In this episode of Founders Journal, Alex Lieberman re‑introduces the show and highlights its most popular episodes, noting that the top‑performing content tends to explore the mental and emotional side of entrepreneurship. He then pivots to a deeply personal discussion about his evolving relationship with money after the sale of Morning Brew. Drawing on his upbringing—where his family shielded him from financial realities—his father’s death, his first six‑figure salary, and the massive liquidity event that made him financially independent, Alex explains why he feels more anxious about money now than ever. He identifies four primary drivers of this anxiety: (1) a learned scarcity mindset rooted in childhood and his dad’s passing, (2) heightened visibility into the true cost of life, (3) constant comparison to other ultra‑wealthy founders, and (4) the societal importance placed on financial success. He frames these as the “paradox of success,” where the pursuit of freedom through wealth paradoxically creates a new, addictive drive for more wealth, eroding the very freedom sought. To mitigate this, Alex shares three practical habits: surrounding himself with people who don’t validate him financially, deliberately engaging in non‑money‑motivated hobbies (inspired by a conversation with Tim Ferriss), and setting balanced monthly/quarterly goals across family, health, work, finances, and leisure. Throughout, he references insights from Scott Galloway and Tim Ferriss, provides concrete anecdotes (e.g., a $7,000 dog purchase, a $37,000 startup spend), and emphasizes the ongoing, imperfect nature of staying grounded amid success.
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What's up everyone? Welcome back to another episode of Founders Journal. This is Alex Lieberman, co-founder and executive chairman of Morning Brew. There are a ton of new listeners to the show this month, so I want to provide a quick reintroduction. Founders Journal is my personal audio diary made public for the world. The show comes out 3 times a week, Monday, Wednesday, and Friday, and episodes range from 10 to 20 minutes long, so it's very digestible. Before we hop into today's episode, I wanted to quickly share a conversation that I had with my producer yesterday. I asked him, what are the 5 highest performing episodes since we brought back the show? And I want to share the list of the top 5. Number 1 was Be the Idiot in the Room, the episode about getting good at asking questions. Number 2 was Why Successful Business Minds Have Paranoid Brains, the episode about an invaluable characteristic of my co-founder Austin and so many other great CEOs I've met. Number 3 was Why Standard Operating Procedures or SOPs Suck, where I talk about how to create great playbooks. I think that's a better name than SOP, how to create great playbooks in your business. And then I actually provide you a template to do so. Number 4 was 10 Valuable Lessons from a Successful Show, where I break down why Morning Brew's daily show has become the largest daily business news show in business in the world. And number 5 is 4 Takeaways from Threads, an episode covering my thoughts on Instagram's competitor to X, recorded right after they launched. First off, I will link to all 5 of these episodes in the show notes so that you can check out our fan favorites if you haven't already. Second, something I found interesting looking at this leaderboard is how the 2 most popular episodes are not at all tactical or strategic, but more around the mental and emotional parts Of the entrepreneurial journey, and for that reason, I'm going to keep the momentum going with a more psychological topic for today's episode. It's one that's very personal to me. I'm going to talk about my relationship with money as I've made more of it, and the scary trap that so many entrepreneurs and successful professionals fall victim to. Let's hop into it. I was listening to a podcast episode by Scott Galloway about his financial situation. And if you don't know Scott, he's a serial entrepreneur, an angel investor, a podcast personality, and an NYU professor. He actually writes a really good newsletter called No Mercy, No Malice as well that you should check out. According to Scott, he is worth more than nine figures. He is burning up to $500,000 in cash per month, $6 million a year. And he talked about his journey to making money and how he thinks about it today. Now, there are a number of things that struck me about this podcast episode, and I'm going to link to it in the show notes. I found it so interesting because I've had the same exact experience. I actually never worried about money growing up, not because I thought we were rolling in dough, but Because my parents sheltered me from it. I never knew how much we had. When I asked for something, I got it. And I had no idea how much life cost in general. And my first anxious thought about money came when my dad died. This was a week before my junior year of college. He was 46 years old. For the first time ever, I felt a pit in my stomach thinking about the breadwinner of my family being gone and only money flowing out of the Lieberman household with no money flowing in. Even still, I wasn't wildly anxious about money because my cash burn was so low. And then once I graduated from college, my starting salary of $85,000 in finance was more money than I had ever seen before. And I was living a very cheap life other than living in a high cost of living city. And even still, you know, the cost of my rent wasn't that high. If you're interested, I was paying around $1,700 a month in rent to live in a 5-bedroom apartment. On the east side of Manhattan. Fast forward to today and things look very different. We sold a majority stake of our business, Morning Brew, in 2020, and through the sale of my shares, I made enough money where I rationally would never need to work again, assuming I live the life that I want to live. And just for reference, the life I want to live is pretty nice, but it is a simple life. 3 kids, 2 homes, one in the tri-state area, one in Colorado, A nice vacation each year, experiencing new foods and entertainment without really thinking about the cost, kids going to college debt-free. That's it. And first, let me say, that is an incredibly lucky and privileged life to live. I wanna make that very clear. But what it is not is it's not a private jet, own a sports team, own a $50 million home in Beverly Hills type of life. But despite all of this, despite running all of the calculations on a spreadsheet 100 different ways of the exact life I just described, and knowing that I can afford it, I've never been more anxious about finances. And I'm not anxious in the sense of constantly thinking about how much things cost and keeping a spreadsheet budget to know where every dollar goes. I'm anxious in the sense of money being the undercurrent of all of my decisions that I make in life. When I'm picking a new hobby like photography, my first thought is, can I eventually make money from it? Not just how do I get skillful at this art form? When I'm launching a new business, my financial upside is the immediate thought in my head, not the mission or the impact. And I exclusively try to start businesses that require little capital investment. StoryArc, my ghostwriting agency, started with literally $0, and I felt very financially anxious when I started my backyard sports game, The Plunge. For OG Founders Journal listeners, you'll remember that company that I was launching, and I felt very financially anxious about spending $37,000 on it before bringing it to market. On the flip side, I feel amazing and a great deal of pride when I save money or I spend very little. To be specific, after selling Morning Brew, my cost of life changed negligibly. My largest purchase was $7,000 for my dog Rambo, which, by the way, I would pay 10 times that amount knowing how much joy he has brought to my life. And there have only been 1 or 2 purchases greater than that in the 2 and a half years since. So if I'm not rationally in need of money, why am I still motivated by money? I want to explain, but first, a quick word from our partner. Enter the paradox of success. I believe there are 4 reasons that I still think actively about money, and it gives me anxiety. The first 2 are learned behaviors, and the second 2 are extrinsic motivators. So let's break it down. First is a learned scarcity mindset. I think the combination of not having any visibility into my family's finances, family members of mine talking about money in a worried way, as well as my dad passing— these things have all taught me to believe we don't have enough. On top of that, there is definitely a bit of imposter syndrome in business, which makes me think that what I have in the bank is all that I will ever have because I was more lucky than good with my first business. So I better protect my nest egg as much as possible. The second is greater visibility into the price of life. I never realized how expensive life was growing up, but now that I'm married, living in a high cost of living area, and my eyes are wide open to the costs of a family, the knowledge of the price of life definitely makes me ruminate more about it. Now, I may talk about these first 2 drivers of money anxiety in a future episode, but it is these next 2 drivers of money focus that create the paradox of success. The third is comparison to others. When talking about money, wealth is all about your reference point. I am in a text group of founders who sold their businesses. It's about 400 people. Every person has sold a business in the last 10 years. Maybe to some I am wealthy, but when some of the folks in my group are worth well into the 9 figures and talk about flying private and building their 4th billion-dollar business, I do not feel wealthy financially relative to these people. And that's why, you know, it sounds like a cliché, but comparison really is the enemy of contentment. And the fourth is a feeling of importance in our society, especially in the United States. Professional success and financial success are treated as high status. They command respect. They get you access. They create attention. We all want more of what makes us feel important and valued. And I am not immune to this feeling. Now, you may already know what I'm going to say, but the paradox of success is this idea that you strive to succeed in order to achieve freedom, financial freedom, which eventually leads to time freedom because you can then spend each minute exactly as you'd like. But success can also lead to a desire for more success. It's almost addictive in nature, and that deprives you of the exact freedom that you were striving to achieve in the first place. So the question here is, how do you escape from this unwinnable game? How do you know what's enough and then stay content when you reach enough without moving the goalposts further and further? Because I can tell you right now that I have zero desire to be the billionaire that lies on their deathbed lonely, unhappy, and regretful for chasing a mirage. But also, if I'm being totally honest, I do find it very hard at times to spend time on things that fill me up and that I know are truly intrinsically motivating. Motivated? Because when I'm posting on Twitter about some random business idea that I have, am I doing it because I'm enjoying the act of creative expression and teaching others and learning from people's feedback? Or am I doing it because it makes me feel important, because it's building up my social status as an entrepreneur, and now because I can get paid out as a creator on the platform? Or when I'm starting a new business like StoryYard, my ghostwriting agency, am I doing it because I'm excited about the problem that we're solving and the opportunity to learn a lot? Or am I it to feel important as a co-founder and a chairman, and because I'm money anxious and I want to create another opportunity to accumulate more wealth? The short answer is I don't know. If you're going to do something that opens you to external validation like money, status, or power, you will never 100% know that you are not chasing the mirage that success creates. But there are a few things that I do keep in mind to keep me grounded and avoid the paradox of success. The first is I try to surround myself with people who don't care about my professional success or validate me for my money or influence. The more I spend time with these people, the more that I realize that true connection feels way more filling than superficial relationships based on meaningless material things. The second is I try to do things that are not money influenced at all. And, you know, I got this idea from actually a conversation that I had with Tim Ferriss a few years ago where I had asked him, you know, what are you deep diving on right now? Like, what are areas of the world that you're trying to learn more about? And he explained to me that he was learning a lot about compound bows and I think hunting. And he said the reason is, is because the people who are in the top 1% who spend all of their time on this, they love it. They consider it an art form, and it would be foolish for them to spend time on it if they cared a lot about money, because these are not hobbies that make a lot of money. And so That's kind of where I got this idea of doing things that are not money influenced at all, because you can have more pure motivations. So whether it's Legos, photography, or golf in my life, I like finding things that make me feel playful like a kid again and would make no professional sense for me to spend time on, because then I'm able to compare the joy I feel in these experiences against my professional endeavors like this podcast or my businesses to try and better understand how much my professional life is driven by extrinsics versus intrinsics. And the third thing I do is I set monthly and quarterly goals that touch all the areas of life that I care about, not just work. So for me, that's family, work, health, finances, and hobbies. Those are basically the 5 big things. And so for example, my goals this month include everything from growing Founder's Journal by 20% to planning a weekly experience with my wife to 5 hours per week practicing golf. And I treat each of these goals with the same level of importance as I treat this podcast. So that is the paradox of success. It is a very real thing, and I've seen so many people fall victim to it. I have no interest in making choices that provide me no long-term fulfillment, but I'd also be lying if I've totally figured out how to make choices completely removed from the dopamine-filled status and money game. It is a process, and I hope where I sit in the process today and some of the things I do to keep myself in check are helpful for you as you think about the life that you ultimately want for yourself. As always, thank you so much for listening, and I'll catch you next episode.
