Jan. 17, 2023

How an Entrepreneur Turns Self-Hate into Love

How an Entrepreneur Turns Self-Hate into Love

Episode 16: Today, hosts Alex Lieberman (@businessbarista) and Jesse Pujji (@jspujji) discuss some of the highly self-critical beliefs Alex has been reflecting on as a founder, and how he’s learned to reframe them for himself. 


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Alex Lieberman (@businessbarista)

Jesse Pujji (@jspujji)




Alex Lieberman: Also, if at any point you see me going off camera, it's because I have my toilet paper roll that I'm blowing my nose with. Because, of course, on the day that we're doing a double header is when I sound like Squidward from SpongeBob. So just how it goes. What's up, everyone? I'm Alex Lieberman.

Jesse Pujji: Yo, this is Jesse Pujji.

Alex Lieberman: And this is The Crazy Ones. What's up, Crazy Ones listeners? This is Alex.

Jesse Pujji: Hello, hello, this is Jesse.

Alex Lieberman: Joined by my co-pilot, Jesse. As I promised last episode, we're going to be trying some new shit this year. This is a new format. We're going to try out and see how it lands. So after you've listened to the episode, shoot us an email at thecrazyones@morningbrew.com and let us know what you think. Rather than the classic style of three topics, 45-minute roundtable discussion, we're going to focus on one thing, go deep in that. And then make sure you listen to next episode that comes out, because we're trying a new format there where we introduce a guest. So let's do this damn thing.

Jesse Pujji: Here we go.

Alex Lieberman: Okay, so I posted or tweeted a tweet two or three weeks ago, and it was titled "Eight Self-Hating Beliefs that I've Reframed Into Self-Love." I wrote this thread because I'm a journaling guy now, and I've been journaling for the last month or so, and it's been great. One of the topics was...

Jesse Pujji: I can't get into journaling, by the way, just a sidebar.

Alex Lieberman: I couldn't for the first 29 years of my life. And then...I really believe in habits that have a trickle-down effect, so I've gotten really into health and wellness over the last two or three months. Got a nutritionist, got a trainer. My whole view was like, if I could get disciplined about my food and exercise, it would have an impact on other things. So this may be mental or not, but now I've gotten into the habit of journaling after that happened.

Jesse Pujji: How'd you get into it? What'd you do?

Alex Lieberman: How did I get into journaling?

Jesse Pujji: Yeah.

Alex Lieberman: I went online; I searched "journaling prompts." I also just brainstormed some prompts. I made a note with 50 prompts so that it decreased the friction, where every day I don't have to think about a new thing to write about. I put a 30-minute block on my calendar every morning where I turn my phone on, the Freedom app. Can't even do anything on my phone, it's useless. And so then I just write for 30 minutes. I have my seat right by our window that looks out of our place. You see the New York City skyline, and I just write for 30 minutes.

Jesse Pujji: What's the app called? I gotta get that app.

Alex Lieberman: Oh, Freedom is great. It's on your computer or your phone. You basically make a blacklist of all of the things that steal your attention, so text message, Slack, certain websites, certain social media apps. And so then I go to the app every day during times of focus, I hit Start and you select the time, and you go to access any of these things, and it basically just comes up with the Freedom screen saying that you've been freed.

Jesse Pujji: Love it, dude.

Alex Lieberman: Yeah, yeah, it's incredible.

Jesse Pujji: So that's helpful. That's helpful. I'm going to try it.

Alex Lieberman: Yeah, try it out.

Jesse Pujji: And then what do you do with the journaling? Do you do anything, or you just learn?

Alex Lieberman: I haven't done anything with it other than it forces me to be reflective. I've saved all of them in Evernote. The range on these is crazy. It's like I've got everything from, "What are all the ways I think of business ideas," and for 30 minutes straight I just jotted down every way I could find business ideas, to, "What are the fondest memories of my dad," to if I wanted to write a Pixar movie, and the one rule is it has to have a lesson as a through-line through the whole movie; write a short movie. And so I've done all three of those in the last week.

Jesse Pujji: That's sick.

Alex Lieberman: It's just fun.

Jesse Pujji: Yeah. All right. Well, sorry, go back to your...so you wrote about self-hating versus self-loving beliefs.

Alex Lieberman: Yeah. I wrote about this because, I think I've told you about this, but right after I moved out of the CEO role for Morning Brew, I would say I was the most self-deprecating and self-conscious I've been in my life. I totally lost my swagger. And so I think part of my journey was figuring out what were all these self-limiting beliefs I've had. And so I wrote them down, and then I've tried to figure out, "How do I turn those actually into things that serve me in my life? So should we just run through them and just see where it takes us?

Jesse Pujji: Yeah. One quick thing before we do those, like self-limiting beliefs, I don't know, should we spend a minute on that? Why do people have them? I have my thoughts and experience with it, but...

Alex Lieberman: Yeah, I mean, I actually will explain what I think my self-limiting beliefs are. They all fall into a similar bucket, which is, in my professional life, I have an image of the people who I look up to that I want to be more like. I think my comparison to these people from the best entrepreneurs of all time like the Musks and the Bill Gates, to even my co-founder Austin, these have always been my reference points. I think the reason I care a lot about being more like them, honestly, just goes back to when I was younger and not feeling like I belonged. And so I need that validation from the people that I really want to emulate. And so my self-limiting beliefs, I think, all are bucketed into things that I feel like these people have that I don't have, which means I am not enough.

Jesse Pujji: Yeah, that's interesting. I've told you about the upper limit problem stuff, right? Have I ever told you that? There's this book...

Alex Lieberman: I think you have, but just define it again.

Jesse Pujji: Yeah, so there's this book called The Big Leap. I mean, one of the big things with all these upper limiting beliefs is, and I've never done therapy, but I've done...obviously been coached heavily, which is very similar. And a lot of it is you just explore your childhood and different things you learned. By the way, one time I asked my coach, I'm like, "If you wanted to change someone's life the most you could in the shortest period of time, what would you do?" And he had a very good answer. And it was...

Alex Lieberman: What was it?

Jesse Pujji: In the first, you have 30 minutes and you have to change someone's life. He goes, "I'd spend the first five to 10 minutes trying to drill down." And every human has basically one to three core beliefs that were ingrained in you as children in some way or another through some set of trauma experiences. Could be anything, right? And then I would try to get them to see that the opposite of that belief is just as valid as their belief. Try to get them to basically go, not that they don't have to stop believing it, but they have to see that another way could be wrong. So for me, for example, one of them was immigrant parents. My dad was a businessman. It's like, money is success, security, money is good...and he drilled into it and he's like, "But you know, there's people who make less than you or have less than you, that feel way more secure, way more happy, way more successful." And I'm like, "Yeah." I totally saw it intellectually, and he was trying to get me to believe it inside. And that was really hard. It was just really, really...

Alex Lieberman: Oh, that's always the hardest thing, right? It's like rationally, like it takes so much time for the body to actually catch up to the brain when it comes to knowing what probably is right for us.

Jesse Pujji: But anyway, so I think a lot of limiting beliefs come from there. And then the upper limit problem, there's this book called The Big Leap, and the way that he frames it is super cool. He basically says like in your childhood, your happiness or whatever satisfaction thermostat is set by your parents and caretakers by a whole series of different things. Anytime you get above your temperature of happiness, you will actually do things like self-sabotage or a series of behaviors to bring yourself back into the zone that actually feels comfortable for you. And you'll do the opposite, too. If you have a really bad set of events happen to you, you'll do these things to bring yourself up. But the more common thing is, "Hey, I'm like..." and there's all these fundamental beliefs. "I'm not worthy. I'm not supposed to be here. If I do this I've abandoned my family."

There's four, I forgot exactly what they are. And once you learn this framework, at least for me, I then notice it everywhere. A really good thing happens in my life and I start to worry about something bad is going to...and anything that brings you down a little bit. And so I think the core of self-limiting beliefs are actually, in my opinion, the upper limit problem. I call them...some of my friends who know this, the framework, and I will text, I'll start texting you going, "I'm upper limiting today. Things are going well and I'm creating things to be worried about," or the thoughts going through my head are bringing me back down, as opposed to enjoying being up and being high.

Alex Lieberman: It's such a classic thing that I experienced like even recently. I've generally felt like things are going well. I feel really good about the direction of the show. I feel really good about just like my family. I feel good about the stuff that I'm building on the side. I feel good about Morning Brew. And always the first thought that comes to me is, things are too good. Things are too good.

Jesse Pujji: When's the other shoe gonna drop?

Alex Lieberman: Something bad has to happen, and honestly, and I think the place where something bad happens, where my brain goes, is it has to be something with my health, my health. There's going to be something that comes up with my health because everything's too good right now...

Jesse Pujji: But even that worry, just to be clear, even that worry you have is a form of you upper limiting yourself.

Alex Lieberman: Totally.

Jesse Pujji: Even if the bad thing never happens, the fact that you're giving cycles to worry about is like, "Ugh, I can't be this happy. I gotta lower this a little bit. It's too good." And I think it's a really powerful...once you learn it, and I wrote a thread about it on Twitter at some point, it's such a powerful paradigm because you'll notice it all the time. And even small examples: Someone gives you a compliment and you're like, "Oh, no, no, no, no, it's not me. It's somebody else." You'll misdirect that or push it to someone else.

Alex Lieberman: Well, I want to go into some of these self-limiting beliefs in a second, but what is your strategy now for basically when you know you are upper limiting, to not have it hold you back? What do you do?

Jesse Pujji: Yeah, well, so the book actually has stuff, and I did this for probably a year. He has a mantra, and I could probably remember it because I reminded myself of it twice a day. And it was like, "I am," it's like some affirmation, right? It's like, "I'm happy with my success and letting other people be more successful, and I want to bring more love and success into the world." Or something along the lines of raising yourself to being like, it's okay to have that thing. I think typically if I notice it, it's typically I'm feeling threat from somewhere. I'm scared, and I'll usually do some breathing or I'll just try to say it, even just going, "Oh, I think I'm upper limiting...I think I'm trying to bring myself down right now instead of enjoying it."

Alex Lieberman: Totally. Yeah. That's interesting.

Jesse Pujji: All right, let's get into yours.

Alex Lieberman: Let's do it. There's eight of them, but because you are now, in my brain, the chronic late person, and we only have 28 minutes left, and I am publicly shaming you to see if that leads to behavioral change over the next few weeks, we're going to just pick the best ones or the ones that you find most interesting. So I'm going to start, and once you feel like we've covered one, it's fine. Just be like, "We're done with that; we'll move on to the next one."

Jesse Pujji: For the record, you needed to record two episodes and therefore we moved up an hour into an otherwise busy schedule.

Alex Lieberman: Yes, but a commitment was made to that time. It's so funny, I say this also in jest because, not to say you're late in other things you do, but for the longest period of...

Jesse Pujji: I am, by the way, for what it's worth.

Alex Lieberman: Okay, I didn't know. But I would say for the first 25 years of my life, I was always late. And I don't remember actually what happened, but there were a few events that happened that I started really feeling bad about the impact it had on other people. So this is only a change in the last year. Before that, I was incredibly selfish with my time. Okay. So first belief: Great entrepreneurs must be deeply opinionated to lead well and take big swings. And so then the self-critique I have of myself is, I don't have strong enough opinions or enough contrarian views. So that was, I would say something that I've always felt self-conscious about, because within the context of Morning Brew, I always felt like my co-founder seemed way stronger in his views than I was. And it always made me wonder if I didn't have enough strong views, does that mean the vision for the company wouldn't end up being mine, because I'm not standing for enough things or for enough points of view?

Jesse Pujji: And so how'd you change that to self-love?

Alex Lieberman: Yeah, so the way that I've thought about it or reframed it is, I'm open-minded, and that actually is a huge benefit because it creates safety for others. People know when they talk to me that I'm not gonna judge what they're gonna say. I'm not going to say it's wrong up front. I'm going to try to think through it with them, and that I have the capability of taking bets once I'm informed and they're needed, and I don't have to have a strong view on everything. And what I'll say is this plays into a broader framework that I think of, that I think there's this kind of x axis and y axis. I think there's a y axis of, you're either highly opinionated at the top or weakly opinionated at the bottom, and then the x axis is, on the far right, you're closed-minded and on the far left you're open-minded. And so I think most people fall into two of these, whatever you want to call, quadrants. I can't remember geometry or math or whatever.

First, I think people are either very closed-minded and strongly opinionated, or open-minded and weakly opinionated. And my view is the sweet spot is kind of the old adage of, "strong opinions loosely held," but I think it's very hard to achieve. And I felt self-conscious that I sit in the open-minded weakly opinionated quadrant.

Jesse Pujji: Hmm. Do you think you actually sit in that, though?

Alex Lieberman: I don't feel like I have that strong of views, and I get very self-conscious about it. What's been your experience with me?

Jesse Pujji: I mean, I think you have quite a few perspectives. I think you've lived through a lot, and maybe the way you're defining perspective...like I think that's another thing we do, people, like entrepreneurs, beat themselves up on is like, I had this period too where I was like, "I don't have a passion. Bill Gates was passionate about software, and somebody was passionate about flowers, and somebody was passionate..." And I was like, I don't have a passion. What's up with that? And it took me a long time to go, "No, I do." It's like business entrepreneurship, it's leadership, it's people. It's just not like a thing. It's not a specific product or [inaudible]. So I feel like you have opinions. They may just not be on the future of journalism. Maybe they are...

Alex Lieberman: Totally.

Jesse Pujji: But you walked in with a lot of predictions last time we chatted, and you have perspective on how certain people do things or how they want to live their life or what to do around different problems and situations. So I'm not even sure I agree with the premise.

Alex Lieberman: And again, maybe some of it comes back to, like, we're always anchoring based off of other people, and so it's like maybe even just my co-founder sits far on the spectrum. And so relative to him, I don't feel like I'm far, but that doesn't necessarily mean I don't have opinions.

Jesse Pujji: Yeah, I think that's a huge...I mean, one of the things I've told you, like Nic and I obviously worked together for 20 years, including starting Ampush, and there's a lot of...now he's working on something and I'm working on something separately, and him and I are still best friends, so we'll talk a lot and we'll go, "Man, I didn't know I had this gear in me because you were always doing that gear. And I always thought I didn't have that gear, and now I have it." And he's like, "I can sell, Jesse, but I'm sitting next to you and you're such a good salesperson that I always let you sell." And so I think there's a ton of that.

Alex Lieberman: It's so true.

Jesse Pujji: Sort of relative to your co-founder, especially.

Alex Lieberman: To your point, it's like something that I've found is a consistent thing that's said to me when I'm just helping other founders work through challenges is they always are like, "Wow, it's fascinating how your brain works, your ability to break down these problems in such a clear and simple way." And the reason I say that is not to brag. It's actually because for the longest time, I felt like I didn't think about things in an analytical enough or simple enough way, because my view is like, that's always what my co-founder was great at. And so it's just very interesting when you pull yourself...you create a little bit of distance from your business, what you find.

Jesse Pujji: Yeah, I think that's right. All right, what's the next one?

Alex Lieberman: Okay, number two, the belief is, you must be a horse with blinders maintaining deep focus for a long time. The self-critique I have of myself is, I'm distracted to the point of procrastination and lack of prioritization. And the reframe is, I'm creative and always think of new ideas. This can be maximized if I find a great operator. But what I'll say is I feel like part of me is playing it safe and shorting myself by saying, "This can be maximized if I find a great operator." I'm basically just assuming I'm shitty at focus, I'm shitty at operating, and so I need someone else. I feel like that is the easy copout.

Jesse Pujji: Right, right, right, right. Oh, this is such a good one for me. I have the same exact one. Have you ever done the Enneagram?

Alex Lieberman: No.

Jesse Pujji: Oh, dude, we gotta get you to do the Enneagram and talk Enneagram on the...

Alex Lieberman: I'll do it...

Jesse Pujji: On the thing.

Alex Lieberman: Yeah. I'll do it.

Jesse Pujji: It's been a crazy tool. I like MBTI also, Myers-Briggs. Have you done Myers-Briggs?

Alex Lieberman: I haven't done that either. No.

Jesse Pujji: You haven't done that. Oh man, you would love these things.

Alex Lieberman: We should do an episode of just doing these tests.

Jesse Pujji: Yeah, yeah. We use MBTI a ton at Ampush, and then my coach introduced me to Enneagram, and that's like...my type, it's so interesting, it's a funny story is, I took it...and my type is a, it's called the Enthusiast. It's like excited, loves a shiny object, gets excited, and then kind of falls off or gets distracted easily, frays easily. And literally the examples they gave, some of them are like, "You're the kind of person who goes to an ice cream restaurant or an ice cream store and you have to order two flavors because you can't just settle on one." And I literally...

Alex Lieberman: That's amazing.

Jesse Pujji: I do that to this day, or my entire life. I bought my wife two cards for every occasion because I'm like, "Well, I want a funny one, but I also want one that's really sweet." And I've always bought her two, so she has two cards for every single occasion.

Alex Lieberman: At first I thought you said two cars. And I'm like, "Wow, you're a good husband."

Jesse Pujji: Two cards, one goofy. Anyway. And it's so funny because my brother-in-law did it and he's the same type as me. He's also an entrepreneur. And we had a phone call about it. It kind of happened around the same time and I was like, "Oh god, I'm never going to be successful. I don't know how to focus. You clearly have to focus. Look at all these people, look at Bill Gates. There are all these billionaires..."

Alex Lieberman: We've clearly thought about the same things, but you've explored it more.

Jesse Pujji: And he, dude, but hold on, this is the best part. He was like, I don't know if he talked first or I talked first. He's like, "I'm so excited. This is who I am." And he really, he flipped it completely on his head, and it sort of blew my mind. He was like, "I need to figure out a way to take advantage of this unique enthusiasm and ideation I have, because this is who I am, and I want to build a business that I want to help myself figure these things out to be this way. I'm gonna lean into this. This is a strength, not a weakness." And so it was just so funny because it's exact same thing. It was just, one of us viewed it as a strength, one of us viewed it as a weakness based on some stories we held about what's what.

And I think it's a real one. I do think...I don't know. A lot of this, a lot of self-hating and self-love is about grace with yourself and just being comfortable being like, "This is who I am." I mean a lot of Gateway X was designed around this issue, and I find myself, I've told my coach, I'm like, "This is way better." Dude, when I was running Ampush, I would distract the hell out of the team because I would come up with new ideas and like, "Let's go do this. Everyone go in this direction." They'd be like, "Jesse, we just went in this direction. What are you talking about?"

Alex Lieberman: Yeah, you and I are so similar in that regard.

Jesse Pujji: And so I'd say the setup today, having the right types of people around me in those leadership roles...I sent you the investor overview we did for Kahani, and it was all Nak. It was all the COO who's like, he's a badass. He put that together, but we're just very different. Our strengths are in very different places. So I don't think it's a copout. I don't know. I don't think it's a copout.

Alex Lieberman: And I think there's probably a reason that the way I'm thinking about what does chapter two of my career look like is quite similar in structure to what you've done with Gateway, just because...

Jesse Pujji: Well, by the way, one thing that might...like I saw Ric Elias do this and it might help you circle the square, is just because you're not the person who has to quarterback everything doesn't mean you're not the person who drives accountability throughout the organization. So that's a big difference...I still, to all the things are accountable. I look at the numbers, I ask people what questions on P&L...

Alex Lieberman: Explain what that actually means in practice.

Jesse Pujji: Yeah, I mean I saw Ric do it. It's like, he lets people run with things and drives them and he's looking over everything. But you spend time with him, he'll look at your P&L in 15 minutes and he'll ask you 10 hard-hitting questions or he'll ask you your priorities and you'll have a very clear sense for the priorities. So he sets the tone for culture and what's important and what's not important and what are the expectations. So I think that is still an important part to retain as a leader if you want to...Elon has to do those. Clearly, he must have lots of people around him doing all the day-to-day stuff, but he doesn't absolve himself from that stuff. And so I think that, at least for me, is how I circled the square on this one.

Alex Lieberman: I like that.

Jesse Pujji: I didn't give myself the copout. I say, "I'm still accountable."

Alex Lieberman: Totally. Okay, so first one, the first one you don't necessarily agree with; you think I have opinions. Second one, you think building the infrastructure around yourself so that it respects all this energy and creativity actually has validity to it. Third one...

Jesse Pujji: And hold on. Second one, one of the last things, just for anyone listening, there is a spectrum to these things. If you're so afraid you can't...like I've met entrepreneurial people at Twitter. They'll tweet me and they have 10 ideas in 10 days and they don't make progress on any of them. That's an extreme version of the same type seven behavior, like my type is a type seven, the enthusiast. The other extreme is you or me. We've started companies. So we need to hone ours and kind of improve it and be mindful of it, but it's not so crazy that it needs a whole wholesale change.

Alex Lieberman: Yeah, it makes me think of the age-old question of, do you spend time strengthening your strengths or strengthening your weaknesses? And my view has always been you triple down on your strengths and you improve your weaknesses...

Jesse Pujji: Mitigate them...

Alex Lieberman: ...just enough so that they don't hold you back from your strengths.

Jesse Pujji: Totally. Or from what you want.

Alex Lieberman: Okay. Exactly. Number three, the belief is, being an entrepreneur means spending time on things you don't enjoy. This self-critique is, I don't work hard on things that are not interesting to me. The reframe is, my body keeps the score and allows me to get excited about the journey when the destination aligns with my values. And so just to give context here, by the time that I had transitioned out of the CEO role at Morning Brew in April 2021, very honestly, I was working less hard on the business. I would say part of it was because I was dealing with my own things in life: anxiety, OCD. But also part of it was I felt like I lost some of that fire that propelled me in the early days and I wasn't sure why. And at least one of the ways I thought about it is, I just wasn't loving the work that I was doing and I couldn't motivate myself to do it.

And it was a mindfuck for me because in the past, even if I didn't love the thing I was doing, I still worked really hard on it. I still had that fire. And so then I guess my question is, how do you think about when you not enjoying doing the thing still warrants you working hard on it, versus when it may actually be a really good sign that you're not working on the right thing anymore?

Jesse Pujji: Oof. Getting deep here. So the thing I was taught, which I very much ascribed to, and I had a similar experience to you, is there's five types of motivators. There's fear, there's extrinsic: money, titles, there's intrinsic, like beating your own score. There's play genius, which is like, "Oh, this is just fun. I'm having a blast." And then there's love. And it's sort of like the empathic love. It's like the love of the human experience, helping the human experience. And we all use all of them all the time, but we tend to default to a few of them. And especially entrepreneurs. We love fear. We're addicted to it. The example, the most classic example, is Travis Kalanick, like chip on his shoulder. He's got to prove himself to the world, right? And one of the things that happens is when you have success, for entrepreneurs, you go, "I don't feel scared anymore."

So different people do different things. Some people go, "I gotta set the number higher. I'm going to keep setting the number higher because oh, man, I'm fine here, but I got to look to that guy who makes all this money, I'm not that guy yet." Or in Travis Kalanick's case, some people would say he subconsciously sabotaged his way out of this job. He really hurt himself to the point where he had to start another company and he had to do it again. And so fear is the most common...by the way, it's the most effective. So I'm not judging fear.

Alex Lieberman: So fear is considered the most effective?

Jesse Pujji: You put a gun to your head, you're gonna run faster than you've ever run. But the downsides of fear are that they leave a negative residue on you and others, and they're not sustainable. And they use Bill Gates as this example. He was the fear-driven guy, and then he became the richest man in the world. He was like, "I'm bored." And then he jumped all the way to empathic love. "I'm going to go cure polio. That's what's next for me." And that's what has sustained him actually longer than Microsoft sustained him. So the other downside of fear is it's not sustainable. And so when I hear your version of this hard work and all these various things, it's like, well, especially first-time entrepreneurs, anyone listening, we did everything and anything. I did anything and everything, you did it, because all we were like, "I have to be successful. I'm so scared this is gonna fail. It doesn't matter. I'll grind through anything." Right? And I think, I don't know that there's another way to do it. Maybe if you're super meditative, whatever. I think as you think about the second time journey...

Alex Lieberman: It has to change.

Jesse Pujji: It has to, if either...well, there's two doors I think people choose. One is, "Dude, Alex, why aren't you a billionaire, bro? What's up, man? Come on. Look at all these other guys. Zuckerberg was worth 10 times you by the time..." And you're like, "Oh, I must beat Zuckerberg." And you get even bigger fear. No, seriously. I think a lot of people use it. A lot of people motivate themselves that way. I'm not judging it, I'm just saying it has the same...that's the way they create sustainability as they keep moving the goalposts.

What I've tried to choose, and I'm not perfect. I choose fear all the time, or I end up in fear constantly. But the thing I've tried to pick more of is player genius. And in some ways empathic...the love. What human experience can I improve? Can I teach other people how to be great leaders? Can I coach my Gateway X CEOs? That really lights me up. And then the play genius stuff, the best example I can think of there is Warren Buffett, who clearly, the guy just loves what...he doesn't care about the money. He's like, "Oh, this is fun. I get to think about companies. I get to run this thing. I wake up every day. I eat McDonald's and I do my thing." And so I think a lot of where I've spent time with Gateway X, and it's a little scary. You have to trust it. It is truly trusting that the things that make me, that I enjoy, my zones of genius, are if I do them really well, they're gonna lead to a lot of success.

And I don't need to look at the books in the business because I don't...I mean, I look at the books, but I don't need to keep the books in the business because that's boring for me. I don't need to set the investor materials together because that's boring. This is not what I want to do. And so I have to solve for it and know that's important. But I also have to trust that if I don't do it and I actually do the things that bring me joy and my genius, and I think theoretically, if a first-time entrepreneur could do that, they would also be very successful, but it's just so hard.

Alex Lieberman: Yeah. It's just not as realistic. And I think also it's why it's so important to find the right people to surround yourself with, because this only works if you can find the people to do the things that you don't want to do. We should honestly do an entire episode, whether it's journal style or whatever on zone of genius, because I feel like there's so much to talk about there.

I want to cover two more of these before we hop to the second part of our double header. Fourth belief is, a great CEO must scale from idea to IPO. And the self-critique is, I didn't scale from zero to 100. So I am not great. The reframe is, I love finding problems and building from scratch to flex my strengths, which are creativity, marketing, and sales. And I'm grateful to have partners who are A plus stage 2 CEOs. Now, just like to provide a little bit of color there, like I said before, I felt like a huge failure after moving out of the CEO role for Morning Brew. I had this story of what it meant to be a great CEO. You have an idea, you create a product, you prove that the product has value in the world. You scale that product into a business and you take your business public. And because I didn't do that, I didn't feel like I was a successful founder or CEO. And even to this day when I'm feeling my most self-conscious, I'll ask myself, "Have I said to the world and to myself that I love doing the zero to one because I actually love doing it, or because it protects me from the reality that I'm just not great at scaling a company?"

Jesse Pujji: It's like a defense mechanism. Hmm. Yeah. Are you not great at scaling a company?

Alex Lieberman: I think actually the short answer is, is I don't think I actually took the bet on myself to find out.

Jesse Pujji: Yeah. That's what I was gonna say. It feels like an unknown.

Alex Lieberman: I actually, yeah. I actually think, I don't know. And it's just a question of, at some point will I want to know that? And it just comes back to the motivators of like, I don't know. We'll see, based on what I'm enjoying doing.

Jesse Pujji: Yeah, what do you want? I mean, one interesting reframe with all of these is they all seem to be framed through somebody else's eyes of what is the right...like, there feels like a lot of, you're trying to get the right or wrong answer, versus what does Alex want? What do you want...like in that question, for example, do you want to be that CEO?

Alex Lieberman: I think the hard answer there is, I don't think I want to be that CEO, but I always, just in the back of my head, I'm worried that it's an excuse. You know what I mean?

Jesse Pujji: Yeah, totally.

Alex Lieberman: It's an excuse that because I don't think I'm capable of it, I've created this story that it's not what I like doing and I could find someone else to do it.

Jesse Pujji: Yeah. That makes sense. What if you...one thought for you, you've never actually scaled a company because like you said, maybe you didn't give yourself the chance to, is I wonder if you just held this whole conversation slightly more lightly and just said, "I don't know. Today I'm not. Today it doesn't feel like that's what I want. Tomorrow I may want that. And if I feel like I want that..." Like one of the biggest things I've practiced with my coach is preference, like how to listen to my own preferences. And it's so hard, and it takes a lot of time, and I'm still okay, just like okay at it. But the easiest way is like, are you trying to get an answer right, or are you trying to just do what you want? And if today you wake up, you're like, "I don't think I want to be that." That may change, by the way. You have the right, in a year, to go...

Alex Lieberman: Totally.

Jesse Pujji: ..."Okay. I've launched two more companies." Now, by the way. I have the same issue. I'm like, mine is a little bit different than yours, which is like, I've seen guys like Ric or Jeff Bezos and I'm like, "It seems so cool to run a large-scale organization with an amazing culture, with this great campus." I get excited, I think, imagining myself in that. And then I look at what I've actually done, and I'm really good at the zero to one, and I'm like, "Which part of me...like am I lying to myself about...

Alex Lieberman: Exactly.

Jesse Pujji: ...what I want?"

Alex Lieberman: Yeah, exactly.

Jesse Pujji: But I actually say, "I want that." I think I want Gateway X to be a 1,000-person company or a 10,000-person...

Alex Lieberman: And the question, it sounds like the question that you still think through and it's so hard to figure out is, what's driving that want?

Jesse Pujji: Yeah. What's driving that want? Or mine's a little the reverse of yours. Am I okay settling at just launching a couple companies that get it to eight figures in revenue, selling them, and moving on with my...like which is what I've sort of done to date, and maybe I don't actually want that. Maybe that's my ego that's wanting that, and maybe the reality of me wants to build businesses, sell them, and just chill.

Alex Lieberman: Yeah. I think it's going to be cool over the lifetime of this show, just seeing just how your psychology changes around that question, because it's inevitably going to evolve. Okay. Last one before we hop. Fifth belief: Skepticism and paranoia is a must to be a strong operator. The self-critique is, I'm too tolerant, which prevents me from building high-functioning businesses. The reframe is, a bomb-sniffing dog of business is key to find cracks before they become craters. But it doesn't have to be me. Again, assuming someone else can be the person who does it. And so just the thought process here was, my natural way is being levelheaded, not being rattled, not thinking anything is that big of a deal, and we'll figure it all out. I think this honestly comes from, again, just a place of experiencing a really big trauma in my life when I was 18. And so everything in relation to that is a nothingburger.

Jesse Pujji: Totally.

Alex Lieberman: And so I think it can be really good when it comes to regulating emotions and instilling confidence in people in a business and not making people feel like they're on a roller coaster. But I worry that numbing myself from anxiety and paranoia makes me susceptible to missing cracks forming before they turn into craters. So to me, in a perfect world, I'm someone that's constantly thinking about where are the bottlenecks and the cracks in a business, but I'm also staying optimistic and levelheaded when running the business.

Jesse Pujji: Yeah. This one feels like one of those classic false dichotomies that you have...not you, people have, right? Okay, like why can't both be true? Forget about someone else for a second. Why can't you spot the important issues and address them without feeling paranoia? Paranoia has an anxiety element to it, right?

Alex Lieberman: Exactly. Yeah.

Jesse Pujji: My dad would quote to me as a teenager, "Only the paranoid survive." That was the famous Andy Grove. So I had to...I've worked on getting rid of that. I'm not sure, again, I fully have, but it almost feels like you have what everybody wishes for, which is, "I see the issues, I spot them. I see they're important, and then I methodically drive to solve them, but I don't have to fret about it." Like why do you have to fret for that to...that feels like the false dichotomy part of it.

Alex Lieberman: Yeah. I think the story is that you have to have that tingly sense, that fret, that feeling that something's always chasing behind your back to even get to a place where mentally you can find and think of these things. And I think you're right. I think you can probably just set up the right questions to ask in life or set aside the right time to find these things without feeling...

Jesse Pujji: Well, the question is, have you missed issues because you're too chill, because it doesn't rattle you? Have you, actually?

Alex Lieberman: I mean, I don't think so. Again, I would say in the scaling part of Morning Brew, it wasn't necessarily my job to think of them. But yeah, I would say, yeah, I would say, probably not.

Jesse Pujji: Yeah. So to me it's like if you're missing things, if you're genuinely aloof to the point where you're missing important stuff, yeah, sure, pay more attention. But I don't know that you have to...and by the way, all of your things have a bit of an interesting underlying belief, which I think is common. So I just want to call it out, which is, "I have to suffer to be successful."

Alex Lieberman: Yeah. Yeah.

Jesse Pujji: "If this is not hurting me, if I'm not whipping myself, then I can't be a successful businessman. That's just not allowed."

Alex Lieberman: It's two things. It's, I have to suffer, something has to be wrong for me to be successful, and I have to...I'm not as good as my co-founder at a number of things. And because I don't feel like I'm as good as my co-founder at a number of things, it means there's weakness in how I am as an entrepreneur.

Jesse Pujji: Right, exactly. And therefore, and then it explains why I'm maybe not as big as the other guy as a company, or some of those other pieces to it.

Alex Lieberman: Totally.

Jesse Pujji: But I think like, imagine, here's a fun one for you. Imagine...this is such a...if I could go into your operating system, your hard drive, and delete those beliefs, who would you be?

Alex Lieberman: I'll think about it.

Jesse Pujji: How much more powerful...if I just said, "No, you can have fun and be successful and make a lot of money and touch a lot of people." I don't know. Doesn't that feel great?

Alex Lieberman: Yeah, no, it'd be pretty powerful. I told you I'm out next week, but when I'm on the beach, I'll make it a journaling prompt one day. 

This was a fun one. I like this episode. I like the format, but we want to hear what you think. So let us know what you think of this kind of one idea, one-track format, maybe a little bit shorter than our past ones. Shoot us an email at thecrazyones@morningbrew.com, and we'll catch you all next time.

Jesse Pujji: And believe in yourself.

Alex Lieberman: Believe in yourself. Later, guys.