Alex Lieberman (00:03:22):
Basically what has happened is the void of identity. My identity was so tied up in MorningBrew… Alex, the CEO of MorningBrew, that’s how the world knew me, that’s how I knew myself. So I started feeling a lot of anxiety around what next? I felt anxiety around not feeling I was growing anymore. I felt anxiety around kind of imposter syndrome. And it probably sounds crazy to people on the outside of like, “Dude, you just built a successful company, you sold it.” But 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. 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?”

Alex Lieberman (00:04:07):
And I say all of this with the caveat that I don’t think I try to spend a lot of my time now triangulating around 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 who am I trying to stay relevant for?

Trey Lockerbie (00:04:34):
You are busier than ever, it would seem, 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 super fast, and now it’s almost like the personality comes first and that’s the powerhouse, and the brands are secondary. People are going to the source of this individual to follow, then going to the commerce from there. And you’ve become this expert at growing an audience, first with MorningBrew and now your own brand. So I’m curious if you follow this theory and if I’m onto something here.

Alex Lieberman (00:05:21):
I mean, I hope you’re right, because we’re betting the house to have MorningBrew on this, and in a lot of ways I’m taking fully levered bets on my career on this exact notion. What I think is that there hasn’t actually been a behavioral change, meaning, I think individuals have always followed individuals, aspire to be 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. 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 owning the channels and owning the infrastructure to get TV to homes. Radio stations having broadband.

Alex Lieberman (00:06:24):
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 it’s so costly to distribute content because it was the internet. And then finally, the final piece on top of social platform forms was I would say the tools that gave creators the ability to not just build audiences, but to create products and monetize products. So yeah, I think we’re in a fascinating time right now where you see media companies like MorningBrew going all in on building that are built on the back of a creator, and I can talk about what that looks like at MorningBrew, all the way to creator led businesses being launched.

Alex Lieberman (00:07:28):
So even talk 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. But Mr. Beast, arguably the most powerful creator on the planet, and not just the most powerful creator, the guy gets more views than late night TV gets. 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. So in an age where paid marketing is more expensive than ever before, I don’t know the exact number, but for example, for MorningBrew, the cost of acquiring a high quality subscriber today relative to six years ago, when we are the company, multiples higher. So cost of marketing is going up, tools are in the hands of creators to build audiences.

Alex Lieberman (00:08:29):
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 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 skillset. You also get naturally 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. So there’s such a collateral effect.

Alex Lieberman (00:09:06):
And also think about, say they’re selling these products via ecommerce, but they want to break into retail, 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 by at their closest Target.” These massive companies clearly want younger foot traffic. To me, it’s a layup. So I just think having basically built in creative R&D and marketing paired with a great product and brand is a massive unlock.

Trey Lockerbie (00:09:41):
You can almost see how Mr. Beast goes public, someday. 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 it was at the time, I think, around 60% of all the ad spend in the world is going to these two companies. And of course Google has YouTube and a number of other things. So is that what’s driving the competition? You have this huge wave of people trying to get attention through ad spend, but it’s a thousand people through the exit trying to get through to these two companies?

Alex Lieberman (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. And that’s why these sites do everything humanly possible to keep you on these sites. 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 harder to be able to monetize your attention and eyeballs if you’re not staying on their site.

Alex Lieberman (00:10:51):
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. 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 the privacy changes with iOS, with Apple, where no longer can these companies follow people around their devices, so it makes advertising on these platforms less precise than it was before these policy changes.

Trey Lockerbie (00:11:23):
And yet the cost is going up.

Alex Lieberman (00:11:25):
Yeah.

Trey Lockerbie (00:11:26):
Interesting. So Feastables is an example of your angel investing that I know 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, where things are coming across your desk more often, people are wanting you attached to the gig. Is that a good or bad thing? I mean, I would say obviously there’s some good and some bad, I’m just curious which way’s out. And then also what have been some of the trials and tribulations of just becoming an angel investor over the last year?

Alex Lieberman (00:12:02):
I think the hardest thing for me as an angel investor has been twofold. 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 in my career, but imposter syndrome. Who am I to be able to make great picks around companies with very little experience? And if I’m not confident in my ability to do that, why am I allocating my own capital to do that? That’s 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 this intangible ROI of the osmosis that happens from just spending a ton of time helping founders, helping them fundraise, helping them connect with investors, helping them think through their product strategy, helping them think through their content strategy.

Alex Lieberman (00:13:03):
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. 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, 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. So I try to be active with all the businesses I work with as it relates to deal flow. To me, that is not only 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 leave yet that I can be a better than average picker.

Alex Lieberman (00:13:58):
Basically I operate under the assumption that I am going to be an average picker in the beginning because I need to get enough reps to understand what to look for. So the only way that I’m going to be able to drive above average returns is see above average deal flow. So to me, creating content and 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 an Andreessen, 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. So I think being considered or thought about it as one 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.

Trey Lockerbie (00:15:00):
So with that, I’m curious, 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 where like, “Well, that’s not for me, but it’s definitely a good business.” What does that look like?

Alex Lieberman (00:15:17):
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 am not very familiarized with. I even talk about always building MorningBrew, not that it was easy, but it was far easier than if I was not the consumer myself. I was the consumer of my own product. So yes, if I look at a number of my investments, I am a consumer or a hypothetical consumer of this product. What does that mean? Well one, I do try to stay within 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.

Alex Lieberman (00:16:00):
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 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 check as an LP because I’m betting on them and I believe there’s opportunity in the space.” 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 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 rabid audience to start. And the final would be businesses where content strategy is a very clear remit of their strategy, so I can actually be value add as an investor to help them think through how they build out their content program as an accelerator to their business.

Alex Lieberman (00:17:02):
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 US citizens is incredibly laborious, takes a ton of time. So the product basically streamlines everything from, call it, 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, profiling some of the people who are their customers and are their travelers, content is a big part of their strategy to drive demand. So I knew that was a place I could actually add value and truly help increase the value of the business over time.

Trey Lockerbie (00:17:52):
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 DAOs or… What’s the takeaway here? Why are people so attracted to this kind of model would you think?

Alex Lieberman (00:18:09):
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, that is a creative’s dream, really to be a trail blazer within 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, throughout time. That is a behavior that will never change. So I think a lot of what you’re seeing even in the world of NFTs entirely opportunistic. And again, 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.

Trey Lockerbie (00:19:08):
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, invest alongside of me.” I’m sure a lot of people would want to do that with you. What has been your hesitation with that?

Alex Lieberman (00:19:22):
Look, I think doing that makes a ton of sense. We’ve seen everyone from il Lavingia, to Naval, to my co-founder Austin, to il Bloom, these guys have all created funds or rolling funds, and I think it makes a ton of sense. Not that right now is necessarily a hard time to raise capital, but having an audience… people Can raise 10 million that off of the back of the correct Twitter audience 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.

Alex Lieberman (00:20:13):
In my mind, when you raise a fund, you are an entrepreneur, 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 the investor route. I’m not convinced that’s the route that I want to go yet.

Trey Lockerbie (00:20:36):
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 having what you’ve called social and financial currencies.

Alex Lieberman (00:20:56):
So this idea of a personal moat, actually I got the concept from Eric Thornberg, who is one of the founders of On Deck. He wrote a Twitter thread about this. But based the idea of a personal moat is you can think about it just a company 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 7 Powers is the Bible for understanding what generally creates sustainable power. Things from switching costs, to economies of scale, brand power, et cetera.

Alex Lieberman (00:21:41):
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 what is my personal moat 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? So when I think about a personal moat, basically I think of it as a compilation of skills and knowledge that when combined together in this recipe gives you sustainable advantage. 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.

Alex Lieberman (00:22:26):
So 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 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 moat is defined by your interests, 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. 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 VeeFriends. Baseball cards and collectibles, he did that before it became big. Early investor, I believe, in Uber and in Twitter.

Alex Lieberman (00:23:21):
So for him, what is the asset that he’s built from this 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 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 and self-awareness, 8 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. So for me, as I think about my career, whether it’s with MorningBrewer or building other businesses, I’m constantly thinking about 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 align those up with my deep interest to create an asset for me over time?

Alex Lieberman (00:24:11):
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 and engaged businesses with strong cultures. That doesn’t have to be the combination to build an asset such as an audience or a business, but it is an example of how to do that.

Trey Lockerbie (00:24:34):
Speaking of the creator economy and this web3 thing, I feel like the word of the last, maybe year, six months, whatever you want to call it is community. You have everyone and their mom talking about how community is the new… It’s not customer acquisition costs, it’s community acquisition costs nowadays. But one of the key moats 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, if you think about it. The more people come in, 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 the negative network effect around communities.

Alex Lieberman (00:25:13):
Look, I’m running a founders book club right now. I love this book club. And why did I do it? It was when I was… After moving out of my role as CEO of MorningBrew, I was fiending for something to build and grow, and I didn’t care what it was, I just needed to something. So I started picking 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 investors. Basically predicted everything from crypto to COVID.

Alex Lieberman (00:25:54):
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, gearing up for round three. I was thinking about opening up the group. What do you guys think about it?” And there was 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 their own lives, their own motivations, and I think their concern is as we open it up, not only how is the quality of the new entrants 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.

Alex Lieberman (00:26:41):
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 a thing right now, because community has, as far back as time… Religion is one of the the first versions of community. Even before that, the primal version of ourselves, there’s community to protect ourselves from predators. Community has always been a massive thing because it’s hardwired into us, the importance of connection to others. So I find it interesting and peculiar why it’s so zeitgeisty right now. So all I’d say is yeah, it’s really important. 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 the community, and it’s a ton of work.

Alex Lieberman (00:27:27):
And to give props to one community I’m in, there’s a crypto community called Crypto Packaged Goods, CPG, that was started by Chris Cantino and Jamie Schmidt, and it’s exceptional. The amount of time and effort they have put into cultivating this now, I don’t know, 2,000, 3,000 person community is crazy. There are people basically working full-time jobs to moderate this community. 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. Is the number one thing. When I invested, the second angel investment I ever made was in this sneaker community, SoleSavy. So savvy, I’m incredibly bullish on what they’re doing, because going back to my interest in passion communities, sneaker collectors are insane people in the best way about their sneakers. 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 hits the secondary market makes a ton of sense.

Alex Lieberman (00:28:31):
But they’ve had to do a lot of different things 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, they would have to create a new Slack instance. So now they have multiple slack instances for SoleSavy members. None of them are over 1,200 people, and they’ve had to build out the technology for when they post something to SoleSavy members, it cross-posts to every single community.

Trey Lockerbie (00:29:03):
That’s fascinating. I’m curious, that reminds me almost of early days in email marketing, before you had MailChimp and some other things. What’s the solve for that as they continue to scale?

Alex Lieberman (00:29:15):
It’s a great question. I think what’s going to have to happen is technology’s 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 intimate group with 8 or 10 people, even if the group actually is 50,000 people. But that is incredibly difficult to do. And you see little glimpses of this, you see it with Zoom doing their breakout rooms. But if you’re talking about building a business truly around community, something like a Discord channel with 15,000 people and getting hit up by bots on the side is not going to cut it

Trey Lockerbie (00:30:02):
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 that. You were in New York. Drive around any street where there’s a new nightclub and you see 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 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 gotten into equities at any point. Are you looking at SoleSavy as much as you’re looking at Berkshire Hathaway or something like that? I mean, are you playing those markets as well?

Alex Lieberman (00:30:41):
Yeah. Basically my approach has been I feel so incredibly fortunate to have built up a really strong capital base at 28 years old. So basically my goal as it relates to getting smarter about scaling my wealth is really… So when I’m talking about studying the equity markets or reading through a 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 my capital. I also don’t have the personality where I’m looking at my portfolio every day seeing what my single name stocks are doing.

Alex Lieberman (00:31:33):
I have an interest in it, but really I would say 75% of my portfolio… Actually 70% is basically just index funds in the S&P. 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 start putting some money into real estate via Blackstone, via their REIT They’re doing a bunch of single family home rental investing. I’ve allocated, 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 and growth stocks that I’ve set and forget basically for the next five decades.

Trey Lockerbie (00:32:25):
That’s a good way to sleep well at night. I respect it. I really do. It’s an interesting almost dichotomy between your background and where you’re going now.

Alex Lieberman (00:32:33):
It is. And I think also, again, people look at entrepreneurs and I think they assume they’re super risk loving. And I would say I’m not a super risk loving person. 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 raising tens of millions of dollars from VCs, that even me uncomfortable, because I like the idea of running cash flowing profitable businesses 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 hemorrhaging cash. So I always say that because I think there’s a spectrum of risk tolerance for entrepreneurs, and I would say I stick closer to risk mitigating than risk loving, and I think that shows also in how I invest. It’s not like I have all my money sitting in treasuries or munies, but all I want to just do is compound my wealth by on average 7 to 10% a year for the next several decades

Trey Lockerbie (00:33:35):
Makes a lot of sense. Couple more points around angel investing. One I’m particular interested in. One upfront issue I saw right away is that everything looks great. You get a deck to you and it’s going to be the highlight reel, it’s going to be polished, it’s going to have… And that’s where I’m like, “Okay, I got a new found respect for venture capital because they have sift through everything and they all look great.” So I’m curious, has that been your experience and what have you done to build a filter for that?

Alex Lieberman (00:34:03):
Yeah, it is really, really hard. I think also, to your point, it really depends on the stage you’re investing in, the way that you think about it. Whether you’re investing pre-seed and seed, or let’s call it series A and beyond, how much you’re thinking basically about the intangibles and the traits of the founding team versus how much you’re actually looking at the financials of the business, the growth in terms of whether it’s users, customers, or revenue. So for me, just to give context, I have focused generally on pre-seed and seed, and I struggled exactly with what you’re talking about because my natural way of… I think there’s two very different brains, especially in building businesses. I would say one, I’ll call it the eternal optimist, 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.

Alex Lieberman (00:34:59):
The trade off is maybe you’re a little bit too 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 trade offs. So what is the trade off with the bomb sniffing dog? Well, you can come off as pessimistic, you could come off as not seeing possibility, you could cut things off too early because you only see the negatives. For the first, the eternal optimist, again, it could prevent you from being proactively intellectually rigorous. 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.

Alex Lieberman (00:35:49):
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.” 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. It’s the Seinfeld rule that Tim Ferris talked about with Seinfeld, where Seinfeld the way he thought about the rule was he would write new jokes and he’d 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 use it in the same way, use time to separate emotion in action.

Alex Lieberman (00:36:33):
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, to show past investment memos they’ve sent or answer questions over email, because to me what that strips people of is salesmanship, which is an incredibly valuable skill, but I think it can be limiting from an investor’s because you can be wooed by the wrong things. And 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 6 to 12 months from now, why did it hit the fan? And I should never leave that blank.

Alex Lieberman (00:37:27):
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 Farnam Street, and it’s 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.

Trey Lockerbie (00:37:51):
Are you actually going back and… Is it the simple act of writing that’s powerful? Are you actually going back and reviewing those a year later and finding them through the notebook and saying, “Oh, here’s what I was thinking.”

Alex Lieberman (00:38:03):
Yeah, it’s a combination. 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 within 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 raise. 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?

Trey Lockerbie (00:38:47):
I want to talk about luck because I’ve heard you bring it up a few times, especially around meeting the right co-founder as you did with Austin. And I feel like recognizing luck is underrated and I 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?

Alex Lieberman (00:39:11):
This is the first time I’m saying this, but I think the way that I think about it is 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. You actually had a hand in the luck that occurred versus luck that you had no hand in. So I’ll give you an example 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 6 to 12 months when I tried to start my business. 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.

Alex Lieberman (00:40:07):
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 it was my first semester, senior year at Michigan, that rather than spending nine hours a day playing FIFA, 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 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.”

Alex Lieberman (00:40:43):
The luck is the fact that Austin decided to reach out to me. He decided to say that he wanted to get involved, and that I brought him on as 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… Everyone says 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 describe controlled luck. Uncontrolled luck is you haven’t done anything to your surface area, you’re just lucky.

Trey Lockerbie (00:41:21):
I love that. It reminds me of this discussion I had with Jim Collins, who reminded me that there’s also bad luck. And that is also a variable here. And when he studied, through his research on thousands of companies, he basically found that… He would call it return on luck. So every company he 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 won out.

Alex Lieberman (00:41:49):
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 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, 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. It shows how you leverage skill in the face of luck.

Trey Lockerbie (00:42:37):
I love this concept of control and I think it’s a good segue to talk about something we haven’t really talked about a lot on this show, but it 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 Pema Chödrön, 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 onto it and control.

Trey Lockerbie (00:43:17):
And that word just resonated with me as you said it, and I’m curious about your experience with mental health and anxiety, and especially as you’ve been talking about it with your new show, Imposters, what is really interesting to me about you is the success you’ve had to date. So for example, a lot of people, myself included, I’ve been a founder, I’ve been an entrepreneur, and I’ve had anxiety tied to my business as I’m growing it. But with this idea that as soon as we get somewhere, then I won’t have anxiety. I will have arrived. And it sounds like you’ve somewhat identified your anxiety post, let’s call it, your first success. 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?

Alex Lieberman (00:44:03):
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. 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 like noise falls to the wayside. 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, and it’s like, “Hmm, are they talking about me?” So in that moment, I got really anxious about it. Because the last thing I would ever want to be considered, or one of the last things is an idea stealer.

Alex Lieberman (00:45:10):
So what I couldn’t control 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, 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. 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.”

Alex Lieberman (00:45:47):
So asked them for their number, got on a phone call, basically talked for the next 45 minutes. The first 30 were us basically talking through this, the remainder was… It was like we were good friends. And I gave that example, and 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 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 clean OCD. The guy was Purelling his hands everywhere. He passed when I was a junior in college, but we always joke now, COVID would’ve been the worst thing. He would’ve been a head case during this.

Alex Lieberman (00:46:38):
But for me, one of the ways it manifested was in different forms. One of the forms was 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. So what would happen is I would 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. And I would ask myself, what can I control here? What can I control?

Alex Lieberman (00:47:13):
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 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. So 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. Just even talking about Imposters, the reactions to this show, about people feeling 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.

Alex Lieberman (00:48:03):
And then the other piece, going back to the money part, is 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, so the best investment I can make in myself is giving myself the tools to see the world clearly. So that’s why I spend 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 is 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.

Trey Lockerbie (00:49:00):
Well, I think it’s resonating with a lot of people, especially over the last couple years, we’ve had a lot of existential external forces also adding to the anxiety. 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 relationships. But the other day on Instagram, he was sharing what he called his quote unquote medicine, and it was this laundry list of sauna, breath work, running, marathon, two hour swimming, ice baths, et cetera. All these things he has to do to calm his nervous system, so to speak.

Alex Lieberman (00:49:41):
I saw him do one of those ice plunges.

Trey Lockerbie (00:49:44):
Oh yeah, it’s incredible. And I’ve had had this talk with other people because I follow a similar format, but mine is also inclusive of therapy and CEO coaching and massage, acupuncture, meditation. And all of a sudden it becomes a second or third job just to 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, 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’ve developed it over time.

Alex Lieberman (00:50:19):
Well and just to quickly react to what you’re saying, managing your mental health, especially when it’s a challenging place, is a full-time job. There were absolutely times as CEO of MorningBrew that I did not do my job effectively because I was literally just trying to… Survive isn’t the right word, but get through the day. There was a time in… It was in 2018 when I had my first panic attack, I had a sleep induced panic attack. Basically it’s normal for people when they first fall asleep to kick their foot and jolt their self up or have saliva in their mouth. For me, I literally choked on my saliva where it normally wouldn’t do anything, but because I was in a certain head space, I basically told myself I’m not breathing correctly. And when you get the thought that you’re not breath incorrectly, it’s over. Then you start not breathing correctly. And then you’re asking yourself, are you breathing correctly?

Alex Lieberman (00:51:13):
So basically for two or three hours, my mom on speaker phone had to talk me off the ledge of, “You’re going to be okay. You’re not going to pass out.” But for the next month before seeing a psychiatrist, getting prescribed for medication, I had panic attacks every day. 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 jolt of anxiety would hit me and I would feel like the room was closing in on me, 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 attacks or anxiety to the point where it can be debilitating, that at times it was absolutely my full-time job over running MorningBrew. That’s the first thing.

Alex Lieberman (00:52:04):
The second, as it relates to my mental health stack, basically I think about it is I think of my mental health on a spectrum from one, it’s called 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 base level steady state anxiety, and bring that down or bring it up if it’s not taken care of the right way. And then there are things that help basically lower the fluctuations. So for example, 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 that big of an impact.

Alex Lieberman (00:53:06):
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 as good a 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 me educating myself. So reading books, like Buddhist texts, reading people like Pema, reading Jay Shetty Think Like a Monk, reading Ryan Holiday’s Daily Stoic, all of these things to give me 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. 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.

Trey Lockerbie (00:54:16):
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, when you bring a diet, for example, that Buffett almost jokingly gets teased all the time for having this child-like diet where he eats hamburgers and ice cream and Coca-Cola every day. In fact, I’ve seen him at 6:00 AM getting an interview with a bowl of Oreos next to him. That’s what he’s munching at 6:00 AM. And people tease him for it.

Trey Lockerbie (00:54:55):
I’m like “This is his vice. This is his vice.” And 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, and you brought up your OCD and how it’s a tendency… I remember Carson Daly was on your show talking about GAD, so generalized anxiety disorder. When I hear that kind of stuff, sometimes I think about, “Well who doesn’t?” Is there someone… Maybe Will Smith, but who doesn’t have this that they have to manage?

Alex Lieberman (00:55:40):
So I think this really… This hits at the heart of what is mental health? Because some would say that mental health is basically the clinical disorders per the DSM, the the main mental health, basically, encyclopedia or textbook. The way I think about mental health is 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 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.

Alex Lieberman (00:56:35):
It’s almost 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. And I think, unfortunately, it doesn’t give enough power that our brains have over all of us. So the way I think about defining mental health, and as you’ll see this with Imposters, not every person that I have on the show is going to be someone that had anxiety, depression, bipolar disorder, addiction. That will be some of the episodes, but some of the episodes will also be mental challenges that were created by acute challenges in life, like someone who lost their child or someone who came from poverty. They didn’t necessarily have a diagnosable mental disorder, but they absolutely had mental struggle. So my definition of mental health is more like mental fitness, which is what are the tools all of us use to think clearly about this world and navigate struggles mentally.

Trey Lockerbie (00:57:41):
What’s coming to my mind right now when you’re talking about mental health also is… I just watched the Kanye West documentary. He’s diagnosed bipolar, et cetera. But there’s this interesting line where he’s captured and he’s got this Muhammad Ali energy where he’s like, “I am the greatest, I am a god.” And he’s 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 there’s obviously a fine line. I’m curious how you think about that, if anything comes to mind there?

Alex Lieberman (00:58:19):
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’d kind of brush it off and say, “No, I’m fine in terms of success. In terms of my abilities, yeah there are a few things I’m good at, 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. 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 give a lot of to actually works.

Alex Lieberman (00:59:10):
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. Literally what I’m spending my time on today, the work that I do, 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. So once you understand the power of story, you also understand the power it has if you can trick your brain to new stories. So I didn’t say this before in my mental health stack, and it’s because I haven’t done it recently, and bad Alex, I need to start doing it again, is… I used to, every… And this sounds crazy, but every day in the shower do loving kindness mantras where I would literally say I am beautiful. I am strong. I am focused. And I am loving.

Alex Lieberman (01:00:05):
And the reason I would say that, and I would repeat it over and over for five minutes is… Was I expecting to feel 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, language and stories have such a biological impact on us, both external stories, as well as the stories we tell ourselves.

Trey Lockerbie (01:00:35):
I would argue stories are synonymous with beliefs. 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. 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.

Alex Lieberman (01:01:00):
Yeah, definitely check out Imposters. I think y’all will really enjoy the podcast on any of the podcast players where you listen to audio podcasts, and then you can follow me on Twitter @BusinessBarista. And really appreciate you for having me on the show again. Thanks so much.

Trey Lockerbie (01:01:16):
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 @TreyLockerbie, and be sure to check out some of the other shows we have for you on The Investor’s Podcast Network. And with that, stay safe, and we will see you again next time.

Outro (01:01:32):
Thank you for listening to TIP. Make sure to subscribe to Millennial Investing by The Investor’s 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 decisions, consult a professional. This show is copyrighted by The Investor’s Podcaster Network. Written permission must be granted before syndication or rebroadcasting.