Business Building with Alex Lieberman

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0:34Hope you are having a wonderful day off with friends, family, and potato salad with heaps of mayonnaise. We are off for the holiday, but in true American fashion, the content factory never stops. So we've pre-recorded another special episode for you today. We spoke to one of the co-founders of Morning Brew. Today, we are getting to know Alex Lieberman. Alex started Morning Brew when he was just a student at Michigan alongside current CEO Austin Reif. and has been building the company for the better part of the last 10 years. We're going to talk to Alex about his journey with The Brew, how it felt to step down from being CEO of the company he founded, and discuss his own podcast under The Brew umbrella, Founders Journal.

1:18It's Tuesday, July 4th. Let's ride.

1:25Alex, welcome to the show. It's good to have you. Good to be here. So we've been using these special holiday episodes as a chance to get to know different people from the Morning Brew ecosystem. But we're especially excited to talk to you because without you, there is no Morning Brew ecosystem. You are the founder of Morning Brew. You actually hired both Neil and I, and you currently sit as the executive chairman of this huge multimillion dollar media empire. But before all that, you were just a young, ambitious business major at the University of Michigan. for the people who may have just found the pod, but don't have any background on the company that is Morning Brew.

2:02Can you tell us how Morning Brew kind of started? Yeah. Thanks again for having me. It's good to be here with my golf buddies. So I think to understand my background, you need to like go a little bit, even before college, when this was started, I grew up in a wall street family and all I knew was like wall street and financial services. My dad was a trader for 20 years. My mom was in sales and trading for 20 years. Grandpa was in sales and trading. So like my entire life, my dream was to be a great trader. And it's interesting because like, I had no idea what that meant. It was more just like my role models did that so that I was going to do it.

2:41So I went to the university of Michigan was in the business school there at that point, like freshmen, sophomore, junior year, still on that track going after like the ideal trading job. Uh, I was in the business school, studied finance and sales and trading, had internships at Morgan Stanley, sophomore year, junior year. And basically, I got into my senior year at Michigan. I had my job in hand that I had accepted to join Morgan Stanley for after college. I had all this free time. And basically, it ended up being filled by two things, playing a lot of FIFA. And then the other half was helping other students in the business school prepare for job interviews.

3:21And one question I would always ask these students was, how do you keep up with the business world? And they would always say, you know, I read the Wall Street Journal, but it's dense, it's dry. My parents tell me to do it, but I can't get through the whole thing. And at some point I was like, this is crazy. Like all these students are about to spend half of their waking hours for the next 50 years of their life working in business, but they don't have content that gets them excited about their careers. So I started writing a daily business roundup, which was called Market Corner. I would spend five hours a day basically doing what Neil has done for the last six years, reading through, you know, the primary business news sources and what I call remixing them, like a DJ who remixes records, like remixing them into digestible, approachable and engaging blurbs that help at the time the college business student keep up to date with what was happening in the business world.

4:14And I wrote this by myself for like three months. It was an incredibly, can I curse on this or no? No, we might believe it. This, you know, nothing, no F-bombs. It was an incredibly shty product. It was a PDF that I would attach to an email every day. So like it wasn't like an email newsletter with a template. There was no website to sign up. You would have to literally email me and say, Hey, I want to subscribe to your newsletter. And I would go into marketcorner at umich.edu and manually put in emails. And for whatever reason, like after a few months of doing it, there are a couple hundred people subscribed.

4:52One of those people happened to be Austin Reif, one of the OG subscribers to Market Corner. I'd sent out an email basically saying, I'm thinking about taking this a little bit more seriously. People are reading it. Austin was one of the people that responded. I still have the original email of us corresponding. Framed. Yep. I don't have it framed. I need to frame it at some point. But basically it was like, I wrote that email saying I'm interested in people helping. Austin was like, I have ideas for how this could be better. I want to chat. I responded, cool. Let's meet after BPL, which was beer pong league.

5:22Cause we're in the same fraternity at Michigan. Um, and so we met after beer pong league in the winter garden at the business school. And it's so interesting, right? Because like normally you spend weeks or months figuring out who your co-founder is for a business, but we, it was basically like speed dating for us. Like we basically became co-founders of the business in a few days. And I think my intuition was right, but there's also a lot of luck because it could have gone really wrong. Truly. I have a question. How many times do you think you've told that story? Like, I actually want to know.

5:58Uh, it's really interesting. Thousands, but at least I would say maybe 10 ,000, because when you were in the early days of morning brew, you were the salesperson, right? You were the public facing person and you probably had to tell that four or five times a day for 300 days out of the year over seven years. Yeah. So you're talking about, you know, 1500 to 2000 a year right there. Yeah. How do you motivate yourself to continue like telling this story? It's a fun story though. I mean, to be honest, like I, you'll like see my eyes gloss over and I just turn into a machine when I do it now. But the interesting thing about this, by the way, and I'm sure other founders have experienced this, is I don't even know if that's the true story anymore.

6:42Because when you've told this story so many times, you can't remember the original experience. So, for example, there's a part of the story that I don't tell, which is like, you know, part of this was like for selfless reasons of helping students. But there was 100 % a selfish reason, which was I was going to go work at Morgan Stanley. I felt like I wasn't keeping up to speed with the markets. And this was a force function for doing that. So, yeah, I don't even know what the right story is. I have to break it to you, Alex. You didn't go to the University of Michigan. You went to Wisconsin. Very possible.

7:13Ohio State, yeah. Okay, so can you talk a little bit about your decision to leave Morgan Stanley and go work at the brew full time? Because people might think that you just graduated and went to Morning Brew, but you didn't. you still pursued your sales and trading career. Yeah. So I graduated in Michigan in, uh, May of 2015. I think that is correct. You can fact check me. And so then I went, worked at Morgan Stanley, uh, in what was like for me, the perfect job. Like this was my dream job said by no one ever trading agency mortgages at Morgan Stanley. And so I was doing it. And basically my typical day for the first year.

7:57I was basically at Morgan Stanley for a year. And for that year to paint a picture, basically what it was is the entire time I lived in New York city, which is, which I don't live in anymore. I live in Hoboken, which is the greatest city in the world. I I've been the biggest cheerleader for Hoboken, um, lived in an apartment on 26th and third lived in a five bedroom, all five years that I lived in New York city, the five bedroom that I lived in on 26th and third was a true two bedroom, meaning only two of the rooms that there were five complete rooms like with the complete walls but it was an illegal apartment because only two of the rooms had windows hustle baby my overprotective mom told me that i couldn't have one of the windowed rooms like i had the first choice of room she told me i couldn't take one of those rooms because it was on the second floor and she was worried that someone in the night would climb up the fire escape and stab me so i lived in a windowless room for the whole first year i'd wake up at 5 a.m in complete darkness go to morgan stanley work out get to the trading desk desk at 6 30 work until like seven, come home, work on the brew basically until like 11 or 1130.

8:58And I did that every night for a year. And basically what happened was I realized two things at a certain point. One is like, I wasn't that great at trading. The second was I wasn't very excited about it. And so because I was, wasn't excited about it, I couldn't see myself ever becoming great at it. And so I ultimately made the decision a year in to leave my job at Morgan Stanley. And And, you know, when I talk about this decision, it sounds like a very clean process. But like to paint a picture for anyone who's thought about or thinking about leaving their job, it was eight months of just kind of excruciating discussion with my mom every day, leaving work and being like, I don't know what the hell I'm going to do.

9:42How I ended up thinking about it is like, one, I thought about the worst case scenario, like the worst case scenario, if I leave Morgan Stanley and work full time on Morning Brew is the business fails, like statistically speaking. and I was like, okay, say the business fails, then what are my options? And I was like, well, hopefully I've made like good relationships in the New York City startup scene where I can find something else to do. Or hopefully I haven't burned every bridge at Morgan Stanley where they're like, oh, this is a cool experience he's had. This could actually like help make him an even better trader.

10:11Maybe it's a good business school story. So I went like four layers deep of thinking of options. And my view was like, if none of these things are options, if the business fails, then it's actually not a morning brew problem. It's like an Alex maintaining optionality in his life problem. So that was one of the big ways I thought about it. It's a huge step to make. I actually want to jump ahead just a little bit to when morning you did leave Morgan Stanley, decided to go full time in Morning Brew. I want to talk about a very pivotal decision. What kind of went into the hiring process of my good friend, Neil Freiman, and what made you want to hire Neil in the first place?

10:46So I know Neil remembers this. I don't know if you remember this, but we actually didn't give the job to Neil at first. I do. I do remember. Oh, I don't remember that. So, you know, this, I would say, by the way, like in the early hires we made for Morning Brew, one of the best assets you have, but it also is there's real tradeoffs to it, is so many of your early hires are made through like your network. Right. Because today we could have a job for Morning Brew. we could blast it out in our newsletter and we'll get a couple hundred applications that in the early days, like we were like scratching and clawing for applications, not to say that you weren't a good application, but we weren't getting hundreds.

11:28We were getting like 10. And so, so many of our early hires came from introductions from current employees. The benefit of that is if you think a current employee is good and they recommend someone, you can start to like extrapolate, oh, this person probably is good as well. And so, So Neil was introduced to us through our, not original, but like one of our first few writers as well, who had known Neil like his whole life. And so like that added instant credibility to Neil. Now, the downside of this is you do this too long and you have a very homogeneous organization. And that's what happened to us in the first few years of the business.

12:06But with Neil, basically what happened was we actually thought Neil was an incredible candidate. And I remember two specific things that made us feel that way, other than just like he was a really quality writer. And I don't even know if this is how we still evaluate writers. But for the longest time, it was a very simple application where it was like, write 150 word long story about a major business news topic. And basically within one or two lines, I could tell whether the person had the chops to write for Morning Brew. So like his writing, like absolutely hit the mark. But then the two other things were in the interview, I asked Neil, I don't know if you remember this.

12:45I asked him to teach me about something he's really interested in or passionate about. And he taught me about a battle in U.S. history and and the level of knowledge and passion he had about this obscure, like U.S. battle was I turned into a dad. very yeah oh oh is but like to me the type of brain that understands something so eclectic with such specificity is someone who i kind of saw could like nerd out on news and information for a long time and the second is and i'm sure you've seen this video neil used to neil neil used to have a prolific singing career and we watched a video i don't even remember how we got access to it.

13:30Maybe it was on YouTube, but, um, from his acapella group, he wrote a song called chop it off, which was about circumcision and the wit of that song in like his voice was great, but the, the incredible wit of the song, we were like, Oh my God, like he is an incredible creative writer. And so that was the experience. Morning brew daily listeners are going to go digging for that video. I remember applying to morning brew and I did not know anything about business. I was You're a big news guy. You love the news. I love news, but I didn't know why Warren Buffett was famous. I didn't know what an IPO was.

14:02Oh, yeah. No, you didn't know business well. I'm aware. But, again, that's a very learnable skill. Right, right, right. The skill of being, like, a critical thinker, super curious and writing well, that's way harder to teach. But, yeah, for any MBD listeners, if you end up finding how to chop it off on YouTube, in the comments, let us know what you think. Yes, I've retired my singing career, but we're not interviewing me. We're interviewing Alex. So I want to jump ahead. You started this company and you ran it for a couple of years and then you stopped running it. So you made the decision to step down as CEO.

14:38And that is a very interesting decision that I think a lot of founders may want to make in the back of their mind, but don't. So can you just maybe talk about your thought process for saying, you know, I founded this company, I ran it for a few years. I'm not the person who should be leading it going forward. Yeah, totally. So what I'll start by saying is, again, I think I make it sound like a very easy transition. I want to kind of preface by saying it was actually one of the hardest things I had to do in my life. Because, and you always use the analogy of like a college athlete or a professional athlete.

15:10when you've been doing something for a long period of time, your identity is so tied up in it. And so when ultimately I stepped down from the brew, you can imagine like, let's say I was spending 70 hours a week on Morning Brew for at the time six years. And then I went to basically spending 20 hours a week on the business and now having this remaining 60 hours to think about the fact that I wasn't spending 80 hours on the business. It was incredibly difficult. Like I would say for me, I was spending, It took me, it's called eight to 12 months to figure out like, who is Alex Lieberman outside of this business that he's been working on since college?

15:48Honestly, I was very kind of like self-loathing or self-defeatist after that. I was like, what am I even good at? How much did I contribute to the growth of this business? Right? Like things I think from the outside people like would be like, what are you talking about? Like, these were the thoughts that I had. Like, how much was this luck versus skill? How much did I help versus did my co-founder pull me along? Like these were all the questions I had. And, you know, for me, the reason that I got to this place is I viewed as like there's two very clear stages in the journey of a business. There is what I would call like chapter one of being CEO, which is your number one job is to find product market fit and create a business out of that first product you create.

16:31Right. So in the early days, it was write, grow, sell the best daily business newsletter for millennials, bar none. And that was our entire focus at some point. And I want to say it was like middle of 2019 where we really started thinking about this. You want to switch into company building where you create like the infrastructure in order to scale beyond a single product where really the big change you make is going from reactive to proactive. up to 2019, it was like fires were being put out for that day. Like a success was putting out the newsletter that day. And we wanted to get to a place where we could be thinking about what are our goals three months, six months from now.

17:13And what I'd say is like, I I've realized over time, the first chapter, the, the product market fit chapter is like what I am most energized by, probably because it lends itself best to my skillset. Like I'm naturally creative. I would say I'm natural. I naturally have an ability to kind of like persuade people to move behind a cause like storytelling and selling. Like those are my things. Yeah. And I would say in chapter two of business, not that those aren't important, but those are less important than chapter one. And chapter two is really about, um, setting strategy, like setting a very clear strategy, staying later laser focused on it, setting really intentional goals, sticking to them, building up a leadership team of people who are way better than you in given functions and managing those people well.

18:00And I think a hundred percent, like my co-founder Austin is way better at those things. And that's what, what his skill sets are best lend themselves to. And so, you know, it wasn't the type of thing where one day I was just like, Hey, you know, I'm throwing in the towel. I'm going to stop being the CEO of the business. basically what had happened is from like middle of 2019 until April of 2021, which is when like, I kind of stepped out of the business. Austin had started doing the jobs of a chapter two CEO, meaning like building a senior leadership team, setting quarterly goals, running our leadership meetings.

18:37And so I think in doing those activities, he basically in some ways shifted into the CEO role. So actually when I stepped out of the CEO role, wasn't this like very difficult transition because I was still like focused on like creating interesting new products, which is what I loved. But that wasn't the job that needed to be done of the CEO. You just talked a lot about making difficult decisions like over the course of your life. Do you have a process for making decisions? Like, do you have a decision matrix that you do have a pro and con list? Like, do you have you developed some sort of system for making big decisions?

19:11I mean, I think there's a few things that come to mind. Like one is I think about things in terms of regret. Like that's what I think about a lot. Like what would I regret more? So when I was leaving Morgan Stanley to do Morning Brew full time, I basically put out two scenarios. One scenario is I go full time on Morning Brew and it fails. And then I'm kind of searching for a job after. the second scenario is I stay at Morgan Stanley shut down morning brew and watch someone else build the thing and I asked myself what would I regret more and that second situation where I watch someone else build the thing because they were willing to take a little bit of a leap that was so much scarier to me and so that's why one of the reasons I made the decision to go full-time on the brew I think as it related to the decision of stepping down to CEO I basically said what what would I more regret?

20:06Would I more regret leaving my CEO role, becoming chairman, having to deal with like kind of reconciling my identity but watching the business continue to grow because the right person is in the right seat then? Or stay within Morning Brew, take back my responsibilities, which would largely be ego-driven, and potentially not be the best person to drive the business moving forward. And it's like that second one is 100 % what I would regret more. And I think what that exercise actually does is it tries to separate kind of like my emotions and the stories that I tell myself from like the fact of the matter.

20:45And so that I think that's what I'm constantly trying to do is like you're I'm 100 % like 100 % of the time felt emotions toward this idea of stepping down to CEO. It was super ego provoking. I worried about becoming irrelevant. So I needed some sort of like shortcut to not allow my emotions to make the decision. So you operate under regret minimization. Yeah, yeah, yeah, exactly. You should read a book, Daniel by Daniel Pink, who just who wrote about the fact that you should lean into regrets. Actually, I read it like you should regret things more. Yes. It's like, you know, it helps you learn.

21:23No, he's not saying you should lean into regret, but he's saying don't shy away from it because it actually can help you become a better person. That's interesting. Well, let's talk a little bit about what you're doing in the current day. But actually, first, I remember when you launched this podcast, a little podcast called Founders Journal, back during the pandemic, which was basically like an audio diary of what you were thinking about on a daily basis as a founder. You actually sunsetted that podcast, had a couple of podcasts in between, but now you're bringing Founders Journal back. Can you tell us a little bit about Founders Journal 2.0 and then what you kind of hope to accomplish with that?

22:02Yeah, totally. So I would say one of my, talk about regrets, one of my biggest regrets is not documenting the journey of building Morning Brew more along the way. Like I would say one of kind of my biggest realizations in life, and I think about this in the context of building Morning Brew and not remembering some of these like amazing memories, like for every memory of like interviewing Neil, there are nine others that I can't remember, which I hate the feeling of. And I feel this in life also, like, you know, one of my biggest regrets is not document, like, you know, you guys know, like I lost my dad when I was in college.

22:34And one of my biggest regrets is not having more videos and images to kind of relive some of the experiences that I had with him. And so as I thought about it with Founders Journal, the original thought was it was during the pandemic uh things were a little bit slow and i was just like i want to start documenting my journey i haven't been able to force myself into the habit of journaling on pen and paper so what can i do to force the habit and so the idea was if i create a podcast that is a journal now i am accountable to listeners and so i'm not going to let them down i've been letting myself down in the past i'm not going to let them down so i started doing that the crazy thing is Founders Journal started as five days a week, which is just who would ever do a podcast five days a week, which is just the definition of like an over ambitious, overextended founder.

23:27So I started with that and I would just talk about everything I was learning within the brew, like lessons about everything from like how to fire, how to hire, like how to goal set, the decision to step down as CEO, et cetera. And then what happened was I did like 350 episodes of it. I think at its peak, it got to like 350 ,000 downloads a month. And what happened was I'd moved out of the CEO role. So this was probably like mid 2021. And I was in that period I was describing before of like eight to 12 months of soul searching and not doing a whole lot. And honestly, like coming up with at the time, three episodes a week where I didn't have like subject matter and experience to talk about felt very forced and inauthentic.

24:10So I took a break from that for a period of time, did imposters for a while, which I love doing, and I still get messages about it. I just think it's a business that there's still potentially behavioral change that needs to happen in society for it to be large enough. Can you tell us a little bit about that? Yeah, the whole idea of imposters was the intersection of mental health and career. So it was interviewing, you know, really big names, like everyone from, you know, Jay Shetty to Mark Cuban to just other execs like Andy Roddick. Basically, people have had a wild amount of success talking to them about deep challenges they've experienced in their career.

24:49So like one of my favorite ones was with Apollo Ono. And, you know, this guy, the winningest winter Olympian of all time. And he was retired from speed skating by the age, he was like 22 or something. And so like he had to kind of deal with like, how did he pivot himself after like when he was basically ending his career when most people start their careers. And so I thought the whole idea was if you get really successful people to be vulnerable, it'll bring them eye level with everyone else in society where other people will feel the permission to be vulnerable. And the show did really like to me, the most impactful part of the show was the emails we'd get of like literally these like novels about the impact it had.

25:32But honestly, I think the economics of the show didn't get nearly big enough to be, let's call it like worth the time from a business perspective. So that was imposters, did crazy ones for a little while, which was like entrepreneurship talk show. And it was really good. But basically what happened was in the last six months, I've gotten back into kind of like being more active, like in terms of building businesses, talking to other entrepreneurs, advising companies. So I have a lot to talk about now. And I made the decision that Like I loved Founders Journal. Like I really love the process. It gave me so much energy of documenting the journey.