Jan. 3, 2023

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

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

Episode 14: To kick off the new year, host Alex Lieberman (@businessbarista) is bringing you a very special episode of The Crazy Ones featuring Morning Brew Co-Founder and CEO Austin Rief (@Austin_Rief) and special guest Sahil Bloom (@SahilBloom). In this conversation moderated by Sahil, Austin and Alex recount the early days of building Morning Brew, the scrappy ways they grew their subscriber base, and the biggest mistakes and lessons learned along the way. 

 

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(00:51) - Intro

(02:25) - How Austin and Alex handled the doubters early on in creating Morning Brew

(07:18) - What Austin and Alex imagined their careers would be prior to starting Morning Brew

(11:03) - How Austin and Alex met

(16:39) - How Austin got involved with Alex’s newsletter

(19:48) - How the original newsletter looked in its first iteration

(21:06) - What allowed for Morning Brew to be successful in the early days

(27:46) - The scrappiest tactics Alex and Austin used to grow the newsletter readership early on

(33:40) - The marketing strategy that continues to shape how Alex and Austin approach the business today

(36:40) - How Alex and Austin scaled voice as Morning Brew grew

(40:20) - What sealed the deal for Alex and Austin to hire the current managing editor

(43:44) - The biggest mistakes that Austin and Alex made along the way

(47:47) - What led to Alex deciding to step down as CEO and Austin becoming CEO

(52:19) - Alex and Austin answer whether success and wealth has made them happier

 

Links:

Transcript

Austin Rief: We said, "You know what? What if Alex pitches and Austin walks around with a printed out Excel document basically, and basically stares people in the eyes until they give you their email?" That's what we did. So I would spend 20...

Sahil Bloom: That's like door-to-door sales, though. I like it.

Austin Rief: I would walk around the big lecture hall, 500 people, and I'd kind of just stand there, "Give me your email. Give me your email." Seriously. 

Sahil Bloom: Did you get big on 'em? Did you puff your chest up and hand it to them like, "Give me your email, give me your email." 

Alex Lieberman: He would look into their soul.

Austin Rief: If I...at the time, if I spoke in front of 500 people, I was getting 500 emails, because there's a whole classic thing, like the number two fear in life is public speaking, number one is...or number one is public speaking, two is death. 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." 

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

Sophia Amoruso: And I'm Sophia Amoruso. 

Jesse Pujji: Yo, this is Jesse Pujji. 

Alex Lieberman: And this is The Crazy Ones. What's up, everyone? This is Alex Lieberman, co-founder and chairman of Morning Brew, and we are 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. 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. 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. 

Sahil Bloom: 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 be here. 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 actually said it. It will 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. 

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?

Austin Rief: Yeah, I can start. So in 2015, Morning Brew wasn't a business. 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. 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. 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. 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. 

Sahil Bloom: Do you remember it being fuel at the time, though? Or was it just a blow?

Alex Lieberman: Yeah. 

Sahil Bloom: It's easy to call it fuel in hindsight. These types of things are easy to say, like, "Oh, yeah. I knew I was going to keep grinding," whatever. 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?

Alex Lieberman: It's so hard to know how much is actually revisionist history. 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 that the original story?" Because we've told it so many times now that I forgot there's some principle where it's like if you tell a false truth enough times, that becomes the truth. So 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. 

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. This teacher was not a dick in the tweet. He was constructive; he gave reason for why he wouldn't invest. For me, actually, when we were fundraising, the worst thing was family and friends or people peripheral that would just string along these conversations and be like three 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 three months tell you that they didn't want to invest. 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 middle school and high school, and I felt a chip on my shoulder from that, for sure. Then I think a piece of it also was just, 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 of senior year at Michigan, and so there was, I would say that was actually the number one driver, was this just focus to create something of value so the Lieberman household wouldn't have to worry again, because that was actually probably the number anxiety that was taking up space in my brain. 

Sahil Bloom: I don't think I knew that, the timing connection between your father passing away and the starting of the Brew, which is a really interesting insight. Were you an entrepreneurial kid prior to your father passing away? 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?

Alex Lieberman: Yeah. It's funny, 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. 

Austin Rief: Ugh. That's so strange. 

Alex Lieberman: And the reason was, again, that's what my parents did. So it wasn't 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." 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. I remember as early as first or second grade, this is the smallest thing, but I remember wanting to create a pen/highlighter combo; they didn't sell those at the time. So I snipped a pen in half and snipped a highlighter in half, I taped them in the middle so I could both write notes and highlight with the same instrument. 

And then at sleep-away camp, I had a shoe shining business. So I liked tinkering, but no, I never had the thought, like, "I'm going to go start my own business." My co-host for The Crazy Ones, Jesse Pujji, his dad's an entrepreneur with a travel agency; he always knew he was going to start something. That wasn't me. 

Sahil Bloom: What about you, Austin?

Austin Rief: So I grew up in the suburbs of Baltimore, and no one I knew, no one's parents, were in finance. 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 into investment banking." That was the thing at Michigan, and so I followed the herd. I was a sheep just following the herd. 

Sahil Bloom: Was it like a fraternity thing? I mean, were you guys in fraternities and they had a pipeline to Wall Street? Or was it just all your friends, people around you?

Austin Rief: It was a frat thing, but it was a business school thing. If you were in the business school, goal number one, work at an investment bank. Goal number two, if you can't do that or you're really crazy, go work at McKinsey. That's really unique, that's really different. 

Sahil Bloom: Scraping the bottom of the barrel at old McKinsey. 

Austin Rief: Exactly. So that was the goal, but I think looking back in hindsight, looking at my parents even, they're both entrepreneurs, just not in the sense that we think today. They're not internet entrepreneurs. My mom was a dentist and she's owned her own dental practice for 20 years now, and so she's a business owner. So the people I aspired to were small business owners. Small is relative; there were some very wealthy people in Baltimore, but 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. 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."

Sahil Bloom: Part of me likes those kind of things. It's a good story, and then part of me is like just rolling my eyes, like, "All right, guy. Come on." 

Austin Rief: He was ready to drop that nugget for years. 

Sahil Bloom: He probably dropped it on 100 young people that are out there. 

Alex Lieberman: But it worked. 

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

Alex Lieberman: Is that what you did?

Sahil Bloom: I did that, and it is not pretty. You get asked to do, like, "How many golf balls fit in a school bus?" On the fly. Don't recommend it. Okay, so you guys knew each other or didn't at Michigan?

Alex Lieberman: I would say, knew of each other, we were in the same fraternity. 

Austin Rief: I wouldn't even say knew of each other. We kind of, but barely, because you were two years older. But we really knew each other through TAMID, which was a club we were in. But we were in the same fraternity, but barely knew of each other, the most distant knew of each other possible, I'd say. 

Sahil Bloom: So then what happened, actually? 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, you were tutoring a lot of kids as a side hustle and making some money doing that; you realized that a lot of them had this need for simplified business insights. 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.

Austin Rief: 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. 

Alex Lieberman: Well, so I think I only had to take two classes my whole senior year. 

Sahil Bloom: Did you already have a job lined up?

Alex Lieberman: Yeah, and the way that it typically works in finance is you have your junior year internship; I received a job offer 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...

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

Alex Lieberman: The party we had for someone who left Morning Brew? 

Sahil Bloom: Did you show up really, really late for a party?

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

Sahil Bloom: 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. 

Alex Lieberman: If there's one thing that you take from this podcast, it is that Hoboken is wildly underrated as the sixth 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 two classes, I was spending a lot of time playing FIFA and NHL, living on off-campus housing. 

Sahil Bloom: Like a good frat boy. 

Alex Lieberman: Yeah. I was the most non-fratty person in a frat. Actually, the very...

Sahil Bloom: I actually can see that. I feel like Austin is way frattier than you, as an overall person. 

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

Alex Lieberman: I'm just like a little nerdy schneebly. 

Sahil Bloom: I looked at your old Facebook pictures; I definitely agree with that. 

Alex Lieberman: The very funny quick story of how I got into a fraternity at Michigan is when you do a fraternity at any school, you're supposed to do a bunch of them, 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...

Austin Rief: They call it rushing. 

Sahil Bloom: Shows how much of a frat boy he is. "I just did recruiting at AEPi."

Alex Lieberman: I was asked that question about fitting tennis balls in a 747 at AEPi. The only reason I got into AEPi...true story.

Sahil Bloom: Oh, it was AEPi, I was just throwing out the only Jewish fraternity I know. 

Alex Lieberman: 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 can talk about it now. Yeah, he was celebrating his 21st birthday, was joyriding his dad's Mercedes, and as my mom was making a left turn, crushed her driver side door. They had to use the jaws of life to get her door off. She was totally fine, but it was very scary. So if she wasn't driving a big truck, it could have been an issue. When I first met him there, I knew who he was and I was like, "By the way, I just want to make the connection here."

Sahil Bloom: “You almost killed my mom.” 

Alex Lieberman: He just never looked at me in the same way after it. 

Sahil Bloom: You were in, you were a shoo-in from that day. 

Alex Lieberman: It is 100% why I got into the fraternity, and it explains why I'm not fratty at all. 

Sahil Bloom: That is a pretty good story. I like that. So then how did you guys actually meet?

Alex Lieberman: 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 lived 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 two classes and play FIFA the whole year. 

Austin Rief: But you didn't drop the name of your class, I don't think. 

Alex Lieberman: Well, that wasn't senior year...maybe it was senior year. I took a class called "Water." 

Sahil Bloom: Like David Foster Wallace? Like, "This is water." 

Alex Lieberman: It was just a class about everything that...

Austin Rief: It's a senior elective. 

Alex Lieberman: It was a senior elective all about...

Sahil Bloom: What were you guys doing up in Michigan? Man, this Ann Arbor life. 

Alex Lieberman: So one of my two classes was Water. 

Sahil Bloom: 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. 

Alex Lieberman: Honestly, that sounds cooler than Water. So I would say I partially started writing this because I was worried that my brain was going to just atrophy during senior year, and it was a function for me to keep up to date with markets. Then the selfless side was 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 had 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. 

Sahil Bloom: Daily?

Alex Lieberman: I would say it was daily, other than days where I missed it. 

Sahil Bloom: How many people were on the list in those early days?

Alex Lieberman: So the first email went out to 45 or 50 people, and it started with AEPi people, people in the business school, and my family. Then I would just start getting messages from people saying, "Hey, I heard about your daily roundup; can you add me to your listserv?" 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 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 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 our first conversation. 

Sahil Bloom: So what piqued your interest about it, Austin? Why did you get excited? Because you were, if I recall correctly, you were younger then at the time, but you were on a similar finance-y looking path. 

Austin Rief: Yeah, so I was a sophomore and I'd say there were two 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 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 kinda terrible; it seemed pretty awful. 100-hour weeks and building Excel models and eight to 10 years before you have any real responsibility. I said, "I kinda want to hedge, in case this thing doesn't work." I had a couple friends who were more entrepreneurial minded. 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; Paul Graham does one. 

Sahil Bloom: Was it How to Start a Startup?

Austin Rief: Yeah, I think it's called How to Start a Startup. I listened to that and I was like, "Whoa, this is way cooler than the whole banking thing. 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 99% thought I was going to banking, and 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, and I was like, "This is actually pretty good. No one reads The Wall Street Journal." You'd 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, I agreed with that professor. But I don't know, there was something there about it. And also, to be honest, people were signing up and I was reading, but it wasn't good. The no PR answers? It looked horrible. It was terrible. I don't know if you have a picture that we can put up, but the original newsletter looked terrible. There was a bull and a bear like word art fighting. It looked horrible. I was like, "If I'm reading this thing and it's written like okay and it looks like shit..."

Sahil Bloom: It's written okay. 

Austin Rief: He was reading the entire Wall Street Journal cover to cover and summarizing it in three hours. How good could it have been? But I still read it every day. So I think it was that; it was the classic thing where the product sucks, but people still use it. It's like Amazon. Amazon looked terrible, it's the worst designed site that I used, yet people used it. So I thought that was interesting. 

Sahil Bloom: The thing that's so interesting to me when I hear the story recounted is, we're doing a podcast called The Crazy Ones. This is kind of a crazy idea at the time, from a business standpoint. Today, it's super obvious to say you can start a newsletter, you can monetize it via sponsors, you can build a business, you can do courses, product, there's so much opportunity around an email list. At the time, that wasn't really a thing. The creator economy. There was no VC that was like, "Yeah, I'm a creator economy investor." 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 sucked and you weren't that excited about it. 

Austin Rief: Yeah.

Alex Lieberman: Go ahead. 

Austin Rief: I think there's just a few things 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. 

Sahil Bloom: That's an incredibly important insight, by the way, for all listeners. I talk about this constantly of like, whenever anyone started something, they were just pursuing it out of 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 and I'm going to build my six-figure revenue stream." 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 I think that's a super important insight for people to take away. 

Austin Rief: Totally, and we got there, right? 2017, we kinda saw the math and we had so many people saying, "Hey, this newsletter thing is dumb." Alex and I would sit down 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 numbers are going to double. And then I think if we get to 200,000..." 

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, "We have the numbers, so either no one else sees this or we're complete idiots." I think there were times where we second-guessed ourselves, because we were 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." 

Alex Lieberman: Yeah. 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 would 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 interviewed Tim Ferriss, and one thing he had said was, he loves interviewing non-business people, people who are just on the fringes of the internet and society. When I talked to him, I said, "What are you going down the rabbit hole of right now? He was like, "Archery and compound bows, animal tracking, and one other thing." 

But he gave me the reason. He was like, "Because the people who are best point-one percent 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." There's something so amazing about that to me. You actually go to people who can't be motivated by money, and you find just this unbridled passion for the thing and for the journey of it. I think that's huge. 

I think the other thing is—you talk about this a fair bit, you've talked about it on Twitter: increasing your luck surface area. And I think that was absolutely a part of it. There were things we did in the early days to increase our luck surface area, like making the decision to write this thing. 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 a no, increased luck surface area. But there's also another piece where I think there truly was luck. 

I do think the fact that Austin was a sophomore, I was a senior, we were still in college, we had two years now to not have to think about something as a business, because we weren't in our professional lives, so the trade-offs of life didn't increase in cost yet. 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's this. You can just scale the margin." So I'd say there was luck that came out of just well-intentioned strategy. 

Sahil Bloom: Have you guys seen, I think it's Charlie Weingroff, the investor, has the matrix of complex...level of complexity of the business, that you want to be operating in a place where the business is complex...sorry, boring, but then difficult to execute against. And you guys kind of...and then 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, you're shooting fish in a barrel a little bit. 

Alex Lieberman: I feel like I think of Plaid, when I think of that type of business, or Notarize. 

Sahil Bloom: I mean, Stripe, when they first started. It's super complicated to do, very difficult and challenging to do, but boring. Not a sexy space to go build in, in those spaces. Versus space, like SpaceX, super, super complex, but really, really sexy. 

Alex Lieberman: Totally. Again, at the time, just to give a sense of the competitive landscape at the time, I don't know how long The Skimm had been in business.

Sahil Bloom: They had raised their seed or A, right? They became big and they started 2012, they raised a seed or an A in 2014, so they were probably maybe at a million subs, maybe a little less? 

Alex Lieberman: I remember at that time, us thinking, like, "It is absolute craziness to think we'll ever be at the size as them." They were 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, to...

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

Alex Lieberman: Totally. 

Sahil Bloom: We'll get into that too. 

Alex Lieberman: It's also funny to hear about now, 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. 

Sahil Bloom: That's sort of what Sam Parr did with The Hustle. It was really The Hustle in the early days, and then they built Trends, which was really, I think the big money-making business. 

Alex Lieberman: It was actually something before the newsletters. It was an event. It was Hustle Con.

Sahil Bloom: Oh, yeah. The conferences. Conference, blog...

Alex Lieberman: And then it was a blog, and then Kendall Baker, who writes Axios Sports now, he was one of their first writers, and 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. 

Sahil Bloom: Interesting. I want to talk a little bit about something around growth. So we're talking a lot about the very early days, and not being able to ever aspire to this idea of having a million subscribers, which obviously in hindsight seems like a small number relative to what you have today. Every single entrepreneurial success story that I've encountered has a common thread of these dirty, crawling through the mud growth tactics, hacks, whatever you want to call them, that they had to do in order to 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 dirty, nasty thing that you had to do to get off the ground in those early days?

Austin Rief: Yeah. So I'll give three. Number one, to get to, let's call it 1,000, and again, this goes back to Alex's relentlessness, there were so many times Alex would present something and I'd be like, "Dude, that sounds horrible." He'd be like, "Yeah, but obviously we're going to do it." So the first thing we did was we would...and Michigan was a big school, big business school. Econ 101 lectures: 500 students. Accounting 101: 250. Compared to a 2,000-person list, that's a lot of people. So Alex is like, "Let's ask the professor if we can have five minutes, just five minutes at the beginning of class and let's pitch Morning Brew." 

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, then we check the website. Two subscribers. Maybe two subscribers. We're defeated afterwards and we're like, "What do we do?" Then we figured it out. 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…sign up. So we said, "You know what? What if Alex pitches and Austin walks around with a printed out Excel document, basically, and basically stares people in the eyes until they give you their email?" That's what we did. So I would spend 20...

Sahil Bloom: That's like door-to-door sales, though. I like it. 

Austin Rief: I would walk around the big lecture hall, 500 people, and I'd just stand there. "Give me your email. Give me your email." Seriously. 

Sahil Bloom: Did you get big on 'em? Did you puff your chest up and hand it to 'em like, "Give me your email, give me your email."

Alex Lieberman: He would look into their soul.

Austin Rief: If I, at the time, if I spoke in front of 500 people, I was getting 500 emails, because there's a whole classic thing like, the number two fear in life is public speaking, number one is...or number one is public speaking, two is death. 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." Then afterwards, we didn't have 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 zero to 1,000. 

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

Sahil Bloom: Rather than just scrapping the ones that were unclear, you actually were writing three or four down. 

Alex Lieberman: Two of them would bounce, one would work. 

Austin Rief: So that's zero to 1,000. We can go three stages. Then let's call it 50,000 to 200,000, or 50,000 to 250,000. 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 is, we really started tracking the opens of readers by source, and what sources would open the most. We found that when we did cross-promotions with other newsletters, it was really successful. Those people engaged more, and it makes sense. They were people who were 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 came in; we acted as like sales consultants for two or three companies, and in exchange we'd buy their first month of ads. 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. 

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

Alex Lieberman: So there's two more. 

Sahil Bloom: I love the Excel spreadsheet one, that's just so good. 

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

Sahil Bloom: Typing in hand emails? You do a lot of that these days?

Austin Rief: The grind.

Alex Lieberman: Just finding the most creative, scrappy ways to acquire audience. I don't know why it is, but I just love the feeling of it. 

Sahil Bloom: I asked people recently, I asked, every time I was running into an entrepreneur that had a success story, I would ask them, like, "What is your favorite thing about the entrepreneurial journey?" Ankur Nagpal just started this new company and he's getting back into it. That dude has made a ton of money, 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?" He said, "I love the feeling of that 'aha' moment where I feel like I've figured something out that no one else knows." You're hitting on the same thing. You figure out this little cheat code that for some reason just works and you're able to go and exploit it. 

Alex Lieberman: 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 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. That was the definition...

Sahil Bloom: It was the shock of the cha-ching thing?

Alex Lieberman: That's exactly what it was, and we'd also get it when people hit certain referral landmarks like five, 10, 25. 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, I think the marketing strategy that continues to shape our thinking in everything is this hub and spoke model. Your hub are like, who are the people who give you access? People are channels who give you access to a bunch of the right people, so if you can get to them, it's a very leveraged act of acquiring more people, right? 

So a lecture with 500 people, very leveraged action of the lecture was the hub. 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. So in the early days, a lot of our ambassadors came from us literally poring 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 call chronic newsletter advertisers; they've advertised in 10 other newsletters. We'd look at our list. Who has the domain from, at the time, Brooklinen and Casper, et cetera. Look up that...

Sahil Bloom: It was all the DTC brands, is that what it is?

Alex Lieberman: 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'd say that was a big one. 

Sahil Bloom: Smart. 

Alex Lieberman: 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 what I thought was a really smart marketing strategy. So we just 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, went through resumes, we had an interview process, and we're like, "We're going to pick the most impressive people on college campuses. Who is the student body president, in five 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 that's going to say, "We've received your applications. It's very selective. We're going to talk about it and 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. So it was just fun to just iterate on this program over years. 

Sahil Bloom: How did you actually scale voice? That's one of the things that I find most interesting and incredible about what you guys did, in that you went from 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?

Austin Rief: Yeah. 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. 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 team of the first eight 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? Let's build a criteria, let's build a rubric. Let's see if we can find a writer who..."

The first one we were launching, or the second one, was retail. And we said, "Okay, what if we have someone who is a seven out of 10 in retail knowledge, and eight out of 10 in writing, but a two out of 10 in Morning Brew's voice. Would we hire them?" The answer was no. But we did get to a point where like, "Okay, if the daily newsletter's a 10 out of 10, what are we willing to accept?" 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, a 10 out of 10 on editorial ability, and a 10 out of 10 on tone. So we had to understand, where were we willing to acquiesce? Where were we willing to give up something?

Sahil Bloom: It's like you had multiple burners and they all have a dimmer switch. You need to figure out what the optimal thing is across all of them in order to scale. 

Austin Rief: Exactly. The second thing is, we were in person, we were a tight-knit community, and our managing editor, Neal, is unbelievable. He is so good and he did such a good job training people and making that voice ubiquitous.

Sahil Bloom: Is he still here?

Austin Rief: Yeah, he's still here. 

Sahil Bloom: You know I knew him growing up?

Austin Rief: I did know that, because he messaged me. 

Sahil Bloom: We went to a bunch of Jewish holidays growing up together. My mom, when she came over from India, was…her host family in college was his grandparents, his family. 

Alex Lieberman: That's wild.

Austin Rief: So you probably don't know this, but Neal Slacked me. I can look it up later. Neal Slacked me, I think when you had 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 2020 when you started?

Sahil Bloom: Yeah, 2020. 

Austin Rief: So for us to even think about how we're partnering with creators, that wasn't even a thought. It was like, "Eh, it's cool, but I'll let it go." 

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

Alex Lieberman: Nothing personal. 

Sahil Bloom: Look how far we've come, guys. 

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

Austin Rief: Oh, I know it is, because I've seen those DMs.

Sahil Bloom: I think I brought it up, I think I brought it up. 

Austin Rief: It's not just you, I ignore most DMs. 

Sahil Bloom: 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 to everybody. 

Alex Lieberman: By the way, one last thing I just want to say on voice. So one thing about Neal, 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 more, let's call it like traditional journalistically trained writers over time as we've gotten a sense 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 wanted 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. 

So all of our initial hires were not writers by training. So Neal, 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 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 two sentences, we know whether you're going to be the person or not. With Neal, what actually sealed the deal with him in his interview process was two 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 Neal.

Austin Rief: He's going to kill you for telling this story, by the way. 

Alex Lieberman: He knows this. But I would say that's one of the bigger mistakes we've made is if he wasn't available, the trajectory of the business would be so different. But with him, there were two things that stood out in the interview process. One, I asked him to teach me something that he's super passionate about. It doesn't have to be about business at all, and he's a US history junkie and he basically taught me about the Battle of Ticonderoga for 30 minutes. To me, the amount of detail and nuance he understood, I was fascinated by. 

The second thing, really what sealed the deal, is Neal's an a cappella singer, and he's going to absolutely kill me for telling this story. There was a YouTube video...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 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 like, "This is how we know he has the voice." So yeah, Neal...

Sahil Bloom: Can we still look that video up? 

Singing: Na na na na na na na yeah, yeah, chop it off! Na na na na na na na yeah, yeah, chop it off! 

Sahil Bloom: We'll put it in the show notes. "Chop It Off," Neal Freyman. 

Alex Lieberman: It's incredible. 

Austin Rief: Neal may quit if you put it in the show notes. 

Alex Lieberman: And the final thing I'll just say that we did from a voice perspective, and this is why I love...the early days of business are so intuitive, you don't know naturally 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."

In excruciating detail, we would describe that person, which I think brand or marketing people would call it building personas. We didn't know that. It was just like, how do we have a proxy for making decisions when we write a newsletter and we're editing, whether the Morning Brew voice would say this or not?

Sahil Bloom: So you mentioned that one of your biggest mistakes, jokingly, was not hiring Neal immediately. What are the other ones that jump out to you? What are the worst, I mean like actually bad ones? Not the like, "Oh, yeah. My biggest weakness is I'm too attention...I have too much attention to detail." Don't give me the fake interview answer. The real ones. What are the big mistakes that you guys made along the way?

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

Sahil Bloom: You're the CEO.

Austin Rief: But it really is all about hiring. I'll get specific, but it's all hiring. There's two types of mis-hiring, 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 four to six 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 then. That sucks. 

But what's even worse is you hire someone who the company outgrows too fast, and so they're good, they're really good, and they're going to thrive somewhere else, but you need a C-blank-O, you need a C-suite officer and you hire an SVP or an EVP. That's difficult, because what happens is they then, after four, six, eight 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 forward, so what do I do? I'm going to hire a bunch of people below me to help me solve that problem." 

But those people are too junior, because this person's too junior. Maybe the person below them should be at their level. 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. That I think we've got wrong a couple times, and you may not find that out for two or three years. 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 at...

Sahil Bloom: Across the tech world. 

Austin Rief: Exactly, in venture cap companies. They hired so quickly. This is a problem that's so pervasive at these companies, and it will just crush a company. 

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

Austin Rief: Totally, and it's not that these people, these founders, are bad, these are great founders, but there's the saying: "It's impossible or it's very hard to feel, to be able to fathom what compounding is like." Even when you think about compounding, you can't actually think about compounding. It's impossible, because that's what compounding is. So if you're going to grow 3X for the next two years, I can conceptually know what 3X is; 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? The answer for definitely first-time founders, but probably even second-time founders is no, that's really, really hard. 

Sahil Bloom: Alex, worst mistake? 

Alex Lieberman: I actually think probably the biggest, and I know we're going to get to this, but I think I've spent so much time 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 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 there was a lot going on in, let's call it starting in 2019. But I would say the biggest thing that happened was we made this big...I would say the most important shift that you make as a business when you go from 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 still operating in this mode of, "Just get the newsletter out. Just get our next advertiser for the next day or next week. Just find that next subscriber." Everything was reactive, and not proactively thinking about who do we want to be three months from now, six months from now, 12 months from now? I remember Austin and I had talked about, how do we get more proactive, and then he had...one of our early investors is the founder of the Snuggie, and he recommended you the book, right?

Austin Rief: Yeah, and coincidentally, Adam Ryan also had been reading it at the same time. 

Sahil Bloom: Oh, really?

Alex Lieberman: So he had recommended Austin this book called Traction, which is by Gino Wickman. There's now this set group of business planning frameworks out there: OKR, scaling up, this one's EOS. Austin read it and I would say this is 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 your vision: right people, right seats, 10-year, five-year, three-year, one-year, and quarterly goals. It's the roadmap for planning your business. 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." It's probably the one time, or one of few times in 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 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 cover to cover. I would say what happened there is that was 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, it forces you to 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? It forces you to set quarterly goals, run leadership meetings, et cetera. 

I think after that point, I kind of knew it in my heart of hearts that what I was spending my time on was largely the stuff that I was still energized by, so new products like our new podcast, our new newsletters, our education business. But what I wasn't spending my time on, or not naturally 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. I would say 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 acknowledge this truth earlier, and because I think I had always 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, 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. I think that ego held me from actually doing what I think was right actually for everyone: for me, for Austin, for the business. 

Sahil Bloom: 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, et cetera. You ended up selling at least a portion of Morning Brew—I know you guys are still owners—to Business Insider in 2020?

Alex Lieberman: Yes, October of 2020. 

Sahil Bloom: 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 close to 100%, 90+% of the business at the time. You made a lot of money in this transaction. Are you happier? Do you feel like creating tens of millions of dollars of personal wealth has made you a happier person on a daily basis?

Austin Rief: Yeah, I can start. So I was reading a book or an excerpt from a book that Will Smith wrote, and he had this quote. It wasn't about money, but I think it translates so well. The quote was about fame, and it was 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%, I think I'm absolutely happier because I have more money. I think there's that whole $70,000 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 make me not happy. So on the net, I am happier, but there are also tons of things like, for example, when you have money, money is step-wise, so making an incremental 5% on net worth means nothing to me. So that motivation just changes and the drive is just different. So net, I'm happier, but the risk/reward profile, everything just changes. It just complicates everything and just makes things more difficult. So I think I'm happier, but again, when I lose a dollar I'm like, "That sucks." One small thing is I used to love to go to a casino and gamble, and now I'll probably never gamble again in my life. 

Sahil Bloom: I'm the exact same way. I can't stand losing money. 

Austin Rief: What's funny is when I, before I sold Morning Brew, I would love nothing more than to go play three hours of blackjack for a couple hundred bucks. Now, betting $300 isn't exciting to me, but I would never bet something, because I hate losing it. I hate it. So just 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 what makes me happy now that I have a certain threshold of money. 

Sahil Bloom: Alex?

Alex Lieberman: 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. 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...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. 

I would say after the deal, and especially after moving out of the CEO role, because these are two big moments, they happened relatively close to each other. The deal was October of 2020, moved out of the role in April of 2021. My happiness actually went down a lot. It went down because of, one, I realized I had money anxiety in life actually not tied to my net worth. I still have money anxiety today, 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, 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 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 any money or doing anything that jeopardized it. So I would say I've realized actually in this how risk-averse I am. 

Sahil Bloom: 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. They think they're going to end up totally broke, which is almost impossible unless you royally screw something up. 

Alex Lieberman: 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 four to six months, I was very much, not this existential or 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 going to 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 going to 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, that I truly have the ability...I don't set an alarm in the morning; my body just wakes me up. I can choose what to do with my time both in Morning Brew and outside of Morning Brew. I see, for example, how hard those around me work in 9 to 5 jobs, and I just feel very grateful that I can choose what to do with my time. I know that's a cliché also, but that is the number one thing. 

Austin Rief: It sounds like I made the wrong decision here. That sounds pretty good. 

Sahil Bloom: 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 conversation and getting to dig into some of the details, especially around those early growth stories that I absolutely love. So thank you so much for the honesty, and thanks for having me to moderate this. 

Alex Lieberman: Thanks for doing this, man. 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. 

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

Alex Lieberman: Yes, yes, you gotta 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.