#39: Alex Lieberman, Cofounder and Executive Chairman of Morning Brew — Mental health for founder...

Welcome to From Startup to Grownup, the podcast. My name is Alisa Cohn. I'm an executive coach, an angel investor, and the author of From Startup to Grownup. Each week I talk to founders, creators, advisors, investors, and builders of all kinds about their insights and experiences in going from startup to grownup.

My guest today is Alex Lieberman. The co-founder and former CEO of Morning Brew. Alex is now the executive chair of Morning Brew and the creator of 3, count 'em, 3 podcasts, The Crazy Ones, Imposters, and a video podcast, The 60 Second Startup. We had such a rich conversation about how Alex got into the startup world, his decision-making frameworks, and what it was like when he sold Morning Brew, a very surprising story of how it all went down. We also had a real talk conversation about his own struggles with mental health and how important it is for founders and everyone to identify and address their own mental health issues. We also talked about Alex's strategies for healing and how he maintains perspective right now. We also talked about Alex's super cool tool that he's building for other founders. This is an incredible discussion, super honest, super practical, Alex is wise beyond his years and has a lot to share, and you're gonna enjoy it and learn a lot. So please enjoy my wonderful conversation with Alex Lieberman, executive chair of Morning Brew.

Alex, welcome to the show. I'm so excited to have you today.

Thanks so much for having me. Excited to do this.

It's exciting to be in real life here in New York City. And Alex, I'd love to start by just asking you about Morning Brew. So you're the co-founder of Morning Brew. What, What was the insight? How did you start Morning Brew?

Yeah, it's one of those stories of an accidental business founding. I was a student at the University of Michigan. I was largely there for two reasons. One is because I wanted a, a college experience that was very different from my high school experience, which I got with Michigan. I went to a small private school in New Jersey. Michigan was about as different as it gets. But also I was planning for basically my entire life through college to be a Wall Street trader. That's what my entire family did. And so I went to Michigan for the business program and I was in my senior year at Michigan. I already had my job secured to work on Wall Street at Morgan Stanley as a trader. So I had a lot of free time my senior year. I started spending that time by writing a daily business newsletter. I wrote that newsletter for two reasons. One was, I would say, selfishly, I wanted to keep up to date with the business world. So because I was concerned that my brain was going to atrophy if I just did nothing my whole senior year. The second part, I would say, was more selfless, where I talked to a lot of students. I asked them, how do you keep up with the business world? Every student said, I read The Wall Street Journal, but it's dense, it's dry. My parents told me to. I thought that was crazy. And so I started writing this thing. It was called Market Corner. It was— it started as a Microsoft Word template. That I would convert to a PDF, attach it to an email, and send to people through a listserv. The original listserv was themarketcorner@umich.edu, and that was the start of Morning Brew, not as a business, something simply to pass the time and solving a problem that students told me about.

So that's fascinating because part of this is like senioritis in a way. You just had to keep—

100%.

But then how did you know that it had real heft? Yes.

So I would say there are a few things that I saw. One was there was a lot of traction in the first few months of doing this, and traction is all relative. But I would say we went from the original newsletter going to, let's call it, 50 people to, I don't know, 300 people after a few months. And that sounds small, but to put it into context, there were only 3,000 people in the business school at Michigan max. This product was very mediocre. It was impossible to actually use the product without asking me for it. So there was no website originally. You would have to message me, say, hey, Alex, I heard about your daily roundup. Can you add me to your listserv? And so the fact that people were so excited about this, yet it was impossible to sign up, that's what made me really excited. And then I would say part of it was I was just really enjoying it. Like, I didn't actually think about this in as a business until, I don't know, a few months before quitting my job at Morgan Stanley to do this full time. But I was just enjoying it. Like I would say I was getting so much energy from being creative, thinking strategically, creating something from scratch. Like that is something that I've learned about myself is I love the process of creating something from scratch. Seeing what people like, seeing what people don't like, and continuing to evolve it based on what I think people will like over time. And so, yeah, I think part of it was we saw traction, but I also just kept pushing it forward because I was enjoying it.

It was just fun for you. Yeah. And you love that sort of tinkering and evolving.

I love this.

That's amazing. Now we're going to get to Morgan Stanley in a second, but before that, you— when you say we, you mean you and Austin, your co-founder. How did you meet Austin? How did you get involved?

Yeah. So Austin Reiff is my co-founder. He's now the CEO of Morning Brew. He was the COO for the first, let's call it, 5 years. So between March of 2015 and April of 2021. In April 2021, I moved from the CEO role to the chairman role. He went from the CEO— COO role to the CEO role. Austin is 2 years younger than me. He went to Michigan as well. We're actually in the same fraternity, but we didn't— we really know each other. He was just one of the early readers, so one of those first 500 people to get my PDF. And I want to say around December or January of 2014 or 2015, I had sent an email out to my readers saying, things are going well. I want to take this a little bit more seriously. If you're interested in helping me out with this project, let me know. And I ended up meeting up with Austin, uh, because he raised his hand.

He emailed back and said, I'm into it.

Yeah, he did a digital raise of the hand. He emailed me saying, yeah, I'm interested in helping out. I have ideas for how it can be better. I still have saved the email about us meeting up because it's a pretty funny email. It says it's us scheduling when we're going to meet with each other and it says like, let's meet up before BPL. BPL was Beer Pong League in our fraternity that we were both a part of. Yeah, we met in the Winter Garden at Michigan, which was kind of like the main area of the business school. And I just— I don't remember the exact details of our first conversation, but I remember the feeling that I had. I remember feeling like, wow, this guy's really intelligent and he has such a different brain from me, you know, where my brain is constantly thinking of ideas around the product of kind of like the customer and the reader and the feedback that we've gotten. Like, I've always kind of just thought from either creative mindset or like a people-first mindset. Austin was just an unbelievable linear thinker around very practically, these are some of the problems I see, this is how to fix them. He is the most kind of A to B thinker I've ever met. And I feel so grateful that I would say my original intuition was strong because again, we weren't even thinking about it as a business at the time. So I wasn't like, oh, this is going to be my co-founder. I was just like, this guy is really smart and he has such good blinders and focus. I just want to learn from him. And it just so happened that we ended up becoming co-founders and the success that Morning Brew has had to this day wouldn't have been possible without Austin.

Yeah, that's great. We such complementary skill sets. Just, just to ask, your intuition was good and you probably started evolving into working together. At what moment did you agree to be co-founders? This was your thing and he was helping you. When did that shift?

Yeah, I, I want to say it was— I don't remember exactly when we actually filed to be a business. So, you know, we first filed to be a Michigan LLC. The reason we did that was Michigan, the schools in Michigan, and we were working with the law clinic there. So there was like this pro bono legal clinic where law students would help student entrepreneurs. With formation documents and equity agreements, etc., for free. And so we probably did that around April of 2015. The, you know, the interesting thing is we actually had 4 co-founders. So it was Austin, myself, and I brought on 2 other guys who were in the business school in Michigan as well. They ended up moving on from the business call within 6 months of joining for different reasons. You know, one of them was interested in going into finance. They had their internship coming up and, you know, they were just more interested in doing the finance thing than the Morning Brew thing. And that's great. Like, to me, you know, that's what happens a lot where naturally a co-founder or two could end up going a different way because it's just not exciting to them. And you really can't fake being excited about something for 8 years. And so it was 4 of us, 2 of the co-founders left. Austin and I ended up together, and I would say we probably consider ourselves to be co-founders. In April or May of 2015, and then I ended up graduating from Michigan in June of 2015.

Got it. Okay. And then you went to Morgan Stanley, and then at what point did you get enough confidence from Morgan? Like, you were at Morgan Stanley, you had a normal job and doing everything you always wanted to do, be a trader on Wall Street. At what point did you realize, no, no, no, I'm going to give that all up and I'm going to focus full time on Morning Brew?

Yeah. So I made the actual decision right around Labor Day of 2016. Um, but I would say it was 9 or 10 months in the making that there were months of basically kind of the same story every day where I would wake up at 5:15 AM in my windowless room in, uh, Kips Bay of New York.

New York City. Very glamorous.

Oh, the best. Yeah. The classic 5-bedroom apartment that was a true 2-bedroom and had 3 rooms that didn't have windows. Right. Uh, would go to the office, work out, be at the desk by 6:30, work in, you know, mortgage trading, the dream job, from 6:30 until, let's call it like 7 o'clock at night, come back from Times Square to the apartment, have dinner, work on The Brew for a few hours, go to sleep. And that was like every day for 10 months.

Wow.

And there was a point a few months into doing that routine where I was just like, This doesn't feel great. And the reason it didn't feel great is because I felt like I was diluting my finite abilities. I feel like it's such a cliché at this point where a lot of people say, you know, I wasn't the smartest, but I worked the hardest. That is how I felt. I felt like the way that I did well at Michigan was simply by just spending more time in the library than other people. And so it was this really defeating feeling where I was like, if I want to be the best trader in the world,, I would be dedicating all of my time to trading. If I wanted to be the best entrepreneur in the world or the best at building Morning Brew, I'd be spending all my time at that. But I wasn't doing that. So this feeling of dilution felt defeating. I also had this feeling like I enjoyed the time spent on Morning Brew in kind of the late hours of the day far more than I was enjoying trading. You know what I realized about, about my time in trading? Was it wasn't creative at all. And I've just realized about myself that I need to spend time on creative work, kind of purely quantitative or analytical work. It just doesn't land with me. I don't get excited about it. And I feel so grateful that I'm surrounded by people in life that do get excited about those things because, right, like that's how you build something bigger than yourself. And I would say the other thing is I just had this notion that I was going to love trading. Not because I actually understood what trading was, but just because I wanted to be like my parents. And that is what they did. And so I think by doing the act of trading, I realized for myself that like there was kind of that cognitive dissonance that existed. I committed to something that I didn't truly understand. And I think that's very common for people going into first-time jobs is they're just like, I'm going to do something like my parents. I ended up making the decision to go full-time on Morning Brew for a few reasons. I basically thought about, you know, what's the worst-case scenario? So what's the worst-case scenario if I decide to go full-time on Morning Brew? The worst-case scenario is that it fails because the majority of startups do, especially media companies. Like, you know, it's very hard to build a media business. And so I said, okay, if that happens, then what are my options? I basically went through these layers of like, one option could be me going back to Morgan Stanley if I keep my relationship strong and I have this new interesting experience that provides side texture on my resume. I was like, okay, let's say that doesn't work. Business school, maybe, because building a business in media with the finance experience could be an interesting story. If that doesn't work out, you know, maybe I've met people in the New York City startup scene where I could go build something else. And I went through all these layers and I was like, if, if none of these things work out, it's not like a Morning Brew issue. It's an issue of me not keeping options open and not keeping relationships strong.

Yeah.

So that was one way I thought about it. The other way I thought about it was just like, what would I regret more?

Yeah.

Would I Would I more regret staying at Morgan Stanley and watching someone else build Morning Brew just because they dedicated the time, or would I more regret leaving Morgan Stanley and working on Morning Brew, seeing it fail, and then not be able to get a job back at Morgan Stanley? And to me, it was like such an obvious answer that I would more regret watching someone else build this thing.

Yeah.

So those are a few of the ways I thought about the decision.

You know, Alex, I have to say, how old were you? You were like 22, 23.

Um, yeah, I was— so, I mean, I was 21 when I graduated from Michigan, so yeah, 22.

Okay, so here's what's normal in my world. I'm a coach. Normal people who come out of school and they have a first job and they're experiencing some, oh, what if I do this and what if I do that? Oh no. And what I say to them is, well, you know, even if you fail, you'll be able to get something else and keep your relationships strong. What really matters is build the experiences and all the things you just said. How did you at that young age know that by yourself? Like, that's my job to tell people that.

Yeah, yeah. I think there's a few things. One is that I make it sound very clean right now, but when I was 22 or 23 thinking through this, I don't think it was such a kind of organized thought process. I just think, you know, as over the last years, uh, 8 years I've built a business, I've spent time around a lot of smart entrepreneurs. My thinking has gotten more organized, so I don't want to kind of like confound things. I think I describe it in a really clean way right now, but I don't know that it was actually that clean at the time.

Yeah.

And so I hope that gives relief to people who are thinking like, am I not thinking about things in a sophisticated or organized enough way? Say most days was me getting home and calling my mom and being on the verge of tears, being like, what do I do? Like, that was the average.

Yeah, yeah. That sounds more realistic.

Yeah. And I would say, and I would say, you know, on the flip side, you know, part of the question that is like, how has my thinking gotten more organized over the last 8 years? You know, now I'm 29. I would say it's been through the act of building a business. It's been a force function for thinking more clearly. It's been— I, because I am just a lover of media and content, I consume a ton of content. So I focused on consuming content by people who I consider to be like the clearest thinkers in the world. And then going back to having Austin as my co-founder, that was one of the things that I was most attracted to when I first spoke about— spoke with him in the Winter Garden was his ability to think at a more sophisticated level than people twice his age. So I think also just through osmosis and spending— talking every day with him for the last 8 years, it has made me a better thinker.

I see. And so that kind of helps you reflect on your experience now and maybe make sense of it.

Yeah. And so, you know, was I kind of like the most disorganized thinker at the time? No. Was I as organized as I describe it today? No. It was probably somewhere in the middle. There were some days where I went through kind of these tradeoffs and other days where I was just like kind of acting in an irrational, emotional moment where I was just like, you know, fuck this, I want to go do something else.

Right, right. And also the whole notion of just that feeling of despair.

Yeah. And then one other point I would make is that the other kind of lens that I looked at things through that I didn't mention before is— and I've talked about this in the past, but I would say losing my dad was like a massive— it really was like a light switch. And again, I think it feels cliché to say, you know, having a moment like that gave me perspective, but it really does. You know, it's It's interesting because on my podcast, The Crazy Ones, one of my co-hosts was telling the story of an amazing business called Red Ventures. Red Ventures is a huge $12 billion media business, and this guy Rick Elias has been building it over the last 20 years. But Rick, you know, a big part of his story is that he was on the flight that landed in the Hudson., and he gave a great TED Talk about it. And he talks about how like that moment really changed his perspective. Before that, he was planning on just building Red Ventures, flipping it, and going on to his next business. And everything changed after that where he was like, I'm going to build this for the rest of my life. I'm going to have balance in my life where I get home to my kids at 6:00. And from my understanding, as my co-host Jesse tells the story, like he has stayed true to that. And so I would just say like decisions have become easier for me, because if I do not feel energy around those decisions, I won't do them. Or around those actions, it's like I can't fake enjoying things. And so I feel very grateful kind of on the other side of tragedy, the clarity that it has provided me.

Yeah. And maybe your realization, maybe you could share more about that. Like, I understand, obviously, losing your dad.

Yeah.

Is just a moment and it is a tragedy. And it sounds like it clarified everything for you. What, because life's too short or what specifically?

Yeah. I would say there's a few things. I would say one thing was the job that I was doing at Morgan Stanley, I was trading mortgages. That is what my dad did for 20 years. So I think part of it was possibly fear-based decision-making, whereas Wow, my best friend just passed away suddenly. He's been doing the job that I just started doing, the exact role. We had the exact role. He's been doing this for the last 20 years. If stress created from this job is what led to him ultimately having a stroke, an assumption my always-on brain made is like, this feels like Groundhog Day. Why is this not going to happen to me 20 years from now? That was one way of thinking about it. I think the other way of thinking about it was very simply, yeah, like all I can control are the things that are in my control and what I can control is the things that I spend time on and that I feel energy around. I felt greater energy and excitement around Morning Brew. I can control how much time I spend on that. And now one point I'll make is that I only have the ability to control that decision. Because I had the privilege of my mom covering my rent for 10 months after I quit my job at Morgan Stanley and went from an $85,000 salary to a $0 salary. The decision-making wouldn't have been nearly as easy if I didn't have the opportunity of falling back into a comfortable situation with my family.

Yeah. Thank you for sharing that. That's so honest. Yeah, I think people sometimes rush over that.

Yeah.

Yeah. And when you talk about a cliché, by the way, about Rick's story, I heard about his story on the Peter Attia podcast. Yeah. And I was also struck by that. And, you know, as a listener, it feels like a cliché. And then if you're the one— I've had my own moments of truth before, and I hear that, you know, obviously you have too. When you have that moment of truth and it makes that change, it really is real. I think that's why it's a cliché, by the way. And so I think it's just so important. Important to recognize those moments and to just honor them for what they are.

Yeah, totally. And I would say what I've realized, at least for myself, is my life and kind of my psyche is this always existing kind of like tug and pull between, let's call it, like old stories and new stories, or intrinsic drive and extrinsic drive, right? Like there's always the kind of one side of me that's pulling myself to just spend my time in the way that best fulfills my values and what gives me the most energy, no matter what anyone on the outside has to say about it. That's like kind of the part of me that I want to get stronger and stronger. There's the other part of me that's like the, the external storytelling that has existed for a long time, like I would say since I was a kid. This kind of this focus on making more money because I came from a Wall Street family. And interestingly enough, like we didn't talk about money a lot. So I actually think in a weird way I have a scarcity mindset around money because I never knew, actually knew our financial situation as a family. So there were more, always more questions than answers. I would say also just like coming up into entrepreneurship, I had this idea of what it meant to be a successful entrepreneur. It meant having the CEO title forever. It meant starting a business, building your business for decades, taking your business public, and just kind of riding on into the sunset. It meant not just building one business, but after you have a successful business, building a second one that's even bigger and a third one that's even bigger than that. It meant going on and angel investing after being a founder, because that's what every founder does. All of these stories are stories that if I just latch onto it and do it, I'm doing it because of my desire to fulfill the story, not what actually provides me the greatest level of joy. And even though I can rationally talk about that, I think having my actions mirror the story that I want to be stronger in my life, which is kind of like my inner desires, the things that give me the most joy, is a constant tug and pull.

Yeah, that— there's so much there and there's so much to unpack because I know that you really struggled with that. So you sold Morning Brew in, if I'm not mistaken, 2020. Yeah, you sold Insider. And so can you take us back to that Zoom call where you consummated the deal with Insider? Like, what was that like for you?

Yeah. So, you know, just to give some context on the deal, it was many months in the making. It was 11 months. We started talking with Insider in November of 2019. The deal probably would have happened faster, but in March of 2020, you know, the world that ended changed. Everything happened. And so it was this constant ebb and flow for basically 11 months of like, feels like we're doing the deal, feels like we're not doing the deal, feels like the world's ending and feels like our advertising dollars are going to zero. We're definitely not doing the deal. Deal. Oh wow, the deal's back on.

Wow. By the way, before you get— go on, that's so fascinating. What was that like for you? Because that's what entrepreneurs have to always do, navigate that roller coaster and the ups and downs. If you were saying, oh, the deal's happening, it's not happening. Oh, we're gonna not die. Oh, we're gonna die. What was that like for you? Just briefly.

It was, I would say it was a little bit discombobulating. I think I had kind of this, faith that the deal was going to get done. There was a period of time in late March, early April. That was the time where I was like most uncertain about everything, because in that time from, call it like March 15th to April 15th, that's when it felt like our business was going out the window. There was a period of a week where dozens of advertisers canceled their deals with us. Austin and I were worried about advertising revenue going down. By like 50%. We spent a ton of time literally just brainstorming any possible way we could make money as a business, whether it was literally starting a Patreon and getting donations, launching an education business, which is one of the things we actually ended up doing. So I would say that period of time was kind of like the most uncertainty I've ever had around the business. And I would say just the decision to do the deal itself is such an interesting and complex thing, and it's so different for different founders. For me, I would say what has driven me, what drove me to build Morning Brew and drove me ultimately to do the deal, I would say is some combination of love for the game and money. I don't know, let's call it On average, it was 50/50. If you had to ask me what it is for Austin, and you'd have to ask him for the exact number, but my guess is for Austin, it was more like 70% or 80% love for the game, 20% money. And if you were to ask me, why does your balance look this way? I would say, one, it goes back to kind of the scarcity mindset around money and this desire to hoard money because I think that I need more of it and protect it. I also think generally, like, it had this connection to happiness for a long time, even though the rational brain has always said, like, doesn't define happiness. And I would also say that to me, after my dad passed away, I just felt this level of obligation to my family where, you know, there was a period of call it when my dad passed my right before junior year of college to when we did the deal, I kind of assumed this role of I'm going to take care of my family like I and quite literally assumed the role in like when my dad was in the hospital, when I knew he was going to pass and they hadn't pulled the plug yet, I in the room with him in the hospital said to him, I'm going to take care of everyone. And it's, it's one of those things like I, I think there's so many layers of like subconsciously I don't even think I realize what that did by saying those words to him. It just dictated all of my behaviors from that point on. My behaviors in terms of like the focus that I put into school and how hard I worked in school to make sure my like GPA was great so that I could get a great job on Wall Street. Like my grades after my dad passed were far better than my grades before my dad passed. And so once I knew that there was a life-changing number that Insider was putting in front of us, I would say that part of my brain kind of overpowered other parts of my brain because I was like, you know, this is the moment where I can be set for the rest of my life and my family can be as well. And I don't any longer have to worry about the fact that the Lieberman household only has money outflow and not money inflow.

Yeah. So, wow, there's a lot there. And so that was both probably conscious and unconscious.

Totally.

In those moments. And so the deal did come together, as you said. And what was it like for you to be— I heard you talk about this and I'd love you to share with our listeners, like, what was it like for you to be on the Zoom call when you were like wiring the money?

Yeah.

Because you made this decision and again, it was rational and also subconscious, like in some ways paying a debt to your dad., but there you are in the actual moment.

Yeah, I would say, uh, underwhelming is, is the word. Um, yeah, yeah. I mean, I just, I still have a screenshot of the Zoom with Austin, myself, Insider folks, Axel Springer folks, and like we're smiling in the picture. If you were to ask me like the feelings I was feeling, it was like I was happy, but I wasn't like ecstatic. I wasn't crazily excited. I would say my mom and my fiancée were more excited. Like they had champagne in our— it was in my mom's place in New Jersey because it was during the pandemic and we were living with my mom. Like she had champagne and balloons and they were, well, you know, when the Axel folks said that like the wire transfer was starting, like my mom and my fiancée were like cheering for me. But I didn't feel any of that. I think part of it is because the deal was 11 months in the making. So it was like for 11 months, I think I had these opportunities, these micro opportunities to prepare myself mentally for the deal. And it was like I knew for 11 months what, what the— what was going to happen. So even though, like, you know, the bank account number went up, I knew what was going to happen for a pretty long time. And say the other part of it is I think that sometimes my body protects itself from feeling deeply in either direction. My guess is that it's a combination of my parents not showing a lot of emotion growing up. I think being in a Wall Street family, like I never saw my dad cry once. I only seen my mom cry a handful of times. So like I would say kind of like our emotional range as a household was, you know, if, you know, some of my friends, it's, let's call it, I call it a negative 10 to a 10. Our emotional range was more like a 3 to a negative 3. I think my dad passing away also impacted my ability to feel deeply or express deeply because it was like everything was anchored from that moment. And it was like, how could anything be as bad as this moment. Um, and again, I think that it makes sense rationally, but I think also feeling deeply is such a beautiful thing to experience life fully. So it's like something I work on all the time. Um, and I also think it was a coping mechanism for Austin and I to be level-headed operators because, you know, back to your question of like, what was it like to be in the ebbs and flows of the deal? That's not just the deal, right? That's kind of the arc of an entire business. And so I would say Austin and I got really, really good at not celebrating things and got really, really good at when shit was hitting the fan, whether it was our website being hacked, whether it was our first employee quitting, whether it was being told no by dozens of advertisers on advertising deals. We were able to stay very cool, calm, and collected. And so I think that is effective in building a business. It's less effective in every other aspect of life.

Right. And you, you know, for all of us, we get sensitized and we learn a certain set of skills, and then it's not like you just turn them off when you go home.

Totally.

Right. Yeah.

And, and those skills, again, they can be useful for certain things, but not in other contexts.

Totally. And to your point about the ups and downs, I mean, every single founder I've ever dealt with, talked I've talked to, coached, experienced anything, they all talk about the surprise of the ups and downs, even though everyone talks about the ups and downs, but it's actually a surprise when it's happening to you. Did you find that way?

Um, I, I didn't find it to be particularly surprising. Again, like, I think Austin and I got so good at being numb to the ups and downs. Like, I think Austin by nature is a kind of more stoic figure than I am. And I think I just got very desensitized. So yeah, I would say like our level of reaction to the ups, like the ups and downs absolutely happened. But I think our level of reaction, you know, it reminds me in some ways of— have you ever heard of Alex Honnold? He's the rock climber.

Yeah, the rock climber.

Yeah. So Alex Honnold, you know, they're considered the world's greatest rock climber. There's the documentary about him called Free Solo.

He—

free soloing, for those who don't know, is where you climb up a mountain without any harness, ropes, or support. And he has climbed some of the crazy, craziest mountains. One is called El Capitan. It's like a mountain that very few people have done with ropes., and he did it without ropes, and he gave a TED Talk about his free soloing. And they did MRIs on his brain around triggering kind of the, the visuals and taking him back to the moments when he was free soloing and that he could have fallen to his death, etc. And they basically said the MRI scans were the exact same as a typical person walking through the park. And it's like, it's— I'm not at all, at all Alex Honnold, but to me that's a relatively good analogy for, I think, what our emotional state was with things in the business that if someone who wasn't running our business looked at it, they'd be like, oh my God, like this all is going on. Whereas for Austin and I, we became so just like normalized to these things.

Yeah, well, I have to ask you though, Was that always that way or was that a learned skill just from repetition? Because I think that founders, entrepreneurs who go through the rollercoaster, they do finally come to realizing, okay, this is the way it's going to be for 8 years.

It's so honestly, it's so hard to remember. Maybe the answer is yes, but yep, yes, but I'm not entirely sure.

Yeah, yeah, I get it. So then after you did the sale and went through the sale, you then became the executive chairman.

Yep.

And your co-founder Austin replaced you as CEO. Talk about that decision.

Yeah. So, you know, the long short of it is that April of 2021 is when I officially moved out of the CEO role. I think really kind of that transition, not by title, but by just time and behavior, was probably 6 months in the making. You know, I think the, the short answer of it is I was good at being a builder CEO. I was particularly bad at making the transition into an operational CEO. And now I think there's a few reasons for why, and I think understanding the why is valuable and understanding kind of how do I level up moving forward. I think one reason why is because I, going back to me wanting to spend time on the things that give me energy, I just continued to spend my time on kind of building, tinkering, creating new things. So rather than, let's say, goal setting, long-range planning, thinking about building out an executive team, I was thinking about What's the next B2B newsletter we're going into? When are we launching a podcast? What is that podcast? So I think I was assuming a lot of the role of just like, I don't know whether you want to call it chief innovation officer, whatever it may be. But I think what I wasn't assuming the role of is the first job of a company. YC says this, Paul Graham says this. First job of a company is to find product market fit. Second job of a company is to build a company. That second job, I just don't think like kind of the light switch ever got turned for me to spend time on it. And I would say that transition in our company was kind of made in the middle to late of 2019. I vividly remember in our WeWork space, Austin coming to me with a book that he was recommended by one of our investors. It was actually our investor who invented the Snuggie, and he's an amazing entrepreneur. And he told us about book called Traction by Gino Wickman.

That's a great book, right?

And it's all about the EOS, the Entrepreneurial Operating System. Basically, for those of you that don't know what it is, EOS is a— it's a standard operating procedure for building and scaling a company. And so what it includes is it starts at— it goes most macro to most micro. So it's mission, vision, values, people, then it goes to what's your 10-year, 5-year, 3-year, 1-year goals. And then at the most micro level, what are your 90-day goals? Those are called rocks. And then it also sets up like your standard operating procedure for meetings. So how often do you have your all hands or your pulse meetings? How often are you doing offsites and what is the agenda for offsites? And so Austin was like, at this point in the business, it still felt like we were operating for today. Like everything we were doing was making sure the machine was still running today. And Austin had made the comment at some point, he's like, I think we need to start thinking more proactively so that we can be planning for weeks, months, and quarters ahead. And everything we're spending our time on today is to help the business months from now. And I think at the time, probably my less mature brain was like, yeah, but that stuff's not fun. And I remember Austin had told me to read that book. Of course, the first time he asked me, I didn't read it. And then he followed up and he's like, dude, you got to read the book. Like, this is literally about the future of our business. And in retrospect, like, it was such a, you know, a rightful comment to make. And so, yeah, I think a big part of it was I didn't make the mental transition from building to operating nearly soon enough. And then, you know, the other piece of it was around just my own mental health. I've had OCD since, I don't know, I can remember. And I was in kind of a very intense period of OCD or obsessive compulsive disorder for probably all of 2018 or a lot of 2018 into most of 2019. And so during that period of time, it's when I had my first panic attack ever. Woke up in the middle of the night gasping for breath, thinking I was going to pass out. Had panic attacks for probably a month straight until seeing a psychiatrist. And so, you know, probably to take a little bit of the pressure off myself and not just kind of deliver all this critical feedback to myself. There was also a part of me that I think was not present enough in mind to be thinking about the transition in the business. Because I would say for a year to a year and a half, I was— it was a full-time job managing my psyche where when you're building a business, if you're really enjoying the process, I'd say 90% of your thoughts are about the business. You go to sleep thinking about ideas for the business. You wake up thinking about kind of the biggest blockers to remove in the business. For that year to year and a half, that was not what was— what I was thinking about. I was going to sleep thinking about my obsessions. I was waking up thinking about my obsessions.

That must have been so difficult.

Yeah, yeah, it was brutal. And again, I don't know why it is, but I always look for the opportunities in things. So what I find is the experience with OCD, the experience with my dad have given me a beautiful skill of seeing the best in people, of empathizing with people, of having an emotional toolkit that I feel very grateful for. But yeah, it sucked. It absolutely sucked.

Yeah. I also didn't realize that OCD was a thing that would kind of go in and out a little bit. Like, you probably always have a backdrop of OCD, but sometimes it's super intense. Yeah. In the background.

Yeah. I didn't know the way that I think about it is kind of my base level of OCD for, let's call it, between 2015 and 2020 was, let's call it, like a 4, a 3 or 4 out of 10. Where there was always some amount of, like, little bits of pressure that I felt on my chest. Like, if you envision, like, a, a 5-pound weight on your chest, that's what it felt like during periods of constant obsession and rumination. You can basically assume that it felt like a 25-pound weight on my chest, that 90% of my thoughts were about my obsession, that it almost felt like a kind of if you visualize like when you have like kind of one of those swimmers in your eye and you like look at your eye and it's kind of blurry. Imagine just like there's a whole film of fog over my eye where like I never— I wasn't— I'm not able to be my most 100% present self in any aspect of life. And I would say my obsessions have changed form over time, the things that I obsess about. But they all have the kind of the same pattern. The things that I obsess about are always extremely important to my identity, and there's no way to objectively answer my obsessions. It's always— there's an unknown piece to it. So to just give one example, something that I was really— that I ruminated a lot about after my dad passed away was my health. And this happened to a close family member of mine as well, where they had very significant health OCD after my dad passed away, and it led to eating disorder for them. For me, what it led to is there was a period of time where I wouldn't run on a treadmill because I was so fearful that if I got my heart pumping too fast, I would be one of the young people who had a cardiac arrhythmia and just drop dead.. And unless I went to a cardiologist and got my heart mapped every week, there's no way to definitively answer if I'm going to drop dead or not. It's an unanswerable question. So what compulsion in OCD refers to is compulsing on your thoughts. So taking this thought of, I am fearful that I am going to drop dead while running on a treadmill, so I'm not going to run on a treadmill. It's avoiding the thought versus what you're taught to do with OCD, with anyone who has OCD. And by the way, something I've learned recently is how prevalent OCD is. At least 5% of adults struggle with OCD. What you're supposed to do is it's called ERP or exposure response prevention, where you actually go and you run on the treadmill and actually test running on the treadmill as fast as you can, where you actually desensitize yourself to the provoking thought. So that's one example of it, but it's manifested in different ways over the course of my life based on what is most important and provoking at that time. Yeah, but there are periods again where I go through like the 3 out of 10 stage where there isn't that thing that my mind is just constantly grabbing onto for weeks or months on end.

Yeah, that's a lot to handle. And I'm curious if maybe some of your OCD was coming up for you when you then stepped away from operational day-to-day of the business?

Yeah, absolutely. I would say partly because I just had more free time, so there was more time for my brain to wander. And I'd say the other big thing that came up for me, and I don't know if this would be considered OCD, I just consider it to be more like self-doubt, the opposite of self-loving, is I found myself to be very kind of self-critical. And self-deprecating after I moved out of the role. Right. Because given the backdrop of kind of my story that I have told myself, and that's a story, whether that's a true story or not, you know, I don't know. But the story I told myself is like, I messed up in my role. I could have been better. And so after I moved out of the chairman role, it was— I wasn't a good CEO. I got lucky with Morning Brew. And I'm never going to be successful again. Now I need to build another business in order to prove to myself that I'm capable of this and I wasn't a one-trick pony. What am I going to do for the rest of my life? I'm a 29-year-old. I have no idea how I'm going to fill my time for hopefully the next 50 years. And so, yeah, there was a period of time where I just felt super down on myself because I didn't know what I was going to do with my time. I felt like my previous time that I spent wasn't time well spent because I wasn't successful in that. So I felt like I had regrets, and so I was just lost.

Yeah. I mean, I'd like to read a little bit of what I read that you wrote. You wrote, right after transitioning from the CEO to executive chairman of Morning Brew, I didn't love myself. I felt lost. I felt self-conscious. I felt a lack of worth. I felt like a failure. And you're hearing this and maybe like, what are you talking about, Alex? You sold your company for a bunch of money and you're executive chairman at 28. Stop complaining, get your shit together. But that wasn't my honest experience. I felt like a failure for feeling like it wasn't the right time to transition. Why did I feel that? Why couldn't I keep running the company forever? And then you talk more about being a one-trick pony and I felt a loss of identity and I didn't know who Alex Lieberman was outside of Morning Brew. And could you maybe, maybe get a little more deep sort of what was in your head or in your heart during that period? And then also, how did you find your way out of that?

Yeah, I mean, I think what was in my head was, this is a really hopeless feeling because for the longest time I thought that kind of like the end goal or part of the end goal was having a lot of money. I got to a point where that was my reality, but I wasn't any happier. I would actually say I was less happy because now I didn't feel like I had the crutch of money. So like that goalpost no longer existed. So I no longer had kind of, let's call it this superficial North Star that existed. The other, the other piece of it is, for whatever reason, I had more money anxiety than ever because now I was like, what do I do with this? And I felt a level of loneliness because everything you just described is a very first world problem, right? Like everything that we're describing is completely a function and problem from privilege. And so I felt, I would say, a level of embarrassment when talking about this because I kind of said to myself, like, people are dealing with so much more shit than this. Why am I going to complain about this? And so what that led to is me only talking to very few people about my situation and my experience. The way that I got out of it was reminding myself to not feel rushed in this process. Not feeling like I have to figure out all of these answers on day one. Also, I tried to make the problems or the questions I was answering as small as possible. So rather than asking myself the question of what am I going to do with the next 50 years of my life, I asked myself, what am I going to do with the next month of my life? To me, that took a lot of weight around the problems I was creating for myself. I spent a lot of time reading. So I reading mostly not business stuff, but I think I would say things more in the genre of like personal development, self-discovery, stoicism, Buddhism.

Yeah.

And I feel like again, that's such a cliché thing for founders to start getting all like hippie dippy and spiritual. Yeah, but like I was just looking for kind of tools. I felt like I lacked tools to navigate this challenge. I was looking for tools. That's basically what I was doing.

Yeah.

I also spent a lot of time talking to people who had moved into chairman roles to ask them what they did in their roles, how, like, if their experience was similar to mine. And of course, it's not all that surprising that their experiences were very similar to mine. Same questions around feel the need to start another business to prove that they're not a one-trick pony. Same questions around feeling lost. What am I going to do with my time now? Same feelings with, was I actually good at this? So I found comfort in that, not necessarily because it gave me more tools, but because there's a level of satisfaction you get in not just being told by other people, yeah, there's a lot of people like you, but actually talking to the people like you. And then I would say for me, the way I started framing things for myself is just like, what would my ideal day look like? Right now and how do I get towards what that ideal day looks like? Try it for a little while and then kind of reassess. And so what I said to myself, my ideal day looks like is spending time supporting Austin and the Brew in the ways that I enjoy most and therefore I think I can add the most value. So for me, that is providing value from a content perspective. Like, I absolutely love -consuming content, coming up with content ideas, uh, providing thoughts on who are great, uh, people we can bring into our business that can create content for us. I love tackling big problems with Austin. So whether it is personnel problems, whether it's strategic questions, I like talking through those with Austin. Something I've realized over time is I think I like thinking through those and talking through those versus those things being my full-time job. And then I also realized outside of Morning Brew that a big thing that I was missing, especially when I was spending a lot of time consuming content and reading, was I loved learning, but I didn't love just learning through consumption. I had to learn through building. And so I was like, I need to find a way to just like tinker and build again. And so it started at the simplest level of I've gotten super into Legos in the last year where I've built a ton of Lego-related things. I've brainstormed businesses for how am I going to build a Lego competitor because I just love building and it's actually been very therapeutic. But also what just happened is I've just come up with some ideas that I I don't even call them business ideas similar to Morning Brew. I just call them like hobbies and side projects that I can build something that I think is gonna provide value to people, that I'm enjoying the process of learning. And in doing this, if it turns into a business 5 years from now, great, that's awesome. And I would say with any of these ideas, there's a small part of me that believes they can be a business that I think gives me enough of an interest in it such that I do it. But I'll give you an example. Like something that I'm working on right now is building what I consider to be the world's greatest database of curated content for founders. So one place where if you are a startup founder and you have a question around how much equity to give to executives that you hire, where to find a coach, or how do you— what does it look like to work with an executive coach in a smart way? How to hire well, how to fire well. So much of this great content exists on the internet. It just hasn't been aggregated in one place. And so I would say the value of curation is higher than ever before. So literally just in my free time that I'm not helping with The Brew, I'm putting together this thing which involves me using Airtable for the first time, creating a database that's connected to another piece of no-code software that turns it into a website. I feel so much energy from that, and I think doing this kind of project has been reaffirming to where I do feel energy versus where I don't. Because a question I would always have for myself about where I don't feel energy is I would always be self-doubting and ask myself, do I not feel energy because I actually don't feel energy here or because I'm not good at this thing? And so I'm creating a good excuse for why I don't feel energy around it.

Right.

I think the short answer is it kind of doesn't matter.

Yeah.

And I should really just spend time on the things that light me up.

Yeah, for sure. Alex, there's so much in what you just said. I have got to go, I want to go backtrack on a number of things. Cool. In particular, I heard what you just said about the curation of the founder's information. I heard that.

Yep.

But I also think you just broke some news that you're creating a competitor to Lego. Is that accurate?

Yes, I'm still—

Breaking news.

I'm still in the early days of—

Watch this space.

Yeah. What I've read is basically getting, uh, creating a physical product that can be connected like Legos but doesn't lead to you getting sued by Lego for infringing on their patents is extremely hard. Like, there are many companies that have tried to do this and they get sued by Lego.

Yeah.

So the big question in my head is, how can you build something that interlocks in a really customizable way but you don't get sued by Lego? So if anyone has an answer, let me know.

Write in. Okay, okay, great. And then just backing up before that, you said that during this period where you were finding yourself and I think healing in many ways from these experiences that you read some books. So like, what are some books that you recommend for people? Yeah, that really were helpful to you. Um, such a cliché.

So I would say any of the, um, books by Ryan Holiday.

Yes.

So, uh, The Daily Stoic. He just came out with, um, a new book, Discipline. Yes. Well, is it Discipline?

Uh, Destiny, I think. Yeah.

Uh, I think that was great as well. Uh, Man's Search for Meaning by Viktor Frankl. Super sad book, but like, I think really profound. I'm trying to think what else I read. I read a number of essays by founders who had moved from CEO to chairman roles where they basically did kind of memos on why they're making the transition. I found those to be really helpful.

Books or blog posts?

They're blog posts.

Yeah.

By the way, some of the best content I read, I think, is personal essays, Substacks, and blog posts. Over books. That's also kind of like a new thing I decided over time is I'm not going to read full books if I don't like them. I think people feel a need to get to completion for the sake of finishing a goal. But I just think if a book starts feeling repetitive after a few chapters or I'm not jiving with it, it's okay, move on to the next one.

Yeah, yeah, totally. There's a lot of good content out there. That's not the book From Start-Up to Grown-Up. That is a page-turner. Every single page.

There you go. Exactly.

Yeah. And then you also, and this is so significant, you said that you talked to other founders who had transitioned into executive chair roles. I think that's so important. And I told you before we were filming this or recording this, I told you that I think part of my biggest mandate for this podcast is for founders to recognize that they're not alone. There's other people going through the same experiences. And then of course, talking to other founders is like the best way to do that. And I guess I'm curious, like, is there one example in mind that you can think of? You may not be able to, but like, is there a story that you remember where you talked to one of the founders who was going through this that you found particularly insightful or poignant or comforting or that resonated with you?

Yeah, I mean, I would say the consistent thing, the consistent story I was told by other founders who had made this transition was like, you should absolutely not feel the need. And you should tell yourself the story that like building a business has to be bigger than Morning Brew is a fool's errand, that even if you complete that, you're just going to keep moving the goalposts. Like, how do you get to a point of where it feels like enough? I'd say that's the first thing. The second thing is I actually think seeing these people who are a few steps ahead and got exciting about— excited about something provided a frame of reference of if I tried those things and I didn't feel a similar level of excitement, it maybe was a good sign that that's not the path I should go down. So for example, I spoke to Ryan Hoover, who's the founder of Product Hunt, and he was the CEO. Now he's the co-founder— or sorry, now he's the chairman and he runs a, a VC now. I think it's Weekend Fund, I think it's called., and he loves investing in founders. He loves it. And again, I think it's such a classic thing for founders to go into angel investing, then start a fund, because I think the playbook is so clear of like, you have a network, you can get good deal flow, you can make a lot of money starting a fund because you get management fees, you get carry. I've been investing in— I saw one of the things I did in this period of time was like, I'm going to invest more to help founders. And so I wrote 15 checks over the last 12 months. And I was just like, I'm going to see what 12 months of doing this is like. I've realized I really don't like investing. I really do not enjoy it. And I think seeing his excitement around it provided a good reference for me, really realizing it's so clear that it feels like work right now.

Yeah.

And like, it should not feel like work, right? The other thing that I didn't mention, aside from talking to founders, is I had a coach. We haven't worked together recently, but it's someone who started as a friend, worked with him for probably a year and a half to 2 years. And something that one of my co-hosts on The Crazy Ones talked about, because we did an episode on executive coaching and what our thoughts were about coaching, when it makes sense to get one, the type of like how you pick the right coach is Jesse. My co-host talked about kind of like this 2x2 matrix of at least one of the 2x2s is kind of like business or strategic consultant or like kind of like spiritual guide, because I would say there's very different flavors to executive coaches. And the big thing with my coach is, you know, he had— he has amazing business savvy. He ran a media business. He started Summit, which is one of like the big conferences. And so he had this media and operational experience, but like he had been committed to kind of like spiritual work for, call it, the last 9 years, started with Eastern work and like Buddhism. And now he's done a lot of Western work. And I would say for me, for what I needed as I was coming out of my CEO role, I had lots of questions, lots of doubts. He was the perfect person to talk to, to help navigate that time.

Yes. I just want to emphasize and highlight that there are so many different kinds of coaches who do different things.

Yeah.

And you've gotta find the person who's gonna be able to help you on your current mission.

Totally.

Yeah.

And, and I think at the end of the day, I think of coaching like I think of, um, finding a co-founder or finding a romantic partner in life where it's a process. Like it shouldn't be like a point and shoot, you found your person. And I say that especially with coaching because I think there's a ton of bad coaches. And the reason I believe that is because anytime you have a career path where it can be lucrative and the bar to enter is super low, you naturally will have people that enter. There's going to be a lot of supply. And so I think what happens is you just have a lot of people that call themselves coaches. They don't have any sort of licensing, whatever it may be.

Right.

It's different than like psychologists where you literally need to have the degree.

Agree.

And so I would argue that actually the best way to find a coach is to talk to 4 or 5 people. Because by the way, some may be bad coaches or they could all be good coaches, but there's a coach who makes the most sense for what your personality is and for the acute challenges you have right now. And so, you know, I talked to a number of coaches before I landed on the coach I ended up going with.

Yes. Also talk to your friends and peers and other founders to figure out who they're working with and why they like that person.—

Totally.—

to get those introductions. And then the thing you're talking about is so, I think, significant. So the idea that the founder either becomes executive chairman or sells the company and steps away, and there is this depression, loss of identity. Why is that, would you say? Why is that so normal?

Yeah, because I think kind of the way The way we as humans work, this is at least how I try to wrap my head around it. The way we work as humans is like we're trying to satisfy our most basal needs that have been with us for tens of thousands of years. And I would say the number one is to feel safety. And the way you feel safety to me is through status and connection. And one of the ways you feel status or at least as a founder, is like you feel status through kind of your role in the hierarchy of the business. You feel status through the accolades that you get externally. And so when you no longer have a place in that hierarchy, when you no longer are getting accolades for being the CEO, therefore you've lost your status. To me, you, you've lost your safety. And Kat Cole talks about this concept of diversifying your purpose portfolio, which, you know, to me what it basically means is don't throw all your eggs in a single identity basket, right? Don't just think of yourself as a founder and CEO. Don't just think of yourself as a parent. Don't just think of yourself as like a friend. Kind of think of yourself in many ways. You are many things. And I think the reason many founders, including myself, fail at doing that, at diversifying kind of their identity, is because your sense of value ends up being attached to the amount of time that you put in certain parts of your identity. And as a founder, inevitably you put a ton of your time in this one identity. And so when that time is very quickly taken away from you, you don't necessarily— there's almost kind of like this whiplash that happens because you haven't yet reallocated your time to these other things in your life. So you have to be really proactive and intentional about giving your time to these other things. Otherwise, you're going to feel this sense of the one thing that I was tied to has been taken away and I haven't given nearly enough time to these other parts of my identity to feel like they truly have given me value and then safety in life.

Right. Wow, that's so well said and especially so true because it's all-consuming.

Yeah.

So you then don't do that diversity. I love the purpose— what is it, purpose portfolio?

Yeah, exactly.

I love that. And I had Svee Bandh, who's the founder of— founder and co-founder and CEO of Contactually, which got sold to Compass. And he said that even before the sale, he kind of realized that it was he talked to a lot of founders and he realized that he had to start diversifying his interests. Otherwise, to your point, the sudden drop is so jarring.

Totally.

Yeah. You have everything like taken away from you.

Yeah, 100%. It is jarring. And I think to that point, again, just like having other people to talk about this with is the most valuable thing.

Yeah. So important. So what are you— so it sounds like right now you have gone through that process. It sounds like you're feeling better about everything. You're sort of tinkering with a bunch of different things. Is that accurate?

Yeah, I would say I've gone through this process of trial and error to find things that I enjoy spending time on.

Yeah.

So like I mentioned, I tinkered with angel investing. I don't really enjoy it. And again, I try to be super intentional with my stories and words because that ends up being my thoughts and my thoughts end up being how I behave. And so like, I don't enjoy angel investing right now. Could that change? Absolutely. But at this point in time, I don't enjoy it. I tinkered with the idea of buying small businesses because that's a very popular thing that my friend Cody Sanchez does. And so for a period of time, I was looking at buying mini golf courses. The idea was to buy a bunch of mom-and-pop mini golf courses, wrap a brand around it, operationalize them a little bit, and then turn them almost into like a Topgolf for mini golf where it's like a tech-enabled mini golf. The idea sounds great, but I realized that like not starting something from scratch. It didn't feel scratch enough for me to get excited about it. So I wasn't excited about that. And so I've gone through, I would say, like 4 or 5 iterations of things I've tried and really haven't gotten excited about them. The things that I am excited about right now is providing kind of like advice and consultation to Austin when he solicits it, to other founders that I'll just kind of like just informally help out. I enjoy creating content. That's why I have 3— 2 podcasts and a video series right now. I have The Crazy Ones, which is this startup radio show, basically Impostors, which is a show interviewing top performers, top performers about critical challenges in their careers and kind of their mental health journey as they navigate those challenges. And then I have 60 Second Startup, which, which is like my version of my short-form version of Shark Tank where I have entrepreneurs pitch their businesses in 60 seconds. Like, I love creating that content partially because I love being creative and partially because I think it leans into one of my skills, which I would consider to be like storytelling, salesmanship, articulation. I enjoy building things from scratch, which is why I have these like little side projects right now. I have the startup database that I'm building.. I also have a backyard game that I'm building, like learning to build a physical product. And it's fun. Yeah, it's a product that like literally worked with manufacturers in China to build it. The hope is for it to be like the next big backyard game for families. So I love tinkering. And so I actually spend a lot of time now looking at models of people who also like tinkering and have built good structure around their tinkering. So One example of that would be like my co-host Jesse Pujji. He built Ampush, which is— was one of the largest Facebook marketing agencies in the world, actually sold that business to Red Ventures. And what he— he's similar to me where he loves building new ideas. He loves going zero to one and then having an operator run the business and kind of like his why, his purpose is to help grow entrepreneurs. And so what he's done is he's built 3 businesses in the last 18 months. He stands them up. He has funded most of them with his own money from his previous business. He gets it to a point where he believes it's hit product market fit. He finds a first-time operator so they can learn how to be an entrepreneur. He trusts them with the business. They scale it. He moves on to the next one to build, stand up, and find the next operator. And, you know, now this has become called like the venture studio model for a while. It's existed for a while, just didn't always have that name. That structure is really interesting to me because it allows me to be kind of like crazy creative and have structure around kind of my scattered brain.

Or your desire to build. Exactly right, right, right. Boy, I really love that. I didn't actually realize you were doing your imposter video series. Yeah, I'm obsessed with the idea of imposter syndrome.

Yeah.

You mentioned how you had this experience with OCD, and actually a lot of people have OCD. I think you said 5%.

Yeah. That's like, I would say, the minimum, the floor for what it can be.

Right. It turns out, you probably know this already, 95% of high performers have at some point experienced imposter syndrome or severe self-doubt. Yeah.

Not surprised by that at all.

Yeah. Yeah. I mean, have you also dealt with that?

Oh yeah, totally. I mean, I would say a lot of what I just— Yeah. It's my entire story.

Alisa, were you listening?

Yeah, exactly. I know. I, um, and that's why I started the show originally, is because I was like, I think so many— beyond creating kind of like groups for people to meet together, how can I kind of provide a solution for kind of like founder and professional loneliness at scale? And the idea was a show where the best in the world open up about their imposter syndrome and their self-doubt. Because it's just a constant reminder in your ears about even the very best are having likely the same exact thoughts that you have.

So true. And the way to get— the only way out is through.

Yep.

Right? You just got to keep putting one foot in front of the other. And your point earlier about, oh, if I fail, it'll be okay. We all need to just own, if I fail, it'll be okay.

Yep. And I think, by the way, I think it's a cultural thing. Because, you know, a startup community that I'm always really— that I admire a lot is like the Israeli startup community because, you know, my understanding is like so many unicorns and big businesses have been founded in Tel Aviv and in Israel. But what I also understand about the ecosystem is like failure is an expectation, like so so many of these successful Israeli entrepreneurs have failed 3 or 4 times before and they don't even use the word failure there. And it reminds me of— I was listening to the All In podcast yesterday, or actually, sorry, I was listening to All In, but I was actually listening to Lex Friedman's podcast where he interviewed Chamath Palihapitiya, who's one of the co-hosts of All In. And Chamath is telling his story and, you know, he basically talks about like his whole thesis, and it comes from him running product at Facebook, right, where the original mantra was, was it build things or like build fast and break things?

Yeah, build fast and break fast and break.

Exactly. And he's like, you know, the entire way to accelerate in your career is actually to just make as many mistakes as fast as possible because The way it works, and this is like an old Charlie Munger mental model, is like there's this very tiny circle of the things that you know that you know. Then there's this little bit bigger circle of the things that you know that you don't know. And then there's a massive circle that's like multiples of those two circles that are the things you don't know that you don't know. And so the only way to start pushing the things that you don't know that you don't know into the things that you know that you don't know and that you know that you don't know into things you know that you know is by making a lot of mistakes that reveal your blind spots. And so on the podcast, he was like, I'm just using the word mistake because that is in the vernacular of our culture, but they're not mistakes. Every one of these things are learning opportunities.

Yes. Or they're not failures.

Exactly.

Right. Wow. I have to say, I'm again so struck how wise you are at age 29 in terms of being able to figure these things out, which I think takes a lot of people quite a long time. I mean, do you experience that you feel like you've kind of gained a lot of wisdom in your young life?

Totally.

Is that from your experiences, your tragic experiences?

I would say it's a combination of, I would say, my experiences that have given me perspective. I would say it's one of the things that really does attract me so much to entrepreneurship is I think it is such an accelerant of personal growth. I also attribute it to, you know, my fiancée being, I would say, so high on the, on kind of the EQ spectrum. And, you know, it's not— I don't think it's a coincidence that every kind of serious relationship that I've been in in my life, the mom of the person that I was with was a psychologist. Like, to me, that is definitely not a coincidence.

Yeah.

It's like, I think you— we look for things that are both really interesting to us or also that, that allow us to grow in areas we weren't necessarily provided the same resource growing up. So it's like, I love my parents dearly, and I think they parented me in such an amazing way. But I think one of the opportunities where they didn't even have the tools to develop me was kind of on the emotional side. And so I think that's why I've really sought that out in life. And I would say, yeah, the other piece is entrepreneurship is not just a vehicle for great personal growth as a function of like, you know, having to make a lot of decisions, weighing trade-offs constantly, using both the left and right side of your brains. But I also think the best hack of entrepreneurship is it gives you unfair access to really smart people. And so it's just like one of those things where meeting really smart people just leapfrogs you years because they just tell you what they've learned over 10 years in 10 minutes.

Yes. Oh my God, I love it. That's so good. Alex, just a couple more questions. What do you wish you had known earlier on your journey?

Um, that it's okay to not be the CEO forever and that is perfectly fine. That it's okay to be motivated by money. That is perfectly fine. Um, and that it's really important to make sure that you're nurturing other parts of your identity. And even if you're a founder and CEO, you're not just— that is not who you are. That is one of the things that you do.

Beautiful. Good. Thank you so much. And what advice do you have for other founders as they embark on their journey to grow into leaders?

I would say the first is give yourself the space to be reflective about how you're spending your time so that you don't end up being the definition of insanity, which my pledge master in college gave me. Shout out to Grinch, which is the definition of insanity is doing the same thing over and over and expecting a different result. And to me, the only way you avoid insanity is by giving yourself the time and space to reflect on what you like about your current situation and what you don't like about your current situation. And the reason I think it's so important to share is as an entrepreneur, it is so easy to get lost in the weeds and the minutiae, especially in the early days of the business. And unless you create a force function for pulling yourself out of the business, the business will consume everything that you are.

Well said. So much wisdom. Alex, thank you so much for joining me today. This was such an important conversation and I think everyone's gonna benefit from it.

So thanks so much for having me. Really, really enjoyed it.

Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alisacohn.com.