We Study Billionaires - The Investor’s Podcast Network - TIP432: The Creator Economy, Building a Personal Moat and Mental Health Stack w/ Alex Lieberman

Starting point is 00:00:00 You're listening to TIP. On today's show, we have Alex Lieberman, co-founder and executive chair of Morning Brew back on the show to discuss his foray into the creator economy, angel investing, and building a personal moat. In this episode, we discussed the benefits of building an audience when it comes to investing, the shift from product first to personality first and what that means, how to build a personal moat that sets you up for success, what role luck has played in Alex's career, how successful people, billionaires especially deal with anxiety and manage their mental health and a whole lot more. We take the conversation to new territories on this show and I hope you enjoy it as much as I did. So without further ado, here's my conversation with Alex Lieberman. You are listening to The Investors Podcast, where we study the financial markets and read the books that influence self-made billionaires the most. We keep you informed and prepared for the unexpected.

Starting point is 00:00:59 Welcome to the Investors Podcast. I'm your host, Trey Lockerby, and today we have back on the show, my man, Alex Lieberman. Welcome back. Thanks for having me. It's always embarrassing to be here because you got the world's greatest podcast voice. And I just always feel so self-conscious when I join the show. Oh, man. Coming from you, that means a lot. Seriously, amazing radio voice. I appreciate that. Well, last time you were on the show, you had just sold Morning Brew. you're kind of, I think, kind of figuring out what to do next. And there is this idea, I think, that when you sell your business for millions of dollars, that gives you the permission to just kick back and relax and, you know, take some time. And, you know, the billionaires we study especially, and it looks like you as well, who I consider to be a future billionaire, would be the exact opposite. And, you know, I heard this quote from Kevin O'Leary recently,

Starting point is 00:01:56 and he said, success is not owned, it's rented. And rent is owed every day. I wonder if you relate to that. What's been your experience as you've been kind of navigating what to do next? Yeah. You know, it's one of those things where you grow up hearing the stat that's always thrown around, right? You only need to make $75,000 a year. And at that point, every marginal dollar, there's a decreasing marginal benefit. The happiness study.

Starting point is 00:02:22 Yeah. Yeah. And you hear that and you're like, oh, that's interesting. That makes sense. But you don't necessarily like, at least for me, I didn't like intuitively believe it. Like, I didn't behave in my life as if I believed that. Because if I truly believe that, then I would, you know, get to $75,000 in salary and then spend time on anything else that maximized my joy.

Starting point is 00:02:42 And, you know, what I found was basically like the hypothesis, like was the happiness study talked about all the time. But I really, I think I had to experience it for myself to realize how true it is. After selling the brew, I would say my happiness was actually significantly lower than it was before selling the brew. And the reason for that was, you know, I had some money that was put away into a bank account. My lifestyle didn't change. You know, what have I done since selling the business? I've moved to Hoboken, New Jersey. I have a dog, and I've gotten engaged, and those are all things that would have happened irrespective of selling a company. But all that, basically,

Starting point is 00:03:22 what has happened is the void of identity, right? Like, my identity was so tied up in Morning Brew. Alex, the CEO of Morning Brew, that's how the world knew me. That's how I knew myself. And so I started feeling a lot of anxiety around what next. I felt anxiety around not feeling like I was growing anymore. I felt anxiety around kind of imposter syndrome. And it probably sounds crazy to people on the outside of like, like, dude, you just built a successful company. You sold it. But like, that's not how I internalize it. For me, it was you were basically pulled along for the ride for the last six years. It was all luck, no skill.

Starting point is 00:04:00 And now the decision you have to make is do you want to prove to yourself or to the world that you're not a one-trick pony? And I say all of this with the caveat that like, I don't think I try to spend a lot of my time now kind of triangulating around like what is the shit that actually gives me energy and happiness when I spend my time? But for sure, right after selling the business, I felt this pull to have to build something else to stay relevant, which again, when I think about that statement, it's so ridiculous because it's like, who am I trying to stay relevant for? You are busier than ever, it would seem,

Starting point is 00:04:36 where you've got multiple podcasts going. Your personality and your personal brand has just shot up. I feel like in the last six months, you've got top 10 podcasts hitting the charts. It used to be about a brand would be the focal point and it would associate itself with the personality. But nowadays, we have this thing called the creator economy that I think is still pretty nascent, but building like super fast. And now it's almost like the personality comes first. And that's the powerhouse. And then the brands are secondary.

Starting point is 00:05:08 People are going to the source of this individual to follow, then going to the commerce from there. And you've become this expert of growing an audience first with Morning Brew and now your own brand. So I'm curious if you follow this theory and if I'm on to something here. Yeah. I mean, I hope you're right because we're betting the house to have Morning Brew on this. And in a lot of ways, I'm like taking fully levered bets on my career on this exact notion.

Starting point is 00:05:31 What I think is that there hasn't actually been a behavioral change, meaning I think individuals have always followed individuals, aspired to be like other individuals. But the platform and the connectivity didn't exist for those individuals to wield as much power. Ben Thompson talks a lot about how the value chain of content has changed significantly, right? It used to be where the most powerful companies or brands, players in media or content were the ones who owned distribution, meaning the newspaper company owning the printing presses and the delivery routes. The TV companies, you know, owning like the channels and owning the infrastructure to get TV to

Starting point is 00:06:20 homes, radio stations, having broadband. And basically with, you think about it in three steps, all of them sitting within the word technology, the creation of the internet, all of a sudden, billions of people with devices could now feasibly be connected with one another. Social media, the platforms now that were aggregating attention, and all of a sudden, they were the most powerful players in the world because no longer was in, you know, it's so costly to distribute content because it was the internet. And then finally, the final piece on top of social platforms was, I would say the tools that gave creators the ability to not just build audiences, but to create products and

Starting point is 00:07:05 monetize products. And so, yeah, I think we're in a fascinating time right now where you see media companies like Morning Brew going all in on building brands that are built on the back. of a creator, and I can talk about what that looks like at Morning Brew, all the way to creator-led businesses being launched, right? So even talking about a recent experience, I invested in Feastables, which is Mr. Beast's new chocolate bar brand, ultimately going to be way more than just chocolate will be an entire CPG brand, right? But Mr. Beast, arguably the most powerful creator on the planet. And that's just the most powerful creator, the guy gets more

Starting point is 00:07:48 reviews than, you know, late-night TV gets. And so not only do I believe he's going to be a billionaire in the very near future, but if you think about it, all of a sudden, you launch a chocolate brand with Mr. Beast, you get many things. One is you get a massive built-in marketing channel. And so in an age where paid marketing is more expensive than ever before, I don't know the exact number, but for example, for Morning Brew, the cost of acquiring a high-quality subscriber today relative to six years ago when we started the company, multiples higher. And so cost of marketing is going up. Tools are in the hands of creators to build audiences.

Starting point is 00:08:29 And so I think it makes a lot of sense the idea of launching brands like companies with creators and partnership with creators who have built large heart loyal audiences because you get the built in marketing. The creator themselves almost acts as not just your marketing department, but your creative and brand department around product design, around the website, because that is their natural skill set. You also get naturally like influencer marketing built in because think about how many people Mr. Beast knows in the creator economy that are going to show and share his new chocolate bar on their videos, right? So there's such a collateral effect. And also think about, okay, say they're selling these products via e-commerce, but they want to break into retail.

Starting point is 00:09:12 I can't think of an easier pitch in the world. Hey, Target, this guy who has 90 million subscribers on YouTube in his videos that get tens of millions of views, he wants to talk about his chocolate bar that people can go buy at their closest target. These massive companies clearly want younger foot traffic. Like, to me, it's a layup. And so I just think having basically built in creative R&D and marketing paired with a great product and brand is a massive unlock.

Starting point is 00:09:40 Yeah, you can almost see how Mr. Beesco's public someday, right? I mean, that could be where we're heading right now. It's really insane. You talked about the ad spend competition, and I've heard you talk about how Google and Facebook seem to have, might be more than this, but at the time, I think around 60% of like all the ad spend in the world. It's like going to these two companies. And of course, Google has YouTube and, you know, a number of other things. So is that was driving the competition? You have this huge wave of people trying to get attention through ad spend, but it's just it's like this 1,000 people through the exit, you know, trying to get through to these two companies.

Starting point is 00:10:13 I think it's the combination of dollars moving from traditional advertising to digital. So that's one big trend. So simply just supply demand imbalance, far more demand coming in than there is supply on these sites, right? And that's why these sites do everything humanly possible to keep you on these sites, right? There's a reason that when you go and post on Twitter or you post on Facebook and you include an outbound link to another company's website. That's why your posts get throttled is because why would Twitter want to send you somewhere else because it makes it that much

Starting point is 00:10:47 harder to be able to monetize your attention and eyeballs if you're not staying on their site. So it's one, this huge shift of traditional advertising dollars moving to digital. The second is over time these businesses just raising the CPMs on their real estate, right? They effectively have a monopoly on a given piece of real estate. They're going to raise their prices on it. And the third is you're seeing, you know, the privacy changes with iOS, with Apple, where no longer can these companies follow people around their devices. And so it makes advertising on these platforms less precise than it was before these policy changes. And yet the cost is going up. Yeah. Interesting. Okay, so Feastables is an example of your angel investing that I know

Starting point is 00:11:31 you've been doing a lot more of in the last year. Now, growing your own brand and your own personality and getting hundreds of thousands of followers on Twitter, et cetera, and getting all this attention, I imagine that increases your deal flow as an angel investor all of a sudden, right? Where things are coming across your desk more often. People are wanting you attach to the gig. Is that a good or a bad thing? I mean, I would say, obviously there's some good and some bad. I'm just curious which weighs out. And then also, like, what have been some of the trials and tribulations of just becoming an angel investor over the last year? Yeah, I think the hardest thing for me as an angel investor has been twofold.

Starting point is 00:12:07 It's been allocating enough time to make sure I'm being thoughtful in how I'm allocating my own capital. And the second has been, maybe this is the through line of my career, but like imposter syndrome, like, who am I to be able to make great picks around companies with very little experience. And if I'm not confident in my abilities to do that, why am I allocating my own capital to do that? That's kind of the imposter syndrome around it. But what I'll say is I get a lot of value out of it because obviously I hope to drive strong returns on my own capital. But beyond that, there's like this intangible ROI of the osmosis that happens from just spending a ton of time

Starting point is 00:12:52 helping founders, helping them fundraise, helping them connect with investors, helping them think through their product strategy, helping them think through their content strategy. And so I've just gotten a ton of value. It has made me more thoughtful as an entrepreneur by spending time, angel investing. And again, you can take two approaches as an angel investor, right? You can be active or passive, passive being you just write a bunch of your own checks or you write checks as an LP into funds. And that's not necessarily a bad strategy.

Starting point is 00:13:20 There's just, it creates different options. For me, I've wanted to be active because to me, angel investing is, it's an investment decision that secondarily is an educational opportunity. And so I try to be active with all the businesses I work with as it relates to deal flow. Yeah, to me, that is not only like the advantage of building an audience, but it is also, I find it to be a necessity for me to give myself a chance of driving good returns, especially early in my angel investing career, when I don't necessarily believe yet that I can be a better than average picker. Like basically, I operate under the assumption that I am going to be an average

Starting point is 00:14:02 picker in the beginning because I need to get enough reps to understand what to look for. And so the only way that I'm going to be able to drive above average returns is he above average deal flow. And so to me, creating content, building audience acts as a natural magnet. And the cool thing that I've also found is a lot of tier A VCs are now looking for both operators to involve in rounds as well as creators. I think it is very much a natural thing now for, let's just use an example of Andresen to carve out a portion of their round for people who have built audience, basically as kind of going back to the idea we were talking about before, a built-in marketing channel for that business when they raise. And so I think being considered or thought about it as one

Starting point is 00:14:50 of many in this category of creators gives you deal flow by way of this new standard of carving out for creators in rounds for startups. So with that, I'm kind of curious, you know, now that you have a personality attached to your investments, does that limit you in any way to only using products that you would use personally? I'm just curious if you've come across something and we're like, well, that's not for me, but it's definitely a good business. What does that look like? It's a great question because to be honest, the hardest thing for me has always been understanding the value prop of a product and the opportunity of a product that I'm not very familiarized with. I even talk about always like building morning brew, not that it was easy,

Starting point is 00:15:32 but it was far easier than if I was not the consumer myself. I was the consumer of my own product. And so yes, like if I look at a number of my investments, I am a consumer, a hypothetical consumer of this product. What does that mean? Well, one, I do try to stay within kind of like the suite of things that I could be a customer for or something I get to a place where I really feel like I was able to empathize with whoever this customer is. So especially right now, do I think I'm going to be the world's greatest B2B SaaS investor? No, I do not. But maybe that's like a space where I'm like, there is someone who's spending 24 hours a day thinking through the ins and outs of B2B SaaS. Maybe I write a track as an LP because I'm betting on them and I believe there's opportunity

Starting point is 00:16:19 in the space. And so I generally focus on businesses where I very clearly can put myself in the shoes of the customer, media businesses where there's an opportunity to invest, which I would say is rather limited from a venture investing perspective, passion businesses. So like I love investing in businesses where the audience is a rabid audience, which is also why, again, creator-led businesses, I love because you're naturally latching onto a rabbit audience to start. And the final would be businesses where content strategy is a very clear remit of their strategy. And so I can actually be value at as an investor to help them think through how they

Starting point is 00:16:58 build out their content program as an accelerator to their business. And so I'll give you an example. One is this company called Atlas, which is streamlining the visa process for non-domestic travelers because getting an international visa for non-U.S. citizens is incredibly laborious, takes a ton of time. And so the product basically streamlines everything from called a three-week to month-long process to a two-day process. Am I the customer? No, but I was able to get to a place where I could see how this was really, really painful and how people would pay because it was so painful. And I also knew that content, like profiling some of the people who are their customers and are their travelers, content is a big part of their strategy to drive demand. And so I knew that

Starting point is 00:17:47 was a place I could actually add value and truly help increase the value of the business over time. I've noticed that a lot of people in the creator economy, let's call it, are flocking to products that are in, so quote unquote, the metaverse or Web3 or have Dow's. What's the takeaway here? Why are people so attracted to this kind of model, would you think? Well, I think there's a few reasons. One is when there's any, new technology. I think two types of people are attracted. One is technologists because it's an opportunity to really be on the frontier. The second is creative people because when you're in a totally blank space, like that is a creative's dream to really like to be a trailblazer within

Starting point is 00:18:30 a new framework of technology. Anytime you have a new industry where there's alpha, a significant alpha or asymmetric information or dislocation, there are always going to be opportunistic human beings. Like throughout time, that is a behavior that will never change. And so I think a lot of what you're seeing even like in the world of NFTs is entirely opportunistic. And again,

Starting point is 00:18:53 I don't think that is good or bad, but as both an investor or an entrepreneur, I think it is your job to spend enough time in it to ask the right questions and cut through the noise. so you truly understand where the value lies. Kind of curious why you haven't taken the route of, let's say, doing an angel list fund, a lot of personalities do that as well, or they'll say, hey, I'm going to invest alongside of me, right?

Starting point is 00:19:17 I'm sure a lot of people would want to do that with you. What has been your hesitation with that? Yeah. Look, I think doing that makes a ton of sense, right? We've seen everyone from Sahel, Lavingia, to Naval, to my co-founder, Austin, to Sahil Bloom. these guys have all created funds or rolling funds, and I think it makes a ton of sense, right? Not that right now is necessarily a hard time to raise capital, but having an audience, right? Like people can raise $10 million like that off of the back of the correct Twitter audience

Starting point is 00:19:50 in a given week, and it's remarkable. So I think it's an amazing opportunity. Honestly, it was a very personal decision where it's just like, I didn't want another full-time job. I like the ability to write checks using my capital when I choose, but also if I wanted to stop doing it or I wanted to just take a break for a month, I had that luxury. In my mind, when you raise a fund, you're an entrepreneur,

Starting point is 00:20:17 you're building a business, you have a responsibility to the people you have raised from. And unless I knew I would go all into that, I don't want another full-time job, at least in that capacity. I'm also not convinced, by the way, a lot of entrepreneurs go the entrepreneur to investor route. I'm not convinced that's the route that I want to go yet.

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Starting point is 00:24:27 Sign up for your $1 per month trial today at Shopify.com slash WSB. Go to Shopify.com slash WSB. That's Shopify.com slash WSB. All right. Back to the show. A lot of people understand this concept of having a competitive moat, but it's most often associated with the business, for example. And we're talking a lot about personalities right now. So I'd love to explore the ways you've thought about building a personal moat, especially around

Starting point is 00:25:01 having what you've called social and financial currencies. Yeah. So this idea of a personal moat, I actually, you know, I got the concept from Eric Torrenberg, who is one of the founders of On Deck. He wrote a Twitter thread about this. But basically, the idea of a personal mode is you can think about it just like a company moat. So company moat you think about is basically what is the strategy or unique advantage of a company that allows it to establish power and maintain power for a long period of time. And if you want to think about what are the things that create moats for businesses? I think Hamilton-Helmer's book, Seven Powers, is kind of like the Bible for understanding what generally creates sustainable

Starting point is 00:25:45 power, things from switching costs to economies of scale, brand power, etc. And so I think about personal moats the same way, just in the context of an individual. Basically, the question you should ask yourself, if you're wondering, you know, what is my personal mode as a professional or as an entrepreneur is very simple. Do I have a unique accumulating advantage in my career? If so, what is that advantage? And so when I think about a personal moat, basically I think of it as a compilation of skills and knowledge that when combined together and kind of this recipe gives you sustainable advantage,

Starting point is 00:26:27 meaning if you're a professional in a company, it makes you highly regarded where your job security is high. If you're an entrepreneur, it makes you really good at leading your business. And so, you know, there's a few examples that come to mind when I think of people who've built personal moats. The first is, and it's going to be controversial that I say this, but like Gary Vee, I love Gary Vee. I think the guy's a genius. I know there's people who think that he just shouts on the internet, but basically, I break it down into your personal mode is defined by your interests,

Starting point is 00:26:57 your skills, and then the asset that that moat creates. So Gary Vee's interest, his deep interest that motivates him is building businesses. His skills are the combination of self-awareness, empathy, and storytelling. And so empathy in my mind relates to his ability to have his finger on the pulse of what consumers are doing, which gets him involved in new technologies or businesses early. So NFTs, it was V-Friends. Baseball cards and collectibles, he did that before it became big. Early investor, I believe, in Uber and in Twitter. And so for him, what is the asset that he's built from this kind of compilation of skills? It is a massive, engaged audience that accrues value when he sleeps. And the way that I think about this combination of skills is all you're trying to do

Starting point is 00:27:45 is basically it's less about being a 10 out of 10 in any given skill, but it's more of if you're an 8 out of 10 in self-awareness, eight out of 10 in empathy and 8 out of 10 in storytelling, well, generally you're a 10 out of 10 in that mix. It's what David Perel calls the personal monopoly when it comes to writing. And so for me, as I think about my career, whether it's the morning brewer or building other businesses, I'm constantly thinking about what are the,

Starting point is 00:28:08 basically what are my unique skills, my natural superpowers that I'm just willing to spend more time sharpening, than anyone else I know. And how do I line those up with my deep interest to create an asset for me over time? And so for me, my skills, I would say, are vulnerability, empathy, and creativity. And I believe over time, what that will allow me to do is to build large engaged audiences and large engaged businesses with strong cultures. That doesn't have to be the combination to build an asset such as an audience or a business,

Starting point is 00:28:42 but it is an example of how to do that. Speaking of the creator economy and this Web 3 thing, I feel like the word of the last maybe year, six months, whatever you want to call it, is community. You have everyone in their mom talking about, hey, how community is the new, you know, it's not customer acquisition costs. It's community acquisition costs nowadays. But one of the key modes that I think a lot of people are familiar with is a network effect. And I've heard you talk about how a community can have a negative network effect over time, right? If you think about it, the more people come in, kind of the wider out the bell curve you're going and the quality can decrease from that. So I'd love to hear you talk about

Starting point is 00:29:20 the negative network effect around communities. Look, I'm running a founder's book club right now. I love this book club. And why did I do it? It was when I was like, after moving out of my role of CEO of Morning Brew, I was fiending for something to build and grow. And I didn't care what it was. I just needed to build something. And so I started picking like time-bound projects. So I didn't have to commit myself to the next seven years to something. So I was like, why don't I just build a book club? I'm trying to read. I can force accountability with other people and I get to meet other founders. So anyway, we're two books into this thing. The first book we read was the sovereign individual, which is a big book, especially in the crypto community, written in 1998 by well-known

Starting point is 00:30:00 investors basically predicted everything from crypto to COVID. The second book we read was the Will Smith memoir, phenomenal book that I think investors and professionals can learn a lot from. But anyway, there's 20 of us in this group. When we do our book club meetings, there's eight people in a meeting. And I asked the group this week, I'm like, okay, guys, you know, gearing up for round three, I was thinking about opening up the group. What do you guys think about it? And there was like palpable anxiety from the group around opening it up at all because I think they feel like such a special and safe space to have open conversations, not just about the books, but just like their own lives, their own motivations.

Starting point is 00:30:37 And I think their concern is, okay, as we open it up, not only how is the quality of the new entrance going to stay high, but also how do we moderate quality conversations when instead of eight people on a Zoom, we have 30 people on a Zoom. And so it's a very real thing. I think a lot of people espouse the value of community. It's also just fascinating that it's like a thing right now

Starting point is 00:31:01 because a community has as far back as time, Like, religion is one of the, you know, the first versions of community. Even before that, like, you know, our kind of like primal, the primal version of ourselves, there's community to protect ourselves from predators. Like, community has always been a massive thing because it's hardwired into us, the importance of connection to others. And so I find it interesting and peculiar why it's like so zeitgeisty right now. And so all I'd say is, yeah, it's really important.

Starting point is 00:31:29 It's always been important. Very few people can actually build strong community because, You talk a lot about it, and then you go and try to manage a community, and it's a trying to work. And to give props to one community I'm in, there's a crypto community called Crypto Packaged Good, CPG, that was started by Chris Cantino and Jamie Schmidt. And it's exceptional. But the amount of time and effort they have put into cultivating this now, I don't know,

Starting point is 00:31:53 2,000, 3,000 person community is crazy. Like there are people basically working full-time jobs to moderate this community. And so what I would say is it's super important. there's a huge difference between community and brand affinity, which I think people conflate a lot. And the hardest thing about community is how to scale it. You know, it was the number one thing when I invested. The second angel investment I ever made was in this sneaker community, soul savvy. I'm incredibly bullish on what they're doing because going back to, you know, my interest

Starting point is 00:32:21 in passion communities, sneaker collectors are insane people in the best way about their sneakers. And so to have a community where you get to share your collection, talk shop with other collectors, also get notified of upcoming drops so you can buy things on the primary market before it's the secondary market. It makes a ton of sense. But they've had to do a lot of different things

Starting point is 00:32:45 to preserve community while scaling a business that's all based on community. And the example I give is, I'm not sure if they still do it, but early on, basically they had a rule that every time their community got to 1,200 members in Slack, they run it through Slack,

Starting point is 00:32:59 they would have to create a new Slack instance. So now they have more. Multiple Slack instances for sole savvy members. None of them are over 1,200 people, and they've had to build out the technology for when they post something to soul savvy members, it crosspost to every single community. That's fascinating.

Starting point is 00:33:15 I'm kind of curious. That reminds me almost of like early days in email marketing so before you had MailChimp and some other things. Where do you see what's to solve for that as they continue to scale? It's a great question. I think what's going to have to happen is technology is going to have to just get better and better at managing communities while maintaining their intimacy. I just think that there's basically platforms are going to have to be built. That allows people to always feel that they're in an

Starting point is 00:33:45 intimate group with eight or 10 people, even if the group actually is 50,000 people. But that is incredibly difficult to do. And you know, you see little glimpses of this. You see it with Zoom, you know, doing their breakout rooms. But if you're talking about building, a business truly around community, you know, something like a Discord channel with 15,000 people and getting hit up by bots on the side is not going to cut it. Community being around since religion is a great example. What also has been around, I feel like forever, is exclusivity and how valuable that is and what the value that comes from. Just you were in New York, drive around any street where there's a new nightclub and you see

Starting point is 00:34:24 the demand out the door. It's not that dissimilar. I'm kind of curious because you started your career in New York, you were at Morgan Stanley. And then you start this really, you know, equities focused email letter, I would say, obviously equity related. But as you've entered angel investing, I'm kind of curious, have you bolstered up or kind of gotten into equities at any point? Are you looking at soul savvy as much as you're looking at, you know, Berkshire Hathaway or something like that? And are you playing those markets as well? Yeah. Basically, you know, my approach has been I feel so incredibly fortunate to have built up a really strong capital base at 28 years old. And so, you know, basically my goal as it relates to getting smarter about scaling my wealth

Starting point is 00:35:09 is really, like so when I'm talking about like studying the equity markets or reading through 10K, I literally just want to get smart enough to ask the right questions. And the reason I say that is I now have financial advisors who are managing my money. And I want to just be smart enough to ask the right questions as they're deciding how to allocate my capital. I don't want it, at least right now, to be my full-time job to allocate my capital. I also don't have the personality where I'm like looking at my portfolio every day, seeing, you know, what my single name stocks are doing.

Starting point is 00:35:44 I have an interest in it, but really, I would say 75% of my portfolio, actually 70% is basically just index funds in the SMP. My view is just take the base that I've built up and literally don't look at it for 50 years. That is my view. And then the other 30% is to hopefully create some alpha in the portfolio. So, you know, start putting some money into real estate

Starting point is 00:36:08 via Blackstone, via their REIT. They're doing a bunch of single family home rental investing. I've allocated, you know, let's call it somewhere between 5% and 10% to other alternatives. So that be crypto, that be angel investing and private equity. But again, 75% is sitting in just large value in growth stocks that I've said and forget basically for the next five decades.

Starting point is 00:36:35 That's a good way to sleep well at night. I respect it. I really do. It's an interesting almost like dichotomy between your background and where you're going now. It is. And I think also like, again, people look at entrepreneurs and I think they assume they're super risk-loving. And I would actually, I would say I'm not a super risk-loving person.

Starting point is 00:36:54 There are people in the startup space that I know basically have 95% of their net worth tied up in crypto right now. Even the idea of like raising tens of millions of dollars from VCs, like that even makes me uncomfortable because I like the idea of running cash flowing profitable, that you can then reinvest in yourself, even if it means you have to grow a little bit slower, but you can sleep at night because you're not a hemorrhaging cash. And so I always say that because, like, I think there's a spectrum of risk tolerance for entrepreneurs.

Starting point is 00:37:27 And I would say I sit closer to risk mitigating than risk loving. And I think that shows also in how I invest. You know, it's not like I have all my money sitting in treasuries or munis. But like, I just, all I want to just do is compound my wealth by on average 7% to 10% a year for the next several decades. Makes a lot of sense. a couple more points around Angel investing. One I'm particularly interested in.

Starting point is 00:37:51 One kind of upfront issue I saw right away is that everything looks great. You get a deck sent to you and it's going to be the highlight reel. It's going to be polished. It's going to have, you know, and that's where I'm like, okay, I got a new found respect for venture capital because, you know, they have sift through everything and they all look great. So I'm kind of curious, has that been your experience and what have you kind of done to build a filter for that? Yeah, it is really, really hard.

Starting point is 00:38:16 I think also, to your point, it really depends on the stage you're investing in the way that you think about it. You know, whether you're investing pre-seed and seed or let's call it series A and beyond, how much you're thinking basically about like the intangibles and kind of like the traits of the founding team versus how much you're actually looking at the financials, the business, the growth in terms of whether it's users, customers, or revenue. And so for me, just to give context, like I have focused generally on pre-seed and seed, and I struggled exactly with what you're talking about because my natural waves, I think there's two very different brains, especially in building businesses. I would say one, I'll call it the eternal optimist,

Starting point is 00:39:01 which is really the person who just always sees possibility, what's possible. And it's a great way of being, but there's trade-offs to that, right? The trade-off is maybe you're a little bit to reactive because you don't see cracks when they start forming. Maybe it gets you to not ask if something should be done differently enough. On the flip side, there's the other brain, which I would call the bomb sniffing dog of business, which is the brain that is naturally saying what's wrong? Not inherently bad, either of them, but there are tradeoffs. And so what is the tradeoff with the bomb sniffing dog? Well, you can come off as pessimistic. You could come off has not seen possibility. You could cut things off too early because you only see the negatives.

Starting point is 00:39:44 For the first, the eternal optimist, again, it could prevent you from being proactively, intellectually rigorous. And so I think understanding where you live on the spectrum of bomb-sniffing dog to eternal optimist is really important. I sit closer to eternal optimist. And so to your point, in the beginning, as I was getting decks, I'd be like, yeah, this looks great, this looks great, oh, I talked to that person, they're awesome. And so there's a few things that I've done. to try to take the emotion out of it and the excitement out of it. One is I never make an investment decision anymore while I'm talking to the founder. I always create a separation of at least 24 hours.

Starting point is 00:40:24 It's kind of like the Seinfeld rule that Tim Ferriss talked about with Seinfeld, where Seinfeld, you know, the way he thought about the rule was he would write new jokes and you feel really excited about those jokes. And he would never show them to anyone else for 24 hours because he didn't want people to ruin the feeling of excitement that he had, but I used it in the same way, use time to separate emotion and action. The second is, and I actually heard my co-founder Austin talk about this, which is why I started doing it, is forcing founders to show memos, like to show past investment memos they've sent or answer questions over email, because to me, what that strips

Starting point is 00:41:00 people of is like a salesmanship, which is an incredibly valuable skill, but I think it can be limiting from an investor's perspective because you can be wooed by the wrong things. And, you know, the third is that I force myself every time I approach a decision around an investment, I write an investment memo for myself. Basically, the eight Alexes in my brain are just the investment committee for me. And I always ask the same questions. And part of the questions, or one of the questions I ask is, basically, if it hits the fan, six to 12 months from now, why did it hit the fan? And I should never leave that blank.

Starting point is 00:41:38 And the other thing I do is I write down what my emotional state is when I've made that decision. And I basically got this decision journaling framework from Shane Parrish from Farnham Street. And it just helped me basically all these exercises are what I would say is to necessarily strip yourself of excitement and optimism for a brief period of time to think clearly. Are you actually going back and read, is it a simple act of writing that's powerful? Are you actually going back and reviewing those, you know, a year later and finding them through the notebook and saying, oh, here's what I was thinking. Yeah, it's a combination.

Starting point is 00:42:15 I'd be lying if I said I reviewed every single decision journal that I've written. The act of writing it, not only super helpful for me, but I send it to other people to have them poke holes in it. But for some of these, I am adding into my calendar six months from now, a calendar invite with an attachment to the memo, or when I end up hearing about one of my portfolio companies raising another round, I'll just have the natural trigger in my mind of looking back on the memo and seeing how my thesis is playing out. And whether it's a really strong raise or not a strong rays, I basically get to look back and say, was my decision-making sound here? Or is the result that is happening right now based off of luck versus skill? I want to talk about luck because I've heard

Starting point is 00:43:00 you bring it up a few times, especially around, you know, meeting the right co-founder as you did with Austin. And I feel like recognizing luck is underrated. And I kind of perk up when I hear people bring it up or talk about it because I'm like, that identification of luck is just rare, too rare in my opinion. So how do you think about luck in life and business and now investing? This is the first time I'm saying this, but I think the way that I think about it is, right, luck absolutely exists. And I think in my mind, there's two types of luck. There is controlled luck and uncontrolled luck, meaning skill that is disguised as luck, right? Like you actually had a hand in the luck that occurred versus luck that you had no handed. So I'll give you an example

Starting point is 00:43:43 of both. Uncontrolled luck, luck that I had no hand in would be me being born as a white man in a privileged neighborhood in New Jersey, being able to quit my job from Morgan Stanley because I had the privilege of having a parent who would cover my rent for six to 12 months when I try to start my business. And so when people say I took a big risk, I remind them of exactly how things went down and how the risk I took was so much less than many other people in this country. That is what I call uncontrolled luck. I had no hand in that. Controlled luck is what I would call meeting Austin. The skill or the say that I had in this is that I made the decision when I was my first semester senior year at Michigan that rather than spending nine hours a day playing FIFA,

Starting point is 00:44:33 I was going to spend three hours a day playing FIFA. And the other period of time writing this newsletter because I saw a problem and I also wanted to keep myself sharp around business. I had, I would say, I had a hand in it that I reached out to people saying, I'm looking for help on this newsletter. Let me know if you're willing to help me. The luck is the fact that Austin decided to reach out to me.

Starting point is 00:45:00 He decided to say that he wanted to get involved and that I brought him on as kind of this co-founder for a hobby and he ended up being the perfect partner for a very significant business. So that's where I think, you know, everyone says, you know, create more luck surface area. I think creating luck surface area is really just saying, where do you have a hand or where can you leverage skill to make luck occur more frequently? Because you're just giving yourself more shots at luck. That's how I described controlled luck.

Starting point is 00:45:27 Uncontrolled luck is you haven't done anything to your surface area. You're just lucky. I love that. It kind of reminds me of this discussion I had with Jim Collins, who reminded me that there's also bad luck, right? And, you know, that is also a variable here. And when he studied, you know, through his research on thousands of companies, he basically found that what he would call it return on luck. So every company studied had good luck and had bad luck. And it was those who could mitigate the bad and capitalize on the good and actually get an ROI on it that were the ones that

Starting point is 00:45:58 won out. I think that's really interesting. And I think the reason that's such a powerful thought is the idea of luck, I think the reason it's an uncomfortable idea, is like we as human beings like being in control. And when you're dealing with luck, it purports that you're no longer in control. Something happened that was out of your control. What I find fascinating, I don't know if this is what Jim was thinking about when writing about return on luck, is that the idea of return on luck to me puts luck back in control, basically saying something happened as a function of something you couldn't control, but it's what you control, like what you do after the fact because of you make a decision based on what you can control. And that really shows your abilities beyond luck.

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Starting point is 00:50:12 And I think it's a good segue way to talk about something we haven't really talked about a lot on this show, but it kind of ties into your latest project, which is mental health. And as you're a founder especially, you got to find ways to control your mental health and support it. And control, in my mind, is reminding me of this book I read by Pemakodron, who basically it's called Life is Beautiful. And basically summarizing it, a lot of human suffering comes from this idea of trying to find stability in a world that is just fundamentally unstable. Things are fluid all the time, constantly changing underneath you, and you are just trying to grab onto something and hang on to it and control. And that word just kind of

Starting point is 00:50:52 resonated with me, as you said it. And I'm kind of curious about your experience with mental health and anxiety, and especially as you've been talking about it with your new show, Impostors, what is really interesting to me about you is the success you've had to date. So, for example, a lot of people, myself include, I've been a founder, been an entrepreneur, and I've had anxiety tied to my business as I'm growing it, but with this idea that, okay, but as soon as we get somewhere, then I won't have anxiety, right? I will have arrived. And it sounds kind of like you've somewhat identified your anxiety,

Starting point is 00:51:26 post, let's call it your first success, right? And I'm curious if you became more attuned to that having sold your business or is that something you've been mindful of all along? Yeah, you know, there's so much here. But to comment for a second on control, the reason I think the idea of control is so profound is because everything that gives us anxiety or causes fear is based on something out of our control, right? And so if you think about if you mentally shift, every day, if you focused your attention on the stuff that you could actually control, control what you can control, you very quickly see how things kind of like noise falls to the wayside, right?

Starting point is 00:52:11 I'll just give you a random example. There was someone who had posted or had tweeted basically saying that there was a founder with a big audience on Twitter who copied my idea. What should I do? And I saw this and this person I had been DMing with recently. It's like, hmm, are they talking about me? And so in that moment, I got really anxious about it, right? Because the last thing I would ever want to be considered or one of the last things is like an idea stealer.

Starting point is 00:52:43 And so what I couldn't control in that scenario was how they were feeling. What I could control is taking the impetus to reach out to that person rather than through the grapevine communicate with them. So I sent them a message and I said, hey, Hey, is this tweet about me? And they said, yes, period. And they explained why they thought I had copied their idea. And I said to them, look, I understand what you're saying. And I understand why you're concerned about this.

Starting point is 00:53:09 If you'd be open to it, I would love to explain to you all of the facts from my side. And that's all I can do. I can't control how you feel about this. But what I can control is giving you all the information so you can decide what you think happened. So ask them for their number, got on a phone call, basically talk for the next 45 minutes, the first 30, Ross basically talking through this, the remainder was like, it was like we were good friends. And I give that example, and you know, the long story short is I can very confidently say that I did not steal this person's ideas, but it didn't matter what I thought. The whole thing

Starting point is 00:53:40 was I could control the information that I gave them. And I think for a large part of my life, the things that I was anxious about were things that I couldn't control. So I'll give you an example. my whole life I've had OCD. It's hereditary. My dad had OCD. For him, it manifests in the form of like a clean OCD. The guy was Pireling his hands everywhere. You know, he passed when I was a junior in college, but we always joke now, like, COVID

Starting point is 00:54:07 would have been the worst thing. He would have been a head case during this. But for me, one of the ways it manifested was in different forms. One of the forms was like health OCD, where after my dad passed away, I was obsessive about my health. And I was worried as someone who exercised a decent amount that one day I'd be running on the treadmill and my heart would just give out. And I'd be one of those people who died really young from their heart stopping. And so what would happen is I'd spend a lot of days where I'd just be so fearful of working out. I would have the fear of dying each time I worked out.

Starting point is 00:54:43 And I would ask myself, what can I control here? What can I control? And what I could control these scenarios was pushing myself to be uncomfortable and work out every day. And for the person who's not experiencing this, right? It sounds kind of crazy because most people aren't worrying about their heart popping while they're running. But that was a thing for me. And what I controlled was the thing I could control was the action of facing that fear. And so, you know, to bring it back to mental health, I've been aware of my anxiety and OCD for a long time. The reason I think I've spent a lot of time recently thinking about it and helping people with it is one, I've found the profound effect that me talking about it has had on people, right?

Starting point is 00:55:22 Just even talking about impostors, the reactions to this show about people feeling like they were heard for the first time in their life about struggles they've endured for decades. It makes me feel more purposeful than anything else I've ever done in my life. And then the other piece, going back to the money part is, you know, when I realized that selling the company and having the proceeds from the exit did zero to impact my happiness. I think it acutely focused me on one very simple truth, which is that the way that I and we all perceive the world is truly the most powerful thing in a good way or a bad way. And so the best investment I can make in myself is giving myself the tools to see the world

Starting point is 00:56:10 clearly. And so that's why I spent so much time on it is because I realize no matter what happens, whether I have a lot of money or I don't, my perception of everything that occurs in my life, whether I perceive that as good or bad as based on the clarity of my thinking, and to think clearly you need the tools to navigate that, especially at times when it's really hard to think clearly. Well, I think it's resonating with a lot of people, especially over the last couple of years where we've had a lot of existential external forces also adding to the anxiety, right? And, you know, someone we've had on the show multiple times, Jesse Itzler is someone I look up to a lot. I just feel like he's found this amazing balance of meaningful work, meaningful

Starting point is 00:56:53 relationships. But the other day on Instagram, he was sharing what he called his quote unquote medicine, right? And it was this kind of laundry list of sauna, breathwork, running marathons, two-hour swimming, you know, ice baths, etc. It's like all these things he has to do to kind of like, you know, calm his nervous system. I saw, I saw him do one of those ice plunges. Oh, yeah. It's incredible, right? And, you know, I've had this talk with other people because I follow a similar format,

Starting point is 00:57:24 but mine is also inclusive of, you know, therapy and CEO coaching and massage and acupuncture, meditation. And all of a sudden it becomes like a second or third job just to kind of, you know, manage. And I'm kind of curious because I've heard you frame this up as something I hadn't heard before, but it's called your mental health stack, you know, similar to a tech stack that people might be used to running a company. Talk to us about your mental health stack and how you kind of developed it over time. Yeah. Well, and just to quickly react to what you're saying, managing your mental health, especially when it's in a challenging place, is a full-time job.

Starting point is 00:58:01 there were absolutely times as CEO of Morning Brew that I did not do my job effectively because I was literally just trying to survive isn't the right word, but like get through the day. There was a time in, it was in 2018 when I had my first panic attack, got a sleep-induced panic attack. Basically, it's normal for people to either when they first fall asleep to like kick their foot and kind of like jolt their self up or like have saliva in their mouth for me, I literally like choked on my saliva where it normally wouldn't do anything, but because I was in a certain headspace, I basically told myself, I'm not breathing correctly. And when you get the thought that you're not breathing correctly, it's over. Like, then you start not breathing correctly. And then you're

Starting point is 00:58:45 asking yourself, are you breathing correctly? And so basically for two or three hours, my mom on speaker phone had to like talk me off the ledge of like, you're going to be okay. You're not going to pass out. But for the next call it month before seeing a psychiatrist ending up getting prescribed for medication, I had panic attacks every day. And so there were times when I was in the office and I would just be sitting in a meeting and I wouldn't be talking. And then all of a sudden this like jolt of anxiety would hit me and I would feel like the room was closing in on me.

Starting point is 00:59:14 Like everyone was focused on me in that moment and I'd have to leave the room. I would literally have to go walk outside because I felt like I was going to break down. I hope it just paints a picture, especially for people that have not experienced panic, panic attacks, or anxiety to the point where it can be debilitating. That at times, it was absolutely my full-time job over running morning brew. That's the first thing. The second, as it relates to my mental health stack, basically the way I think about it is I think of my mental health on a spectrum from like one, it's called like perfect calm, 10 being the worst anxiety that I've ever experienced in my life. And to me, there are a group of things on my mental health stack that take my

Starting point is 01:00:02 base level, steady state anxiety, and bring that down or bring it up if it's not taking care of the right way. And then there are things that help basically lower the fluctuations. And so, for example, kind of the trio of self-care things that I do, So exercise, sleep, and diet. When I have not taken care of one of these things for more than three days, my baseline moves from what I would argue is typically a three or four to a six or seven. It's like that big of an impact.

Starting point is 01:00:40 And of course, I haven't given up drinking, but on days that I drink, the next day as a function of probably the alcohol itself as a depressant slash me not getting is good of sleep, baseline always higher. The other things that I do, so I have a therapist, I have an executive coach, I meditate, and the fourth is like me educating myself. So reading books like Buddhist texts, reading people like Pema, reading Jay Shetty's Think Like a Monk, reading Ryan Holidays, Daily Stoic, all of these things to give myself the mental tools. And the way I think about those is those are the things when I am experiencing heightened anxiety, those are things that lowers the peaks. Basically, what is the toolkit that allows me to react to things happening?

Starting point is 01:01:32 And so that is my mental health stack. And it's different for everyone. But I guess the secret here is, I would say 90% of it for me is those first three things that I named. Again, super boring and simple. But I just find has the biggest impact on my mental fitness. You see, I absolutely love this discussion because this is another side of success that isn't often explored. And we talk a lot about billionaires on this show and we study them and how they became successful. But this is such a huge component. I mean, to get someone where they need to be, I would argue, you know, when you bring a diet,

Starting point is 01:02:08 for example, that, you know, Buffett almost jokingly gets, you know, tease all the time for having this childlike diet where he eats hamburgers and ice cream and Coca-Cola every day. I've seen him at 6 a.m. getting an interview with a bowl of Oreos next to him. And that's what he's munching at 6 a.m. And, you know, people tease him for it. I'm like, this is his vice, right? This is his vice. And like, he's got $145 billion on his mind. I mean, that's just the cash he has. Not to mention the half a trillion company he's dealing with. That puts a lot of pressure on you. And you have to manage that. I just find this so interesting. And you're doing an interesting thing here, studying successful people and talking about their anxieties.

Starting point is 01:02:54 And you brought up your OCD and how it's kind of a tendency. I remember Carson Daly was on your show talking about GAD, so generalized anxiety disorder. You know, when I hear that kind of stuff, sometimes I think about, well, well, who doesn't? Like, is there someone, maybe Will Smith, right? But like, who doesn't have this that they have to manage? Well, so I think this really, this hits at the heart of, like, what is mental health? because, you know, some would say that mental health is basically the clinical disorders per the DSM, that, you know, the main mental health basically encyclopedia or textbook.

Starting point is 01:03:31 The way I think about mental health is like everyone lies on a spectrum of mental health. And also people experience mental health, I would say chronically and also mental health acutely based on situations in life. The reason I say that is, I believe the art, like the suggestion that everyone lives on the spectrum also makes it that much more important, that everyone builds their toolkit. Because at some point, even if people don't have, say, generalized anxiety disorder, I'm willing to bet that the vast majority of people on this planet at some point in their life are going to feel intense anxiety. It's almost like basically a bad, a false shield, a false sense of protection for people who don't believe they're anxious to never have the motivation. or the need, the quote unquote need to develop these tools.

Starting point is 01:04:22 And I think, unfortunately, it doesn't give enough power that our brains have over all of us. And so the way I think about defining mental health, and as you'll see this with impostors, not every person that I have on the show is going to be someone that had anxiety, depression, bipolar disorder, addiction. Like those will be some of the episodes, but some of the episodes will also be kind of like mental challenges that were created by acute challenges in life, like someone who lost their child or someone who came from poverty, right? They didn't actually have a diagnosable mental disorder, but they absolutely had mental struggle. And so that's my definition of mental health is more

Starting point is 01:05:07 like mental fitness, which is what are the tools all of us use to think clearly about this world and navigate struggles mentally? You know, what's coming to my mind right now when you're talking about mental health also is I just watched the Kanye West documentary, you know, he's diagnosed bipolar, et cetera. But there's this interesting line where, you know, he's captured and he's like got this Muhammad Ali energy where he's like, I am the greatest, I am my God. And he's like mentally training himself in that way to think that way. And it's actually not that dissimilar from what I've seen someone like Tony Robbins do with other people. There's a certain amount of that, that mental training to stay fit with, that

Starting point is 01:05:46 there's obviously a fine line. I'm curious how you think about that. Yeah. If anything comes to mind there. Yeah, it's a great question because I've thought a lot about this. And the reason is a lot of people have far more confidence in me and my abilities than I have in myself. If you were to ask me, Alex, do you feel successful? Alex, do you feel like you are really good at the things that you do? I kind of brush it off. I'd say, no, I'm fine in terms of success. In terms of my abilities, yeah, there are a few things I'm good at,

Starting point is 01:06:18 but there's a whole lot that I'm not good at. It's so interesting. I optimistically look at everything in the world, but when I look internally, I look at what's wrong, right? So I think to the point of what Kanye is doing, without judgment of his own practice, I think this idea of loving kindness, this idea of manifestation, which people I think give a lot of shit to, actually works. And the reason I think it works is at the end of the day, the stories that we tell ourselves dictate our behaviors for our entire lives.

Starting point is 01:06:50 Like literally, like what I'm spending my time on today, the work that I do, you know, what you're spending your time on with your startup with this podcast, it is dictated by deeply ingrained stories. that were formed earlier in your life, whether you're conscious of them or you're not. And so once you understand the power of story, you also understand the power it has if you can trick your brain into new stories. And so, like, you know, I didn't say this before in my mental health stack,

Starting point is 01:07:18 and it's because I haven't done it recently and, you know, bad Alex, I need to start doing it again, is I used to like every, and this sounds crazy, but every day in the shower do like loving kindness mantras where I would literally say, you know, I am beautiful. I am strong. I am focused and I am loving. And the reason I would say that, and I would repeat it over and over for five minutes, is, you know, was I expecting to feel like super energized after just saying that? No, but my belief is if you do that for long enough, you subconsciously start to believe it. And it changes biologically how you feel about yourself. I really do believe that because I just think stories at the end of the day, like language and stories.

Starting point is 01:08:03 have such a biological impact on us, both external stories as well as the stories we tell ourselves. Yeah, I would argue stories are synonymous with beliefs, right? Well, I'm super excited for you and all the things you're working on. It's always great to catch up. I really loved this wide-ranging discussion we just had and also touching on stuff we've really never explored on this show. And I've really enjoyed it.

Starting point is 01:08:23 So I would love to keep doing this and keep following up with you. And best of luck with imposters. Before I let you go, absolutely hand off to our audience where they can learn more about you, the show, anything else you want to share. Yeah, definitely check out Impostors. I think you all will really enjoy the podcast on any of the podcast players where you listen to audio podcast. And then you can follow me on Twitter at Business Barista. And really appreciate you for having me on the show again. Thanks so much. All right, everybody, that's all we had for you this week. If you're loving the show, please be sure to follow us on your favorite podcast app. You can find me on Twitter at Trey Lockerbie.

Starting point is 01:08:57 and be sure to check out some of the other shows we have for you on the Investors Podcast Network. And with that, stay safe and we will see you again next time. Thank you for listening to TIP. Make sure to subscribe to Millennial Investing by the Investors Podcast Network and learn how to achieve financial independence. To access our show notes, transcripts or courses, go to theinvestorspodcast.com. This show is for entertainment purposes only. Before making any decision consult a professional,

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