Startup Hotline

What's up, everyone? Welcome back to another episode of Founders Journal, my personal diary made public for the world. I'm Alex Lieberman, co-founder and executive chairman of Morning Brew. And on today's episode, we're doing a little startup hotline where you ask me questions and I answer them. Let's hop into it. So it is Thursday, December 28th, and we're, I guess, on holiday break right now. And because I haven't been working nearly as much or consuming as much content, I wasn't feeling particularly inspired, which, you know, if you're in the content game when you're creating stuff every single day for years on end, it happens. And that's just par for the course is some days you're not going to feel nearly as inspired. And one of the things I do when I'm not feeling as inspired by a specific topic or content that I want to talk about or a lesson is I'll just crowdsource content. And the way that I do that is I go to social, I ask people if they have any questions for me, and I turn that into an episode. And that's what we're going to do today. I call it Startup Hotline. So I'm going to read posts that I put on Twitter, LinkedIn, and Instagram for you so you kind of have the same foundation of knowledge that everyone on these platforms has. And then I'm going to pick some random questions I got from folks. I'm going to answer them to the best of my ability. Also, as you're listening to this episode, if If you have any questions for me that you want to hear me answer because it wasn't a question that came up during the episode, please shoot me an email to alex@morningbrew.com and I either will answer you over email or maybe I'll turn it into an upcoming episode. So here's the post that I put out on social earlier today. I'm bored listening to Adele on record, which was true. Just got Adele on vinyl. Phenomenal. And I need to record a podcast episode. Ask me anything. Topic thought starters. My dream was to work in finance. I quit After a year, I went to the University of Michigan, big state school, after hating my small private high school. I lost my dad to a stroke at 46, which was one week before my junior year of college. I started Morning Brew as a senior in college. I scaled and sold the business with my co-founder Austin. We sold it to Axel Springer in October of 2020 during the pandemic. I dealt with significant OCD and panic attacks while building the Brew. I stepped down as CEO in April of 2021. I felt lost, unmotivated, and unskilled for 12 months. I angel invested for 12 months and absolutely hated it. In 2023, I started a personal holding company. I launched StoryArb, which is my media company for non-media executives, basically a personal brand accelerator. Started that 6 months ago. We have over $1.5 million in annualized revenue and plan to double this quarter. I got married in May of 2023 and traveled to Africa for our honeymoon. I'm launching other holdco businesses this quarter in addition to StoryYard. And finally, I picked up other hobbies that allow me to feel like a kid again— Legos, piano, and golf, just to name a few. So that is the foundation I gave everyone. And now I'm going to just go through some of these questions and answer them, and hopefully they're enlightening for you. And again, reach out to me if there are any questions you think of that I don't cover. From Judith Arden, Judith said, how has your perspective on business changed over the course of your experiences? I said, you don't have have to like every stage of business. You know, something that I realized while building Morning Brew is I had this story in my head, which is that if you are the founder of a company, you need to be the person who comes up with the idea, the person who builds the initial product, gets it to product-market fit, scales the business from 1 to 100, meaning you are an exceptional operator as well as an exceptional visionary. And then you end up ideally taking the company public and you just kind of stay with the thing for decades. And what I realized over time is that's not realistic. Most entrepreneurs do not build in that way. Of course, there's like the Mount Rushmore of entrepreneurs that people build in their head, whether it's Elon Musk, Bill Gates, Jeff Bezos, and that's the story for them. But that is not the typical story. And what I realized about myself, at least at this point in my life, I love the early stages of business and ideating businesses, finding problems, building the first product, proving that it's valuable to customers, getting it to product-market fit. I like that stage of business so much more. It's more exciting to me. I love when you feel like you're building with a ragtag team of a small group of really talented people who are kind of— have this underdog mentality in an industry that has big players. And I also feel like I get to flex my biggest assets, which are storytelling, invention, and creativity, which feel like they lend themselves most to the early days of a company. So that was the first thing that I said to Judith is you don't have to like every stage of business. And in fact, you probably aren't going to like every stage of business. Second, I said, you can never be too customer-centric. I think it is so easy when you're building a company to get bogged down in the minutia of everything not related to serving your customer. So let me just use the example of Morning Brew. It is so easy to get bogged down in what is our revenue strategy, how are we selling our advertisers, What is our strategy for our website? You know, how are we thinking about our growth strategy on social? How are we thinking about scaling our YouTube channel? And these are all important questions to have, but if the highest priority questions aren't about how do we just continue to serve really good shit to our listeners, our viewers, and our readers, then you're not focusing on the right things. And, you know, like just taking the example for StoryArc also, within StoryArc, we have really ambitious goals, right? Yeah. double this quarter to be a $2.5 million a year business. We want to double our number of customers. We have 3 hires we're going to be making in an editor, a content coordinator, another content strategist. It's all really exciting. But again, this is all in service of our customers. And so what my co-founder Abby and I talked about is, as we set goals for the quarter, we need to have some goal related to the satisfaction of our customers. Because that is, at the end of the day, every action we take in this business has to be in service of that and can't be the opposite way around. So you can never be too customer-centric in your business, and you kind of want to have a spidey sense as a founder when you kind of get this itch or you kind of have this paranoia if you feel like you haven't thought about your customer recently enough. And then the third thing I said to Judith is there's this really interesting thing that happens when you start a business young and you end up having some level of success and you sell your company, is you would You would think that a young founder who started a company in college feels this very high level of confidence in their ability to build businesses. And that, that's true in some senses, but also in a lot of senses, you actually know very little about building a business if you built a company very young. And here's what I mean by that. We started Morning Brew when, again, I was a senior at Michigan. My co-founder Austin was a sophomore. I'm 30 now. He's, I believe, 28 or 29. If you were to ask us, what are we really good at? It's like there's so many intangibles. I would say like we are good at understanding how content and distribution on the internet works. We're good at knowing how advertising works and what advertisers care about. You know, we're good at being scrappy. But because we built a business right out of college versus, I would say, what is more typical, which is someone builds expertise in an industry over time and then launches a business that leans into their expertise, I would say there's actually— there are so many fundamentals of business or Specializations in business that Austin and myself— I definitely feel this way— I want to learn for the first time now that I've had kind of this one success under my belt. So, uh, you know, a classic trajectory a lot of people will take is, you know, they'll go to college, they'll study engineering, then they'll go work at a big tech company as an engineer, then they'll go work at a startup as a product manager, they'll scale as a senior product person, then they'll go launch a company. And so when they've launched their company, they have deep subject matter expertise in product for 2 founders whose like really first job was building a company, it looks very different for us. And so, you know, even a goal that I've set for myself for this quarter is to take a course in product management because I think it's such a valuable skill and I literally know nothing about it. I just have kind of like this intuitive approach to product that I take, but I have no idea how to actually product manage a company. So I thought that was interesting as well, which is we've had success, But there are so many fundamentals to business that I feel like I haven't actually learned. Okay, let's go through a few more of these. Nancy said, today happens to be 43 years since I lost my dad. I was 15 and he was 48. So much respect for you. How did you navigate that loss and how do you feel like your grief has evolved over the years? So what I said to Nancy is, at the time I handled it as best as a 20-year-old knew how to, which was burying feelings. So in a lot of ways, I'm reprocessing that grief little by little. Now that I have a greater set of tools. And so, you know, the way I think about this is when I was 20, I didn't know how to navigate my emotions. I didn't know what to do with kind of such a severe trauma and emotion that all came at once. And so as I reflect on the loss of my dad, you know, it sounds crazy, but I think I only cried once when my dad passed away. And that is not at all indicative. of the loss that I felt or the importance that my dad had in my life. Like, my dad was my best friend. We spent all of our time together. He knew everything about me. I think it was largely because I didn't know how to kind of accept all of the feelings and the depth and the gravity and the, the amount of feeling that one can feel when you lose someone that important to you. I think it's very hard to actually, like, face it and handle it. And the easier thing to do is, of course, to To bury it, to bury it in your body. I think overall it's a relatively gendered thing where men tend to be taught, sometimes consciously, sometimes unconsciously, to not display emotion or to emote. And I think also, you know, it requires having tools to know how to deal with significant emotions like this. And so As I, as I think about the processing of, of the grief around my dad, what I actually realize is I think a lot of that processing is happening now. Now that I have some more tools to identify emotions, identify feelings in my body, sit in those feelings. Now that I feel more kind of permission to feel, and I actually have this deep desire to feel more, I think I'm thinking about my grief more than I ever did when I was 20. And so I think it's a really— there's nothing good or bad to it because I dealt with it in the way that I could at the time. But to say that I fully grieved the death of my dad, I actually think isn't right or complete. And I think over the next 5 to 10 years, I will still be grieving his loss. And beyond just kind of grieving his loss to completion, I think the other kind of beautiful thing that will come out of it is deeper access to emotions than I've ever had. And I think in having that deeper access to my emotions, in kind of reprocessing this grief, my hope and my belief is it will allow me to connect more deeply with everyone else in my life, whether it's my wife, my kids when I have them one day, my sister, my mom. Because I think full deep connection happens when you have the ability To to kind of feel the range of emotions, and I think in some ways I actually am inhibited in the in the sadness category because I was stunted from the experience of losing my dad. So that's kind of what comes up for me as I think about processing that grief. Okay, next question from Rohan Garg. Wow, quite a journey you've been on. How did you manage your OCD while building the brew? So for those of you that don't know what OCD is, OCD stands for obsessive compulsive disorder. It's I can't remember like the exact definition in the DSM, but basically it's the proliferation of unwanted thoughts or feelings, uh, that you can't get rid of. Um, and so I've had a lot of manifestations of OCD over the years. I think it is hereditary. I'm pretty sure my dad had OCD. He had clean OCD. Um, it's why at my sister's bat mitzvah we literally had a Purell cake for him. But what I'll say about OCD is when it's at its worst It was a full-time job for me. It was a full-time job. Basically, I felt a 25-pound weight on my chest at all times, and it felt like a full-time job to basically do a lot of the strategies and tactics I was taught by my therapist. The kind of the two main ones are CBT, cognitive behavioral therapy, and ERP, which is exposure prevention therapy, to try and get relief from the feelings of obsessive thinking. And obsessive thinking, again, can be about anything. It could be around touching a door handle and then obsessively thinking, oh, it must have been dirty, must have been dirty. I'm gonna get sick, I'm gonna get sick, and not be able to get that out of your head. All the way to, I've had obsessive thoughts where I'm worried that I have a heart defect, and if I get my heart rate up too much, uh, I'm going to drop dead. And so to Rohan's question, I think the answer to how I manage my OCD while building Morning Brew is I probably managed my OCD not extremely effectively, again, because I was young and I didn't have all these tools. And I think because of that, I also didn't manage Morning Brew effectively. Like, I think I was probably a subpar CEO because I had my full-time job managing my OCD, my part-time job being CEO of Morning Brew, and at the same time, because I was young and I, you know, didn't really understand what it meant to be an effective leader and manager. I don't think I communicated my needs and what I was experiencing well enough with my co-founder. So I don't think he had the ability or knowledge to kind of show up for me in the way that I needed, to no fault of his own, but because I never communicated what I was dealing with. So all in all, again, you learn from these experiences, but I actually think I probably was not a great leader during the, call it, 6-month period where my OCD was at its worst. Okay, let's see. Let's take a few more questions from Todd Allen Rose. How did you navigate the transition from finance to Morning Brew? And I'll bundle this with another question, which was someone had asked me like, how did you know that finance wasn't for you, especially if you wanted to spend your whole career in finance or you grew up thinking that? So I'll answer both of those questions. So how did I navigate the transition from finance to Morning Brew? The short answer is I stayed at Morgan Stanley as long as humanly possible until I had to make a decision of staying with Morgan Stanley or going to Morning Brew. And the reason I stayed as long as possible is it gave me as long as possible to get Morning Brew into a place where it had a foundation to be a business such that making the transition felt like it was de-risked as much as possible. And the way I think about it is people talk about this leap of faith, but I actually think if you build a business effectively or if you mitigate risk effectively, if you treat something as a side hustle before it becomes a full-time job, you should be looking at your transition as a calculated risk rather than a leap of faith. Like, I actually don't think leap of faith is the best illustration of what people should do when they go into entrepreneurship most of the time. And so, you know, when I ended up leaving Morgan Stanley, it was because I literally had to make a decision because my co-founder Austin had to decide if he was going to go full time to work in investment banking for Moelis. And he had no more time to wait. He had to make the decision. So we made that decision. And when we made the decision, it was after a year of being at Morgan Stanley, which means that we had already spent, call it like 2 years working on Morning Brew. When I quit my job, I can't remember the exact number, but we probably had 40,000 subscribers. We roughly knew how much money we could make with advertising on those 40,000 subscribers. So we knew we could have a, a business that could roughly cover our salaries to live in New York. And so then kind of the big risk to take, if we knew we could monetize it, was the risk of are we going to be able to convince advertisers? So that was a risk we took on ourselves. And are we going to be able to raise money? Because we would have to hire a writer before we could get advertising revenue. And so those were the 2 risks we took. But it wasn't like this massive macro risk. It was like we knew exactly what risks we would be taking if we decided to go full-time on Morning Brew. Now to the second question of how did I know finance wasn't for me? You know, it reminds me of the Jeff Bezos podcast with Lex Fridman, which I recently covered on another Founders Journal episode where Lex Fridman had asked Jeff Bezos, like, how did you decide that you didn't want to be a theoretical physicist? Because that's what he thought he wanted to be when he was at Princeton. And Bezos was basically like, I knew that I didn't want to be a theoretical physicist when I realized that there are like 3 people in the world who actually make a difference on the world of physics. And it's largely based on your brain being wired in a certain way that you can't get to through hard work. Like you literally have to be wired in this way. And he's like, I knew one of those 3 people in college at Princeton who was just like orders of magnitude smarter than me in the world of theoretical physics. And by seeing this person, He was basically like this guy, not because he intentionally did it, but this guy basically showed me that I shouldn't work in theoretical physics because he's going to be one of those 3 people. And I kind of had a similar feeling, not that I'm Jeff Bezos, but a similar feeling of reference point when I worked at Morgan Stanley, which is like I was working with all of these extraordinarily intelligent math majors from Ivy League schools trading mortgage-backed securities with me and I realized as I was trading with them, no matter how hard I work, I'm never going to be as skillful as them in trading this product because they're oriented in this way. This work lends itself to what their uniques are. And so then I kind of like— I always had some level of awareness of my unique skills, and I knew it was about storytelling, relationship building, invention, and creativity. Like, it was that group of things. And I knew I was using none of those skills to trade mortgages at Morgan Stanley. And in the hours of call, like 7:30 at night to 10:30 at night when I would get home from work, I was using all of those skills for Morning Brew. And so it was just very clear to me that like in career, you want to stack the deck in your favor. And the way you stack the deck in your favor is you have self-awareness of the 2 or 3 things that you're really good at, and you work your way into a job or a position where 80% of your time is spent on those 2 or 3 things. That you're exceptionally good at. And so that's how I ultimately knew that trading for Morgan Stanley wasn't for me. Okay, we're at 23 minutes, so I'm going to just see if there are any other good questions and then we're going to call it. And remember, shoot me an email if you have any other questions about my background or things that you think I could be helpful with on your entrepreneurial journey. It's just alex@morningbrew.com and I'll either email you an answer or response or I'll include it on an upcoming episode. Okay, we'll take 2 final questions from Brad Dye. He said, favorite Lego kit? Had to include a Lego question. So I've built 4 or 5 Lego sets over the last few years. I've built the Taj Mahal. I've built a boutique hotel. I've built a globe, a typewriter, an island. And I think by far and away, my favorite Lego kit is a typewriter. Oh, yeah. It is not functional in the sense you can't actually type something on it, but the keys actually move. The thing in the back actually moves. So it's very cool. So typewriter is number one, but I ordered a set recently that is a custom set made by a Lego YouTube creator. It is a ski slope that plugs into your wall and skiers ski down the slope and get pulled up by a lift. So that could be in the running for favorite Lego kit ever. I will absolutely Let you know once I build it. And then the last question from Tiago on LinkedIn. He said, if you could improve just one thing in Morning Brew's operation back in the day, what would it be? And my answer is delegate faster. I didn't realize at the time what it meant to delegate. And so it's kind of crazy to think about now, but like I ran sales at Morning Brew for 3 years and of course I couldn't instantly delegate sales at the Brew because we needed to get to a place where we were making enough money to be able to hire a salesperson. But now, as I'm spinning up businesses, I want to try to delegate too fast because I think I was so far on the opposite side of the spectrum in building Morning Brew. And to me, the only way that you can end up spending your time on the things that you are most qualified to do and are highest leverage for your business is through exceptionally good delegation. It's why, you know, it's funny, my friend Jesse Pujji always says like he believes he's a good entrepreneur and delegator because he's really lazy. And I don't know if he actually means that in truth, but I do think if you're a lazy person or like you're lazy about the things you don't like doing, you could be a great delegator because you're never going to do those things, but they need to get done. So yeah, I think a big lesson from the early days of Morning Brew is you need to delegate faster and get out of the weeds as quickly as possible so you can be the captain of your ship who's actually steering the thing versus, you know, being kind of one of the workers on the deck that has no visibility into where the business is going. And so that, that about covers the Startup Hotline. Love doing these things every once in a while. I hope you enjoyed it. And again, reach out to me if you have any questions you want me to answer. As always, thank you so much for listening to Founders Journal, and I'll catch you next episode.