How To Grow A $75M Newsletter Business | Morning Brew Co-Founder (#398)

All right. So we have Austin here, Austin Reiff, founder of Morning Brew. I know how big you guys are. I don't know what the public numbers are, so I'll let you kind of say, like, how big is the company now?

Yeah, $70, $75 million of revenue this year, double-digit profit margin, 250 people or so.

And it's kind of crazy, kind of a crazy story. You guys started this, you guys were at college, right? You were, you were at, is it Michigan where you guys went to school?

Yeah. So, so we're at the University of Michigan. I applied to Duke, didn't get in though, unfortunately.

Yeah. Sorry.

Wow. And so went to Michigan. Yeah. I went to a small private high school. Our condolences. So I, no, Michigan worked out well. It was a little cold, a little bit colder than Duke, but I, I mean, my goal was to go to the biggest school I could get into other than, you know, an Ivy or Duke. So I got into Michigan, had no idea what I wanted to do. and everyone went to finance at Michigan. So I was like, oh, I gotta, I gotta follow the herd. I was a sheep following the herd straight into the world of corporate finance or investment banking, uh, and then stumbled upon this guy Alex Lieberman, who was like— I wouldn't even call it a newsletter. It was a PDF attached to an email. He actually took a— he made a Word document, he would PDF it and put it to an email, and that was the first newsletter.

So he was, he was already doing it. Was it called Morning Brew?

No, it was called Market Corner. It was way more markets-based, way more finance-oriented.

Was he in college as well, or was he— had he graduated?

Yeah, so he was 2 years older than I was, and that's a big part of our success, to be honest. Uh, if I was his age, we probably would have went out and raised venture capital. So, you know, 20— 2015, you have BuzzFeed raising money, Vice raising money, and the only reason we didn't follow that path was because I was in college and no one was going to fund a sophomore in college. And so Alex went to work at Morgan Stanley for 14 months. I spent summer in investment banking and was like, holy shit, this is miserable. Get me out of here. And so I was like, all right, well, I got this Morning Brew thing. I might as well do it for a couple of years. What's the worst thing that happens? I come back here. And that was the— that was the start of going full time.

What did your nice Jewish parents think about you not becoming a banker and instead working on a newsletter?

So my parents were actually okay with it, except I told them after my junior year, I said, I have one more year of college. What if I just don't go back? What if I don't finish? And the idea of them spending $150,000 on 3 years of college and not finishing my senior year drove them nuts. So the deal we made is if I, if I graduated, they were cool with me doing Morning Brew for a year or two after.

And then fast forward, you guys. So it was funny, right when we were in the process of selling, you announced that you had sold like months or 2 months, uh, in a, before us. And so you guys sold a portion of the business, I think the majority of the business for at something like a $70 million valuation in that ballpark, right?

Yeah, right around there. I think we were actually, we were doing M&A at the same time. We were even talking to some similar partners.

I, I think we were. And the reason why like Sean and I wanted to have you on, because we wanna talk about newsletters, which every, all 3 of us have a newsletter business, but you and I have an interesting background. We're like on paper, we kind of hated each other. Like the whole time.

I hated you, dude. I hated you.

So I didn't entirely hate you. I just— it was—

I hated you.

It was like I— it was like just sports, opposing sports teams where I was like, I have a lot of respect for this person. I don't know anything about their character, but I'm going to make up this story in my head to, like, motivate me. And the reason why I wanted to do that was because we— so I launched— we technically launched The Hustle in April April 2016. Were you before us or after us?

We were 2015 when we launched the first newsletter, but it wasn't— it was a very small thing.

So we were going like back and forth. It was like The Skimm was like the thing, and then it was you and I, Morning Brew and The Hustle. And you guys were this like New York kind of buttoned up crew. I was like a little bit of a crazier person. It was tech, San Francisco, but it was like everyone kept comparing us. And I remember like wanting to like crush you guys. And then after we built so old, Alex called me and, uh, you and I became buddies. And I was like, oh no, I actually love these guys. And now at this point, you and I are great friends and I have a ton of respect. But, uh, yeah, like, I wanted to crush you. I didn't, I didn't really hate you. What did you feel?

Yeah, look, I think it's always good for a business to have an enemy. I think in the early days our enemy was The Skimm. Very quickly though, we were like, you know what, they're not our enemy. We realized, I think we both realized pretty quickly that you can't raise $25 million for a newsletter and have a good exit. And so I think it was you and us. And so I turned you into that enemy. And I was so immature at the time, right? This was my first thing out of college. I knew nothing. So I was like, here's this guy. He's so abrasive. He's so aggressive. Like, what the fuck? And like, I was so— I wasn't principled. I didn't have real values at the time. And so I just saw you who are super valued, right? You have strong principles, very strong principles, which some people love, tons of people I'm sure don't like. And I was like, this guy is just so abrasive. And I've learned to love that about you. But at the time, it just— it rubbed me the wrong way. And I was like, we're going to make this guy your enemy and we're going to crush this guy.

I used to get mad because everything that I was bad at, you were good at. And everything that I was good at, I thought you guys were bad at. And I'm like, shit, they're just stealing all my ideas from my ads that I'm running or they're stealing all my content ideas. And then I would see how you guys operate and I'd be like, no, we got to have all these salespeople just like them.

Like, I remember I was at your office and I— and you were talking about Morning Brew and you were like, I thought you would just hate them and be like, they suck. Because, uh, I feel like that's how we used to just talk about most people at most startups was just like, oh my God, they suck. And especially one that's doing what you're doing, then it's like, oh, I already want you to suck. So I'm going to say that. And instead you were like, God, why does this email look better than ours? And you would just like show it to the whole team and you're like, look at this. Why does this look so much better than our email? Look at what they do at the top. Like, God, there's some, like, you're just like, they're so much better at that. You know, like the, the formatting or the cleanliness or like the brand that they are doing at the, I remember at the top of the email and I was like, wow, he just respects the actual like craft so much that he can't even hate them fully. He's like, ah, they're doing good at these 3 things.

Sam, I'll give you a story. I don't think I've ever told you, which is You know, there was a time where I thought our copy was much better than yours, our editorial. And then there was a time where I thought you guys passed us, right? And Alex in particular was maniacal about this. He would print out Morning Brew and The Hustle every single morning.

That's so funny.

Line by line, we'd sit down line by line and we'd be like, that line's better. No, our line's better. No, that. And we go line by line. And some of the early Morning Brew employees, they really hated you because when you wrote a story, that we wrote and when yours was better and Alex thought yours was better. People, I mean, people were pissed. There was like a revolt in the morning brew office one morning 'cause people were like, "No, ours is better." And I think ultimately it wasn't better or worse, right? It was just catered towards different people. But I mean, yeah, we printed out your newsletter every day and read through it for, I don't know, 6 months, 9 months. Like we were just so focused. Like I've never been as hyper-focused as I was in 2018 on us writing the best newsletter, growing the best newsletter, and selling it. Like I woke up every day, Write, grow, sell. Write, grow, sell. Like we wrote it on the wall and at 11:00 AM every single day we had the Great Wall of Opens and we track our open rate and write down the wall. And we had that for probably 2 years running every day. What was our open rate?

And your strategy was to— our, our strategies were, they diverged and they were different. So we were gonna launch, we were gonna stay in this space and verticalize and launch subscription services and all this other stuff. You guys launched multiple different newsletters, which meant from my eyes, you grew your revenue quicker. I personally hate that business because I don't like advertising that much, but you grew your revenue way faster than us. Well, I think you did. Like we— if we were one year behind you, I think we were tracking one year. So the year we sold, I think we could have done $18 or $20 million in revenue, which is around— you were, I think, the same year. So we were like tracking perfectly, which is really interesting. But you went this horizontal route where you launched multiple, multiple newsletters. Which route do you like looking back?

Look, I mean, it's tough to say we took the wrong route, but I also think it's what we had to do, right? We didn't have the choice you had because our content was more general business, right? You wrote with an edge, with a tone. You were targeting entrepreneurs or maybe like account executives who want to become entrepreneurs. And so you had way more opportunity to launch a Trends or to launch a HustleCon. For us, we we thought, you know, a general Morning Brew subscription wasn't going to work. A general Morning Brew event wasn't going to work. The tone wasn't specific enough. The target customer wasn't specific enough. But we fell in love with this B2B business, which I know both of you got a little bit of Twitter shit when you, when you spoke about the B2B world and, you know, Industry Dive. But we, I fell in love with that business. I'm like, wow, if you can get in front of retail professionals and HR professionals and we have them in our newsletter, and it was the craziest business where we'd launch a newsletter and it'd be break-even before we even hired the writers because we'd pre-sell, you know, an advertiser, let's call it like a B2B SaaS company, into one of these newsletters. And so I don't think there's better or worse. I think your— our opportunity was easier to get to $100 million of revenue. Yours was easier to get to, let's call it like a billion-dollar company, right? Because you could have subscription, multi-revenue stream much easier. It just was going to take another, you know, 8 to 10 years.

That's great. I'm happy I'm learning that now after I sold it.

I'm happy I got to see it because I just got to copy both of your playbooks and do that, do it for the Milk Road. Like, all three of us were able to win with the same playbook. Mine was the easiest path of all because I could just text you guys and be like, hey, uh, think about doing, uh, your thing but for crypto, uh, what do you think? It was like, yeah, I think it's gonna work, let's do it.

Did the playbook work perfectly, Sean, you think?

I mean, it has so far, right? We basically, in less than a year, we built the number one like the biggest daily crypto email. It's profitable. It's, you know, 7 figures. It's, I don't know, like it worked as well as one could expect. Bootstrapped it, you know, in our spare time. Like that's like as good as I could have expected that to go.

Dude, that's why these businesses are awesome is people don't realize. That's why I always hate when people say, if you're going to start it over again, what would you do? I'm like, do the same thing. Like it works. It consistently works. I know, uh, Austin, you're way more like pessimistic. You got— you're like, I'm pretty paranoid. You're way more paranoid. And I know you say like, oh, it can't work again. And I'm like, well, no, man, I think it— I think it can.

Austin, you have like a framework around— you have like a lot of opinions around email newsletters. Give us that and put it in the context of Milk Road. Like when I told you I was going to do that or you saw I was going to do that, what did you think? And did that fit your framework for what you thought might work, or was that maybe an outlier? What was it?

Yeah, so it perfectly fits the framework. So I'm pessimistic on relaunching the next Morning Brew, a general business, 4 million person email. Uh, but basically I split up newsletters into 3 categories. One are the editorial newsletters, right? You have your Substackers, your, your Packy McCormick's full newsletter, maybe 2,000 words, maybe 10,000 if you're some of these writers. Uh, that's like category 1, right? Category 2 is what we did, aggregation, right? And Sam and I kind of went more general, general business, went for scale. And then, uh, after that you kind of have like the, let's call it Morning Brew for X, right, where you, you still have that aggregation of summaries, but you're more niche, right? And maybe the TAM is smaller, but you think because of your tone and because of the way you cover it, you can have a larger percent of that TAM reading your product, which Sean, I think is what you're doing. And the third is more of like your classic, hey, I'm going to give you 5 links, your 5 Bullet Friday or things like that. I think the biggest opportunity is, Sean, what you did, which is Morning Brew for X. You find a growing industry, you ride that tailwind and you just own that and build a brand, something really distinct in one of these, you know, niches.

And if X is finance or X is something that's more B2B or like, you know, a professional, you know, something that's a job title, then X works better than if X is, you know, fly fishing or, or, you know, basketball or something like that.

Yeah. So I think if you're going to go consumer route, right, target consumers, it's got to be high dollar. It's got to be, you know, the newsletter for Ferrari owners or the newsletter for Rolex owners, right? Something where people spend, you know, hundreds of thousands of dollars a year on this. B2B is great as well. That's the other place I would go. And so you were kind of like, I call it maybe prosumer, right? It was the best of both worlds. You could hit on both worlds. You got the consumer-oriented readers and then also the people who work in the crypto industry.

Did you agree with our— I know that I and we actually did, or I'll say it myself, I did sound like a douchebag when I was talking about Industry Drive. I didn't mean to like phrase it that the way that I did. But when we were talking about Industry Drive, you know, they're a $600 million, uh, company that mostly is a newsletter business. And our criticism towards the B2B industry was like, the content's pretty whack. Do you agree with that, uh, that assessment? Like, do you still think there's a lot of opportunity to build really big B2B media companies?

Yeah, I just think you have to do it the way Sean did it, right? Which is go the complete opposite route, right? So they're, they're pretty dry. They have a standardized process. They go in every single vertical. Look, I think their business model is simple, but it's not easy. I don't think what they did was easy at all, but I think it's very simple. The playbook is very well-defined. There's no crazy tech. They're not, you know, building some AI machine learning thing. It's they create great content, they resonate, they sell ads into it. But the way to compete, I think, is to treat B2B like consumer, right? To treat them like people, like, you know, the Milk Road does.

Why is it not— you're saying it's simple but not easy. Why is it not? What do you mean it's not easy?

I mean, I think to scale across all those verticals, right, to your point, ad businesses are pretty tough, right? And so you take on a lot of costs and you can't, you can't mess up, right? Because if you go wrong in verticals, you have a bunch of writers and salespeople. And, and the thing about media businesses, even when they're profitable, the difference between 20% profit margins and losing 20% is way, is way like it's easier to flip that because of all your fixed costs. It's not SaaS. You don't have locked in, you know, you're a B2B SaaS company, you have locked in 100 or 110% of your revenue the next year because of renewals. Every day with ads, it's another grind. You got to go sell more ads. And so it's not easy. You know, the ad business is an absolute grind.

We found this guy. I'm going to give a shout out here.

His name's—

I don't know, I think his name, you pronounce it Volter, and he's from the Netherlands. and he, uh, I think he's at school right now. I don't know what happened, but I, I did a video. I thought, okay, maybe, maybe we'll start doing YouTube content. I did this video when Luna collapsed and I did this video like, oh, I lost a bunch of money on Luna. And I did this video. I thought it was gonna be like, I remember that. I was like, ah, might go viral, whatever. We came out late. We came out like 3 weeks after the news. So that was kind of stupid. So it didn't, didn't go super viral, but one good thing came of it, which was this kid, this kid on Twitter was like, Hey, your thumbnail sucks for your YouTube thing. Like, it should be like this or like this or like this. He did this thread and I was like, yo, you're great. I don't know if I'm going to do any more YouTube videos, but like, you want to just come in our Slack because I just— I like what you just did. That was like helpful and it was quick and like, you know, he's like, sure. Yeah, that'd be amazing. I love the Milk Road. And so he joins our Slack. First, we're like, what do we do with this guy? Like, what the fuck is this guy? Like, imagine like a 2-person meeting and I just invite this third guy from the Netherlands to a meeting. You'd be like, uh, like, is this guy gonna talk? What's— why is he here? And for 2 months, no one knew why he was there. But then something amazing happened. We were like, ah, we need to sell ads like for the next month or whatever. And it was like nobody wanted to do it. It was just like, uh, do we have to? Like, it's just gonna be a pain in the ass.

It sucks.

It just sucks to sell ads. Like, I wish I hired a sales guy. It's like, uh, even hiring a sales guy is kind of a shitty task. Okay, let's procrastinate a little bit. And, uh, along the way, this guy had been wanting— or this guy had been always just messaging us ideas. Like, because he's like, I don't know, he's like in the Slack, so he's like trying to be productive. So he would just nonstop message ideas of things we could do. And, uh, it got to the point where Ben was just sort of like, dude, this guy is like, you know, incessant. Like, he won't stop messaging. And it's like, you know, it's at first it's a good, but like, Nobody can handle this volume of ideas. Like, this is crazy. And then he's like, he's like, you got to do something about this. And I was like, okay, I'll, I'll talk to him or I'll kick him out of Slack. And I was like, hey, what if we just point the machine gun like outwards instead of like right now the machine gun shooting us with ideas? What if we just made him like sell the ads and he just bothered the hell out of everybody else? And so that's what we did. And this guy is single-handedly crushing Milk Road ad sales through the crypto bear market. Like we are fully sold out for months on end. Just one guy, just one kid who's not even 20 years old, just absolutely pillaging the market. And the advertisers will privately DM me and be like, yo, I shared this guy's name with our sales team. Cause I was like, this is how you sell. Like this guy is relentless. And I was like, wow, that was a, that was just like an incredible, I don't know, like incredible thing. He is so impressive.

Dude, let's talk about that real quick. Ad sales. Ad sales suck, Austin. They suck. And what I learned getting into the hustle, I, I did you sell? I sold our first ads. I think I got us, I sold like the first maybe $100,000 worth of ads. And then in order to scale, we had to hire a sales team and they would show me like the conversations that they are going to have. I'm like, there's this conversation will never work. Like you're using all this jargon and you're wearing like these like button-up plaid shirts and like these brown leather shoes. Like you guys look like dweebs. Like this is never going to work. And it worked perfectly.

Nobody wants to go skateboarding with you right now.

Yeah.

You are not ready if they want to skateboard.

Dude, I was like, dude, you look like a, you look like your name's Todd or Kyle. Like this is not gonna work.

And, uh, he's like, my name is Todd.

It fucking works. Yeah.

Yeah.

It, it worked perfectly.

You're, you're not cut out. Your personality is not cut out for the, the, the media buying world.

Did you do it?

You're a— well, no. So yeah, in the early days we bought, right? But we sold all direct response ads, right? It was Casper Mattress, it was Away Luggage. It was, you know, hey, buy your placement here, you're going to get 300 clicks and 3% of them convert and you're going to make $1,000 and we'll charge you $800. As we've grown, though, I think there's another difference between us. We were in New York City and it opened up this whole world that I had no idea about, which was the world of, of media buying and these big ad agencies and they have huge budgets, right? We're not talking about $100 grand from Casper. We're talking about $5 million from the biggest brands in the entire world. And it really is a black box to people who aren't in it. And I think it's one of those things where it's a black box intentionally so people can't get in, right? Finance is the same thing. Every year there's a new term within the ad industry or finance just to keep people on the outside.

It's crazy. It's crazy. It's like not based in logic or fact. It's based on relationships and like, it's so weird. It's like, oh wait, I have to realize that this person, this lady I'm trying to get to buy ads, she just has to spend this $20 million this quarter and she just wants to find somewhere to place it where she won't get fired. That was such a weird feeling.

Yeah. I mean, the idea of like media budgets, right? Hey, they— if they— if they don't use it, they lose it. And so you're incentivized to spend money. It's interesting. And it's something that we learned again by hiring people in New York, which I think was a big difference. Between us and you, you had a lower cost, more like inside sales team, a really efficient one, right? You took that route. We didn't take that route. We went for these big brand dollars. And, and I think both routes work. It depends what you're, what you're looking to sell. We just took the route to say, hey, we're going to, we're going to dive right in this black box and we're going to learn all about it. We're going to get $1 million. I mean, one of our first advertisers, Discover, gave us $1 million. I was in college. I'm a senior in college living in my frat house, right? Like, beer cans everywhere. I get an email from the CMO of Discover like, here's an RFP. I'm like, what in the fuck is an RFP? Like, what are you talking about?

No clue.

I open it up and it's like, hey, give us media plans for like half a million, a million bucks, right? For $1 million, she could own the company 7 times over. The company was not worth $100 grand. And here's this woman asking for a million-dollar RFP. And we just— we learned it. But it really is a relationship-driven game.

What are some—

how did you— How did you justify that? Like, how do you— like, if, if, if Amex says we're going to spend $5 million this year, be real. Do you actually think that's going to help them, like, sell more shit?

Yes, I do. Right. We do a lot of brand lift studies and things like that.

Right.

It's different, right? It's not— we're not— no one's trying to, you know, like Lexus, for example, or car company. Lexus doesn't—

how many brand lift studies did you do?

We used to do that, but I'd be like, what the fuck is a brand lift study?

Like, I'm like, are you kidding me, Todd?

What the hell is a brand lift study? I don't know what the hell this is. Or we would do all this other stuff like an RFP. Like we had been doing it for like 6 months and I was like, hey guys, like at this point I'm a little bit too afraid to ask, but what the hell is an RFP? I don't know what this stuff means. I didn't know what any of this stuff— it's so challenging if you don't work in the industry. And then they like, they talk about agencies and I'm like, wait, what the hell is an agency? Why don't we just go straight to the brand? Like this stuff from an— from a small business owner's perspective, all of this stuff is crazy inefficient and stupid. Now that I've been at a big company, HubSpot, I understand. I'm like, okay, I get like these guys are having to like give out $1 billion of marketing. Like now I understand a lot more. But when you're just a 10-person company, you're like, do you guys realize this market study shit doesn't work? Like this brand study, that's bullshit, right? Or like, you're going to give me $20,000 to write this article. It took me like 20 minutes to do it. Like, so it doesn't make sense when you're small.

Yeah, but, you know, people are, people are buying the audience, they're buying the relationship with, with you. They're not buying, you know, purchases or things like that. And so, you know, I think at scale, when you get to 4 million subscribers, if you can change the perception of half a million or a million people and have make them because of a marketing campaign, have a, you know, 10% of people have a higher perception of, of Credit Card X's programs. Like that is really valuable when you're Visa or you're Mastercard, you're American Express and you spend $1 billion. Like that's so much money. How do you deploy $1 billion of marketing spend? You go through agencies and that's how it all happens.

Sean and I are really good, I think, at starting stuff. We, we've got pretty good vision where we can spin things up and get 'em to like a million in revenue pretty quickly. The thing that I was always envious of you, because it's my, it's a, it's a fairly big shortcoming I think I have, is you are just so good at— I don't know exactly how to explain it. You've got this like almost private equity-like ability to like look at numbers and be like, oh, the margin here is shitty. And I'm like, I've never used that word margin in my life. But you'll like talk about like the margin here and like, well, if you just change that by like 10%, probably by doing this, your outcome is going to be like this, this, and this. Like you just have this really good operational ability. You're also really good at saying like, well, if you just improve this, this, and this and only focus on that, then in 6 months I think your outcome will be this. You're really good at that and you were really good at that at a very young age. How did you figure out how to do that? How did you learn how to do that and have that insight and have that ability and also have that faith in like, well, if you just do this, this and this, the outcome might be this, this and this in 8 months. Yeah.

I mean, so I got an undergraduate business degree and I always used to shit on undergraduate business degrees. I'm like, what a complete waste of time. Like, those 4 years were so dumb. But as I look back, it really did give me a pretty good overview of what it takes to run a business. Not actually the day-to-day of running a business, but like, what is accounting? I took like 7 accounting classes, or I don't know, maybe 5. Those were actually really valuable to be able to really dive deep into a P&L, to real— and my summer spent in investment banking to understand what's a financial model, what drives a model. Those things that within the context of finance, like, yeah, you know, they're okay. Within the context of running a business, was super helpful to understand what levers you need to pull. But the other, the flip side is I looked at you 3 years ago and I, before we knew each other, maybe even 2 years ago, and I was like, both of you, I was like, I hate these guys because they're so good at going zero to one. They're so good at coming up with ideas. Like I'm the opposite, right? I, I'm not an ideas guy. I can't come up with ideas, but I do think it is certainly cooler and sexier to do what we do.

You know, listen, there's no doubt about that.

It is definitely, yeah. But like, dude, what, what would you, I mean, You know, we all— we need to like partner because 0 to 1 is cool, but then like 1 to 100 million a year is pretty fucking cool too.

Yeah. How about you guys take things, you get them off the ground, you take them to 3 employees and $1 million of revenue, and I'll take them from 1 to 100 and we can just pair up and just every couple years—

I asked him about his margin and he thought I said margarine. He brought me some butter.

Yeah, dude. Like, we— like, I didn't understand a lot of that stuff.

For all we know, The Hustle was either a billion-dollar company or worthless. Sam just has no idea.

Yeah, well, I like, I remember when we were negotiating to sell and like there was just all these things that people were giving me advice on and I'm like, man, I just didn't even think about that. Like it's just, and I actually know a lot of people that are really successful, like we're talking billion-dollar successful and they know so little about operations. And there's a lot of people like that, like who are just, they're good at hiring. Like Richard Branson, I think he famously said, he's like, dude, I didn't know what a P&L was until we hit like hundreds of millions in revenue. Like I didn't know how to read it.

Um, and I think the same thing, which is super cool. Uh, so Austin, you, what I like, uh, that you said on the operation side, like Sam saying is, um, like when you were talking earlier, you were like, you know, write, grow, sell. We wrote that on the wall. We woke up every day and said, write, grow, sell. We had the great—

that's what I'm saying. He's so good at that.

Those are the things that like, I used to do this such similar, literally we had the wall, but not with Milk Road actually, but this is kind of my earlier startups. And at Monkey Inferno, I remember, Sam, you probably remember this when people used to come in, we would always have all this shit on the walls and these sayings and these posters.

The indoctrination things.

The indoctrination. And I always felt like whenever I would meet founders, one of the highest predictors of success was, do they even know what the main thing is? And it sounds like a stupid question, but for a lot of founders, they didn't really understand what the main thing was for their business. They didn't know their business's version of right, grow, sell.

Okay.

And even if they understood like that, that's kind of generic. Okay. What are you gonna do with that? They didn't understand to translate that into the Great Wall of Opens is the number we're gonna write down every day. We're gonna look at it and if it's bad, we're gonna do something about it. And if it's good, we're gonna like double down on that. And that's what daily work is, is around this one number. And so it was like, uh, I remember we had these founders in, in, in the office and they would be like, I'd be like, all right, what's the, you know, how many new customers you guys get today? Or like, what's the revenue? And they'd have to like, oh yeah, let me check. And they would like, at first they didn't have a dashboard. They were like going into the database. I'm like, bro, you haven't ever built an easy way to know this number. And then they, then finally they built that and then they always had to check. And I was like, how do you not know? Why am I asking this question? Like it's 3:00 PM. One of y'all two should have asked this question by 3:00 PM, like every day. This is crazy. And they just didn't do it. And I was like, these guys are gonna fail cuz they don't know how to keep the main thing the main thing. Is that something that you see or like did consciously? Like where, where'd you get that? Cuz that wasn't, uh, obvious to me right outta college, but it sounds like you got it right, right away. I can't find this client info. Have you heard of HubSpot?

HubSpot is a CRM platform, so it shares its data across Every application, every team can stay aligned.

No out-of-sync spreadsheets or dueling databases. HubSpot.

Grow better.

Yeah, I mean, for us, I mean, it's almost an insult, right? We were— we— people like, why didn't you do this? Why don't you do that? Why don't you go into video? We were too dumb to do that. Like, we had no— we're like, video? How the hell do you make a video? We can barely get our newsletter out. I mean, there were days where we'd finish the newsletter like 2 a.m., we'd be coding the thing ourselves. And so I think it was partially, you know, a little bit of foresight, but also partially a forcing function. you know, we just looked at, we're like, if we do these things, we will get here. And we looked at the math and we're like, everyone's telling us we're crazy, but if we grow subs $50,000 every, or 50,000 subscribers every single month and our costs don't change, we're gonna go from $50,000 monthly revenue to $75,000 to $100,000 to $125,000. And by end of this year, we're gonna be at a million subs doing a million dollars of revenue a month. And I tell that to investors and people, they'd be like, that doesn't make any sense. I'm like, I don't know what to tell you. Like, I'm just looking at the Excel and people could— I mean, we spoke to investors and they were like, what do you mean your business only has $100,000 of costs? I'm like, it's people, it's growth marketing, and it's an ESP. That's it. That's all we spend money on.

What was that last line? I don't even know what that last line is.

Email. It's like provider, email service provider. We use SailThru.

Oh, ESP. Okay. I think I was like, SP. I was like, what the hell is SP? All right. Yeah.

But it, but it's, it's one of those things where like, it was just when you boil it down to numbers and run it in an Excel model, it's like, it's so simple. And people, these investors were like, well, people like, you're not accounting for this and that. I'm like, it's all bullshit. Like, none of that means anything. I'm just trying to make money. Like, I'm just trying to make money.

You also did some scrappy stuff. I remember, like, uh, didn't you get your first, I don't know, a few thousand emails just by, like, standing in a classroom?

We, I, I think we may have, we may have broken a couple laws to get our first couple thousand.

People would walk out and you'd have a piece of paper and be like, hey, just write your email down.

No, we, we wouldn't let them walk out. So we go in the beginning of a lecture, these Econ 101 lectures, like 1,000 people. And I hated public, I still do, but I hated public speaking. And I was like, look, if I'm going to this lecture hall and I'm gonna talk in front of 1,000 people, I better get every damn email. And so what I would do is I'd speak in front of these people and then I'd walk around.

You'd like, the teacher would let you speak or you would just stand up and speak?

Yeah. No, no. The teacher would let us speak cuz there's, there's this thing called Michigan time. So you actually had 10 minutes in between each class. So if the class started at 10, it actually started at 10:10. And so at 10:05, I'd get up there, I'd pitch on, pitch them on Morning Brew, and then I'd basically print out an Excel document and I'd walk around. I would just stand in front of people and just stare them in the eyes until they gave me their email. And I'd sit in the back of the class and type every email in and I'd be like, shit, Alex, that an A or a C or an E? He'd be like, who cares? Put 'em all in. And we just had like every, like 6 permutations of every single email. And that's how we got to like 10 or 15,000 at Michigan. And then we're like, do you have a friend at Penn State? I have a friend at Penn State. Let's do this at Penn State. Let's do it at Miami. Let's do it at NYU. And next thing you know, we have like 50,000 people across the country, college students reading Morning Brew.

Are your parents wealthy? Did you grow up wealthy?

I'd say middle class, upper middle class. But what's interesting is, so I grew up in the suburbs of Baltimore and like, I didn't know— I thought I knew wealth. And then I moved to, I went to Michigan and I met people from LA and New York and I moved to New York and I saw people from New York and I never saw that kind of wealth. And to me that was inspiring. That was exciting. Uh, cuz I came from, again, it was like a very well-off, I had everything I needed. But you know, I know people, I met people at school who were flying private planes. I knew what a private plane was.

You got rich pretty young, right? Like when did you guys sell? You're, you, you're pretty young right now. I think you guys sold at what, 26 or something?

Yeah, I think 25.

Well, the reason— but hold on real quick. The reason I asked was because, like, you've got this, like, this immigrant hustle. And before I knew you, I stereotyped you as this, like, everything's been given to this rich kid, like, and, and, and hearing this story, I'm like, oh no, these guys were like just as gritty as I was for sure. Sometimes more. Yeah.

I mean, Alex has his own story about, you know, his family and, and his dad passed away. And so he was— I mean, I learned so much from Alex about hunger. Like, Alex, again, he broke things down the same way I did. Alex would be like, hey, You know, I'd be like, Alex, we need 100 advertisers this year. I'd be like, I don't know how we're gonna do it. We have zero. He goes, I know exactly how we'll do it. I'm gonna go on LinkedIn and I'm not gonna sleep until I message 1,000 companies and we'll get a 10% reply rate. I'll be like, you're gonna message 1,000 companies? He's like, well, isn't that what you need to do to get to 100 advertisers? I'd be like, yeah, but that sounds crazy. He goes, well, let's start working. And we just like, you know, sit there, drink beer at WeWork and just, you know, crank out cold DMs. The head of, I mean, I must know the head of growth at every New York City direct-to-consumer company, cuz Alex incessantly emailed them and we would like, we would laugh at the response. Like we would get excited when someone respond to be like, hey Alex, this is your 9th email. Like you gotta stop following up. Like number 8 was good, but 9, you, you passed it. And so yeah, I think we both had that hustle.

What did it feel like to back, back to what Sean was saying, you're 25 and you, I don't know how much you made, but let's just say 8 figures. What's that feel like when you're 25? Fucking dope.

Yeah. I mean, so first of all, it was very cool. It's great. So it's interesting, right? I got the wire, the sum of money. It was during COVID So I get this— like, listen to this juxtaposition. On one hand, I just made a boatload of money, more money than I thought I'd ever make.

Right.

On the other hand, I'm living in my childhood bedroom, sitting next to my parents as the wire hits my account. And everyone's like, what are you going to do now? I was like, I don't know. My mom's cooking like meatloaf. Yeah, yeah.

Tell your mom, mom, make me breakfast.

Yeah, it was the most anticlimactic thing ever. It was unbelievably anticlimactic.

You should have just moved into the master bedroom.

Yeah.

Like, move over, Mom and Dad. This shit's mine.

No, but I think, look, I think getting a quick win early in life or a win early in life is so important, right? Just having that swagger, that confidence, that brand allows me to do so much that I wouldn't have been able to do otherwise. Like what? But get into any room. I can get in touch with anyone, right?

What other opportunities do you think you get?

I mean, again, like get into any room, right? So meetings, investing.

What are— what are some cool rooms you got into?

I mean, again, like, it's the same things that I think you guys are— you guys also have a witness, right? I don't think anything is— is that—

well, I don't like to leave my house. And then Sam's only interested in, like, people that are like, this guy's the best axe thrower in the country, and he's, like, super pumped about it. I'm like, I don't think you needed to, like, you know, pull your, you know, rich guy card to get in touch with him. But I feel like you— I don't know, like, Have you met Leo DiCaprio? I feel like you might have just bumped into Leo DiCaprio somewhere. I feel like that's more your vibe in New York.

Well, so, so I bumped into Justin Bieber in the Bahamas, which is pretty cool. But no, I mean, like the weekend we had with, with what's his name, MrBeast and Haasim was cool. I spent a weekend with Kid Rock on his ranch. Yeah, tell me, that was pretty sick.

What was that like?

I mean, he's a unique, unique character. Again, this is all according to him. So I mean, I haven't fact-checked this, but I'll assume he's telling the truth. He told me he's the only person to play at both President Obama and President Trump's inaugurations. He played at both and he knows both super well. He's close to both. And he has this— this— he lives in this huge ranch outside of Nashville, right? I went there. It was my friend. His name's Shane. He works in tech. He's good friends with Kid Rock. Kid Rock, obviously music guy. And Shane put together 10 people in tech, Kid Rock, 10 people in music. We go to his ranch. And I mean, you get there and it's like out of a movie, right? You walk in and Kid Rock's back is to me. He's got a cigar sticking out of his mouth. He's got a shotgun and he's just shooting clay pigeons. And the whole weekend was out of a movie, right? His studio, unbelievable. We pulled an all-nighter together just telling stories about Eminem. I mean, he's a— it's really, really cool.

He's a— a lot of people don't realize this, but Kid Rock got famous right before CDs went down. And he's one of the best-selling artists of all time. And I, I, it wouldn't surprise me if he's probably worth $200 or $300 million because he was famous when CDs were $18 and $21. And so like, it's wild.

Yeah. So, so now though, I think he's a new source of wealth. So he owns, uh, again, this is what I've been told. He owns the most popular bar in all of Nashville. And whereas most of the other ones, like Luke Bryan has one and a bunch of other country singers, they just license their name to the bar. Right, and they make a couple percent. I think Kid Rock's like a 50-50 owner.

Probably makes $2 million a month.

No, I've heard more. Really? Like, it's a project. I've heard— again, I don't know if it's true. I've heard it's big, big money, you know, high, high, uh, tens of millions, you know, which is crazy, dude.

The one of the best things, uh, about our companies and, um, like the culture that us three have kind of built with our friends because we kind of like got into this media game a little bit early. And I don't know about you, Austin, but when The Hustle was starting, there wasn't that many people who we could look at and be like, well, let's just do what they do but different. Like, I remember I told this one media guy who I'll tell you afterwards, he's the founder of a multibillion-dollar media company now. I was like, here's what I'm doing. He goes, bro, this will never make more than $2 million a year in revenue. And this other person who I'm now good friends with was like, dude, what are you talking about? This— I'm like, it doesn't matter. It's just a small screen. Who cares? Like, if you're an email or on a website, it doesn't matter. The math shows X, Y, and And so we had to hire like 24-year-olds who like were promising, but like, and then we had to learn about it as we grew. And but because of that, both Morning Brew, The Hustle, and the, and the crew that now— I mean, Sean's great at this as well. We've, we've done a really cool job of like finding smart, inexperienced people who now have gone on to do a lot of really cool stuff. And that makes me really, really proud to like see like this crew that we've all built. And so there's like The Hustle crew, the Morning Brew crew, and then Sean was like the hustle thing. Now he's got his own thing. Have you noticed that, like, we all have this little, like, army of people who have, like, been through, like, this, like, self-created, like, training camp? It's kind of neat, right?

Yeah, 100%. I mean, it's— we in the early days, we could not get people to work with us who didn't want to be entrepreneurs. And the pitch was simply like, hey, we're starting a business. You'll be in on the ground floor, right? You'll see what it's like. And that's, that's all you get. Like, you know, we didn't have— for the first year and a half, I was so cheap. For the first year and a half of Morning Brew, you didn't get a company computer. You had to bring your own computer to work.

Dude, I was famous because on Facebook I would put, hey, I'm buying, I'm buying laptops. Does anyone have a Mac for sale for $500?

No, we were not dropping any money on company computers. We didn't have health care in the early days. You got nothing. You got— I mean, and we, we couldn't afford it because I was so against taking venture capital. I was like, we're going to make every penny count.

One more story.

Fridays at 3:00, we'd all go pencils down. Work would stop because we had a referral program. We'd send out stickers and t-shirts and that whole thing that, you know, I'm sure we've all seen.

But you had to pack it.

We had no— we had no packing. And so we'd sit down, we'd like wheel in the WeWork keg into our office and we'd convey, you know, we'd do like an assembly line. The first person would, would like open the envelope. The next person would stick the sticker in there. The next person would lick them. The next person would put the label on. And for like 3 or 4 hours, from like 3 PM till 7 PM on Fridays, that's all we did was just pack envelopes of shit.

Well, you're one of your early guys. Tyler Dank has gone on to start Beehive, which is a really cool company. He seems like a really good entrepreneur. He's pivoting or iterating really quickly. And then I've got a couple of people have done that. And then like, it's just cool to see like these people who are young and not dumb, but like just young and like inexperienced. Go on to like build cool shit. And then like your ex-people are now at other newsletter companies. And then Sean has hired a couple of my ex-people or— and probably it seems like a couple of your ex-people. And it's like this incestuous thing, which at first I would be jealous. I'm like, well, what the hell? Why are they working with this person? But now I'm like, oh, this is awesome, man. Like, we've created this like tiny little industry of newsletter nerds and it's actually quite cool.

Yeah, I love it. Yeah, I think it's really cool. I think there's to be so much more value created. I think what Tyler is doing at Beehive is amazing. I think what I've been so impressed with him is like the maturation from the Morning Brew days of, you know, it's like 6 of us and he's doing a little bit of everything. So the way he's been able to scale himself and scale that team is amazing. And so it's really— and Trung's the same way. Like what Trung's done is incredible. And there's— I mean, there's a ton of examples and it's really cool to see.

Do you regret selling?

No.

That's—

that's—

you answered that quickly, even though, like, not even a little bit. So you sold part of the business. What do you think the, the entire business is gonna sell for in the future? Hundreds of millions.

I think many multiples of what we sold the first, uh, half for, but we structured the deal in a way that I thought was great, right? I mean, the ability to have life-changing money, if anyone has the option, like I always think it's good to take half your chips off the table, right? And maybe I'm biased cuz I did that and, and it's worked, but I thought it was really important. But I still have enough upside where I'm excited, right? Right. It's not like a tiny earnout that people sign where it's like 10% of the deal. It can, you know, it can be really, really meaningful. And that drives me. That keeps me excited. It keeps me on the hunt. I love the company. I love the people we work with. I love the executive team. But I would— I mean, during COVID or during— I wouldn't have slept at night. I just— I sleep very well at night knowing that, like, I have my nest egg.

And so what'd you do with money? Did you do anything cool with it or do you You touch it right away. What— that money hits the bank, you're at your parents' house. What happened to that money over the next— I don't know how long it's been, like a year or two?

Yeah, so I haven't— I'd say in terms of everyone's like, oh yeah, do like make a splurge purchase. There was nothing out there that I was that excited about buying. So I ended up buying a car, which is expensive. I didn't buy like a Mercedes. I bought an Acura, right? Nothing crazy. I doubled my— or I—

yeah, a pre-owned Acura.

My dad just—

it wasn't pre-owned, brand new. 2022 sports boat, sports edition, ATEC. ATEC air conditioning.

That's air conditioning. What?

Why, dude?

You really do have that immigrant mentality, man. I think we need to get you like a 23andMe test. I, I feel like, uh, there's something going on here. You got too much immigrant energy. I love it.

No, but I mean, I, I, I increased my rent 4 to 5 times, right? I live in a great apartment. Um, I went on an amazing vacation last summer. You know, I, I actually love— I know you guys know Ramit Sethi, or Sethi, I'm not sure how to pronounce the last name, but like that idea of like your rich life and spending on— because I mean, lifestyle creep is real.

Totally.

That is real. And so like, look, I spend money on the things that I find interesting and that I like, and I love traveling and staying at really nice hotels and spending a ton of money on business class flights and things like that. I like living in a nice apartment, but I live in New York City. What am I going to do, drop another $50K on a car that sits in a parking lot 361 days a year? It's a complete waste of money. It's just stupid. And Morgan Housel actually tweeted this, and I read this too. In Will Smith's book, he has a great quote. He was talking about fame and becoming famous, and the quote was something like, becoming famous is awesome. Being famous is cool. And losing any fame is horrible. And I feel the same exact way about money, right? I feel the same way. And so I have no desire to like spend money on things I don't actually care about. I don't want to, I don't want to lose my money because I can, you know, change the A to a, you know, an M or whatever on a Mercedes. So I spend money that I, on things I actually care about so I can make sure I maintain my wealth.

So what do you invest in? Or do you just— are you conservative? Are you aggressive? Like, what's the pie chart of like of the 100%?

Where did it—

where did the money go?

Yeah, so I probably took like 85, 90% of it and put it into very, very boring stuff, right? S&P 500 or Vanguard, like target date funds, like 2065 or something like that.

You did this yourself or you hired like a wealth person?

I hired a team. It's a good thing I did, because if not, I would have went off the rails, right? and then I put, you know, 5, maybe 7% in crypto, right? And I put another 5% in venture investing, right? Uh, but the vast, vast majority is in really boring real estate, S&P 500, uh, and like bonds, right? But like really boring shit.

Nice. Let's talk about some non-newsletter stuff. So you got a bunch of ideas, uh, when we were hanging out at, at Camp MFM. You were telling me about like this thing you're doing and this thing you're doing. I was like, oh, this guy's like way more dynamic and interested in a whole bunch of different things. What are some ideas that you think would be cool to share?

Yeah. So I'll throw out a bunch of ideas I have, but one general framework I think people should think about is when you're in shitty economic times like we're going into now, I think the framework you should use is you should look to save companies money or earn individuals side income, right? Before, companies' money didn't matter, right? Capital was abundant. And so companies, they were all about just grow, grow, grow, right? How can you help me grow? It's a 180 now. You know, people were trading their money for other people's time, right? Now they're trading time for money. And so, you know, if you can help companies preserve money you can, I think, build really, really great side hustles. So a few ideas, right? I think it's like what's old is new, and then there's a bunch of agencies I think can be really interesting to start right now. One is outsourced talent. I knew nothing about the outsourced talent game. I recently became a co-owner in a business. Uh, it's a really interesting business called Oceans. They found talent in Sri Lanka, right? Really cool talent in Sri Lanka where they've— US graduates, uh, come to tech startups, work there. Uh, really interesting. And I think there are ways, right? They have a unique advantage going to Sri Lanka, which we don't really have to talk about, but I think there are companies who were hiring a full-time copywriter, let's call it, or a full-time, you know, marketer, and they probably only need them for 25, 30 hours a week. 2021, screw it, right? We'll need them at some point. I think now companies are really questioning FTEs, right? Do you need a full-time hire? And so you can create these niche marketplaces. I'm getting investment opportunities for them all the time, and they're just not venture scale. But you bootstrap a marketplace, let's call it like a content marketing agency or content marketing marketplace for B2B companies, right? These stocks are down 90, 95%. They're trying to drop FTEs, but they still want content, right? We all know how valuable owning audience and content is and building that marketplace, helping them find people. I think simple services like that are going to come back into vogue and be very, very profitable.

What's that company where the founder got in trouble for not converting the stock? Converting the convertible notes, but it was a marketplace for developers and it like bootstrapped its way up practically with TopTel. So TopTel, they got in trouble because they only raised like $800,000 or $1 million, but they didn't convert the, the, the, the note or whatever. So it was controversial, but they basically bootstrapped it to this point to like north of $100 million in net revenue. And so these marketplaces are like, can be, they can be pretty freaking powerful and seem, they seem too hard to get off the ground, but they don't seem that hard if you already working in in the industry and it's a super niche, a niche topic because people ask me all the time, they go, hey, I want to hire writers, who should I hire? And I'm like, I don't know, man, it's hard. I don't know who you should hire.

Yeah.

Yeah.

I mean, the one I, the one I'm now a co-owner in has gone from 0 to 7 figures of ARR in like 8 months. Right. You pick a very specific target customer.

That's in gross?

Unique talent.

Gross or is that just—

Yeah. Margins are— No, no. Well, now both. Right. Both are 7 figures of ARR. That's crazy. Yeah.

And then, uh, what's his name? Marshall from, uh, Marshall Haas. He did Shepard. What's the URL?

It's the same thing, right? Same, same business.

And I, I, it seems like he's scaled that to high 7 figures in like less than a year. It seems from the outside.

Yeah. Yeah. I think they're a bit different, right? Ours is, I think theirs is more like strictly EAs. The one we have is more, you know, you have people in finance, people in operations. What's interesting about Sri Lanka is they have Big Four accounting firms, right? And so you can poach people not just from local businesses, but from people who've been trained by Ernst Young and Deloitte. And so it's an interesting, an interesting demographic to go into.

Yeah, I love that one. I think that's a great one. What are, what are some other, like, you know, help businesses save money, help you? The other one you said is help individuals earn side money. What's a, what's an example of that?

Yeah. So here's one I think is interesting, right? So you built Morning Brew for crypto, right? I know a lot of people have spoken about this, but I don't think anyone's really built the brand yet. I think Morning Brew or The Hustle for AI is going to be huge.

Dude, how's that feel, by the way? I think you're just like calling Sean the Morning Brew of blank. It's okay. It's okay.

We did kick your ass in crypto. I mean, it's okay. It's okay that that happened. No, we can just Let it go though. We could tell, we could take a collective deep breath and just let it go if you, if that would help.

No, no. I mean, you, again, you guys did a really great job. I, I thought that was awesome. And I think someone's gonna do the same thing in AI, right? And so the bootstrap version of this is to do what you did, right? The AI newsletter, right down the fairway, have a unique tone, integrate yourself into the audience. The way I think to take it to the next level is The last 3 months, thousands of entrepreneurs have all started tinkering on little AI side projects, right? And they all have $50K, $100K of ARR. And I've been reaching out to all these founders like, you know, different little tools, right? These are not real big businesses. They're all side hustles, right? I went home for Thanksgiving. I asked all my friends from home, my family, hey, like, have you guys been playing around with ChatGPT? Have you been playing around? And they're like, what in the hell are you talking about? Right? And so clearly it's the same customer. For all of these different things, right? And so I think there's this opportunity for the AI for Morning Brew to start a little tiny capital or a little holding company where you can start to invest and buy these businesses, right? Give an off-ramp to these founders who've built these $50K or $100K or $150K ARR businesses and start cross-promoting them, bundling, marketing them. You write reviews for your little AI tool and then you promote it. And instead of having advertising, which again, Sam has spoken about how it's difficult. You're just promoting all your products. You have this portfolio of 10, 20, 30 little AI tools, and maybe each one is half a million or a million of ARR, but altogether you can get, you get pretty big pretty quickly.

That one seems harder to me. I feel like, like I like the idea, but I'm like, okay, realistically, if I did that, I feel like I would— I like ideas where The idea is so good, my execution can be like a 7 out of 10 and I still win because—

Yeah, but this is his thing, man. This is his thing. He executes some of these things really well.

Yeah, yeah, yeah.

I don't think it'd be that hard. I'm telling you, I've been talking to a bunch of these, like, these founders, these little AI side projects, and I've been— I'm like, what are you doing with it? And they're like, I have no idea.

I think it's hard is not because you can't roll them up, you can't buy them. I think it's hard because it's like the Lindy effect, right? So when something's been around for 3 months and it's at $50K MRR and it seems great, like, you don't know if that thing's gonna be around 3 months from now because the next model will come out or the next chat— like, for example, uh, you know, Stable Diffusion comes out, then, and then, uh, you know, ChatGPT comes out. Well, people were— you know, I've invested in a couple of these that, you know, the AI writing tools They're getting better and they're pouring millions into marketing to get, to get customers for their, you know, AI writing tool. But everybody's building on the same foundations, the same models, and then they're trying to say how they're going to be differentiated. And the reality is they could differentiate it on, I don't know, customer acquisition. And so I think that like it is, you know, I think about when I buy something like, you know, the Tiny Capital model works because he buys stuff stuff that's kind of been around and forgotten and ignored for a long period of time. He buys Dribbble. It's like, oh, it's been around for years and I could buy it and it's going to be around for years and I can improve it over that time versus buying the things that are really new and quick. I think you have a challenge with the durability of those businesses because what happens as you know, the AI just keeps improving, you know, either these things become obsolete or it starts to consolidate into like one app that can do 4 of these things. And so you don't need one for posting on social media and one for writing emails. It's like, ah, it's the same Chrome extension that's just gonna do both. And so I think there's a good chance you can kind of get like, you know, um, you know, just sort of blown away by, by, by the rate of change that's going on in the industry. So that's the thing I would be worried about with that, similar to, I remember telling Andrew Wilkinson about Thrasio and I was like, oh, this is super smart. Like, these FBA stores are super cheap and there's, you know, like each one of them is small, but you could go and just like scoop up all these and look at this. They're buying them on this like crazy low multiple. And he goes, yeah, it's like picking pennies up in front of a steamroller. And, um, it was his first reaction. And I was like, yeah, I could see what you mean. What, like if the platform changes? He goes, if anything happens, he's like, you know, these aren't real durable brands. They haven't been around for a while. Maybe it's that Amazon changes the algorithm. Maybe it's that there's, you know, more competition. Maybe it's that the multiples go up. There's, there's 4 or 5 different ways where you just get steamrolled. And that's actually what— how it played out pretty much in the, in the Amazon aggregator space was for a while the getting was good, and then those companies went all in on it, and then they kind of got steamrolled. That, you know, they're getting steamrolled as we speak.

Yeah, I think you bring up a great point about AI, right? And that's why, while I think the technology is great, I've been very skeptical of investing in these companies that just really build on top of, you know, OpenAI, because it's like you have a nice wrapper, right? It's nice marketing, it's great. But what do you have long term? What are you actually going to do?

They all do that.

What are you going to do?

Who doesn't do that? Nobody's doing their own AI. Everybody's building off OpenAI or Stable Diffusion.

And that's why I'm skeptical of investing in that, right? I think there's so many popping up, right? It's the next crypto wave, right? There's going to be a huge— huge bubble and, you know, and they're raising not at crypto prices, but I'm seeing, hey, two guys left some, you know, Andreessen Horowitz-backed company, we're raising $5 on $25. Like, what do you have? They're like, oh, well, we have a deck, but since we created the deck, we've already changed our mind. It was this and now it's this. And it's like, guys, come on, you can't— you can't be serious. We've seen this play out.

And they're like, while you say that, they're like, we just got another offer for $35. The price has gone up.

You You know, like, I always felt this way about you. And as I've gotten to know you, I feel this way even more. The way that you know someone's an interesting founder is when you talk to them and you're like a little fearful of them, where you're like, I don't want to have to go against this person because they're going to be very, very challenging to kill. And you totally have that vibe. You've got this like weird mixture of neuroticism where you're like, no, I have to go. Like, I have to win. We're going to lose. Like, everything's over if I don't win this thing. But then you also have this like really good work ethic. I remember I asked you the other day, I'm like, hey, at what point at Morning Brew did you quit grinding? And you're like, what? Never. I'm still grinding. And I think that's just a really— that's really fascinating.

Are you weirdly good at like some random thing? Did you like channel that obsession towards some other thing? Yeah.

Like growing up, we— we like— we— tennis or some bullshit.

Yeah. I mean, I was obsessed with video games, right? Sports, video games. Uh, but nothing, nothing specific, right? I wasn't like Travis Kalanick, like number 2 Wii tennis in the world. Um, no, it was that. And now I'm like into that for cooking, right? I'm— I've thought about like would I go to culinary school and take night classes because now I'm obsessed with cooking. I love to cook.

Wow, did not see that coming.

You got to come over for a meal. You got to come to me. I know you don't leave San Francisco, but when you do, you have to come to New York.

So what, where do you, what's— you said something about Ramit and like your rich life. What do you think your rich life— how old are you now? 28. What's your rich life going to be at 35 and 40? Like, what are you working towards?

Yeah, I think for me, it's all about time, right? Like, to me, wealth is all about having time and spending that time how you want to. Right now, I want to spend that time building this company because I constantly see more growth and more opportunity and not just like 2x, but 10x. But ultimately what I would be able to do at 35 is spend my time how I want to spend it on any given day. Right. And that means a lot of travel. I love traveling. Like, I want to go at some point in the not too distant future, hopefully go on a 6-month trip, 3 months to Europe, 3 months to Southeast Asia. I never got to do that. A lot of my friends in college, when they graduated, they went to Thailand and wherever else. I drove from Michigan to New York and started working the next day. And so for me, it's a lot of traveling, you know, nothing crazy, spend time with family, doing fun stuff, right? Like being able just to say, hey, like today I'm gonna, you know, drop $500 and go, you know, do something, you know, $1,000 and go do some fun activity, right? Adventurous activities. But it all comes back to just waking up and saying, hey, here's how I wanna spend my day. And then doing that thing.

Are you able to do that now?

I can, right? But I, I choose to spend that time on Morning Brew. Like I am maniacally focused on growing Morning Brew. I think there's a ton of opportunity, but as soon as I don't think that, like, I'll change. I'll say, hey, you know, today I wanna do something else.

Do you like having 200+ employees? It sounds like fucking hell, particularly New York, Manhattan, like woke employees that like in the New York media scene, like everyone's talking about unionizing. Like when I think about that, I'm like, this sounds miserable.

Blink if, blink if it's miserable, cuz I know you can't say anything.

Yeah.

What, what are you gonna say?

No, no, I mean, look, I think there's a couple things. One, we have a lot of remote employees, so we do have a really good distribution of employees across the country, which I think does help, right? I think having employees everywhere gives different perspectives, right? Our engineering team lives, you know, in the Midwest, and we have people all across the country, which I think is cool. But to be honest, as the CEO of a 250-person company, I'm not interacting with that many people on a daily basis. But what I love is like the one of the reasons I stay is because we built this team of people who are reporting to me who are just A+ all-stars, like absolute rock stars. And that's what makes me so happy is when I can just come to work and say, hey, you know, Chief Content Officer, hey, you know, Person X, like, what are you doing? Like, tell me more about it. How can I help you? But also I'm like a vacuum, right? I'll hire someone new, a Chief Content Officer, a COO, I'll be like, I'm going to learn as much as humanly possible. And my goal is to catch up to you in knowledge as fast as possible. So if you're 38, you're 40, you're, you're 10 years older than me, I want to just vacuum up those 10 years of knowledge you've gained working in these 4 or 5 places in the next like 2 months. And I'm just going to pester you and sit with you and just learn as much as humanly possible so I can be better than you and know more than you. And it's like this competitive nature.

That's exactly what I'm saying about being like someone that you're, you're be a, you'd be really hard to compete with. You were hard to compete with. Uh, that's a really fascinating mindset. It's very intriguing. I, I saw Sean smirk. That's always a good sign.

You were like, yeah, I wouldn't wanna compete with you. It's like, oh, you did for like 5 years training.

I did.

Yeah. And like, uh, I mean, it was fun. I, I think that, I think maybe I'm the same way where someone's like, I don't know if I wanna compete against you, but, but But like, you know, I think it's, it's, it's, it's, you're, you're intriguing. You're interesting. I think you have got a really good mindset. I think you got that good inner game.

Yeah, I think, I think I can't remember if I said this before, but I think the thing that really, I've changed my thinking about you so much is I used to think you were like rude. And now we've been working together on like a few side projects. And what I've learned is that Your style's not for everyone, but you are what I would call like admirably abrasive, right? And we were on a call. I don't know if I'm supposed to tell a story, but we're on a call. I won't say names. We're on a call and this guy gives us like a 3-minute pitch and I just see the look on Sam's face and I go, oh no, this guy's spiel is not good. And the guy goes, Sam, what do you think? And Sam, no smile, straight face goes, I don't know why I'm even on this call. What are you talking about? Well, I just start dying.

But, but I'm not trying to be rude. I'm not trying to be rude.

Exactly. Exactly. And it's not for everyone, right? That style is not for everyone. But I can see how you so quickly grow things with the right people because that type of radical candor that like, hey, I'm going to tell you what I think and we're not going to have an ego and we're going to work together to solve problems is so much better than sitting in the corporate media being like, Oh yeah, no, that was, that was great. And then sending an email later, you should look this guy straight in the eyes and you're like, I don't know why I'm here.

Yeah.

I mean, and the person who we were speaking with, I think they're great. And I was just like, you're, you're great. This is stupid though. You, you know, be different and, uh, be better than you are right now and, and achieve your potential. I think you're, I think you're great. That's typically the way that I work with people. And I don't like hearing when people say that I'm rude, that kind of hurts my feelings because I'm like, oh shit, I don't wanna be like I don't want to be known as a jerk. I'm a pretty kind guy, I thought. So I hate hearing that, but it is the truth.

All right, Sean, you work with Sam. What's it been like?

Deal with that on your own. Yeah, I think Sam's intimidating to work with. Uh, you know, I think that I've seen a bunch of people around the podcast that are intimidated, but it's a good thing. It's a standard. Like the people who have really high standards for how they want things to go, they're intimidating to work with. Like for me, we come on here, something's messed up— the camera, the audio, whatever— I'm, hey, don't worry, it's gonna be a great show. I'm trying to put that person at ease. I'm like, they probably feel like shit. I know they didn't want this to happen, uh, you know, like, and a lot of these things are— I know, like, that's not you intentionally messing something up. That's like something is going wrong, somebody's late, so something out of your control is happening. Whereas Sam gets frustrated, I could see that person start to sweat, and I don't think that's rude. I just think that's like I think you're focused and I think you, uh, you know, you're just like, you're like a blunt object. It's like, what are you gonna say? Like, this hammer is not very soft? No, it's a fucking hammer. We— that we— that's why we like it. That's why it has— that's why it gets the best spot in the tool set, because it's this like really like heavy blunt object and that's what you need. And like, for the podcast, the podcast would not be successful without Sam. Like, that's just— he brings that to the pod. And so I love that. Now with that comes, well, I, you know, sometimes it's not going to be, you know, not everyone's going to get treated with soft gloves and that's okay. Like, you know, if you know the guy's intent is good, then you don't really worry about it. So I don't know. That's, that's my, uh, I don't know, my feedback.

That's good.

Yeah, no, that's on brand. And then Sean, let me, I know I'm here for you guys to ask me questions, but I want to ask you a question. Which is, you know, like, you obviously are a great storyteller. You're very good on camera. How much of that do you think is natural? Like, you were just born with it? Let me answer this.

Keep going, keep going, keep going. Let me, let me answer it first.

Keep going.

I was going to say, I was going to say, how much of it do you think you're born with and how much are you— have you studied? Like, are you— and what are you doing to get better at it? Because I've listened to the podcast for 3 years. And you just increasingly upped your game and gotten better. And I mean, it's pretty, it's pretty incredible.

So let me give my perspective and then he should answer. But so from the time I knew Sean, he was always pretty good. He would, we would, we would do these like the podcast stemmed because me, him and Siva and a few other guys would meet weekly or monthly and like do kind of what we're doing now. And Sean was always good at like I would explain something and he'd be like, well, so what you're really saying is this. So here's how you should look at it. And he would like storytell in such a way where I'm like, oh wow, you've got this like inspirational, like thing about you that's really good. And then so he always had that. I think that was like a— I think he was born with that. And then we started the pod and he was a little rough where I actually think early on I was better than him at like capturing attention. And then he started learning about copywriting. I think I was like, you should learn about this copywriting thing. And then he got really good at copywriting and then he got really good at storytelling, like on a more refined basis. And basically what happened was because he was born with this, I think this innate ability as well as he wanted to learn about it and then he actually studied it, his trajectory and his growth was quicker than mine. And I think he actually surpassed it in terms of like storytelling and ability to capture attention. And if you listen to like the first couple of episodes, you could clearly see like because of his tone of voice and everything, like, all right, this person's intriguing. But then it was like he studied it over a year and you could see that there was a huge change. And I think it was in part of him studying copywriting. And I do think he like actually went and studied like Hasan, Hasan and like all these other comedians. He like figured out— we both like comedians, but I think he studies it and we'll like tweet or message each other like, hey, let's look at how they like told this joke. It was really interesting. And so he actually studied that and truly learned it. And so I think it was a combination of being born and studying over like 2 years. Is that, is that accurate?

Uh, I think some things you said there were accurate for sure. Um, my, and nobody knows, right? Like it's an impossible question to answer, but like I'll give it my best shot. My, here's my honest opinion. My honest opinion is I don't actually think I'm that good at it in absolute terms.

I just think it's relative to tech business, and like podcasts or generally when I've seen you with like professionals and they like comedians and I saw that they were like coming to you for advice. I've seen it.

Yeah.

Okay.

That happens. But I think the, I don't know. I grew up in Houston and Houston's just got like a very high swag factor. And like, they were like, I play basketball in the locker room. There were dudes that like should have been on stage at the Apollo or something like that. Like just the natural charisma of people who are just, uh, you know, that I grew up with were— was just really, really high. So I think that actually has a lot to do with it. When you hang out with people who naturally have a lot of swag and charisma and tell funny jokes or stories or are able to, to just quickly jump in and have quick wit, that just becomes your normal. So I think part of it was that, some environment stuff. My sister, for example, is way funnier, way better storyteller than me, and growing up it was always Sean's the smart, nice one, but he's quiet, he's shy. She's the funny one, charismatic. If something happened to me, they'd be like, Nisha, tell the story about— like, Sean, like, let Nisha tell the story, everyone will love it. So at every family party, it was her doing it. And, you know, so imagine that, like, the person you admire, your, your older sibling, is really great at this thing, and you just constantly see your family and friends are like, everybody loves that about them. So to me, it became like an important thing in my life. I was like, And not in a negative way, not like a jealousy, but I was just like, it was a thing I valued. I was like, oh, that's a really cool skill. I value that. I had no idea how to do it. And when I was younger, I was just super, super quiet. So I didn't talk that much in my friends group. I was just the, I was the laugh track. I wasn't the guy making the jokes. I was the crowd noise. And, um, but I started to, I got a couple lucky breaks. My cousin was in town and was like, hey, you know, there's a movie audition going on, like, you want to come with me? And I just like, yeah, I guess so, I don't know. And so I went with him and I ended up getting cast in the movie. Um, and that like showed me— that exposed me to a different thing. And the guy in the movie who was my brother was, uh, Kal Penn, who was the guy from Harold and Kumar and stuff like that. So I got to hang out with him for like weeks at a time. So now I'm around somebody else who's very charismatic very good storyteller, but he's like a professional actor, right? So he was somebody I admired that I was hanging out with for weeks. He's the only guy I talked to on set because I was intimidated by everybody else, and he was super nice to me. And so we just hung out every day for like, you know, 6 weeks. So that's like kind of a boot camp in like just being around somebody who's got that charisma. Okay, then fast forward, uh, I moved to San Francisco and I'm like, okay, um, I want to be like, you know, I don't know, in my mind I was like, a CEO should be the leader. The leader should be inspiring, charismatic, clear. I'm none of those things. So how am I going to do all that? And so I like tried to do things. I took, you know, I went to the SF Improv. I took classes there all the time, right? Because I was like, I don't know, it's fun. I might meet some people, but also I think this, I think improv is just like a crazy skill set to have, like to be able to on your feet, be able to think of something and, you know, make a crowd laugh. That, that to me is an actual superpower, and it's the superpower I wanted to have. Same thing with comedians. Like, I like that content, but I don't just watch it and let just like drool come out of my mouth and, oh wow, these people are funny. I'm like, I want to be funny. I love how funny they are, and like, what do they do when they tell stories, um, to, you know, that makes it work? And I'll go rewatch it and I'll sort of break it down sometimes. I'll I'll try it myself. Uh, like for example, when I did that Luna video, I did it in the style of like those John Oliver or Hasan Minhaj like skits. And mine is like, you know, 10 times worse. And I texted it to Hasan and he was like, cool, change these 95 things. And I was like, ah, dude, that's a lot to change. I'm just gonna ship it. Like, you know, I don't have time to do all that. But like, now that you've told me this, I now know what I should have done. But it's just those reps. Like, It's talent helps, but then there's reps and people don't really see the reps. And I would say like that combination of the 3 things I mentioned, like being around people who are, who are better at it than you and you admire them, that plants a little seed inside you, right? Like Austin, you were talking about that with money. Like when you met people with more money, it was inspiring and you're like, oh wow, my world opened up. I now have like people I can sort of like, you know, I can try to embody a blueprint that, that maybe they have. to, to something I want. That's how it was with storytelling and sort of like, I don't know, charisma or something like that for me. And so that, you know, being around people who you admire, uh, putting yourself in unusual situations that are like kind of intensives, like improv or acting in movies and stuff like that. Most people in business don't have that experience, so they shouldn't be as good at it, right? Like if you've never gone through these intense experiences, then, then, you know, how would you have developed those skills?

Why are you asking that, Austin? Are you trying to like get better at talking or what?

Yeah, I want to get better at public speaking. So 2023 goal, I guess I'm going to New York Improv.

Dude, I, I, I think some people are born better, but I think everyone can get at least good. But I do think Sean has this like something that will make him great.

And, uh, it, it is, it's very, uh, well, let me just put it this way, Austin. Have you ever watched back a video of you you speaking publicly in order to take notes on yourself of how you did?

Yeah.

Super uncomfortable feeling, but an obvious thing to do if you wanted to get better.

Yeah.

Right? I just had that moment where I was like, oh, I'm saying I want to get better at this. I've never done any of the obvious things you would do. I've never went and watched myself and said, what the hell am I doing with my hands? And why am I fidgeting so much? And oh man, I keep saying, um, at the start of these sentences. I should just say the sentence. but I had to go review the game film. Okay. Then the second thing was I had to take it seriously. Did I just walk up there unprepared and not warm, or do I warm up or do I prepare? Okay. That added to the game. And then the third one is like, who's the best at this? And I went to a Tony Robbins event and I was like, this guy's the best public speaker I've ever seen. And even if I don't listen to any of his content, if I just literally listen to the rhythm of his words, and the gestures and then the hooks and how he's getting everyone's attention. That's a masterclass right there. Like, okay, I'll take that. And so that's how I started stacking up some of these things. And I don't consider myself a good public speaker because I don't do a lot of speeches or anything like that anymore. But, um, it's definitely something at a time I try to build up. And it accumulated in an epic wedding speech. I gotta say, the best speech I ever gave was at my wedding, unrehearsed, off the dome. And just like, it was, I don't know, the perfect, the perfect speech. I just retired from the game right there.

At your own wedding.

At my own wedding. Yeah.

Is there, uh, is there anything else you want to talk about, Austin? This is pretty cool. You should come on more, by the way, and we should talk about newsletter shit. Cause you're like the only person, or us three are some of the very few people that like I actually want to ask newsletter advice from.

Um, and like, yeah, I'm trying to get out of the, the newsletter guy branding, but just keep on bringing me on to be the newsletter guy.

Dude, but it's, it is so fun. It's a love-hate relationship. It's really— they're really fun to do, but also they're painful and whatever.

Yeah. No, I think that's it. I think we cover most of it.

What do you think you're going to be doing like 10 years from now? You think you'll be running businesses or you're going to be just investing or big business or small ones or what?

So to me it's barbell, right? I either want to have some passive income and work 20, 25 hours a week more casual or I'm going to go all in. But if I go all in, it's got to be huge, right? The potential has to be multiple billions. I don't think I'm going to want to run a business where it's like, it's nice and it's like a double, right? If I win, it's a double. I don't want doubles, right? Either want a home run or I want to, you know, sit in the dugout and just, you know, be, be part of the peanut gallery. I don't want to play in that middle game.

I'm going to look in the future and I'm going to tell you it's probably not going to be you sitting in the dugout. That is not going to be— this is— I think maybe you will for a couple of years, but if I have to make a bet and I would put my money where my mouth is, it's not going to be that one. That's not what you're going to do.

We'll see.

Well, thanks for coming on, dude. This is awesome.

Yeah. Thanks for having me. Let's do it again soon.