Co-founders Austin Rief and Alex Lieberman on Building Morning Brew

We said, you know what, what if Alex pitches and Austin walks around with like a printed out Excel document basically, and basically stares people in the eyes until they give you your email? And that's what we did. So I would spend 20—

It's like door-to-door sales of a newsletter list. I like it.

I would walk around the big lecture hall, 500 people, and I kind of just stand there. Give me your email. Give me your email. And we get—

seriously.

Did you get big on them? Like, did you puff your chest up and hand it to them?

You would look into their soul.

Give me your email.

If I, at the time, if I spoke in front of 500 people, I was getting 500 emails because I, you know, there's a whole classic thing like, you know, the number 2 fear in life is public speaking. And number 1 is— or number 1 is public speaking, 2 is death. Like, people would rather be in the casket than speaking at the eulogy. That was me at the time. And so I was like, well, if I'm going to do this, I need those emails.

What's up, everyone? I'm Alex Lieberman.

And I'm Sophia Amoruso.

Yo, this is Jesse Pujji. And this is The Crazy Ones.

What's up, everyone?

This is Alex Lieberman, co-founder and chairman of Morning Brew, and we were back with another episode of The Crazy Ones, the best startup show on planet Earth. We're trying something a little bit different today. My co-hosts Jesse and Sophia are on a well-deserved break at the end of the year. And so if you're listening to or watching this episode, I believe it is January 3rd. So wishing you a happy new year and a ton of good things to come. So here's what we're trying today. My co-founder Austin and I have talked about the Morning Brew story at length on other podcasts, but very rarely—I don't even know if ever—have we talked about our story together in a moderated conversation. And so that's what we're going to be doing. We're going to be talking about the journey of Morning Brew, the idea, the challenges, the wins, what comes after the brew, what the business is like now, the future of media. And to have us have this conversation is our good friend Sahil Bloom. Sahil is an investor. He's a writer, he's a prolific tweeter. He has done all of the things. And so we're so lucky to be joined by him today. So I'm going to pass the mic to you.

Awesome. Well, thank you guys so much for having me. I'm excited to get to do this. I'm going to set one ground rule at the outset of this, which is no PR bullshit responses to anything that goes on. So that's the only ground rule. And other than that, I think we can kick it right off. But excited to— excited to be here. You know, I want to start with something that you guys both tweeted just recently the other day, which was a screenshot. I think, Austin, you tweeted it first. It was a screenshot of an email with names blacked out. So I'm not going to ask you who, who actually said it. It'll be in the show notes and we'll share it. But basically it was a rejection email from presumably an investor criticizing a few factors about the Morning Brew, in particular criticizing whether or not it was ever going to be able to make any money, any revenue. And what you tweeted was basically like, look, if we had listened to these people that were doubters of the idea, We wouldn't be where we're sitting today. So I want to start there. What's going through your head when you guys are receiving presumably a bunch of emails like this back in 2015?

Yeah, I can start. So in 2015, Morning Brew wasn't a business, right? It was a side project, a hobby, a fun thing just to stay up to date in the business world for ourselves and help our friends. And one thing I remember in the early days that I was actually pretty surprised about And now I look back and I think it's awesome, was how relentless Alex was about getting in touch with everyone, right? Talking to people, meeting people, whether it was advertisers, investors, whatever. And Alex— I mean, it's a professor at Michigan in the email, and Alex emailed the professor, and most people had pretty good answers. Most people— We sat down with most people at Michigan in the entrepreneurship clubs and whatever, and we sent this email, and we had heard that this guy, this professor, was a little abrasive. And we definitely didn't expect to get that email. I don't blame him, by the way. Like, I think at the time we also didn't think it was a business, or at least not a potential big business. So I don't blame him. But that was definitely fuel to the fire.

Do you remember it being fuel at the time, though, or was it just like a blow?

Yeah.

I mean, it's easy to call it fuel in hindsight. You know, like these type of things are easy to say, like, oh yeah, I knew I was going to keep grinding, whatever. Like Alexis Ohanian has his with being called a rounding error by the Yahoo team. This is kind of your moment of that. Was it fuel at the time?

It's so hard to know how much is actually like revisionist history. Like even when we tell the original story of Morning Brew and how it started, like the original insight, I oftentimes will ask myself the question, is like that the original story, right? Because we've told it so many times now that I forgot there's, there's some kind of principle where it's like If you tell a false truth enough times, that becomes the truth. And so, like, I can't remember actually what the thought was in late 2014 when I started writing this thing and when Austin joined on. And so I would say for me, actually, there was probably some fuel from people saying no. And by the way, this teacher— we're definitely not just picking on this teacher because actually Alexis Ohanian, he had replied to Austin's tweet and basically was like, I really like constructive rejections, which I totally agree with. Like this, this teacher was not a dick in the tweet. Like he was constructive. He gave reasons for why he wouldn't invest. For me, actually, when we were fundraising, the worst thing was like family and friends or people peripheral that would just string along these conversations and be like 3 months of them saying, hey, I'm going to look at the materials tomorrow. Hey, I have this question. They would have you answer all these questions and then after 3 months tell you that They didn't want to invest. Like, that was the worst. But yeah, it was this teacher. I remember Mark Cuban. We also asked him to invest. And I give so much props to Mark because he is someone that irrespective of his success, he still emails with founders at the earliest stages all the time. But basically he had a similar response to this teacher where he was like, there are a ton of newsletters. I don't get the difference. What's the differentiator? That was the gist of what he said. I think that was the fuel for me, actually. I think a fair bit of the fuel was people who I think doubted me or belittled me throughout, like, middle school and high school, and I felt a chip on my shoulder from that, for sure. And then I think a piece of it also was just like, you know, you guys know this, but I lost my dad actually right before The Brew started. a week before junior year of college. The Brew started first semester senior year at Michigan. And so there was— I would say that was actually the number one driver, was this kind of just focus to create something of value. So kind of the Lieberman household wouldn't have to worry again, because that was actually probably the number one anxiety that was taking up space in my brain.

I don't think I knew that the timing connection between, between your father passing away and the starting of The Brew, which is a really Interesting insight. Were you like an entrepreneurial kid? Like prior to your father passing away, do you had you always thought you were going to start something and go build something, or do you think that ended up being a spark of wanting to go create something with your name attached to it?

Yeah, it's funny. Like now I couldn't envision doing anything but this. But no, growing up, all I could think about doing was being a trader on Wall Street, and and and so strange. And and the reason was again that's what my parents did. So it wasn't like me thinking on behalf. of myself and what I knew I enjoyed versus didn't enjoy. It was just like, my dad's a trader, that's what he does. My mom's a salesperson at a bank, that's what she does. I just want to be like them.

Mm-hmm.

And so I actually thought it was the opposite of independent thinking, it was dependent thinking for my whole life.

I was for sure creative growing up.

Like, I remember as early as like first or second grade, this is like the smallest thing, but I remember, um, wanting to create a pen-highlighter combo. They didn't sell those at the time, so I snipped a pen in half and I snipped a highlighter in half. I taped them in the middle, and so I could both write notes and highlight with the same instrument. And then at sleepaway camp, I had a shoe shining business. So like, I like tinkering, but no, I never had the thought like, I'm going to go start my own business. You know, like my co-host for The Crazy Ones, Jesse Pujji, like his dad's an entrepreneur with a travel agency. He always knew he was going to start something. That wasn't me. Yeah.

What about you, Austin?

So I grew up in the suburbs of Baltimore, and no one who I knew, no one's parents were in finance. Like, I didn't even know what Morgan Stanley or Goldman Sachs were growing up. But I went to this very small private school. And so I wanted the exact opposite when I went to college. So I went to Michigan. I think you were similar, similar private school. And from that moment on, I was like, oh, all the kids who look like me and sound like me are all going to investment banking. Like, that was the thing at Michigan. And so I kind of followed the herd. I was a sheep just following the herd.

Was it like a fraternity thing? Like, I mean, were you guys in fraternities and like they had a pipeline to Wall Street, or was it just all your friends?

I mean, it was, it was a frat thing, but it was a business school thing. Okay. Right. Like, if you're in the business school, goal number one, work at an investment bank. Goal number 2, if you can't do that or you're really crazy, go work at McKinsey. Like, that's really unique. That's really different.

And scraping the bottom of the barrel at old McKinsey.

Exactly. So, so that was like, that was, that was the goal. But I think looking back in hindsight, like looking at my parents, even they're both entrepreneurs, just not in the sense that we think today. Right. They're not internet entrepreneurs. My mom was a dentist and she's owned her own dental practice for 20 years now. And so, you know, she's a business owner. Right. So the people I aspired to were small business owners. I mean, small is relative, right? There were some very wealthy people in Baltimore. But, you know, a real estate person, a dentist, a lawyer. But I was really attracted to the people who were lawyers, but they were really business owners, and the business they were in happened to be law. And I interned at a law firm senior year, and the managing partner sat me down and he's like, I'm not a lawyer, I'm a businessman. I just happen to be in the business of law. I was like, oh, that's interesting framing.

I like— part of me likes those kind of things and it's like, good story. And then part of me is like, just rolling my eyes, like, all right, guy, come on.

He was ready to drop that nugget.

Yeah, I know. He probably dropped it on 100 Young people that are out there.

But it worked.

By the way, side note on McKinsey, if you ever want to just get absolutely wrecked in life, go and do a McKinsey interview with no preparation.

Is that what you did?

I did that, and it is not pretty. Like, you get asked to do, like, you know, how many golf balls fit in a school bus on the fly. Don't recommend it. Don't recommend it. Okay, so you guys knew each other or didn't at Michigan?

I'd say knew of each other. We were in the same fraternity.

I wouldn't even say knew of each other. Okay. We like kind of, but barely, because you were, you were 2 years older. Yeah. Okay. Well, we really knew each other through Tamid, right? Which was a club we were in, but we were the same fraternity, but like barely knew of each other, right? Like the most distant knew of each other possible, I'd say.

So then what, what happened actually? Like, what is the story of how you guys ended up coming together? Alex, you had the insight around this business from what I understand. It was like, and maybe this is the PR answer that you've given in the past or the narrative revisionist history of like you were tutoring a lot of kids as, you know, you know, a side hustle and making some money doing that, you realize that a lot of them had this need for simplified business insights. Like it was hard to keep up with everything that was going on in the world, whether that was for interviews or things that they were having to go out and prep for or just for life. And there wasn't anything that was speaking their language in a simple way.

Yeah, I'll let Alex tell the story. But first, I just want you to say how busy you were senior year and tell everyone what class you were taking to keep your time busy.

Yeah, well, so I, I think I only had to take 2 classes my whole senior year. And did you already have a job lined up? Yeah. And, you know, the way that it typically works in finance is you have your junior internship. I received a job offer for my— after my junior internship, which is a whole story in itself, because I would say I've most of my life been a perpetually late person. And I would say I've turned a corner in the last year. I've actually been on time or early most of the time, other than a recent breakfast we had where I took a wrong turn. Other than that.

Or how about the party we had for someone who left Morning Brew?

The party we had for someone who left Morning Brew.

Did you show up really, really late for a party?

You were a little late, but we'll get back to that.

I actually remember Alex does have this bad habit of trying to drive from Hoboken to New York City to come to things, which, like, you're going to be late to half of things that happen just from traffic.

If there's one thing that you take from this podcast, it is that Hoboken is wildly underrated as the 6th borough of New York. But anyway, what I was going to say is I did get this job. at Morgan Stanley, so I didn't have to re-recruit my senior year. Only had to take 2 classes. I was spending a lot of time playing FIFA and NHL, living in off-campus housing.

Like a good frat boy.

Yeah, I was like the most non-fratty person in a frat. Actually, the very—

I actually, I can kind of see that. I feel like Austin is way frattier than you as like an overall—

And I wasn't very fratty, but I was way frattier than Alex.

I'm just like a little nerdy schneebly. Yeah.

And, and I looked at your old Facebook pictures. I definitely agree with that.

And the very funny, quick story of how I got into a fraternity at Michigan is, suppose when you do a fraternity admission at any school, you're supposed to do a bunch of them, like not put all of your eggs in one basket so that you don't risk getting rejected from the one you tried out. I didn't know these rules, so I just recruited, or they call it rushing. I rushed.

Shows how much of a frat boy you are.

I just recruited— I just did recruiting at AEPI.

I was asked that question about fitting tennis balls in a 747 at AEPI. And the only reason I got into AEPI—

Oh, it was AEPI. I was just throwing out the only Jewish fraternity I know.

The only reason I got into AEPI is because the rush chair at the time, so the person who's responsible for ultimately choosing who gets into the pledge class, True story. That summer before, he got into an accident with my mom and everyone was fine. That's why I talk about it now. Yeah. Like he was celebrating his 21st birthday, was joyriding his dad's Mercedes and as my mom was making a left turn, crushed her driver's side door. They had to use the jaws of life to get her door out. Like she was totally fine. But like it was a very scary incident. Like if she wasn't driving a big truck, it could have been an issue. And when I first met him, I knew who he was, and I was like, by the way, I just wanna make the connection here.

You almost killed my mom.

He just never looked at me in the same way after.

Oh yeah, you were in. You were a shoo-in from that day.

He was 100% why I got into the fraternity, and it explains why I'm not fratty at all.

That is a pretty good story, I like that. Okay, so then how did you guys actually meet?

Yeah, so I started writing this daily newsletter at the time, which was called The Market Corner, And again, I don't know what the actual reason I started writing this was, but it lives somewhere between selfishness and selflessness. On the selfish side, me feeling like I'm going to be wildly unprepared for Morgan Stanley when I graduate if I only do 2 classes and play FIFA the whole year.

And that's why you didn't drop the name of your class, I don't think. Well, that wasn't senior year.

Maybe it was senior year. I took a class called Water. There's just—

it was like David Foster Wallace, like This Is Water.

It was just a class about everything that—

It's a senior elective.

It was a senior elective.

What are you guys doing up in Michigan, man? This Ann Arbor life.

Yeah. So, so one of my 2 classes was water, but I took a class called Weather and Storms at Stanford.

That was one of the athlete classes that people took. So I can't actually talk that much shit.

Honestly, that sounds cooler than water. And so I would say I partially started writing this because I was worried that my brain was going to, like, just melt, atrophy during senior year. And it was, it was a forced function for me to keep up to date with markets. Then the selfless side was like, helping students prepare for job interviews. They're telling me that they don't like The Wall Street Journal. I want to write something that's better. The true story probably lives somewhere in between. I'd been writing this for a little while, and the original product was a Microsoft Word template converted to a PDF attached to an email. There was no landing page or website. If you wanted to—

Daily?

Uh, I would say it was daily other than days where I missed it.

Okay. Um, and how many people were on the list in those early days?

Yeah, so the first email went out to like 45 or 50 people.

Okay.

And it started with, like, AEPI people, people in the business school, and my family. And then I would just start getting messages from people saying, hey, I heard about your Daily Roundup, can you add me to your listserv? And I would type in email addresses. It was just a listserv I was managing. I got to— I want to say it was December of 2014 or January of 2015, and I sent out an email basically saying, I want to take this more seriously. I like— I didn't even call it a business, but I just want to take this to the next level because there's appetite. Let me know if you want to help out. And I sent that email to my readers. Austin was one of those readers. He reached out saying he had ideas and he wanted to help. And we met in the Winter Garden, which is like the main lobby area of the business school. And we basically just talked for an hour about what the future of this newsletter could look like. That was like our first conversation.

So What piqued your interest about it, Austin? Like, why did you get excited? Because you were, if I recall correctly, you were younger than at the time, but you were on a similar finance-y looking path.

Yeah. So I was a sophomore and I'd say there were 2 reasons. One was high level and one was about the Brew. So high level, by sophomore year, I had started to ask some questions about, about this investment banking path. And I was like, hmm, I'm not sure if this is actually what I want to do. I talked to people who'd done this banking thing, and it seemed kind of terrible. Like, it seemed pretty awful. You know, 100-hour weeks and building Excel models and 8 to 10 years before you have any real responsibility. And I said, I kind of want to hedge in case this thing doesn't work. I had a couple friends who were more entrepreneurial-minded. I started— I actually listened to a podcast series that I'm sure I assume you've listened to. It was the Sam Altman class at Stanford. It's 10 episodes. It's, you know, Paul Graham does one.

How to Start a Startup?

Yeah, I think it's called How to Start a Startup. And I listened to that. I was like, whoa, this is way cooler than the whole banking thing. Like, how do I get into this? So I always had this idea that let me hedge in case the banking thing isn't for me. Still 100%, you know, 99% thought I was going to banking. I spent the summer after sophomore year in banking. And then selfishly, I read the Morning Brew thing or the Market Corner thing at the time. I was like, this is actually pretty good. No one reads The Wall Street Journal. You walk into the business school, you'd walk down the stairs, there's a stack of 10 newspapers and you leave at night and that stack would still be there. Basically, no one would read it. And I bought into the idea that you could actually make the business world more engaging. Now, did I think it was a real business? No. Like, I agreed with that professor. But there was— I don't know, there was something there about it. And also, to be honest, like, people were signing up and I was reading, but it wasn't good. Like, the No PR Answers, it looked horrible. Like, it was terrible. I don't know if we have a picture that we can put up, but the original newsletter looked terrible. There was a bull and a bear, like, fighting, word art fighting. Like, it looked horrible. Yeah. I was like, if I'm reading this thing and it's written like, okay, and it looks like shit.

It's written okay.

I mean, he was reading the entire Wall Street Journal cover to cover and summarizing it in like 3 hours. How good could it have been? But like, but I still read it every day. And so I think it was that it was the classic thing where product sucks, but people still use it. Like, oh, I mean, it's like Amazon. Amazon looks terrible, right? It's the worst designed site that I use, yet people, people use it. So I thought that was interesting.

The thing that's so interesting to me when I hear the story recounted is like, I mean, we're doing a podcast called The Crazy Ones. This is like kind of a crazy idea at the time from a business standpoint. Like today, Today, it's super obvious to say like you can start a newsletter, you can monetize it via sponsors, you can like build a business, you can do courses, products. Like there's so much opportunity around an email list. At the time, that wasn't really a thing like the creator economy. There was no VC that was like, yeah, I'm a creator economy investor. You know, that wasn't a thing that people were going after. And yet you guys had this spark and decided to start doing it and pursuing it. Part of it sounds like it was like you had time on your hands and part of it sounds like your alternative kind of sucked and you weren't that excited about it.

Yeah.

Yeah.

Go ahead.

Yeah, I think there's just, just a few things that, that made it successful in the early days. One, we didn't intend for it to be a business. And if we did and we thought about it as a business in 2015, I think it would have failed. We would have made short-term decisions to make a little money here or there. But because it was a side project, we didn't.

That's an incredibly important insight, by the way, for all listeners. I mean, I talk about this constantly of like whenever anyone started something, they were just pursuing it out of like pure passion, interest, excitement, and joy of actually doing it. The process on a daily basis was so amazing to them. And that paradoxically is actually what allowed it to scale and succeed. They weren't doing it for the like, hey, let me monetize when I get to 5,000 customers, I'm going to build my 6-figure revenue stream. Like those things are really, really difficult because then you're just focused on prize the whole way along the way. You're not process-oriented. So that's like, I think that's a super important insight.

Yeah.

for people to take away.

Totally. And we got there, right? 2017, we, you know, we kind of saw the math, and we had so many people saying, hey, this newsletter thing's dumb. And Alex and I would sit down, like, once a week or once a month, and we'd look at the Excel model and be like, these people are telling us we're stupid, but we're acquiring subscribers for X, we're making Y off them. So if we can get the list from 50,000 to 100,000, I think the profit number is gonna double. And then I think we get to 200,000. And I think there were a couple moments— I don't know if you felt this way— but there were a couple moments where I was like, Either we have the numbers, so either no one else sees this, or we're complete idiots. And, and I think there were times where we second-guessed ourselves, because we're like, the numbers are so clear. It's the most obvious Excel model in the world. Costs stay the same, revenues go up, profit goes up.

Yeah, I mean, I just think the best part about it is how simple of a business it is. Yet no one understood how simple it was. There's a few things that I'd add, which is I think the point about something not feeling like a business from day one is such an important thing because it reminds me of when I, I interviewed Tim Ferriss and what one thing he had said was like, he loves interviewing non-business people, like people who are just like on the fringes of the internet and society who are like— when I talked to him, he— I said, what are you going down the rabbit hole of right now? And he was like, like, uh, archery and compound bows, um, animal tracking, and one other thing. And— but he gave me the reason. He's like, because the people who are best 0.1% in the world at this are so genuinely obsessed with the craft, because they can't be in it for the money, because it doesn't pay well. And there's something so, like, amazing about that to me, is like, you actually go to people who can't be motivated by money, and you find just like, kind of this unbridled passion for the thing and for the journey of it. So I think that's huge. I think, you know, the other thing is you talk about this a fair bit, like you've talked about on Twitter, is like increasing your luck surface area. And I think that was absolutely a part of it. Like there were things we did in the early days to increase our luck surface area, like making that— like making the decision to write this thing. Like if I didn't make the decision to write this thing, I could have very easily just played FIFA and NHL senior year, but I didn't. I decided to write this thing. So that increases the surface area a little. Reaching out to those professors or possible investors and doing it relentlessly, irrespective of if they gave us a yes or no, increased luck surface area. But there's also another piece where, like, I think there truly was luck.

Mmhmm.

Like, like, I do think the fact that Austin was a sophomore, I was a senior, we were still in college, we had 2 years now to not have to think about something as a business because we weren't in our professional lives. So the tradeoffs of life didn't increase in cost yet. Like, that was huge. And I also think we had good thought process for why we started with an email newsletter. It was cheap, it was opt-in, it's what college students were already doing. But we didn't have the thought process around, like, oh, the cost base is this, the revenue is this, you could just scale the margin. So I'd say there was luck that came out of just well-intentioned strategy.

Have you guys seen the— I think it's Charlie Weingroff, the investor, has the, like, matrix of complex, like level of complexity of the business that like, you know, you kind of like you want to be operating in a place where the business is like kind of complex, like, sorry, like boring, but then like difficult to execute against. And you guys kind of— and then like over time the industry might get sexier over time and then more competition comes into play. But when you're operating at the time when it's really not sexy, I feel kind of like you're shooting fish in a barrel a little bit.

I feel like I think of like Plaid Yeah, I think of that type of business or like Notarize.

I mean, Stripe, when they first started, is like a— it's super complicated to do, like very difficult and challenging to do, but boring. Like not a sexy space to go build in, you know, in those spaces versus like space, like SpaceX, super, super complex, but like really, really sexy.

Totally. That like, again, at the time, just to give you a sense of like the competitive landscape at the time, it was— I don't know how long The Skimm had been in business.

They had raised their seed or A, right? They became big and And they started 2012. They raised a seed or an A in 2014. So they were probably maybe at 1 million subs.

And I remember at that time us thinking like, it is absolute craziness to think we'll ever be at this size as them. Like they were the kind of the North Star in terms of how big a newsletter business could be. As we did research, we had heard about Daily Candy, which was a newsletter and failed. It's funny also over the years—

Successful exit, but a failed post-exit, which is interesting. I think that's a That's a theme.

Totally. And it's also into that too. It's also funny to hear about now, like as I've done research on other businesses over time, how many businesses started as newsletters and you just wouldn't know it. They started as newsletters to prove an audience and then they grew into something beyond a newsletter.

I mean, that's sort of what Sam Parr did with, with The Hustle, right? Like it was really— it was The Hustle in the early days and then they built Trends, which was really like, I think, the month— like a big moneymaking business on that.

And it was actually something before the newsletter. Oh yeah, it was an event. The conference.

HustleCon. Yeah. Conference blog. And then it was a blog.

And then Kendall Baker, who writes Axios Sports now, he was one of their first writers. It was like, we should do a newsletter. The newsletter became huge. It was great. And then obviously Trends became their subscription product that sat under it.

Hmm. Interesting. Yeah. Um, I want to talk a little bit about something around growth. So we're talking a lot about like the very early days and, you know, not being able to ever aspire to this idea of having 1 million subscribers, which obviously in hindsight seems like a small number relative to what you have today. Okay. Every single entrepreneurial success story that I've encountered has a common thread of these, like, dirty crawling through the mud growth tactics, hacks, whatever you want to call them, that they had to do in order to, like, get off the ground, to get those early customers, to get some initial traction. What is your— and you can have different ones or you could have the same one— what is your favorite story of the, like, dirty, nasty thing that you had to do to get off the ground in those early days?

Yeah.

So I'll give, I'll give 3, but I'll do them quickly. Right. Number one, we— to get to, let's call it 1,000. And again, this goes back to Alex's just relentlessness. There were so many times Alex would present something. I'd be like, dude, like, that sounds horrible. He'd be like, yeah, but like, obviously we're going to do it. And so the first thing we did was we would— Michigan was a big school, big business school. Econ 101 lectures, 500 students, right? Accounting 101, 250. I mean, compared to a 2,000-person list, 1,000-person, that's a lot of people. And so Alex is like, let's just go. Let's ask the professor if we can have 5 minutes, just 5 minutes at the beginning of class, and let's pitch Morning Brew. And so we did it. We walk into our first Econ 101 class, we pitch Morning Brew. We're pumped up. I'm nervous. I don't like public speaking. We give the pitch and we check the website, like 2 subscribers, like maybe 2 subscribers. And like, we're defeated afterwards and we're like, You know, like, what do we do? And then we figured out, like, no one's listening, no one's paying attention. There's too much friction to go online, go to morningbrew.com. It was actually morningbrewdaily.com. Okay, sign up. And so we said, you know what, what if Alex pitches and Austin walks around with like a printed out Excel document basically, and basically stares people in the eyes until they give you your email? And that's what we did. So I would spend 20—

Like door-to-door sales of a newsletter list. I like it.

I would walk around the big lecture hall, 500 people, and I kind of just stand there. Give me your email. Give me your email. And we get—

Did you get big on them? Like, did you puff your chest up and hand it to them?

You would look into their soul.

Give me your email. If I at the time, if I spoke in front of 500 people, I was getting 500 emails because I, you know, there's a whole classic thing like, you know, the number 2 fear in life is public speaking. And number 1 is— or number 1 is public speaking, 2 is death. Like, people would rather be in the in the casket than speaking at the eulogy. That was me at the time. And so I was like, well, if I'm going to do this, I need those emails. And then afterwards, there was no— we didn't have like a way to scan them. So we would manually type in 500 emails. I'd sit on the floor in the back of the lecture hall. So that was number one. That was like zero to a thousand.

And by the way, the amount of time, like we have spent hundreds of hours debating whether I's were L's because like it was all handwritten. So like we would basically have to put in multiple permutations of people's emails because we didn't know what certain letters were.

Rather than just scrapping the ones that were unclear, you actually were writing like 3 or 4 down.

Just 2 of them would bounce, one would work. Yeah.

So that's, that's 0 to 1,000, right? We can go 3 stages. Okay, then let's call it, you know, 50,000 to 200,000 or 50,000 to 250,000. We, we spent a lot of time talking about the referral program. So I'll leave that. And if you want to talk about it, we can. But the other unique insight we had, and is we really started tracking the opens of readers by source and what sources would open the most. And we found that when we did cross-promotions with other newsletters, it was really successful. Those people engaged more. And it makes sense, right? There are people who are just newsletter people, just like when you want to promote a podcast, you do it on other podcasts, like Mediums promote like Mediums. So we started buying ads on other newsletters. And then we were like, you know what, there aren't enough newsletters to buy ads on. What if we help other newsletter companies build up their ad business? And so we kind of came in, we acted as like sales consultant for 2 or 3 companies, and in exchange we'd buy their first, you know, months of ads. And we grew from, let's call it, 50 or 100 to 250 with a ton of really, really high-quality subscribers from other newsletters that stuck around. And that was huge for us.

Any others that jump out to mind, or does that cover it for you, Alex?

Uh, so there's 2 more.

I love the Excel spreadsheet one. That's just so good.

I don't know why it is, but it's like those things still to this day are the things that I love doing most.

Like typing in hand emails. Like, just like a lot of that these days.

Just finding— yeah, finding the most kind of creative, scrappy ways to acquire audience. I don't know why it is, but I just like love the feeling of it.

I asked people recently, I asked every time I was running into like an entrepreneur that had a success story, I would ask them like, what is your favorite thing about the entrepreneurial journey? Like Ankur Nagpal just started this new company and he's getting back into it. That dude has made a ton of money, right? Like he already had a massive success story. And I asked him like, why are you getting back into this? Why are you doing this again? And he said, I love the feeling of that like aha moment where I feel like I figured something out that no one else knows. And you're hitting on the same thing. It's like you figure out this little cheat code that for some reason it just works and you're able to go and exploit it.

Yeah. It's a very addictive feeling, and I would say there's two other things that come to mind. One, which we definitely do not do today at Morning Brew because I think the legality is borderline. But in the early days, for I would say both growing our list as well as for acquiring advertisers, I remember I don't know how many years it was. Austin and I would get an email every time there was a new subscriber. It was like that was like the definition.

It was like the Shopify cha-ching thing.

It was that. That's exactly what it was. And we'd also get it when people hit certain referral landmarks like five, ten, twenty. And what we would do, especially as we were building up Morning Brew's referral program and ambassador program, which became big, and looking for advertisers, is we would go through— at the end of the day, like, I think the kind of the marketing strategy that continues to shape our thinking in everything is like this hub and spoke model. It's your hub are like, who are the people who give you access? But people or channels that give you access to a bunch of the right people. So if you can get to them, it's a very leveraged ad. Of acquiring more people, right? So like a lecture with 500 people, very leveraged action of the lecture was the hub. And one of the other ways to think about it was if we could turn our newsletter subscribers into champions in some way, they're a hub for other things. And so in the early days, a lot of our ambassadors came from us literally pouring through our list, filtering by domain names of certain schools. We wanted to have a presence at, reaching out to those students and asking them if they wanted to be ambassadors. Same thing on the advertising side. A lot of the initial advertisers we got, we would look at what are companies that we want to work with who are what we would call chronic newsletter advertisers. They, they've advertised in 10 other newsletters. We'd look at our list, who has the domain from at the time Brooklyn and Casper, etc.

Look up all the D2C brands.

Exactly. We'd look up that person on LinkedIn if they worked in a marketing function. We would hit them up, and we knew that we wouldn't have to convince them of what Morning Brew was. So I would say that was a big one. The second one was, I think just the evolution of our college ambassador program was really interesting because at the time, no media companies were thinking about referral programs or ambassador programs. The only other one that did was The Skimm, but for whatever reason, they didn't really publicize like what I thought was a really smart marketing strategy. And so. So we just, we tinkered over semesters of the best way to do a college ambassador program. So the first time we did it, we had 10 ambassadors. We were super stringent. We went through resumes, we had an interview process, and we're like, we're gonna pick the most impressive people on college campuses who's like the student body president in like 5 different clubs because they have access to all of those hubs I just spoke about. That was the wrong strategy because all those people already have spread themselves so thin when they become an ambassador for Morning Brew, they don't have the time to dedicate to it. Then the second semester, we were like, we're going to go and swing the pendulum in the exact opposite direction. We're going to open the floodgates. So we had at one point 300 ambassadors from 200 schools. We said we're going to automate the beginning of the program as much as possible. So we're going to have an automated email sent to people saying apply to the ambassador program. An automated email is going to say, we've received your applications. It's very selective. We're going to talk about it, get back to you. An automated email that says you've been accepted to the program, whereas everyone was accepted. It wasn't like a 5% acceptance rate. And only when you got to say like 25 referrals did you actually get human interaction from Austin or I. And so it was just fun to like just iterate on this program over years.

How did you actually scale voice like that? That's one of the things that I find most interesting and incredible about what you guys did in that you went from You know, the single email, and presumably that was still you guys writing that in the very early days. It started to grow, and obviously it has now branched into a whole ton of different vectors and a whole ton of different emails and products and different things. One of the biggest challenges of doing that is the Morning Brew was so successful because it had such a unique voice, and it really felt like a person writing it to you that was funny and snarky and pithy and also delivered really poignant business insights. How did you actually scale that? Because that seems like a really challenging thing to do.

Yeah. I mean, it's still something we think about today, right? What we're trying to figure out now is how do we scale our voice and our tone to multimedia, to podcasting, to video content? I'm not sure. You know, we don't do a 10 out of 10 job right now. We're still working on that. But in the early days, it was a real question we had. We sat down with the first, you know, the team of the first 8 of us, and we said, hey, What do we want to do next? We got to more newsletters because we thought it was a good business model. But then we sat down and we had that conversation. We were like, but what actually matters in these newsletters? Like, let's build a criteria. Let's build a rubric, right? Let's say we find a writer who, like the first one we were launching or the second one was retail. And we said, okay, what if we have someone who's a 7 out of 10 in retail knowledge, an 8 out of 10 in writing, but a 2 out of 10 in Morning Brew's voice? Would we hire them? Them? The answer was like, no. But we did get to a point where like, okay, if the daily newsletter is a 10 out of 10, what are we willing to accept? Right? Because you're not going to find someone who is a 10 out of 10 on retail content, a 10 out of 10 on business knowledge, right? 10 out of 10 on editorial ability and a 10 out of 10 on tone. And so we have to understand where were we willing to like acquiesce? Where were we willing to give up something.

Yeah, it's like you had multiple burners and they all have like kind of like a dimmer switch and you need to figure out what the optimal thing is across all of them in order to scale.

Exactly. And the second thing is we were in person, we were a tight-knit community, and our managing editor Neil is unbelievable. He is so good and he did such a good job training people and making that voice ubiquitous. And so is he still here? Yeah, he's—

you know, I knew him growing up.

I did know that because he messaged—

went to a bunch of like Jewish holidays growing up together. Like my mom, when she came over from India, was like her host family in college was like his, like grandparents, his family.

So, so you probably don't know this, but Neil slapped me. I can look it up later. Neil slapped me, I think, when you had like 600 Twitter followers being like, hey, this guy, he's pretty interesting. You should check him out. I think he DM'd you. Maybe he's writing some good content. And at the time, that was what, 2020 when you started? Yeah, 2020. So yeah, I mean, for us to even think about how we're partnering with creators, that wasn't even a thought. So I was like, yeah, like, it's cool, but I'll let it go.

You guys both ignored me, by the way. I'm just going to call them out right here publicly. Like, I DM'd both of these guys back when I think I had like a couple thousand followers on Twitter in the early days. These guys were both already like semi-famous and I was just like, hey, you know, eager, like wanted to, wanted to be friends and wanted to like talk about what they were doing. Both ignored me just to, just to say it.

Nothing personal.

Look how far we've come.

I was going to say, we're going to, we're going to have to go back to the tape and actually find if this is the case.

Oh, I know it is because I've seen this DM.

I think I've brought it up. I think I've brought it up.

It's not just you. I ignore most DMs.

So yeah, which is fair. I totally understand it now, by the way, now that I'm in a different position. It's very hard to respond.

By the way, one last thing I just want to say on voice. So one thing about Neil, which I can't believe you didn't mention, is the thing that sealed the deal of why we hired him. So in the early days, I would say none of our hires were journalists, and we've hired a more, let's call it, like traditional journalist, journalistically trained writers over time as we've gotten a sense of kind of what we're looking for. But in the early days, we didn't hire any journalists, I think largely because we couldn't afford them, largely because we didn't think journalists want to come to Morning Brew because there's a very— like the investment banking path, there's a very clear path of if you go into journalism, what you ultimately want to do. And so all of our initial hires were not writers by training. So like Neil, to use the example, he wrote for Maryland's newspaper. That was the only writing he had ever done, but he just had a knack for it. And to this day, a very simple prompt, writing prompt, is like the best proxy for someone getting hired at The Brew. You take a big business news story from the last few days in 150 to 250 words. You summarize this story. in a way that connects with the audience through voice, within 2 sentences we know whether you're going to be the person or not. And with Neil, what actually sealed the deal with him in his interview process was 2 things. Well, first of all, I'll say we actually fucked up and didn't hire him at first. We gave an offer to someone else, someone rejected that offer, and then we came back to Neil. And that—

He's gonna kill you for telling this story, by the way. He knows that.

But I would say that's like one of the big bigger mistakes we've made is if he wasn't available, the trajectory of the business would be so different. But with him, there are 2 things that stood out in the interview process. One, I asked him to teach me something that he's super passionate about. Doesn't have to be about business at all. And he's a U.S. history junkie. And he basically taught me about the Battle of Ticonderoga for like 30 minutes. And to me, the amount of detail and nuance he understood, I was like fascinated by. The second thing, really what sealed the deal, is Neil's an a cappella singer, and he's gonna absolutely kill me for sharing this.

He's gonna kill you for telling this story.

It is— there was a YouTube video, like we, we research all the hires we make, and I looked him up on YouTube, and there was a video of him performing with his a cappella group, and the—

In college?

In college, and the song was called Chop It Off, and it was a song about circumcision, and he had written all the lyrics of it, and it was so incredibly clever. I was I was like, this is how we know he has the voice.

And so, yeah, Neil, can we still look that video up?

Yeah, yeah, chop it off.

Yeah, yeah, chop it off.

Put it in the show notes. Chop it off, Neil Freyman. It's incredible.

Neil may quit if you put it in the show notes.

And the final thing I'll just say that we did with a voice perspective, and this is why I love the early days of business are so intuitive, right? You don't know necessarily all these frameworks, especially if you're a first-time founder. You just do things that you think make sense. We had a one-pager that defined the Morning Brew voice as a person. So it would literally be like, our voice is Sahil. He is 30-something years old, living outside of New York City. He will drink once or twice a week. His preferred drink is whiskey. Other times he'll be reading 10-Ks or watching a TED Talk, and he loves spending time with family. And like in excruciating detail, we would describe that person, which I think like brand or marketing people would call it like building personas.

Mm-hmm.

We didn't know that. It was just like, Like, how do we have a proxy for making decisions when we write a newsletter and we're editing, editing whether the Morning Brew voice would say this or not?

So you mentioned that one of your biggest mistakes, kind of jokingly, was, was not hiring Neal immediately. What are the other ones that jump out to you? Like, what are the worst? I mean, like, actually bad ones, not the like, oh yeah, my biggest weakness is I'm too attention to, you know, I'm too much attention to detail. Like, don't give me the fake interview answer. The, the real ones. Like, what are the big mistakes that you guys made along the way?

This also may feel a little PR-ish, so, so you can feel free to push back.

You're the CEO.

But it really is all about hiring. I'll get specific, but it's all hiring, right? And there's 2 types of mishiring. And I think people usually think about the first that I'll give you, but it's the second that really kills you. The first is you just mess up. You hire a senior exec, you know, within 4 to 6 months, they're the wrong person. hopefully earlier. It takes a month to fire them, you have to replace them, and next thing you know, you've lost a year because you have to recruit them. That sucks. But what's even worse is you hire someone who the company outgrows too fast, right? And so they're good, they're really good, and they're gonna thrive somewhere else. But you need a C-blank-O, right? You need a C-suite officer. And you hire an SVP or an EVP, and that's, that's difficult because what happens is they then, after 4, 6, 8 months when the company passes them, they then go and they say, oh shit, I now feel the pressure because this is the biggest company I've ever run content, sales, marketing for. So what do I do? I'm gonna hire a bunch of people below me to help me solve that problem. But those people—

Compound.

Yeah, those people are too junior because, you know, this person's too junior, right? Maybe the person below them should be at their level. And so next thing you know, you have this bloated org of a lot of people who might be great, but it's just not the right team for where you are. And that, I think, we've gotten wrong a couple times. And you may not find that out for 2 or 3 years, right?

Mm-hmm.

Like, you can really take a long time to unwind that. And I think that's, by the way, what we've seen over the last couple years Across the tech world. Yeah, exactly. In venture— in venture-backed companies, they hired so quickly. This is a problem that's so pervasive at these companies, and it will just crush a company.

Yeah, it was just, you know, when, when money's free, hiring and marketing dollars are like the easiest things to deploy. You can just go hire endlessly and give people, you know, give, give some like SVP the right to hire and build their entire org.

Totally. And it's not that these people, these founders are bad. These are great founders, But, you know, there's the saying it's impossible or it's very hard to, like, feel the— to be able to fathom what compounding is like. Even when you think about compounding, you can't actually think about compounding, right? Like, it's impossible because that's what compounding is, right?

Yeah.

And so it's like, you know, if you're going to grow 3x for the next 2 years, I can conceptually know what 3x is, right? I can look at an Excel spreadsheet. I can even build an org chart. But can you actually feel what compounding is, and can you know who the right exec is for a company when it's 9x bigger? And the answer for, definitely, first-time founders, but probably even second-time founders, is like, no, that's really, really hard.

Hmm. Alex, worst mistake?

Um, I actually think, probably, the biggest— and I know we're gonna get to this, but I think, you know, I've spent so much time just, like, reflecting on the business, and on the last few years. I think the biggest mistake was probably actually staying in the CEO role too long. I think, you know, I've spent a ton of time reflecting on the things I really enjoy doing, the things I don't enjoy doing, the things I'm really good at, the things I'm not good at. And I think, you know, there was a lot going on in, let's call it, 20— starting in 2019. But I would say the biggest thing that happened was like we made this big— I would say the most important shift that you make as a business when you go from kind of product or product to company. And I vividly remember this conversation with Austin where— and this is another sub-mistake, but it was in WeWork. We were, we were still operating in this mode of just get the newsletter out, just get our next advertiser for the next day or next week, just get the next just find that next subscriber. Everything was reactive, and not proactively thinking about who do we want to be 3 months from now, 6 months from now, 12 months from now. And I remember, um, Austin and I talked about how do we get more proactive, and then he had, um— one of our early investors is the founder of the Snuggie, um, and he recommended you the book, right?

Yeah, yeah. And coincidentally, Adam Ryan also had been reading it at the same time.

Oh, really?

Yeah.

And so he had recommended Austin this book called Traction, which is by Gino Wickman. It's like one, you know, there's now this set group of like business planning frameworks out there, OKRs, Scaling Up. This one's EOS. And Austin read it. And, you know, I would say this is kind of like one of the most exciting, excited moments in the journey I've seen Austin, where he was like, this is what we have to do to be proactive because it really sets up like your vision, Right people, right seats. Ten-year, five-year, three-year, one-year, and quarterly goals. Like it's the roadmap for planning your business. And he told me you have to read this. And I remember I didn't read it. And he had asked me, and I was like I didn't read it. And he—it's probably like the one time or one of few times in kind of the whole journey that I would say it felt like Austin was actually mad at me because he was like, dude, how can you not read this? This is like the most important thing. That we have to do to be able to plan our business moving forward. So I remember the next day, I spent the entire day in WeWork just reading this book, uh, cover to cover. And I would say what happened there is that was kind of the turning point of us getting more proactive about the business. And I think in a lot of ways, Austin taking on the responsibilities of the CEO of the company, because I think in a lot of ways, by following that process, process. It, it forces you to, uh, think strategically about what is the plan for the business moving forward, forces you to think about who is your leadership team and who are you hiring into your leadership team, forces you to set quarterly goals, run leadership meetings, etc. And I think after that point, there was— I kind of knew it in like my heart of hearts that what I was spending my time on was largely the stuff that I was still energized by. So like new products, like our new podcast, our new newsletters, new— like our education business. But what I wasn't spending my time on or not necessarily energized by was in a lot of ways what the job was of the CEO as you go into company building and not product building. And I would say it, it largely led to ultimately Austin and I having to have very difficult conversations about him moving from the COO role into the CEO role, me moving from the CEO into the chairman role. I think largely because I didn't kind of acknowledge this truth earlier, and because I think I had always kind of had this perception in building a business that you have to be the CEO forever. Because a lot of who my role models were for such a long time, whether it was Bezos or Gates, like any of these people, they start the business and they run it until it goes public. Basically, they're the captain of the ship forever. And I think that kind of of ego held me from actually doing what I think was right, actually, for everyone, for me, for Austin, for the business.

So I know we're running up here against the end of time. I have one question that I really do want to ask you guys both on a personal level that I think will resonate with a lot of folks out there and founders, builders, etc. You ended up selling at least a portion of Morning Brew. I know you guys are still owners, to Business Insider in 2020?

Yes. October of 2020.

Okay. In that transaction, both of you guys made a lot of money. You had presumably been paying yourself salaries for a while and had been doing well because the business was doing well and you owned 100%, close to 100%, 90-plus percent of the business at the time. You made a lot of money in this transaction. Are you happier? Do you feel like, you know, creating tens of millions of dollars of personal wealth has made you a happier person on a daily basis?

Yeah, I can start. So I was, I was reading a book or an excerpt from a book that Will Smith wrote, and he had this quote that I think it wasn't about money, but I think it, it translates so well. And the quote was about fame, and it was getting something to the effect of getting famous is amazing. It's like absolutely incredible. Being famous is cool. It's nice. But losing fame is horrible. And I think the same thing is true about money, right? Am I happier? I think 100%. Like, I think I am absolutely happier because I have more money. And I think there's like that whole $70,000 salary, you know, study that people are happier at $70,000. I don't think that's true. I think I am happier. But I think there are also a lot of things that that make me not happy, right? And so, like, on the net, I am happier. But there are also tons of things like, for example, when you have money, it's like money is stepwise, right? And so making an incremental 5% on net worth means nothing to me, right? And so that motivation just changes, right? And the drive is just different, right? And so net-net, I'm happier. But the risk-reward profile of everything just changes. It just complicates everything and just makes things more difficult. So I think I'm happier. But again, like when I lose a dollar, I'm like, oh, that sucks, right? You know, one small thing is I used to love to like go to a casino and gamble, and now I'll probably never gamble again in my life.

Same way. Can't stand gambling.

Yeah. And what's funny is when I— when I— before I sold Morning Brew, I would love nothing more than to go play only, you know, 3 hours of blackjack for a couple hundred bucks, right? Now, like, I— betting $300, like, isn't exciting to me, but I would never bet something that is, because I hate losing it. I hate it. And so it's just like, you know, having money has changed my relationship with money. It's made me happier, but it just made it very awkward. It's something that I personally haven't spent enough time thinking about and internalizing, like, like, what, what makes me happy now that I have a certain threshold of money.

Alex?

Yeah, I would say one of the functions of moving into the chairman role and going from spending a ton of time in the business to less time in the business is it left me with time. So I spent probably too much time thinking about this. And I would say a few things. I feel incredibly fortunate to be in the position that I'm in because I would say the thing that kind of add one to the scoreboard for money, is to not have to feel financial anxiety ever again in my life, unless I royally fuck something up, is just an amazing blessing.

Mmhmm.

Um, I would say, after the deal, and especially after moving out of the CEO role, because, like, these were 2 big moments, they happened relatively close to each other. Deal was October of 2020. Uh, moved out of the, the role in April of 2021. My happiness actually went down a lot. Um, and it went down because, one, I realized I, I had money anxiety in life, actually not tied to my net worth. Like, I still have money anxiety today.

Mm-hmm.

Even though it isn't necessarily rational. I think it's potentially because we didn't talk about money growing up. Potentially it's a generational thing, a cultural thing. I don't know. But so I didn't have the crutch of like money was going to remove my money anxiety. So it's now something I know I have to work on irrespective of it. I would say the second thing is I was absolutely motivated in some portion by money in the Morning Brew journey because it goes back to, you know, how I wanted to feel like there was only cash going out of the Lieberman family and none coming in. I'm going to do everything possible to make that reality better. Now that that's a reality, that can't be part of my motivator. I would say also I got very just afraid of losing it, like losing any money or doing anything, anything that jeopardized it. So I would say, like, I've realized actually in this how risk-averse I am.

The intense paranoia, by the way, is a staple of highly successful and highly wealthy people. There's this weird paranoia that a lot of really successful people have about losing it all. Like they think they're going to end up Totally broke, which is almost impossible if you— unless you royally screw something up.

Yeah. Well, I would say the big reason for me actually was because after moving out of the CEO role for, I would say, a period of 4 to 6 months, I was like very much not this existential or like cliché, but like, who am I? Who am I outside of Morning Brew? I was not self-loving at all to myself. I questioned what I was actually good at. So I think a lot of that money anxiety was tied to me being like, I don't know if I'm ever gonna be able to create something of value again, so I better not screw this up, and I better protect this with my life, because I don't know if I'm gonna bring anything else in that will add on top of this. I think the greatest thing that it has done to increase my happiness is give me the freedom of time.

Mmhmm.

That I truly have the ability, like, I don't set an alarm in the morning. My body just wakes me up. can choose what to do with my time, both in Morning Brew and outside of Morning Brew. And I see, you know, for example, like how hard those around me work in 9-to-5 jobs. And it's— I just feel very grateful that I can choose what to do with my time. And I know that's a cliché also, but that is the number one thing.

Sounds like I made the wrong decision here. Sounds— it sounds like that sounds pretty good.

Well, look, I really appreciate all the honesty and candor and Personally, I feel like I've learned a lot from you guys from the, from the conversation, getting to dig into some of the details, especially around those like early growth stories that I absolutely love. So thank you so much for the honesty and thanks for having me to, to moderate this.

Thanks for doing this, man. And we're going to have to have you on a TCO episode in the future to go through your whole journey, which has been spectacular.

I'd love to do it. I'd love to do it. I'll come pitch you on the book, which is around.

Well, yes. Yes, you got to do it. And for everyone, All you misfits out there who listened to this episode of The Crazy Ones, thank you as always for listening to watching the show. Hope you enjoyed this little bit of a change up, and you can expect next week back to normal programming. And as always, say what up, introduce yourselves, give us ideas for the show at thecrazyones@morningbrew.com. Thanks for listening, everyone.