admin related, generally operations related, generally s- trying to sell to advertisers related, completely drain me, so I don't bother doing them anymore. So that's nice.

Alex Lieberman 1:30:19 Yep.

Ali Abdaal 1:30:19 Another thing is that I, 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 v- really value is being an inspirational teacher to other people, um, to k- to sort of help them... Basically, help people live their best life, which sounds super, super cliche, but I think that is a thing that I can imagine that if I could do that, and I'm kinda doing that, I'm doing that at the moment, so if I could just continue doing that, that, that to me feels like a life well lived. And then I've tried this exercise called the ideal ordinary week, which is you fast-forward in your Google Calendar like five years, get rid of all the recurring events that are still there, and then you basically block out what are, um, what do you want to be doing? And for me it's like, oh, you know, I'd like to play squash twice a week. I'd like to do a board games night, 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, share ideas. It almost, almost broadly the schedule that Ryan Holiday has where he just, you know, from 9:00 AM till 1:00 PM he'll just go to his little room, like, with books all around him and just read and write.

Alex Lieberman 1:31:22 Mm-hmm.

Ali Abdaal 1:31:22 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-

Alex Lieberman 1:31:32 Yeah

Ali Abdaal 1:31:32 ... cool 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 kinda 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." Uh, similarly, this podcast right now I'm feeling like, "Yeah, this is sick."

Alex Lieberman 1:31:52 Yeah.

Ali Abdaal 1:31:52 And afterwards I'm gonna think, "Oh, I had a m- you know, amazing conversation with Alex. That was so fun." So it's like I'm, I'm looking out for those sorts of feelings that I get.

Alex Lieberman 1:32:00 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 t- 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.

Ali Abdaal 1:32:28 Yeah, I think so. I think I have a pretty strong idea of that. And I, I, I think also another thing that I, 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, 'cause those-

Alex Lieberman 1:32:42 Yeah, totally

Ali Abdaal 1:32:42 ... are really fun. But it's when money becomes the ex- an extrinsic factor that it crowds out intrinsic motivation. Um-

Alex Lieberman 1:32:47 Right. Because, because it becomes blurred, and you don't know how much-

Ali Abdaal 1:32:50 Yes

Alex Lieberman 1:32:50 ... each one is contributing to it.

Ali Abdaal 1:32:52 Yes. Yeah, exactly. And so when I, when I was dabbling for a few months in 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, "Ugh, I'm, I'm on the phone to radiology and they're not replying and I have to sit here for the next five minutes-

Alex Lieberman 1:33:10 [laughs]

Ali Abdaal 1:33:10 ... 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-

Alex Lieberman 1:33:17 Yeah

Ali Abdaal 1:33:17 ... 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-

Alex Lieberman 1:33:23 Totally

Ali Abdaal 1:33:23 ... than being here on the phone to radiology. So it was... I, I, I think that question is a, a thing I often, I often think about.

Alex Lieberman 1:33:30 I think that makes sense. And, and to make it a little bit harder, what I found to be difficult was how did I know when something didn't give me energy-

Ali Abdaal 1:33:39 Mm

Alex Lieberman 1:33:39 ... versus when something was hard and I was making an excuse for not being good at the hard thing or wanting to work on the hard thing? And so the example I'll use here is like the opp- like the, the parts of the business that, you know, are Austin superpowers, uh, for when we were wor- you know, working hand-in-hand together. So things like planning, things like-

Ali Abdaal 1:34:00 Mm

Alex Lieberman 1:34:00 ... a hiring roadmap, things like, uh, ru- even running like the traction process. Like-

Ali Abdaal 1:34:07 Yep

Alex Lieberman 1:34:07 ... 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, 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-

Ali Abdaal 1:34:31 Mm

Alex Lieberman 1:34:31 ... 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 axis or variable-

Ali Abdaal 1:34:41 Yep

Alex Lieberman 1:34:41 ... was like I'm always thinking in my head on this spectrum from 100% intrinsically motivated to 100%-

Ali Abdaal 1:34:47 Yep

Alex Lieberman 1:34:47 ... extrinsically validated or extrinsically motivated.

Ali Abdaal 1:34:50 Mm.

Alex Lieberman 1:34:50 Where am I living on this?

Ali Abdaal 1:34:51 Mm.

Alex Lieberman 1:34:51 And do I feel like it is at a place on the scale that feels like it's in check and it's a good reason to do the thing? And then the second one was outside of the, the money versus intrinsic thing. Am I... Do I... Uh, 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-

Ali Abdaal 1:35:12 Yeah

Alex Lieberman 1:35:12 ... good excuse to not do the hard thing?

Ali Abdaal 1:35:13 Nice. So you've got your intrinsic ax- extrinsic axis and you have your hard/easy axis.

Alex Lieberman 1:35:18 Exactly.

Ali Abdaal 1:35:19 Nice. And so I guess your con-

Alex Lieberman 1:35:21 You can use that in the book if you want.

Ali Abdaal 1:35:22 Nice. Thank you. I appreciate it. [laughs] Um, and I, and I, 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, I'm enjoying this?"

Alex Lieberman 1:35:38 Ex- exa- exactly.

Ali Abdaal 1:35:40 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, what do I do with my life?"

Alex Lieberman 1:35:47 Yeah.

Ali Abdaal 1:35:47 How did you go about finding that north star? Is... Yeah, how did, how did you think about that?

Alex Lieberman 1:35:51 Well, uh, if I'm being honest, I'm still in the process.

Ali Abdaal 1:35:54 Mm.

Alex Lieberman 1:35:54 I still don't really know what I wanna be when I grow up. I know there are some options.

Ali Abdaal 1:35:58 [laughs]

Alex Lieberman 1:35:58 Uh, w- 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.

Ali Abdaal 1:36:16 Mm.

Alex Lieberman 1:36:16 Because I do think... I, I love the energy of early stage, uh, entrepreneurs. Uh, you know, I've seen the impact that entrepreneurship can have on a country, on an economy, on a group of people, and to me that's really profound. So that's one thing. A third thing that I've considered, which is totally out of left field, is to become a therapist myself. Is like literally-

Ali Abdaal 1:36:40 Ooh

Alex Lieberman 1:36:40 ... to go get a psychology degree, become a therapist.

Ali Abdaal 1:36:44 Yep.

Alex Lieberman 1:36:44 The, the kind of like business or startup variant of that is to become an executive coach. To, to coach-

Ali Abdaal 1:36:50 Yep

Alex Lieberman 1:36:50 ... entrepreneurs. Uh, and so what am I doing today? Well, one, it's like the time I spend on Morning Brew is like creating content, finding creators to launch shows at Morning Brew, and dealing with the biggest, hairiest problems with Austin. And the le- the, the lens that I look through this is like how do I just learn as much as possible in this experience at Morning Brew right now? 'Cause I'm in a really privileged 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, uh, that can selfishly help me in building businesses in the future?

Ali Abdaal 1:37:27 Mm.

Alex Lieberman 1:37:27 And then outside of that right now I'm basically spending time angel investing and seeing kind of how it lands with me to angel invest versus coach people. So I've started to coach a few people. Uh, and, and for me, again, it's not really for money, it's just like do... Am I enjoying coaching? And also part of it, it's like can I prove to myself that I actually can add value to entrepreneurs and like push back-

Ali Abdaal 1:37:50 Yeah

Alex Lieberman 1:37:50 ... on this imposter syndrome? And then the third thing that I candidly wanna spend more time on is like really focusing on, on not optimizing health, because I, sometimes I feel like optimizing is actually a bad word. Like I feel-

Ali Abdaal 1:38:06 Mm

Alex Lieberman 1:38:06 ... like it creates actually a la- a lack of balance. Uh, and to me everything is good in... Not everything, but most things are good in moderation, and optimization sometimes doesn't allow for moderation.

Ali Abdaal 1:38:17 Yep.

Alex Lieberman 1:38:17 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 wanna spend time on, uh, that I haven't yet spent nearly enough time on. And so to answer your question, I am very scared about not knowing at the age of 28 what I wanna do-

Ali Abdaal 1:38:38 Mm

Alex Lieberman 1:38:39 ... for the, for many years. But I'm optimistic that if I'm patient, if, if I'm both patient and impatient, patient macro, impatient in like feeling like I'm not moving fast enough to answer this question, that I'll get to a pla- like that I am where I'm supposed to be and-

Ali Abdaal 1:38:56 Yes

Alex Lieberman 1:38:56 ... that, uh, things will work themselves out.

Ali Abdaal 1:38:59 Alex, thank you so much. This has been absolutely wonderful. Uh, where can people find out more about you? And we'll have links to all of this stuff obviously in the video description and the show notes as well.

Alex Lieberman 1:39:07 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-

Ali Abdaal 1:39:12 [laughs]

Alex Lieberman 1:39:13 ... uh, my reading list and my bookshelf as well.

Ali Abdaal 1:39:15 Nice.

Alex Lieberman 1:39:15 You can follow me, uh, @businessbarista on Twitter.

Ali Abdaal 1:39:19 [laughs]

Alex Lieberman 1:39:20 Uh, and, uh, you can check out my two podcasts, Founders Journal, which is my, uh, startup show about lessons from the entrepreneurial journey, and Imposers, where I talk to world-class performers from Ray Dalio to Jay Shetty about their careers and how they were able to excel in their career, careers even in the face of really deep challenges and, uh, the mental health journey that went along with those challenges.

Ali Abdaal 1:39:49 Amazing stuff. Alex, thank you so much for coming on. Everyone, thank you for listening.

Alex Lieberman 1:39:52 Thanks so much for having me.

Ali Abdaal 1:39:52 I'll 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 gonna be linked down in the video description or in the show notes, depending on where you're watching or listening to this. If you're listening to this on a podcast platform, then do please leave us a review on the iTunes store. It really helps other people discover the podcast. Or if you're watching this in full HD or 4K on YouTube, then you can leave a comment down below and ask any questions or any insights or any thoughts about the episode. That would be awesome. And if you enjoyed this episode, you might like to check out this episode here as well, which links in with some of the stuff that we talked about in the episode. So thanks for watching. Uh, do hit the subscribe button if you aren't already, and I'll see you next time. Bye-bye.