We Study Billionaires - The Investor’s Podcast Network - TIP344: A Deep Dive Into Morning Brew's $75M Valuation w/ Alex Lieberman

Starting point is 00:00:00 You're listening to TIP. On today's episode, I sit down with Alex Lieberman, the co-founder and CEO of the wildly popular email newsletter company, Morning Brew. Alex comes from a family with a career history and finance, but set out on his own to pursue Morning Brew and recently sold it to Business Insider for $75 million. If you want to invest like Warren Buffett, you have to become a student of business, and you do that by diving deep into successful companies to see what their secret sauce is. That's what today's episode with Alex is all about. In this episode, we cover best practices used by Morning Brew to

Starting point is 00:00:41 grow to 2.7 million subscribers, which can be applied to nearly any business, how to develop a unique brand voice with pricing power, how to find the right co-founders and investors, how self-improvement equals business improvement, and much, much more. At 27, Alex's is well ahead of his years with a tremendous amount of business experience under his belt already, but will no doubt be a career to follow along with. So with that, I hope you enjoy my discussion 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 00:01:35 All right, everybody, I'm here with Alex Lieberman, CEO and co-founder of Morning Brew. Alex, I am so excited to have you on the show. I can't tell you how long I've been actually subscribed to Morning Brew, and it's literally my favorite email to open every morning. So congratulations for the success and excited to dig in on it with you. I appreciate it. Never gets old hearing subscribers say they enjoy the brew. And I will say most of the time that I ask people how they found out about the newsletter.

Starting point is 00:02:05 I'm not exactly sure. I'm not sure if that's a good thing or a bad thing. I appreciate the kind of words and I'm excited to dive in. Well, one thing I noticed about the Brew is that it really provides this great sense of the financial landscape, especially with the investing markets right away. Usually at the top of the newsletter, there's the stats, you know, what the markets are doing. But it also offers up these enticing news stories that, you know, I may or may not choose to dive deeper into later in the day.

Starting point is 00:02:32 When I was reading it the other day, it got me thinking that the main story I was reading really interested in diving deeper into was how Morning Brew came to be. So let's start there. Long story short is my co-founder, Austin Reef and myself started Morning Brew when we were students at the University of Michigan. I noticed you're also a big 10 person. I believe you went to I. That's right. So I was a senior at the time at Michigan. Austin was a sophomore. We didn't know each other. We happened to be in the same fraternity, but we didn't know that. But we were both in the business school. I wanted to work in sales and trading. That was like my dream job, which was obviously a very unique dream job, but my dad spent 20 years working for a city group in sales and trading.

Starting point is 00:03:15 My mom worked for Nomura in sales and trading. My grandpa worked for prudential in sales and trading. That's all I wanted to do. And so basically I got into my senior year at Michigan. I had my job in hand that I was going to do after graduating from college, which was to trade mortgages for Morgan Stanley, which again was me living the dream for everyone else. They're like, what are you doing? And Austin wanted to be an investment banking. And so basically, I had all this free time my senior year. I started helping students prepare for job interviews because a lot of students did re-recruit

Starting point is 00:03:46 their senior year. And I'd always start by asking the question in mock interviews, how do you keep up with the business world? And the goal was like, this was supposed to be just like a layup question. Like let's shake the nerves, get the conversation going. but every student would have a really interesting thing to say. They would always say, you know, I read the Wall Street Journal. Then I would say, why?

Starting point is 00:04:06 And then say, I read it because my parents told me I have to because it's a prerequisite to say I'm well read in business, but it's dense, it's dry, and I don't have enough time in my day to read the journal cover to cover. By the way, I don't want to knock on the journal because I read the journal. But I think it was fascinating how students would say that. And at some point, I was like, this is crazy. You have this entire generation of people,

Starting point is 00:04:27 All of these college students are going to go work and banking and in financial services, yet they don't have content that story tells the business world in a fun and engaging way. And it just seemed like a complete mismatch to me. You're going to spend 40 years in business, half of your waking hours working in a job and you don't have content that engages you. So I started writing a daily business roundup. At the time, it was called Market Corner. It was actually more markets focused than even Morning Brew was, where the logo was a bear and a bull fighting. but I didn't have the money to get a designer to design it. So it was literally just a Google image with a watermark going across.

Starting point is 00:05:02 And that all the original DNA, breaking down the biggest stories in 100 to 200 word blurbs. I would do an investor of the day, a stock pitch of the day, and things like that. And basically what happened was after a few months of doing this, students started reaching out to me and were like, hey, I heard about your daily business roundup. Can you add me to your list serve? It was like in so many ways a horrible product. There was no website. It was a PDF that was attached to an email. And so if you wanted to read my roundup, you had to send me an email to say, hey, add my email to your list serve.

Starting point is 00:05:34 Despite all of that, a couple thousand people subscribe to it. And to me, that was enough proof of concept to say, okay, there's something here because people shouldn't be signing up for this thing. It's impossible to sign up for it. That's when one of my readers, Austin Reef, sophomore at Michigan, reached out to me. It was like, hey, love what you're doing with Market Corner, but I have some ideas to make it better. Met up in the main area of business school at Michigan, and he basically gave me all of these

Starting point is 00:06:01 thoughts for what could level up the product. And I didn't realize it until then, but one of the worst things when building a business or honestly, anything that involves intellectual rigor is like being told by people that you're doing a great job is wildly unhelpful. And so I've been told over and over and over, what I'm doing is great, keep it up, keep sending out this newsletter. Austin was the first person to be like, yeah, this is good, this kind of sucks.

Starting point is 00:06:24 This is good, let's change this up. I ended up bringing on Austin as my co-founder. We launched Morning Brew as a proper email newsletter, not a PDF in March of 2015, and we've been doing it since then. So the business has been around for six years. We officially turned six this past weekend, and it's been quite a journey.

Starting point is 00:06:42 Something I heard you talk about, or maybe Austin mentioned about strategy with the product. Now that you've got this product, and you're sending it out. Something that really stood out to me that I thought was a great strategy is the testing involved with the headlines and the subject matter. So talk to us a little bit about how you approach that. It sounds so small and insignificant, but subject line testing is actually a really meaningful thing for our business. When you're sending out to 2.7 million people every day, the difference of like a 0.1 to 0.5% difference in subject line is tens of thousands of readers,

Starting point is 00:07:17 which actually equates to like advertising dollars. And so what we do is our newsletter is sent out at 6 a.m. Eastern, Monday through Saturday. At 5 a.m. we send out four subject lines, an A, a B, a C, and a D to different 20,000 person groups. Basically, what we see is when we send that newsletter out at 5 a.m. to those 4,000,000 person groups by 6 a.m., what is the group that has the highest open rate? Whatever group has the highest open rate, we take that subject line. and we send the remaining 2.65 million people, that subject one. And that is accounted for hundreds of thousands of dollars over time because one of the ways that we charge advertisers or we have in the past

Starting point is 00:08:00 is based on opens of the newsletter. And so we're incentivized to get as many people to open the newsletter as possible. Also just thinking from like a human behavior perspective, we live in the age of abundance, right? One of the things that platforms have done that the Internet has done is made it easier than ever for creators to create content. And so for us, it just means we have to work harder than ever before. Every media company has to do this.

Starting point is 00:08:26 We have to work harder than ever before to compete for people's attention. Because when they are opening their email every day, their inbox is going to have 100 emails. Even if we are a staple in their morning routine, we still need to fight for their attention because, by the way, we're not just fighting against, you know, the Wall Street Journal or other email newsletters, or fighting against someone deciding to do a headspace meditation, not saying people shouldn't do headspace meditations, or fighting against someone playing Fortnite, or fighting against someone reading a book. And so I think when you're in the world of media, you realize the all-out battle isn't

Starting point is 00:09:01 for subscribers or subscription dollars. It's the battle for attention in time. So starting out with this newsletter, I imagine it just started gaining more and more traction. at some point, you probably needed to raise some money. So just being right out of college, how did you approach that? We had never raised money before. The way we had funded the business was basically a combination of money that Austin and I had made from internships.

Starting point is 00:09:28 And then this was one of the benefits of building a company in college is you just have a lot of resources at your disposal. We basically applied for every grant humanly possible on Michigan's campus to help us fund the business. By the way, it's also one of the reasons. we chose email as our distribution for our content because email was really cheap relative to like building an app or something. At some point when Austin and I decided to go full time, so I'd quit my job working at Morgan Stanley in September of 2016. Austin knew that he wasn't

Starting point is 00:09:57 going to accept his full-time job to work in investment banking. We're like, okay, we need to take this thing seriously because we're going from this newsletter that had at the time like 70,000 subscribers, we have to turn this like kind of cool, nice side hustle into a business. And for us, what that meant is we had to do three things extremely well. Great, great content, scale our audience and monetize that audience by convincing the biggest brands in the world, why they need to pay to get in front of that audience. And we knew that we needed to hire writers. We needed to hire people to grow the audience marketers.

Starting point is 00:10:32 And we had to hire salespeople. But it was a chicken and the egg problem because we weren't monetizing the business yet. so we didn't have ad dollars in order to invest in the hiring people. So basically we said we have to raise some money. Originally, I think our number was 250K we were going to raise. And then we spoke to someone about it. And they were like, there are just so many costs you're not accounting for right now. Just trust me.

Starting point is 00:10:52 I can't remember who that person was. And so then we were like, okay, we'll raise 500K. We ultimately raised 750K. And the way we did it was we raised 750K in the form of a convertible note. And we didn't raise from institutions. or VCs, for two reasons. One is we had no relationships to them, so we felt like we would be starting from scratch.

Starting point is 00:11:14 The second reason is Austin and I just had this kind of like, this naive view in our minds that if we raise from VCs, they're going to suck our soul out. We're not going to be able to control our destiny. In all fairness to VCs, I know several VCs now that are not that way at all, but that was our just view of the world. And so what we said is what's the easiest way for us to raise money

Starting point is 00:11:33 from non-institutions and non-VCs? It made the options pretty small, because by the way, another option was like raising debt. Where were we going to be able to raise debt for a business that had no cash flow? And so we ended up doing something, I think that was pretty clever, which was in the early days of morning brew, we would interview on a weekly basis, successful business people and successful investors. So we interviewed everyone from like the owners of the Minnesota Vikings to the founder of the Snuggie to the former CEO of Time Warner Cable to, to the creator of MTV. And when we went to raise money, we basically said, hey, we have that spreadsheet of those 25 people

Starting point is 00:12:12 that we interviewed in the early days of morning brew. They seemed to be really successful. They seem to have a lot of money. Let's go talk to them. And so we basically, that was like the foundation of who we pitch, was leveraging this network of 25 people that we interviewed for our newsletter,

Starting point is 00:12:26 and then anyone in their network that they would introduce us to. We ended up raising the 750K from 28 individual investors So 28 individual checks in like early 2017. And the very interesting thing about it was twofold. One is investors, several of the investors, honestly, I think they were investing for nostalgia as much as they were investing for return. And things worked out in a really cool way where as a function of selling our business, they saw a return.

Starting point is 00:12:55 I don't think they were ever expecting. But also the other learning is we didn't realize just how much maintenance there is to when you are raising money. those were our first shareholders in a way, even though they were convertible note holders, so they were technically debt holders, they were going to be debt holders that convert to equity holders. So those were like our shareholders. And I don't think we realized at the time, how much time and effort would go into keeping up with them, updating them, making sure their documents were all right. We wouldn't do anything differently, but maintaining legal docs

Starting point is 00:13:25 and updating 28 people and trying to get 28 people on a call or a Zoom for an investor update, absolute nightmare. Let's take a quick break and hear from today's sponsors. All right. I want you guys to imagine spending three days in Oslo at the height of the summer. You've got long days of daylight, incredible food, floating saunas on the Oslo Fjord, and every conversation you have is with people who are actually shaping the future. That's what the Oslo Freedom Forum is.

Starting point is 00:13:54 From June 1st through the 3rd, 2026, the Oslo Freedom Forum is entering its 18th year, bringing together activists, technologists, journalists, investors, and builders from all over the world, many of them operating on the front lines of history. This is where you hear firsthand stories from people using Bitcoin to survive currency collapse, using AI to expose human rights abuses, and building technology under censorship and authoritarian pressures. These aren't abstract ideas. These are tools real people are using right now. You'll be in the room with about 2,000 extraordinary individuals, dissidents, founders, philanthropists, policymakers, the kind of people you don't just listen to but end up having dinner with. Over three days, you'll experience

Starting point is 00:14:38 powerful mainstage talks, hands-on workshops on freedom tech, and financial sovereignty, immersive art installations, and conversations that continue long after the sessions end. And it's all happening in Oslo in June. If this sounds like your kind of room, well, you're in luck because you can attend in person. Standard and patron passes are available at Osloof Freedom Forum.com with patron passes offering deep access, private events, and small group time with the speakers. The Oslo Freedom Forum isn't just a conference. It's a place where ideas meet reality and where the future is being built by people living it. If you run a business, you've probably had the same thought lately. How do we make AI useful in the

Starting point is 00:15:21 real world, because the upside is huge, but guessing your way into it is a risky move. With NetSuite by Oracle, you can put AI to work today. NetSuite is the number one AI cloud ERP, trusted by over 43,000 businesses. It pulls your financials, inventory, commerce, HR, and CRM into one unified system. And that connected data is what makes your AI smarter. It can automate routine work, surface actionable insights, and help you cut costs while making fast AI-powered decisions with confidence. And now with the NetSuite AI connector, you can use the AI of your choice to connect directly to your real business data. This isn't some add-on,

Starting point is 00:16:02 it's AI built into the system that runs your business. And whether your company does millions or even hundreds of millions, NetSuite helps you stay ahead. If your revenues are at least in the seven figures, get their free business guide, demystifying AI at netsuite.com slash study. The guide is free to you at netseweet.com slash study. NetSuite.com slash study. When I started my own side business, it suddenly felt like I had to become 10 different people overnight wearing many different hats. Starting something from scratch can feel exciting, but also incredibly overwhelming and lonely. That's why having the right tools matters. For millions of businesses, that tool is Shopify. Shopify is the commerce platform behind millions of businesses around the world.

Starting point is 00:16:50 and 10% of all e-commerce in the U.S. from brands just getting started to household names. It gives you everything you need in one place, from inventory to payments to analytics. So you're not juggling a bunch of different platforms. You can build a beautiful online store with hundreds of ready-to-use templates, and Shopify is packed with helpful AI tools that write product descriptions and even enhance your product photography. Plus, if you ever get stuck, they've got award-winning 24-7 customer support. Start your business today with the industry's best business partner, Shopify, and start hearing

Starting point is 00:17:25 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. Not a lot of people realize, and we've got a lot of entrepreneurs in the audience who may or may not have raised money yet. There's so much psychology that goes into raising money. One that stands out to me is the social proof aspect of it, right?

Starting point is 00:17:57 Because you mentioned the 28 checks you raised. Tell us how important it was to get five of those checks. So small checks and then go to people and say, look, we've got X amount committed. You know, are you in or out? Like just building from a small, nothing to something big is important. It's such a good point because I want to say all in all, it took us four months to raise the $750,000, I think it took us probably three months to get the first check. And I will forever remember our first check. I was in a coffee shop in Brooklyn. And it was one of these people I mentioned

Starting point is 00:18:31 who was a former executive at Time Warner Cable. I'm on the phone with him and I'm sitting by the bathroom in this coffee shop pitching myself, Austin, the business. And the call finishes with I'll invest 100K. Just let me know how to do it. And it was just like not only pure, adrenaline. I was also, it was crazy to me. I'd never met the person in person. And so to be like, wow, I convinced someone who I've never met in person to put 100K into the business, like, that's an awesome feeling. But to your point, it provided incredible social proof, because now every time we sent our investor deck out, we could say former CEO of Time Warner Cable is invested in the business. It provided legitimacy in two ways. One is because no one ever wants to be the first

Starting point is 00:19:15 check in in such an unproven pre-monetization business. The second is especially because someone had put a check in, but it was also like a qualified check. It was a strategic check from someone who knew the media world so well. It was validation for a lot of people who were saying, I know nothing about media. And if I'm going to make a bet on a media company, am I going to do it on two students who have never started a company before who are going against the Wall Street Journal? Think about how hard of a pitch that is. When we had this guy on board, it made it a lot easier because they're like, he clearly knows something that we don't know. Well, it's that zero to one philosophy, right? Going from zero to one is the hardest,

Starting point is 00:19:52 which is a great book, by the way, by Peter Thiel for all the entrepreneurs. I feel like if you read zero to one and you still want to start your business. You're slightly crazy, but you're in good shape. You know what to expect. Well, I think someone in that pool of investors you were approaching early on was Mark Cuban. So talk to us a little bit about that experience. One of the first people that I had reached out to about, and it wasn't even about investing at the time, it was when we had like 1,400 subscribers. And I'd reached out to Mark Cuban because I was a long-time Shark Tank Watcher. And I also just really, you know, respected what he had built.

Starting point is 00:20:32 I think I still have the email from him. I'm trying to pull it up. I reached out to him basically just saying what our business was. I said, we're a newsletter, everything that I've described. we're trying to make business digestible and approachable and conversational for this emerging generation of business leader who is going to run companies in the next five to 15 years. And like, it really is crazy when you think about it. By 2030, 80% of the working population will be millennial or Gen Z. And so there's this massive wealth transfer happening. Obviously, I didn't say it in that way to him.

Starting point is 00:21:03 But I said, what we're doing is emailed by, first of all, I was blown away that he emailed me back. But then he was basically like, I don't get it. He was like, there's so many newsletters out there. What makes you different? I talked about our voice was different. Curation was different. There was this sense of community. And he was just like, I still don't understand how it's different.

Starting point is 00:21:23 And to be totally honest with you, if I was in Mark's seat, I probably would have said the same thing. Because I think in a lot of ways, in media especially, your motive as a business is your brand and your ability to connect with an audience at a deep level. And especially if you are not in that audience, I think it's actually a really, it's a blind spot. Mark wasn't the 25 or 27 year old young business professional who doesn't necessarily like coming through the journal. They want to feel like they're having a conversation with a friend after work at a bar. And since he didn't have that vantage point, by the way, I think that's in a lot of ways why we had so much opportunity

Starting point is 00:22:04 with Morning Brew, because I think Mark Cuban and a lot of people of his ilk never thought that, oh, the Wall Street Journal or the economist or the Financial Times isn't serving this audience. Like, that was never a question in their mind because they weren't the audience. So honestly, in a lot of ways, I'm just thankful that he responded to me. I think this happens in a lot of industries. And I think from an investor's perspective, it's a really interesting place to think about investment, which is like, what are industries that have moats or defensibility that actually is kind of like fake or a little bit of like smoke and mirrors. And I think in the world of

Starting point is 00:22:37 business journalism or business media, I think a lot of people assumed no one is ever going to take audience from the Wall Street Journal or Bloomberg. These institutions have been around for a century. I don't think what they realized is that the Wall Street Journal has never been serving our audience, has never been serving the 25-year-old. The 25-year-old has been reading that content out of necessity because there's nothing else available. But the Wall Street Journal is the 48-year-old who's been working in business for 25 years. And by the way, that's why it gave us opportunity because it's never going to be the Wall Street Journal or ex-traditional business media company's prerogative to go after the 25-year-old today because they risk

Starting point is 00:23:19 alienating a more valuable audience. And I think that's almost one of the paradoxes of large legacy businesses is how do you build innovative products for a young and up-and-coming audience when you don't want to alienate, your more valuable audience today. I'm curious if you, if that early no, quote unquote, from Mark Cuban drove you in any way, right? Sometimes those early knows as an entrepreneur are so important. And I commend you for not letting that knock you back. Instead, it seems like it kind of fueled you forward. And it reminds me of, you know, a fellow Michigander Tom Brady, who was the 199th NFL draft pick, right? It goes on to become who he is.

Starting point is 00:24:00 Like sometimes those early failures lead to successes. I think in a lot of ways, every entrepreneur has a fire. And it's a question of where that fire comes from, right? Sometimes it's intrinsic. Sometimes it's created by your surroundings. I think for me it was a little bit of both, right? I think I just had this competitive spirit from growing up playing sports. I think things like interaction with Mark and there were, that was one example.

Starting point is 00:24:28 You can assume there were dozens of other ones like that in the early emails that I sent. I think those were all the extrinsic things or just like the things that happened that just added more and more of a chip on my shoulder. There was another side of me where honestly, I lost my dad when I was a junior in college. And I think that changed my perspective around everything where in some ways it created this, this idea in my mind that like now I have to be the breadwinner in the family. I need to take care of my family because by that point my mom had retired. There's only money going out.

Starting point is 00:25:02 There's no money coming in. And whether or not the narrative was true, I think in so many ways, that's what drove me to operate at such a intense level for so many times. There's no other option but to have this succeed because I have this deep vision in my mind of giving my mama check, my grandpa check, my sister check, and knowing they're going to be fine for the rest of their lives. And I wouldn't say every entrepreneur has like a story of trauma, although I will say I have met proportionally speaking. A lot of entrepreneurs have gone through some form of trauma or challenge relative to non-entrepreneurs that I've talked to.

Starting point is 00:25:39 But I do think every entrepreneur has a fire. And the question is where does that fire come from? It reminds me of billionaire Ray Dahlia, who we study a lot on the show. His book Principles. He talks about these two types of people in the world, those who are achievable. oriented, finding their own hero's journey of sorts, and those who are more present who cherish the nuance of everyday life. And while they aren't mutually exclusive, entrepreneurs inherently embark on that hero's journey,

Starting point is 00:26:09 right? And a critical milestone in the hero's journey is this abyss that they enter into or otherwise known as the trough of sorrow. And this is more related to the actual entrepreneurial journey, right, that you went through. So I'm curious about Morning Brew and if you had an experience where you felt like the company was entering this trough of sorrow of sorts that you had to climb out of. Things really accelerated in our business in the last two years, just to give a sense of trajectory. It was like revenue in the business in 2018 was $3.5 million in revenue.

Starting point is 00:26:46 In 2017, it was $175,000. That was the year that we raised our money. 2019 was 13.5 million. 2020 was 21 million. And so if you look at it, like the last three years of the business have really become us being a business. We went from a seven-figure business to an eight-figure business in the last two and a half years. And we've been in business for six years. So the first three and a half years of us being a business was scratching and clawing.

Starting point is 00:27:17 We were scratching and clawing for everything, for every subscriber, for every dollar, And we never lost faith. We never thought that the business was going to fail. We just didn't think we were going to be a massive business tomorrow. But it was like we didn't have this timeline in our head. Our view is almost like, however long it takes, we're just going to keep scratching and clung and building until this is something really meaningful. And so the fact that everything has accelerated in the last two and a half years and,

Starting point is 00:27:43 you know, we sold a portion of our business. That's icing on the cake. And it's a wild journey to realize. But yeah, in the early. days, honestly, it was a lot of just like thankless content creation where we were just putting out this newsletter every day, hoping that we would get a couple hundred subscribers. I mean, in the early days of selling ads in our newsletter, I remember our first ad we ever sold was an $800 ad, I think, to the University of Virginia.

Starting point is 00:28:09 Now someone wants to advertise in Morning Brew, you're doing a full takeover our newsletter. It's close to $100,000 a day. I think what this all says to me is like you need to, you kind of have to have a screw loose in my mind. It's like you have to have this uninformed hope that things are going to work out, that no matter what happens, things are going to work out. We always had that view, but then also have like respect for the journey and enjoying it. Like if we didn't enjoy pumping out the newsletter every day, figuring out partnerships to grow it, thinking about what brands we should go to monetize, like the actual act of zero to one building,

Starting point is 00:28:46 we didn't enjoy that. We would have never gotten here. And so to me, I think that's what happens to a lot of entrepreneurs is they have this big vision. They have the first part of it, but they don't enjoy the journey enough. They don't realize how much of a grind it is. If you don't have just like an appreciation for that grind and a level-headedness to not get whiplash from the highs and lows of it, it can be, it's like a roller coaster. It can make you sick.

Starting point is 00:29:12 And I think for us, the first three and a half years was a time of we don't have a big business, we're paying ourselves fine money. We don't have any perspective yet that this is going to be something huge that's going to be a life-changing endeavor, but we were just loving it. And we were loving it more than the jobs we were doing prior. So, like, to us, the opportunity cost was low is go back to something that we didn't enjoy as much. Well, first of all, I'm just not sure people realize that this is available to them, that you can start marketing pretty cheaply and test pretty accurately very early on nowadays. It's a huge advantage that most companies may not be taking advantage of. Is that something

Starting point is 00:29:47 you guys adapted very early on? The reason we got involved in paid marketing early on is because it is so approachable. And again, it's like when people are wondering, why is Facebook valuable, why is Google valuable, these are the largest platforms on planet Earth that have hundreds of millions, if not billions, of people. And you as a small business or a large business have the ability to spend anywhere from tens of dollars to tens of millions of dollars in a week on these platforms getting in front of your audience.

Starting point is 00:30:16 And so to your point, it was like, it was very easy. In a lot of ways, these platforms' goals are to make it as automated as possible, where you can set and forget their platforms. You decide you want to spend $10 in a day. Well, they'll be able to test that $10. Like, you literally have the ability of creating, let's just say for Morning Brew, we could tell Facebook, hey, we're going to spend $100 this week, and we want you to test three different types of creative.

Starting point is 00:30:42 So three different looks of ad units that could be sent to our audience. one will say, get smarter today. Another one will say be a better investor today. And maybe the third will say be a better entrepreneur today. And Facebook is smart enough to get in front of the right audiences, test that creative. And test that creative would say only like $2 of spending. And after spending $2, no, whether the get smarter, become a better investor or be a better entrepreneur, is going to get a cheaper subscriber and we'll put the remaining $8 in that winning creative. And I don't think, yeah, to your point, people fundamentally understand how powerful these advertising platforms are. And to your point also, I don't think people are truly understand how every company in the

Starting point is 00:31:26 world is becoming a media business or an audience business, whether it likes it or not. Everyone from, you know, obviously there's the argument about the Facebooks of the world being media businesses all the way to the largest investors in the world are becoming media businesses. Like, you look at Andresen Horowitz, they have a full-blown media organization now, And there's a reason that they're doing that because they think the investment in owning their own audience is worth enough to generate leads for potential portfolio companies or people they'll hire into their business or for raising new funds. Every company is turning into a media company because what they're realizing is while

Starting point is 00:32:02 these platforms like Facebook or Google are great places to start paying for marketing, you also realize that paying for marketing is really, really expensive and you don't own the audience. Yeah, and it reminds me of even someone like Warren Buffett who is a marketer. I mean, if you really think about it, he's obviously on CNBC a lot. He's obviously an educator and loves educating people. But that also provides this amazing opportunity for him to market his brand. And if you go to one of his Omaha events, he's pitching.

Starting point is 00:32:34 You know, he's like, call me, you know, we're looking for acquisitions and you want to be part of the Berkshire family. I mean, it's a big marketing effort and a huge media empire of sorts he's built in that way. I think it is actually a really fascinating time to think about this intersection of financial instruments, financial services, and media and audience, because I think you're seeing some of the most successful entrepreneurs in the world and some of the most successful investors in the world that are leveraging their personal brand and media to use that as a top of funnel for their financial instruments or financial services, right? You see that everywhere from

Starting point is 00:33:08 some of like the biggest holders of Bitcoin are touting Bitcoin on Twitter. And And I think are truly moving markets from the brands they've built up on social platforms, all the way to Chmoth, who is the CEO of Social Capital, has become the SPAC king. And now it's like he's built a direct-to-consumer relationship with potential investors or people who have interest in SPACs. Or it's like now he is literally posting on Twitter when he goes to SPAC a company, he writes out his investment thesis and posts on Twitter. There has never been a more direct relationship between investor, entrepreneur, instruments,

Starting point is 00:33:46 provider, and consumer. And I think that creates a really interesting and exciting opportunity. But I also think it brings questions of like at what point is there going to be regulation around a lot of this. Same thing with Elon. Elon Musk is, to me, media company first and electric vehicle CEO second. Or Doge coin promoters. Yeah, yeah.

Starting point is 00:34:08 Doge coin promoter number three. Let's take a quick break and hear from today's sponsors. No, it's not your imagination. Risk and regulation are ramping up, and customers now expect proof of security just to do business. That's why VANTA is a game changer. VANTA automates your compliance process and brings compliance, risk, and customer trust together on one AI-powered platform.

Starting point is 00:34:32 So whether you're prepping for a SOC 2 or running an enterprise GRC program, VANTA keeps you secure and keeps your deals moving. Instead of chasing spreadsheets and screenshots, Vanta gives you continuous automation across more than 35 security and privacy frameworks. Companies like Ramp and Ryder spend 82% less time on audits with Vantta. That's not just faster compliance, it's more time for growth. If I were running a startup or scaling a team today, this is exactly the type of platform I'd want in place. Get started at Vanta.com slash billionaires.

Starting point is 00:35:08 That's Vanta.com. billionaires. Ever wanted to explore the world of online trading but haven't dared try? The futures market is more active now than ever before, and plus 500 futures is the perfect place to start. Plus 500 gives you access to a wide range of instruments, the S&P 500, NASDAQ, Bitcoin, gas, and much more. Explore equity indices, energy, metals, 4x, crypto, and beyond.

Starting point is 00:35:37 With a simple and intuitive platform, you can trade from anywhere, right from your phone. Deposit with a minimum of $100 and experience the fast, accessible futures trading you've been waiting for. See a trading opportunity. You'll be able to trade it in just two clicks once your account is open. Not sure if you're ready, not a problem. Plus 500 gives you an unlimited, risk-free demo account with charts and analytic tools for you to practice on. With over 20 years of experience, Plus 500 is your gateway to the markets. Visit plus 500.com to learn more. Trading in futures involves risk of loss and is not suitable for everyone. Not all applicants will qualify. Plus 500, it's trading with a plus.

Starting point is 00:36:23 Billion dollar investors don't typically park their cash in high yield savings accounts. Instead, they often use one of the premier passive income strategies for institutional investors, private credit. Now, the same passive income strategy is available to investors of all sizes thanks to the Fundrise income fund, which has more than $600 million invested in a 7.97% distribution rate. With traditional savings yields falling, it's no wonder private credit has grown to be a trillion dollar asset class in the last few years. Visit fundrise.com slash WSB to invest in the Fundrise income fund in just minutes. The fund's total return in 2025 was 8%, and the average annual total return since inception is 7.8%. Past performance does not guarantee future results, current distribution rate as of 1231,

Starting point is 00:37:15 2025. Carefully consider the investment material before investing, including objectives, risks, charges, and expenses. This and other information can be found in the income funds prospectus at fundrise.com slash income. This is a paid advertisement. All right. Back to the show. So talking a little bit about Warren Buffett, I want to kind of just frame up here why we're talking about your business so in depth because my philosophy comes directly from Warren Buffett, which basically is, in order to be a great investor, you have to understand business and you have to study businesses like their species of animals. And that's what I'm trying

Starting point is 00:37:53 to do here is figure out kind of the recipe for success that Morning Brew has had. One thing I'm really curious about with the success of Morning Brew is that it seems to really come from the tone you mentioned or the voice that you've mentioned. And I don't think people quite recognize how maybe hard it is to distill or filter everything through a certain voice and have basically brand pillars in place that you honor with every word that you pick. Like poetry, right? That's the brand and that's the essence. So what are the pillars or what is the filter that you use? And yeah, talk to us a little bit about that. To me, actually, Morning Brew's job is the same job as an investor. We are master curators. I think there's

Starting point is 00:38:35 two types of currency in the world. It's like money and time. And for us, we are the people have trusted us with their time, right? They trusted us to sign up for our newsletter. And they trusted that every day that they open our newsletter, that we have respected their time. And we have been basically their internet Sherpa to decide of all this stuff that's happening on the internet. all this content that's being created, what is worth their time so they won't be caught off guard in a conversation with a boss or a coworker. And so we are acting as the curator where we're looking at the 15 things that they could care about that could be worth their time.

Starting point is 00:39:12 And we're deciding what are the four or five that are worth their time? And how do we provide it in a digestible and witty way that is going to keep them engaged? And in the same way, like at least when I think about investing, for example, like to me, investors are marketers and curators. They have to market to raise their funds and then they have to curate based on the remit of their fund out of the 50 different companies, 100 different companies that they could be putting their money to work in or their investors' money to work in. What is the best use of their investors' money? To me, Morning Brews, what is the best use of our reader's time? Like investors, the best investors are the best curators in the world.

Starting point is 00:39:53 And I think curation only gets more important as there's more choice in the world. And as there are more tools for businesses to be created, for startups to be started, for content to be created, the act of curation, of great curation knowing who your audience or your customer or your investor is only gets more valuable. And I don't think people truly grasp why curation is so valuable. I love that point. Absolutely. It goes back to the moat that Warren Buffett talks about. you mentioned it earlier, that voice, because I imagine there's a lot of competitors that have

Starting point is 00:40:27 entered this space with the newsletters, especially seeing some of your success. So does that filter into your mind at all as far as who you're competing with, or is it just full speed ahead? We're focused on this, very myopically focused on our mission. So how I think about competition is no, no decision we have made as a business, generally speaking, has been impacted by competitors, the only time we really think about competition is when we're thinking about launching a new product, there's a consumer need or problem that we're interested in solving. And we think our competitors are already solving it well, then maybe we think to ourselves, is this the best place for us to play? But other than that, none of our strategy as a business really has been

Starting point is 00:41:10 dictated by our competitors, I'm sure as you become larger and larger, it becomes more of a consideration. But for us, the world of media and business media and content, consumption is so large. We are still minnows. And if you're a minnow in an ocean, your time isn't best spent trying to bite other minnows. It's trying to explore the ocean and try to not get eaten by sharks. And so for us, the way that I think about our competitors, just so you have a sense of how I think about competitive sets, the first circle our closest competitors are other business newsletters, Wall Street Journal's newsletters, than newer digital age media companies, newsletters like The Hustle or Phenomize or Robin Hood snacks, then there's this second circle,

Starting point is 00:41:53 which is what I would say are non-business newsletters and business non-newsletters. And what I mean by that is non-business newsletters or newsletters like the skim or Axios' newsletters, basically newsletters that are not the same, but they serve a similar need where if someone's like, I just want to get updated on my day and they don't necessarily think it has to be about business. It could be about politics or pop culture. We could lose our reader there. Other example is non-newsletter business.

Starting point is 00:42:23 And that would be like listening to like New York Times Daily or Wall Street Journal's podcast, like a different media format that still competes for our reader's time. The third circle is what I would say is the least similar, but actually is just as competitive, which is what are all of the things in someone's morning routine that compete for your attention? And that could be the book you're reading, that could be playing Candy Crush. that could be, like I said earlier, listening to Headspace, that is the fundamental thing that I think every business builder needs to think about is what is growing is choice, choice of product,

Starting point is 00:42:57 choice of content, choice of businesses that you can be affiliated with. But consumers' time is as scarce as it's been and it will continue to be that scarce. I think it's the fundamental question that every business has to ask itself, which is not just what problem are we solving, but also does our consumer have the space in their 24 hours of their day for us to solve that problem? Because we could be the best, like, damn newsletter. But if it is not a problem that is big enough, that is worth our reader's time in their day, at the end of the day, we're competing for the same 30 minutes in someone's morning commute that someone else is. And so I just think people need to respect scarcity of time when thinking about what they're trying to do.

Starting point is 00:43:37 They have to think way more about that than they have to think about, you know, are they out competing a similar firm? I love that. And you can apply that. to other businesses as well. For example, my business is a beverage business. So instead of thinking about timeshare, we think about stomach share. It's not like anyone's drinking a kombucha or adding it on top of the other sodas that they've been drinking. Typically, they're replacing something with something else because you have a finite amount. That's really interesting. I'm wondering about that competitive landscape you mentioned and the advertising dollars that go to all of those players. Being a leader in the space, are you able to have pricing power

Starting point is 00:44:13 when it comes to advertising, or is there just a big democratization of advertising across all these media platforms now? I would say we have pricing power because we have loyalty. And I think this honestly goes for any business. It's like when you have loyalty and you have retention, you can continue to increase price. If that's part of your brand. And if your brand is about being like a discounter, then obviously that's going to be different. But for us, at the end of the day, If you are a company that is looking to get in front of the young 30-something-year-old professional who's working in finance, investing, tech consulting, making six figures a year, who has big life moments coming up, putting their money to work or getting married or whatever,

Starting point is 00:44:56 moving into a home, having a child, there are only so many places on the internet that you can do that in a high-impact way. You can't go to the Wall Street Journal or places like that because that's not the average audience. If you go to Facebook or you go to Google, you can get in front of that audience, but it's not going to be high impact because it's not like the consumer I just described has this love for Facebook where they're going to be seeking out the advertisements that Facebook is serving them. And so I think the reason we have pricing power is actually less about our size. It definitely has helped us going from originally 100,000 readers to now 2.7 million subscribers. Definitely gives us more credibility to say we are an at-scale player.

Starting point is 00:45:34 There was definitely an aspect of that. And it really happened when we hit like 500,000 subscribers. But I think it's the fact that like we just have a deeply engaged audience. Like to give you the specific example, in the email newsletter world, a 20% open rate. So 20% of your subscribers opening your newsletter is considered good. That is the average. Morning Brews continues to be twice the average. We're 40% daily unique open rate.

Starting point is 00:45:59 And it's just like numbers don't lie. And when you have a conversation with a brand and they realize that Morning Brew is one of the only places on the internet that has the loyalty of the emerging business leader for five to 10 into their day, it makes pricing really easy. Because I'll give you the example, if I am IKEA and I'm talking to Morning Brew and I'm and Morning Brew tells me, hey, IKEA, we have this audience, 75% of our audience tells us that in the next five years, they're going to move into a home or an apartment, they're going to furnish their home. And they don't yet have loyalty to any brand. And by the way, IKEA, we're talking to Crate and Barrel next week, and either of you would have the opportunity to build

Starting point is 00:46:39 habit with this first-time home buyer, it puts Ikea in a really tough position where they're like, well, Craten Barrel could start working with Morning Brew and start to build loyalty with a totally new generation of consumer or we can. And if we don't do it, where else are we going to do it? And so I think there's this pent-up appetite or this price inelasticity because you have a lot of brands that do have marketing budgets to put to work, but there actually isn't so much choice to get in front of an entire generation of people that are going to have a lot of money to spend in the next few years. Well, I found it interesting that you referred to Morning Brew as a minnow in the ocean because

Starting point is 00:47:19 you recently sold a majority of stake in the business to Business Insider for $75 million. So that's a big chunk of change, especially for someone. Are you under 30, by the way? Yeah, I'm 27. Amazing. So talk to us about that decision, how they came around or came to the table. What made you go that route? The first thing that I would say is this deal revalidated for me how important relationship

Starting point is 00:47:48 building is. And I think for a little while, not that I was skeptical of it, but I was wondering to myself, is that considered an old school? Like, you know, people talk about it in the old days, like building your Rolodex and and all these things, is that as important in like a connected age of social media? And I would say what this deal validated for me is relationship building is more important than ever before. Maybe the way in which you relationship build, like the forums in which you do it, maybe now

Starting point is 00:48:15 it's more so done on Clubhouse and Zoom versus just handshakes in a restaurant. It's probably a combination of both. But the reason I bring that up is the way our relationship originally started with Business Insider was almost probably two and a half years ago. And it was in the days of, we were still in zero to one for Morning Brew, and we were trying to fight for every subscriber. And one of the things we tried doing

Starting point is 00:48:41 when we were fighting for every subscriber is we reached out to big media companies and we were like, hey, can we strike a deal together? Is there any way that Morning Brew could be distributed on your website? And we had reached out to Business Insider because they get hundreds of millions of people to go to their website every month.

Starting point is 00:48:54 We thought, like, wow, this is an amazing marketing funnel of people who care about business. And so at the time, I was talking to one of their editors, and I kept bothering him over and over and over, hey, can we partner? Hey, can we partner? And at some point, he just foisted me on another person. He foisted me on the person at the time who was running consumer subscriptions for Business Insider, this guy, Claudius. And there was kind of no agenda other than to talk about partnership and meet each other. But once I was introduced to Claudius, We met up on Stone Street in the Financial District of New York City. At the time, Morning Brew was in its original office in WeWork.

Starting point is 00:49:30 And Business Insider was also in the Financial District. We got beers. We talked about, like, media, the history of media, where media is going. And then we just kept in touch from that point on. We would do like home-and-home ping-pong matches where Claudius would come to WeWork. He'd play ping pong there. I'd go to Business Insider, play ping-pong there. And basically, it was just like a friendship with appearance.

Starting point is 00:49:52 the industry for probably a year and a half before any sort of serious conversation started. And it was like, you know, around the beginning of 2020, that's when any sort of conversation around what could a bigger partnership look like. Ultimately, it took several months, probably like 10 or 11 months for the deal to actually happen. And Austin and I had never been through a deal process before. So never had a sense of how long it would take. But it definitely went in ebbs and flows. Like it was almost like a little business in itself. It was a roller coaster. And I think it was a magnified roller coaster because March 2020 is when really everything happened with what was going on in the world. And so it went and ebden flowed. But I think the thing that

Starting point is 00:50:32 stayed consistent, which is why we saw a ton of opportunity, was because everything that Business Insider was is what Morning Brew wasn't. And everything that Morning Brew was was what Business Insider wasn't. And what I mean by that is we're both media companies, but we couldn't be more different. Business Insider has built just an incredible brand and business by off of one great journalism and a great newsroom. Morning Brew does not have a newsroom and we're not journalism per se. We are curation, remixing, and some original content like original analysis, but we don't break news. Business Insiders focus has been on website content and social media. Morning Brew's focus has always been on email and then podcasts.

Starting point is 00:51:16 And so I think in so many ways, we saw these complementary assets where business insider really wanted to get into the email game, but they saw a partner who had figured it out. We saw for ourselves as Morning Brew that we wanted to evolve from a newsletter business where you go on the streets in New York, you ask someone what is Morning Brew? Nine times out of 10, you would hear the answer of, oh, it's like the skim but for business, or it's that newsletter company. We knew we wanted to evolve into a media brand. And so for us, we were excited by this fact of like this company that started as a newsletter in Henry Blodgett's apartment has evolved into a full media company. There's so much we can learn from them in how they set the foundation for growth. And for them, as they think about do they buy or do they make newsletters and podcasts, I think they saw a ton of opportunity in us. And again, going back to this idea of how important it is to build loyalty with an audience and like being obsessed with that, that's what they saw in us is like they truly.

Starting point is 00:52:11 saw that we built an obsessive audience. And when you have an obsessive audience, there are so many things that you can do with it. And so that was always the thesis, was this complementary nature of our businesses. The deal closed in October of 2020. And so far, it's been a great partnership where everything they promised that we could do is what we've done. I think people in media get worried about acquisitions or investments. And there's generally three types of flavors. There's vertical. there's, I would say, like, more private equity-esque in nature, and they're synergistic. So vertical is like what Barstool did. Barstool being acquired by Penn National, and the whole idea was Barstool is this huge top

Starting point is 00:52:53 of funnel for sports gamblers, for people interested in sports. Penn National wanted to grow its digital gambling presence. The whole idea was Barstool would be this great top of funnel. We'll see over the long term how it does, but if you look at Penn National stock, since the acquisition. I believe it has significantly outperformed the S&P and just like any other comps in the sports gambling space.

Starting point is 00:53:17 That's a vertical. Then you have a private equity style acquisition. I think this is the one in media that people get really worried about, which is private equity firm buys two or three media companies, puts them, basically centralizes all of their main functions, HR, sales, finance, editorial. A bunch of people get fired.

Starting point is 00:53:38 It's not fun for everyone. Melding of cultures becomes a really difficult problem. That's what I think what everyone assumes when they think acquisition and media. The third is more synergistic or horizontal in nature, where it's similar playing field, similar types of companies that are complementary, that when you bring them together, they can learn from one another, and they can also basically contribute to a larger hole in areas that each one has a blind spot. And that's what it's been for us. And from the early days, Austin and I, as entrepreneurs, said it pretty overtly when we were talking about any sort of deal that we need to have the freedom to continue to build and to control our own destiny and guide the ship. That's why we love coming into work every day, and we don't want to mess that up.

Starting point is 00:54:19 And I think what's been awesome is they've truly respected that. I think because Henry Blodgett himself is an entrepreneur, he's been building Business Insider for a long time. And Axel Springer, the German media conglomerate that owns Insider, is a very acquisitive company as well. I think they've done 200 acquisitions in the last five years, maybe. Everyone was on the same page about being founder and entrepreneur friendly. And unless things aren't going well, we have our game plan. Let's stick to it. And they're always there as a resource if we need help.

Starting point is 00:54:50 Amazing. Well, congratulations. Well, now that you have some resources of your own to put to work, have you thought about your own investing approach or your own portfolio? What's taking your interest? It's a great question because I think there's a few options that I've been thinking about. One is, how much do I do my own angel investing? That's been like a part of my mindset. How much do I just write checks into startups that I believe that I can provide a strategic lens as they think about building audience or marketing, etc. The other is how much should I be thinking about putting money with professionals? They're spending all day long thinking about putting money to work. And then there's another model, which I've just thought about, which is like starting my own fund of sorts. Like, you know, it's something my co-founder, Austin has done, he started a rolling fund, on Angel, we've seen people start rolling funds as well.

Starting point is 00:55:41 Talk to us about that. Maybe describe to the audience what that is, because I only found out about that recently. It's fascinating. Basically, the concept of a rolling fund is that it offers investors flexibility to get in and out of funds and not feel so locked in. And the whole idea is that for fund managers, you don't have to start with large amounts of capital. I can't remember last time I checked, I think Austin's fund had $2.9 million committed, but I think it's a great way for people who have large brands and large followings on Twitter to be able to start putting money to work their money and other people's money and do so in a pretty approachable way. The other thing is that normally fund managers need to raise their entire fund's capital

Starting point is 00:56:25 in a short period of time. The whole idea of the rolling fund is you're constantly fundraising. So you don't have to raise a $10 million fund, make whatever, $50. investments a year and allocate the whole fund within whatever that period of time is, it is rolling in nature. And so as a fund manager, I think it takes pressure off of people where you can start the fund with hundreds of thousands of dollars, not millions of dollars, and continue to raise also as you are proving your worth, not even proving your worth from like ROI on the investments, but even proving your worth of like legitimacy in the marketplace and getting involved, getting

Starting point is 00:56:59 checks into deals that other big investors are in. So I think that's a big thing is like, one, as a rolling fund manager, you can constantly be adding funds to your business rather than in a single period of time. So it adds flexibility. And to that point as well, a startup in your or company in your portfolio has a large markup. So say you invested in their seat or their series A, they raised a series B or series C. As a traditional VC, you couldn't necessarily use that event as a promotional moment to raise more for your fund. but it's created the flexibility now that you can do things like that.

Starting point is 00:57:35 Yeah, I think it's amazing. And we'll link to the Angel Co link in the show notes. So everyone can kind of check that out. I think the rolling fund is fascinating, especially for, you know, obviously we talk about the public markets a lot on this show, but a lot of gains are there to be made in the private markets, especially pre-IPO stage companies. And the technology coming to this is really unprecedented.

Starting point is 00:57:56 So I want to hear a little bit about how you would approach an investment now that you've been an operator of your own business? What do you look for in the management? What do you look for in the metrics? How has that shaped your investing philosophy? There's a few things. As I think about things as an investor, as an early investor, one of the things I think about is like playing in my circles of competence, you know, this idea of circles of competence. I think Charlie Munger talks about it a decent amount. But like knowing what I know, knowing what I don't know, and then all this massive space of not knowing what I don't know, I think it's so important to respect those boundaries. Even as I've started to put my own money to work in the form of checks as an angel, I've generally focused on the stuff I know really well. So I know media really well. I know community building really well. I know passion audiences really well. And so I'll give you an example. Like one investment I made was into a company called Soul Savvy. Soul Savvy is a paid sneakerhead community. So if you are obsessed with collecting sneakers, you pay $350,

Starting point is 00:58:57 a year to be in this community, you're with thousands of other sneaker heads, you get exclusive looks at new sneaker drops. And my whole view from building an obsessive audience myself is that if you play into a deep passion, especially like a collectible passion, and you build a good community around that, you're going to get people locked in for years. I'll use another example. A business I invested in was there's this famous Instagram influencer, her name is Something Navy, Ariel Charnas. He launched a clothing brand. And the reason I was interested in that, is, again, she built a passionate audience who cared a lot about following her on Instagram and engaging with her stuff.

Starting point is 00:59:34 And a lot of the content she creates is fashion-oriented. So I knew if she launched a product, it wouldn't totally change the content of what she was doing. The combination of her having a passionate audience and launching this fashion brand with a proven fashion entrepreneur, it was this guy who has launched several DTC apparel brands. To me, that was really attractive. So the first is playing within my circles of competence. because I am not nearly well-versed enough yet as an investor who try to make bets outside of the areas that I know really well.

Starting point is 01:00:05 The second is actually kind of counterintuitive, which is I actually get really scared investing in first-time founders. It's one of those things where it's like you would expect me to say that like, oh, yeah, I'm going to be more empathetic and invest in first-time founders. But from realizing in Austin and my own experience, how many blind spots we had, how many mistakes we made in hiring, how many things that we got lucky when we got it wrong, that it wasn't more catastrophic. It actually just like, it makes me feel way more conviction now more than ever that when I'm putting money into startups or even like growth equity stage businesses

Starting point is 01:00:41 that they're proven entrepreneurs, because I just think there's such from your point that you made to be a good investor, understanding how businesses are built is fundamental. I also just think to be a good entrepreneur, know what makes you an even better entrepreneur, having been an entrepreneur before. And so it's this weird thing where it's like, I was a first time founder. I have so much respect for the people invest in us because there's so many blind spots we had. And to me, if I can invest in things where those blind spots have been uncovered multiple times, I just think the probabilities are way better. Well, you talk a little bit about what you've learned by being a first time founder on your podcast, Founders Journal, which I've just found

Starting point is 01:01:16 incredibly insightful with your very salient points about just really really. transparent, honestly, experience that you've had. I just feel like sometimes I hear myself talking in your podcast. I can just relate to it so much. So I highly recommend that for entrepreneurs to check that out. And you know, you might be a few steps ahead of someone who's a little bit younger or starting out a little earlier on, but there's a lot of key takeaways to talk. So what led you to this podcast? Maybe talk about that. Yeah. So my whole thing was entrepreneurship has taught me a ton about myself as a person. And one of the things that I realized about myself is I love being able to reflect on past experiences, past decisions, as a way of learning and also just reliving moments.

Starting point is 01:01:59 I've also just realized that, like, we as people have really faulty memories. If it's not in photo form or written form, I think memories as time goes on tend to take on a life of their own. And what I thought to myself is there's so much on the internet that allows us to capture memories of our personal life. Instagram, your eye photo on your phone, all of these things. It allows you to memorialize, create a time capsule for personal moments in your life. But when you think about your professional career, which is taking up half of your life, half of your waking hours between the ages of, I don't know, 20 and 65, it's actually a lot harder to do that. Where do you go to remember your professional moments? And at first, I was always like, I really want to keep a journal

Starting point is 01:02:40 because really successful people journal and it's really important for clarity of thinking, is clarity of writing. And for whatever reason, I couldn't get myself into the habit of journaling. It just didn't drive with me. I couldn't get in the flow of it. And so what I said to myself is, maybe if I hold myself accountable to journaling to the world, maybe that will get me in the habit. So now 178 episodes later, Founders Journal has become my journal for the world. And the whole idea is that I document the biggest decisions, challenges, strategies, frameworks, emotions, behind the scenes that morning grew. And very intentionally, I've said that this is for the business builder.

Starting point is 01:03:19 And the reason I use that language is I don't think business builders are just founders or just entrepreneurs. People who are working in large companies are also business builders, whether they're building out of sales org or a new product. And I think they are yearning for the same types of learnings that entrepreneurs are. And so basically it's this three day a week show, 15 minutes. And, you know, I talk about everything from my learnings. of being a people pleaser and losing our first two employees and how I had to deal with

Starting point is 01:03:49 the emotional reckoning of putting our two early employees leaving on me and something I did wrong, all the way to this concept of the Peter Principle, where Peter Principle says that every employee is promoted to the point of incompetence. So the idea is that as employees are promoted, they're promoted because they do a great job. Every additional promotion, they become less qualify at that job where you could probably find someone elsewhere who's better at it, all the way to I saw an executive coach for the first time in the past week, and I just documented what that experience was like. And it validated more than ever before that like every professional investor, business builder, it doesn't matter, probably have someone who serves the purpose of a coach

Starting point is 01:04:28 or a therapist. It doesn't have to be those formal constructs, but having someone to be your intellectual and emotional sparring partner in your career is so important. Well, I loved that one in particular because I recently got my own coach probably in the last, a little over a year ago, and it was after reading the Eric Schmidt book, Trillion Dollar Coach. I don't know if you know this book, but basically it talks about how all these trillion dollar companies use more or less as one coach and how impactful he really was for their business. So I saw that up for myself and I've just seen a tremendous amount of benefit from it. And it also speaks to something you've highlighted about how your personal improvement has directly correlated with the businesses

Starting point is 01:05:10 improvement. And I really resonated with that. So maybe talk to us a little bit about that. One of my core beliefs, this has been one of my biggest learnings as an entrepreneur, is every entrepreneur, every investor is generally going to be exceptional at one, maybe two things. Everything else, you are not going to be the best in the world at. And that's okay. And so for me, I've just learned about myself that there are a few things that I'm really exceptional at. I'm exceptional at storytelling and I am exceptional at creative thinking. Everything else, there was someone better at the job. And so I think, honestly, a lot of my personal improvement has been around me getting out of my own way and being okay with not being exceptional at everything.

Starting point is 01:05:52 And what I mean by that is early in the life of the business, I try to hold on to a lot of things. And this doesn't mean just like with delegation. I wanted to do a lot of the different jobs because I felt as this competitive type A personality that getting better at the things that I'm weaker at was actually investing in myself and investing in the business. I've never been more convinced that that was the wrong approach, that the right approach is what are ways you can double, triple, quadruple down on your superpowers, and then literally just remove yourself from everything else and outsource everything else to people who are better, outsource through hiring, through freelancers, through people who just love doing those things,

Starting point is 01:06:30 and it's their superpowers. And so to this day, it's like, when I think about what I spend my time on with the brew, I always go back to these questions, these fundamental questions as a builder, which is, what are the things that I invest in class at? It's literally just those two things. And it's like, what are the highest leverage things that I can do in the business with my superpowers? And then the third question is, what are the things that the business needs most right now? And to me, the way that I have grown and I think the business has grown is by always basically landing on the two to three things in the business that the business needs most right now that lean into my superpower of storytelling and creative thinking and are high leverage

Starting point is 01:07:10 activities. And I think it was this turning point where I finally was open to this idea of it's okay to keep spending time on the things I'm really good at and let the other things go. It was a really humbling feeling because it doesn't feel, at least for me, as a competitive person never felt good to truly have people that were better than me at those things. Because I think we talk about it in concept that like hire really good people around you that are better than you at those things. When you actually do it in practice, it actually is tough. It's anxiety provoking. It makes you question your value and if you're actually good at things. And when I finally got okay with that or

Starting point is 01:07:45 more okay with it, I think it unlocked a ton of opportunity in the business. What would you say is your co-founder Austin's superpower. You mentioned him being somewhat of the, what Warren would call Charlie Bunger, an abominable no man early on, right? Saying he had a more analytical mind maybe. What would you say his superpower is? How did it complement yours? To me, if I had to say what Austin's superpowers are, it is strategic thinking and linear thinking. Austin is exceptional at taking a lot of ideas, a ton of noise, and finding, literally just picking out the pieces of of gold that are the things we should actually focus on. And especially when you're a resource-constrained startup, there is nothing more important than having this ability to focus your limited resources.

Starting point is 01:08:33 And so Austin is exceptional at setting what our game plan is based on the little resources we have and all the things we want to do. And then also, once that plan is set, he's incredible at constructing just these blinders around himself and around the people he works with to only, only care about those things. I think to your point of the abominable no man, Austin is exactly that way. And I think it is so important for a business. I've always called it like the bomb sniffing dog of the business, which is like the person who has just the naturally critical brain. Like seems negative in nature because they're calling out flaws. But I think when you really, really realize it, they're actually calling to attention a lot of things proactively that could turn into big issues.

Starting point is 01:09:17 They're able to sniff it out earlier than other people. I think it's Austin's ability. to understand the strategy of the business, prioritize what we're doing, and sniff out early cracks that haven't yet turned into big problems. It is such an important thing to have in a partner. Yeah, I think the distinction there is that you want to have potentially a realist to counteract your optimism, but maybe not so much a pessimist. There's a fine line, right? Yep, I think that's exactly right. I think it's this idea of being a realist and putting everything on the table, the good and the bad, but acknowledging, basically just acknowledging, what are the things that can hurt you? What are the things that could sink the ship? And if there's no one to do that,

Starting point is 01:09:59 at some point the ship will sink. Well, luckily, Morning Brew didn't sink. You sold for $75 million, and it's an incredible accomplishment, especially for someone your age. You have a long, fruitful career ahead of you. I look forward to watching it and following along on Twitter like I do already and keeping in touch. And I really enjoyed our conversation. I hope the audience really took this as an exercise as looking into the qualitative measurements of a business, as well as the quantitative measurements. We can all get myopic with the quantitative. But this was such a great exercise, I think, in learning about the qualitative elements of what makes a great business. So thank you for being so sharing with that. So, Alex, before I let you go, I just want to make

Starting point is 01:10:43 sure I give you the opportunity to hand off to our audience where they can learn about more Morning Brew, subscribe to the newsletter, follow along with your podcasts, and any other endeavors you're working on. Totally. No, I appreciate that. So if you want to sign up for Morning Brew, the daily newsletter, just go to morning brew. com. If you want to follow me on Twitter, I am at Business Burista. And if you want to check out the podcast, Founders Journal, just go to Apple Podcasts, Spotify.

Starting point is 01:11:09 It's three days a week, 10 to 15 minutes, and I think you'll enjoy it. Alex, thank you so much for coming on the show. Thanks so much for having me. All right, everybody, that's all we had for you this week. If you haven't already done so, definitely go to the Investorspodcast.com. Check out the wealth of resources we have there for you, different shows, the TIP Finance Tool, and so much more. And lastly, don't forget to follow me on Twitter at Trey Lockerbie, reach out and get in touch.

Starting point is 01:11:38 And with that, we'll see you again next week. 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, this show is copyrighted by the Investors Podcast Network. Written permission must be granted before syndication or rebroadcasting.

We Study Billionaires - The Investor’s Podcast Network - TIP344: A Deep Dive Into Morning Brew's $75M Valuation w/ Alex Lieberman

There aren't comments yet for this episode. Click on any sentence in the transcript to leave a comment.