I recently had the opportunity to be featured on the Post Run High podcast hosted by Kate Mackz where I opened up about my journey in ways I don’t often share publicly.
We covered everything from my Wall Street roots and some of the childhood challenges that shaped me, to co-founding Morning Brew and eventually selling it for $75 million.
I found myself getting pretty raw about some tough experiences — the bullying I faced growing up, personal losses that changed my perspective, and what I’ve learned about scaling a company from the ground up.
We talked a lot about my philosophy around hiring for potential rather than just experience, and why I believe leading with curiosity has been so crucial to everything I’ve built.
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Full Transcript
Alex Lieberman: You can’t fake passion about entrepreneurship because it is such a slog and the odds of success are so low. Alex Lieberman, he’s the co founder of Morning Brew. What they’ve been doing with the Morning Brew is absolutely astonishing. There’s this concept of creating lux surface area. Like the more seeds you plant, the greater the chance that one of the plants is going to bud.
Kate Mackz: What do you think was harder, building a successful company or letting it go?
Alex Lieberman: Letting it go for sure. I just was incredibly lost. And experience, unfortunately, is sometimes the best teacher of the most powerful lessons in life. Building business feels like a game right now. And when building business feels like I’m playing this like fun Internet game, life just feels like easy and in flow.
Kate Mackz: Alex Lieberman, welcome to Post Run High.
Alex Lieberman: Thanks for having me pumped to do this.
Kate Mackz: So guys, for a little bit of context, Alex and I just ran three miles through Brooklyn. We did little Brooklyn Trot and I.
Alex Lieberman: Feel bad that you have to be in close proximity to me right now after definitely sweating a lot. I’m a bit of a hot mess right now.
Kate Mackz: You know, you look great. I was. Honestly, a little bit of sweat is natural.
Alex Lieberman: I’ve realized when I go to weddings, I tend to dance a lot even though I’m not a good dancer. And so I bring an extra shirt to weddings now because I just know I’m going to sweat through the first shirt within the first few hours. I just need to do the same thing whenever I’m doing a run into a podcast in the future.
Kate Mackz: Honestly, that’s really smart for everybody going to weddings this summer. Are guys out there and you’re wearing a tux?
Alex Lieberman: Yeah. You owe it to yourself. Break it down on the dance floor and then feel good in your clothing after.
Kate Mackz: What is an Alex Lieberman? Go to dance. Move on the dance floor.
Alex Lieberman: That’s a great question. I like pulling out the shopping cart and then I’ll be walking down aisle to grab some of the paprika, then look to the left, grab the rice cakes, put them in and just stroll down the aisle.
Kate Mackz: Okay, let’s get into the conversation. So Alex has such a cool story. I’m so excited for everybody to not only enjoy watching this video video but also learn so much from you today. Tell us a little bit about young Alex, where you grew up and what your childhood was like.
Alex Lieberman: Yeah, for sure. So I grew up in Livingston, New Jersey, a small suburb outside of New York. I grew up in a Wall street family. So my mom was on Wall street for 20 something years. My dad Was a trader on Wall Street. My grandpa worked on Wall Street. So like Wall street and finance was in my blood from a very young age. I have one sister, she’s four years younger. And I would say like I had a pretty, just like vanilla childhood in the best way. Like I, you know, family was the most important value in our lives. Spend so much time with my family but like there was nothing out of the ordinary about my childhood. But then I would say, I don’t know, from like fourth or fifth grade until the end of college, there were just a lot of key milestones in life that really were formative for me that had a huge impact on how I think about the world. So it starts with around fifth grade. I went to a small private school. I was bullied from basically fifth grade until 12th grade. So imagine for a period of eight years, little Alex not feeling a sense of confidence, not feeling belonging, you know, at times getting to school and just walking from one end of the school to the other other end of the school just to kill time because he didn’t feel comfortable being in a with a group of people. I think that for a lot of my life, up until college or even starting my businesses, I don’t know that I had that strong of a sense of self. I definitely didn’t have self confidence. I didn’t view myself as like kind of really special or smart or capable. And you know, we’ll talk about it in a few minutes. That definitely changed when I ended up starting a company and building it and kind of that momentum created confidence for me. But then the other big milestone in my life was a week before junior year of college, my dad passed away completely unexpected. He was 46 years old, totally healthy, in the same shape that I’m in, and he died from a stroke. And you know, we’ll never know why it happened. My story that I have is that he worked in an incredibly high stress job for 20 something years and cortisol running through your system for that long had has an impact on you. And so I would say just like those two moments I would say were the biggest forms of adversity in my life and they really informed kind of what I chose to do after college and kind of what created a fire in me to build a company once I went all in on entrepreneurship.
Kate Mackz: Those are two moments that take up such a large chunk of your life because they’re kind of years of, you know, with your dad grieving and then, you know, when you’re getting bullied, it’s that’s a hard mindset to come out of that, you know, attacks your self worth and yeah, your self confidence. So it’s so true. It’s when you’re faced with a little bit of adversity is when you really do grow though. And I mean, it’s so cool to see what you’ve built.
Alex Lieberman: You know, it’s always interesting to think about how much of us is informed by nature versus nurture, because at least my. I would say I came out the other side of all of this with an immense sense of like, gratitude, which people listening may be like, why would you have, like, why do you have gratitude after being bullied? Why do you have gratitude after you lost your dad? But I would say there’s a few reasons I feel gratitude. Like one is life has felt a lot easier since then, candidly, like my adult life has felt, knock on wood, pretty easy. But the other part is, is like when I think about bullying, one part of it could be like me feeling bad for myself. The other part of it is like, it created this incredible resilience that I have today as a person. And it gives me a sense of grounding and confidence that no matter kind of what is put in front of me, I have the tools and kind of the mind to be able to navigate it. And then like losing my dad again in my grief journey, there was for sure a part of that journey, especially early on where I was. I went from like shock to sadness to anger, to ask myself why this didn’t happen to other people who were in way worse shape. Like, I went through all of that. But on the other side of it, I do feel immense gratitude that I spent so much quality time with my dad for the 20 years that he was in my life. And I also feel so much gratitude for the perspective that it gave me and how I choose to lead my life today. And obviously I would do anything to have him back, but I don’t have that choice. But I do have the choice of, you know, what lessons has it instilled in me that can inform kind of what I do moving forward, going through.
Kate Mackz: Hard moments in life, like, if you have it so easy, I often find that those people have a hard time even maybe connecting with people on a deeper level. Right. Like, you’ve gone through stuff that is really hard and really challenging to overcome, but when you do get the other side of it, like, you can also connect with people in a whole new way. I mean, I had a similar experience when I was in high school and through college, I had A really hard time fitting in and finding my people and finding my place.
Alex Lieberman: But.
Kate Mackz: But it was through going through that that I’ve become the person that I am today. And I would. I would not be who I was today if I hadn’t gone through those experiences again.
Alex Lieberman: It’s like. It’s one of those things, like, you don’t hope that it happens to people. But I think this one unfortunate truth that I’ve realized is, like, there’s such valuable lessons to learn in life, and unfortunately, one of the best ways to learn them is through experience. Like, I always say to people, like, spend. Like, spend your time as if it is your last day. Like, would you be spending it in the same way? And, like, it always comes off so cliche, obviously. And I think what I’ve realized is, like, I can tell people a story of losing my dad and how, like, that really has changed the way I think about how am I going to spend my time with my family? How do I want to spend my time in life? But there’s also part of me that’s like, is it. Is it actually going to sink in? Like, is it going to work? Because the only reason I know to live in this way is not because someone else told it to me. It’s the unfortunate reality that I experienced it and experience, unfortunately, sometimes the best teacher of the most powerful lessons in life.
Kate Mackz: And it’s wild that you were going through all of that all while starting your company. Right. I mean, when you were a senior in college is when you started the Morning Brew, which was originally called Market Corner. So let’s talk about what was going on in your life when you started Market Corner. I know that you grew up in a finance family, by the way. So did I. I feel like that was a little bit of a Jersey experience.
Alex Lieberman: Totally. For whatever reason, in my head right now, I like, hear, like, in a deep Jersey accent, someone going Wall street. Yeah, no, 100%. Like, so I went to Michigan, and first of all, going back to, like, I didn’t feel like I fit in in middle school or high school. I was the first person in seven years to go to Michigan from my high school. Most of my grade went to either Ivy League colleges or to, like, the nezcacs, which are, like, the Middlebury’s Colgates of the world. So it was not at all, like, a cool thing for me to go to Michigan. It was kind of a mediocre thing. Now I look at Michigan and it’s such a hard school to get into. But. But when my actually my first choice was Emory, I didn’t get into Emory. And that’s how I ended up deciding to go to Michigan. But anyway, I went to Michigan with the full intent of working on Wall street, spending my whole career in finance. Like my parents, I did the classic internship thing after freshman year, sophomore year, junior year, and I get into my senior year at Michigan and I. The way it typically works, like in finance now is like, you do your junior year internship, if it goes well, you get a job offer. So you don’t have to re recruit your senior year. You just have a job lined up after graduation. So I had that. So I got into my senior year, had my job lined up, so I had all this free time, and I started helping kids prep for job interviews who are doing re recruiting. And I would always ask them the question, how do you keep up with the business world? Like, what do you read? And I would get the same answer over and over and over, which was, I read the Wall Street Journal. And I’d be like, okay, tell me more. Like, why do you read the Journal? And people would be like, my parents told me I have to read it, but it’s dense, it’s dry, I don’t get through the whole thing. And at some point I was like, this is crazy. Like, every kid is about to spend their career, like their working life in a job, and they don’t have content that they enjoy reading that gets them excited about the work they’re doing. Like, why is that? And so I started writing a daily newsletter that at the time was called Market Corner. Mind you, I was not a writer at all. Like, I was. English was one of my worst subjects for my entire life.
Kate Mackz: That’s what I wanted to ask you. Because when you think about business school and people that work in finance, you don’t immediately think about somebody that also has that creative background or that writing capability. And I don’t want to single out all finance people because of course they do. Some people do.
Alex Lieberman: But I think there’s a reason that, like, you know, these kind of truisms have truth to them is, yeah, I would say, like, you think about someone who works in finance, you consider them to be more quantitative and analytical in nature and less creative. And so I started writing this thing. And basically what I would do is I would spend four hours a day reading all the news on the Internet having to do with business. I would consolidate it into a word doc template that would be like, biggest business stories of the day that I wrote in these, like 150 to 250 word blurbs. And then there would be kind of like informational candy at the end, which would be like, trivia question of the day, business game of the the day, today in history. And I would get take that doc. I would export it as a PDF, I would attach it to an email, and I sent it to a listserv. It was the market corner at Umich Edu. And literally it just started with 50 people. It was the kids I was helping prep for job interviews. It was kids in my fraternity, and that was it. And just every day that I sent it out, I would get emails back from readers saying, hey, so and so wants to get added to your listserv. Can you add them? So I then manually add people to the listserv. And so then after a month or two of doing it, there are a couple hundred people reading this. And I was like, okay, there’s enough momentum here that I want to take it a little bit more seriously. So I sent an email to my list during winter break of senior year being like, hey, I want to take this more seriously. Does anyone want to help me with this? My co founder, Austin. He was one of my readers at the time. He was a sophomore at Michigan in. We were in the same fraternity, didn’t really know each other. And I had this email saved to my desktop where he emailed me being like, hey, I have ideas for how to make this better. Do you want to meet after bpl? BPL was Beer Pong League. We met after Beer pong League, and we just completely hit it off. And I would say, like, other than the choice to marry my wife, the choice of picking Austin as my co founder for Morning Brew was the best choice I’ve ever made. Because in so many ways, we’re like, we’re quite similar people. Like, we have dry sense of humor. We’re both like these, I don’t know, like, five, ten Jewish guys from the east coast grew up in, like, traditional Jewish families, but in. In every other way, we’re actually so different in terms of the way our brains work. Like, I am a creative, divergent thinker who is kind of like a bucking bronco that needs to, like, be, like, kept in their, like, in their zone. Otherwise, it’s a mess. Austin is the most focused, linear thinker I’ve ever met. And what I’ve realized as, like, I’ve built more businesses is, like, it wasn’t just at the time that I thought he was an unbelievable, like, operator and linear thinker. He’s a better business operator and like, thinker than almost every entrepreneur that I’ve ever met. Wow. People like twice my age. And so, yeah, it’s crazy. Like, everyone talks about like, the co founder decision is the most important decision you make in business. And because I wasn’t thinking of Morning Brew or Market Corner at the time, as a business, it was just like this side project I didn’t put in necessarily all of, like the time to figure out if Austin was the right co founder. We had a great two hour conversation. I was like, this guy’s brain compliments mine. Let’s do this. And so in a lot of ways, it was good intuition, but also so lucky that this guy was such a good co founder for me, despite not spending months together trying to figure out if we were the right pair.
Kate Mackz: And I also feel like when it comes to bringing somebody onto a business, especially in those early years or have them help you with an idea, it helps having somebody that is a fan of what you’re currently doing, which he clearly was. I’m so curious, like, and even this is just like going back to the very beginning when you had the idea of, wow, I’m reading the Wall Street Journal. It’s pretty hard to digest. These are some complex topics that we’re reading about here. When did you decide to not only make those topics more digestible for yourself, but then also share them with other people? Or were you always the type of person that was like, I don’t do anything just for myself. I want to help other people too?
Alex Lieberman: No, I would say there was like, there were, there was probably a, what we call, like a selfish, driven thing and a selfless. Like, the selfless was like, students told me they did not like business news as it was, and I was like, how can I make it better for them? The selfish part was like, I knew I was going to work full time on Wall street. And I was like, if I don’t stay up to date with what’s happening in the world, like, I may not be prepared for my job after school. So that was one of the other reasons I started this newsletter, was I was like, by creating this newsletter, it’s going to force me to stay on top of what’s happening in business so that when I graduate, I’m actually like, ready to go in my job.
Kate Mackz: It’s so smart in so many ways because I’ve interviewed a few different people that have said, like, I’ve interviewed this one news anchor Dana Perino, who was the press secretary for Bush and She said growing up, her dad always said to her, the one thing that you have to do every day is you have to read the news headlines, just know what’s going on in the news. And you know, I think when it comes to business too, like my dad always said to me growing up, like, you know, you should be familiar with what’s going on in the Wall Street Journal even if you just read the headlines, you know, so it really is this, you know, thing that I’m sure so many parents tell their kids growing up. And then you were able to like really take those articles and make them digestible and conversational and add humor to them.
Alex Lieberman: And, and look, I would say, and every entrepreneur says this after the fact, but I would say that like there is inherently so much luck that happens in entrepreneurship. But if you, if, if you were to ask me, like, what, what is the non luck, like what are the things that caused us to actually be successful? I would say in the early days of the business, like deep curiosity and defaulting to action are the things that like created surface area for luck to happen. Like there’s this concept of creating luck surface area. Like the more seeds you plant, the, the greater the chance that one of the, like one of the plants is going to bud. And so basically, like, I think that like curiosity and defaulting to action is such a valuable thing that anyone can do. And this is like a totally separate thing, but I think it just makes it actionable for people who don’t even necessarily have a business. Today is something that recently happened with one of my businesses is we brought on an intern. And one of the reasons I brought on this intern is they did something that has, is now called like permissionless apprenticeship. Where one way that most people apply for internships is they just like drop their resume or they find like a family member who has a connection and they have them send it in to me. Permissionless apprenticeship. What it is is someone takes an interest in your company. They figure out what is work they can do that’s valuable for your company without being asked. They do the work and then they send it to you. And so this guy Justin, who’s literally interning for one of my businesses now shout out Justin. He’s a sophomore at UCLA in Beijing for study abroad right now he got interested in one of my businesses. He ended up doing a full project like about basically how he could help my business and ideas he had for it. He posted on Twitter, it went viral on Twitter. That’s how I found out about him. And I’M just like, clearly he’s deeply curious. Clearly he defaults to action. And I will pick that 10 times out of 10 versus someone who just like went to an amazing school and has an amazing resume.
Kate Mackz: Absolutely. I mean, I’ve never read somebody’s resume in my life. When it comes to working for us. I agree. Like, I think, and obviously this is a much smaller scale, but yeah, when I’m hiring somebody or looking for people to work on our team, it’s always take initiative, try to see what it is that you want to do for us that can like, make our lives better, make the work that we’re doing quality better. And anyways, it’s always work driven.
Alex Lieberman: There’s this concept of like, slope versus intercept. And what it basically means is like, there’s two ways that people can choose to hire people in businesses. One way is you hire for experience. The other way is you hire for potential. So slope means you hire someone who maybe is at a lower point in the curve in terms of their value today, but you think they’re going to have incredible slope because of their curiosity, their hard work. And their default to action Intercept refers to someone who’s higher up on the curve. Like, meaning they already, they have more value today, but you don’t necessarily think like, you think their ceiling is more limited because yes, they have experience, but they don’t necessarily have the grit, the curiosity and the proactivity to get a lot further. And my general view in life is almost in every role you’ll ever hire for hiring for slope versus the intercept is the right way to go.
Kate Mackz: If you guys are enjoying this episode, please do us a quick favor and hit that like button and subscribe to our channel. It helps more people discover these conversations and it helps us continue bringing on amazing guests. You know, And I also think what’s so interesting about you guys with Morning Brew is I like that you said you didn’t set out to start a company.
Alex Lieberman: Yep.
Kate Mackz: You really set out with this, this problem to solve and with an inherent curiosity and to make your life better. When you graduated and started working in the business world and through having that curiosity and that work ethic and this drive to do this passion project, you started a company.
Alex Lieberman: Yeah, I just think it, it is a weird thing now because, like, now as I start businesses, it’s like weird that for the first time I’m like having to think of a business idea and create a, like, not create a business plan, but like, it just, it felt so authentic at the time where it’s like with Morning Brew, it was not thought of as a business. It was just like a curious hobby. And I actually think the more that a business or something can start as a curious hobby, the better. So I totally agree with that. And to me, one of the best ways to actually make that happen is people are like, I. I think people wonder, like, how can they be more curious in life? And either you’re like, default very curious or you’re not. But I actually think curiosity is a muscle. And. And I think, like anything else, if you have the right exercises to work that muscle, you can build it over time. And so, like, there are actual exercises I do to work the muscle of curiosity. And so I’ll just use a random example. Like, one example is I will walk, like, what. While I’m, like, walking the streets of Hoboken, I will play this game called, like, the why game. And the why game will literally be where, as I’m looking around me, I will ask the question, why? About things that I’m observing, like, why is it that these cameras need to be on stands? Why couldn’t they be hanging from strings? Like, why is it that you need a sandbag to be on top of the light here? Like, why is it that these cups, like, why is it that the design has these ridges in it? Is there a re. There must be a reason that there’s a ridge design. Is it aesthetic or is it functional? And so basically, what that exercise does is it takes your brain off autopilot. Because, like, in life, like, we wouldn’t be able to survive if we ask questions about everything. It would overload our brains. So 99 of the time in life, we’re just going to go about life and not question everything we do. Like, imagine if you were running. As you’re running, you’re going through the. The questioning of, how is my leg working right now to lift my foot and then lift my leg? Like, you wouldn’t do it. But to me, if you do these exercises where you take your brain off autopilot, it actually builds up the muscle of curiosity.
Kate Mackz: I mean, I love thinking about it like that, too. And I think that’s so important, especially in my career as an interviewer. It is so important to keep your curios up and keep wondering about different things and people doing different things, how things work. What are some other exercises that you do when it comes to curiosity?
Alex Lieberman: So another one like, this is as I’m, like, I’m thinking about, specifically for business ideas, like, where do I get business ideas from? And I would say basically anything that I go through in life where I feel emotionally provoked, I ask myself, why am I emotionally provoked? So if I ever like, if, say our average emotional range as People is like 5 to negative 5, when I get from 0 to negative 5, I ask myself, why am I feeling this right now and what is it about this experience that could be changed that would get me closer to zero to five? So like, that’s one thing that I do. Another thing that I do is I will. And this like sounds obvious but like I just talk to people and customers a lot. So like I will literally for, for my businesses, I’ll get on a call with a customer or a user and I will have them screen share and I will have them literally take me through what are like the most mundane and annoying processes they do every day in life or at work and I will have them literally show me on their screen as like a show and tell. And I learned so much through that process as well. So yeah, like, I don’t know, I try to root everything in questioning and as and getting as close to questioning my experiences or experiences of people that I want to build things for.
Kate Mackz: Even hearing about how you co work sometimes when you’re alone with that.
Alex Lieberman: Yeah. With focus, mate. The craziest thing in the world. Yeah, I just, it’s funny, I’m. I’m listening to the audiobook of Ben Franklin right now. Really interesting cat and he, he’s like, it’s like kind of amazing that he’s like, you know, this guy was like, he had a media company, he invented the lightning rod. He was huge in politics. And I think one of the reasons is, is because he basically was like this polymath who knew a lot about a lot of things. And I think the main reason is because he was just an absolute sponge for like learning different things from different parts of the world. And so that like, there’s just no excuse not to be curious if you want to be today because like you have so many things at your fingertips. Especially with ChatGPT now, like ChatGPT, to me, the reason it has been the biggest game changer for me is, is it. It is just literally my personal tutor. And so like, just to give you one example, one of my businesses now, which, like, again, it was the one I was describing before where we help businesses with AI transformation. Most of the employees in this business are engineers. I am not technical at all. I never took a comp sci class, but I’ve always been curious about software and engineering because as Someone who like, I identify more as like an inventor than an entrepreneur because I love building shit from scratch. And, and so I’ve always been interested, like, how do engineer, like how do engineers think? How do they build things? Now all I will do is I use an amazing tool called granola. I don’t know if you’ve heard of granola. It’s like there’s hundreds of these meeting note takers. I just think granola is the best one. It will take notes on my call. So I will have granola set up. When we do one on ones with our engineers, it will take notes of our whole calls. And then I’ll feed granola automatically into ChatGPT and have ChatGPT create micro courses for me on any topics or jargon related to engineering that I likely wouldn’t know which is most things. It’ll turn it into a course for me. So the amount I’ve learned about software engineering in the last three weeks, even though I’ve never taken a class in it, just by literally turning meetings into transcripts, transcripts into prompts, and chatgpt that create little courses for me, it’s just unbelievable the speed at which you can learn today.
Kate Mackz: I mean, that’s so smart.
Alex Lieberman: Yeah.
Kate Mackz: And for anybody listening, where that can be relevant for them and what they do, I mean, do exactly what I.
Alex Lieberman: Apply that to anything.
Kate Mackz: Exactly. I love knowing how people use ChatGPT and I feel like the most important thing when it comes to any AI tool like it is knowing how to prompt it correctly to give you the answers that you need.
Alex Lieberman: That’s everything.
Kate Mackz: Sometimes ChatGPT can be a little bit too of a yes man for me. I need to retrain my model.
Alex Lieberman: Another. Another fun one is I was actually asking it this today is ask ChatGPT what are under the radar or like not unpopular or unconventional use cases for ChatGPT that few people are talking about. And it just unlocks all these things you probably haven’t done with that are amazing.
Kate Mackz: What were some of them like?
Alex Lieberman: An. An obvious one is like now what I do is take a picture of my fridge, take a picture of my pantry and have it tell me every recipe that I can create given the food I have in my home. And then tell me what I need to order to complete certain recipes.
Kate Mackz: Alex, that is so smart.
Alex Lieberman: Yeah. And so that’s the thing is actually I think the, the limit of CHAT GPT and these tools now is actually our own creativity, not the technology that we’re using.
Kate Mackz: Well, I saw the other day a video that this girl did where she said she put every single article of clothing in her closet into Chachi pt. And now every morning Chachi PT makes her a new outfit with the clothes that she already has.
Alex Lieberman: Funny because I literally started doing this and it was taking me too long because I literally was like pulling all the out of my closet taking pictures of it.
Kate Mackz: I have too much.
Alex Lieberman: Yeah, it was taking too long. But yeah, like for me there’s. I basically have four go to outfits that I know are complete outfits. Other than that I have no idea what I’m doing in the closet. And so I’m just like it’d be amazing. And. And it’s also a great business if you think about it where it might it will. I take pictures of everything Chachi Beat GPT tells me what are all the outfits I can complete and then if there are outfits that I could complete by buying an article of clothing, it makes those recommendations and I could buy it straight from the app. And now you actually can do that because Shopify and ChatGPT have an integration for where you can buy stuff straight from the actual application.
Kate Mackz: Okay. I did something really niche with ChatGPT that’s kind of funny in relation to clothes where I’m getting married in September and I wanted to buy a second dress to change into and I had four different options that I was choosing between. I uploaded every single outfit that I’m wearing for my wedding weekend. The first day, what I’m getting ready in my actual wedding dress. And then I uploaded these four options that I had and I said based on the current outfits that I’m already wearing, which one matches the vibe the most. And it gave me a detailed response as to why and picked out my shoes.
Alex Lieberman: It’s. It’s so good. I mean it is to me the barrier for using chatbots now is our own creativity and our own ability to prompt it. Well, one other just like crazy use case I’ll share is there’s a guy who is like a renowned commercial director. Like he used to produce multimillion dollar commercials for health care companies and he started. He’s blown up on Twitter now because what he does is he creates unbelievable like world class quality commercials using just ChatGPT, Google’s new model which is is it vero vo vo vo 3 and that’s it. And then premiere to stitch everything together. You have to check his stuff out. He basically creates like and. And the caption of his tweets are now like I used to create five hundred thousand dollar budget commercials for Pharmaceutical companies. This one I Created with for $500. The world is changing fast. And you watch and you’re like, oh, yeah, like this 1,000% would have cost $1 million to produce before. And it was unbelievable.
Kate Mackz: Can you imagine if chat existed when you were just starting the morning brew?
Alex Lieberman: Yeah, I mean, it’s.
Kate Mackz: It would have saved you so much time.
Alex Lieberman: It’s crazy to think about. Yeah. It also, I will say this is a very niche thing, but it makes me think about now. Is there a world where every person can have their own custom newsletter in their life? Like, if no newsletter is the same for each person, like, there’s this concept of the presidential brief, which is every day the president gets effectively their newsletter, which is everything that they need to know for the day. What if every human had their presidential brief?
Kate Mackz: Do you think there is a world where that starts happening?
Alex Lieberman: Well, I think there’s also even a question, like, if you had your own personal newsletter and you could handpick anything to be in it, what would be in it? And I think that’s an even an interesting question. Like, if I got it every day, would it basically be like, what’s on deck for the day? Like, what’s happening at work? Like, you know what. What’s happening at home? Like, what’s a meal that I can cook later, whatever. So, yeah, I do think that more than ever before, with the right data, people can just have more custom experiences than ever before.
Kate Mackz: Talk about crafting your own reality.
Alex Lieberman: Yep, exactly.
Kate Mackz: Going back to the OG days of Morning Brew, I’m curious, when you brought on Austin, how did you guys initially split up responsibilities? Like, what was he working and what were you working on?
Alex Lieberman: Yeah. So kind of a crazy story is we originally actually had four co founders for Morning Brew, so there were two other guys at Michigan who, like, I think also had emailed me, like Austin did. They became part of the project. And what we very quickly realized. Well, there’s two things we realized is, like, there’s too much of the similar skill sets have for kind of redundant people. But also, you can’t fake passion about entrepreneurship because it is such a slog and the odds of success are so low. So it’s like you either are going to be passionate about the work you do, and if you aren’t, you’ll just, like, quickly realize it. And so that’s what happened. These two other guys that were involved in the business, they just weren’t as passionate, and so they kind of just like, peeled off in a pretty natural way. But for Austin and I, I would say like, I was focused on more of like the creative functions more like, I would say like kind of front of house. So I was focused on content, on marketing and on sales. And then Austin was really focused on like tech growth and like the finances of the business. And that’s kind of how we divided up our work for the the first four years. Like basically the way and, and the way it changed over time was how much of the work we were doing versus how much of the work we were managing versus how many people we were managing that were managing the work. So like just even use the example of content, it’s like it started with me writing the content. At some point I was like, okay, I’m getting better at this content thing, but we can find better people. So then when we ended up hiring a full time writer, I ended up managing the writer and I basically acted as the editor where I was editing everything the writer wrote. We ended up hiring another writer. They were writing and then they were self editing each other. So now I was just kind of like managing what was our content strategy broadly. Then at a certain point it was like, okay, what are we doing beyond just Morning Brew, the newsletter? And so my thinking became like, how do we grow into a true multiplatform media company and just, and not just a daily newsletter. And so I think as time went on, what I was thinking about didn’t actually change in terms of the disciplines. It was just I was getting further and further from like the nitty gritty of the product and more focused on just like what is like the business as a whole. Look like I will say though, it’s why after a period of time in the business, my energy towards the business changed because like the first four years of Morning brewing, it felt like a ragtag crew of people trying to like prove that you can build a media company when everyone was saying we couldn’t. And I was like super close to the product. At a certain time a point in building a company, your job goes from like your number one job is like get to product, market fit and make sure your product is excellent. To you’re a company builder and your job is like build like a six month, one year, three year plan, build an executive team, be a people manager. And I think when things got to that, I just realized I enjoyed it less. And I think that was actually just a really interesting learning for me because when I got into entrepreneurship, I had this certain image of what it meant to be a successful entrepreneur. My Mount Rushmore of Entrepreneurs was like, the classic cast of characters, like Jeff Bezos, Mark Zuckerberg, Elon Musk, because they, like, had this epiphany. They built stuff, and then, like, they kept building their company until they had thousands of employees went public. And so that was my definition of success. And so I think it kind of messed with me at some point where I was like, is this. Like, is this bad that I’m basically not enjoying the job anymore? Once I actually came to terms with the idea that, like, there are certain parts of entrepreneurship I love and there are certain parts I don’t love, I think it took a lot of pressure off of, like, what it. What the journey had to look like for me.
Kate Mackz: Because you sold it after seven years, right?
Alex Lieberman: Yeah.
Kate Mackz: Well, I feel like that’s also because you get. Get into the motions of doing the same thing over and over and over again. And I think the beautiful thing about the morning brew was it was this really consistent thing.
Alex Lieberman: Exactly.
Kate Mackz: That was in people’s inboxes every single morning. But that can get mundane for you, even though the stories are changing every day.
Alex Lieberman: So what ended up happening, though, is, like, we sold the business in 2020, and I think even though I technically stepped out of the CEO role in April of 2021, so we sold the business in October of 2020. Mid pandemic, I stepped out of the CEO role in April Of 2021. I would say that, like, probably middle of 2019 is where, in an unspoken way, Austin and my roles were shifting, where he was really moving from CEO of the business to CEO of the business. And I would say, like, my role was kind of starting to look like Chief Innovation Officer, where, like, I was just excited about, like, the new things we were building. So when we were launching a podcast or we’re launching our new, like, vertical newsletters, like, I wanted to be deeply involved in those projects. And so I think that’s, like, I just started my time, started gravitating towards the things that I naturally loved. But what that also meant at some point was, like, I actually wasn’t the best person to be the CEO of the business.
Kate Mackz: I think the beauty about building a business, from what I’m hearing from you, is when you build a successful business, you also get to learn things about yourself that you can’t learn just doing, you know, a regular job where you’re doing the same task over and over again because you learned that it wasn’t doing, you know, writing the newspaper that fueled you up. It was literally growing this business. And you’re a serial entrepreneur because of.
Alex Lieberman: That 100% and yeah. And I think the more you can like just kind of almost like trick yourself into not focusing on a specific path, the better. Because if you think about it like entrepreneurship by definition people, the reason we people become entrepreneurs is so that they don’t necessarily have a defined path. Like they’re crafting their path. And so it actually sounds quite ironic when it’s like you, if you focus on like a certain path, it’s like that’s the exact opposite reason of why people become entrepreneurs. So I think when I started being okay with a different definition of what success and entrepreneurship looks like and even as like my Mount Rushmore of entrepreneurs has changed a ton over time, I think the journey felt a lot more like play. And I’ve just realized like the more that I feel like three year old Alex, the happier that I am as I’m building my companies.
Kate Mackz: Yeah we talked about this during the run. But you have to gravitate towards what gives you energy. What do you think was harder? Building a successful company or letting it go?
Alex Lieberman: I would say let letting it go for sure because even though building the brew was hard at no point in the journey like did like I’m sure it felt hard at points but like it never felt like excruciating. Like there was just like a love for the journey of building throughout letting it go. Which really in my mind meant letting go of a big portion of my identity that was, I think that’s one of the hardest things I’ve had to ever do. Basically from April of 2021 for about a year I just was incredibly lost. I was incredibly lost. I didn’t know like what I wanted to do after the brew. I worried that I was only successful because I out of luck versus skill. I like convinced myself that my success was a function of having a great co founder who kind of dragged me along the whole way I was worried that I had peaked in life and how sad of a thing it would be if I was like 28 years old and like what life do I have ahead of me if I’ve peaked already. Right. I have so many reasons for why this story is not truth. It also like I, I kind of have compassion for myself and my kind of the way I thought then that like it makes so much sense why you get into these kind of like self conscious, self doubting stories after you leave something that’s such a big part of your identity. My best analogy for it is like when someone plays a sport for their whole life and if someone’s a pro athlete and then they end up retiring and you know, for the longest time as a pro athlete like they felt at the top of their sport, they were externally validated for being great at what they did. And a pro athlete, depending on the sport you’re in, retires at say like their mid-30s. Like you still have your whole life ahead of you but it’s not going to be with the sport. I think the, the kind of almost like the mind of like refinding purpose on identity is a very similar thing.
Kate Mackz: The purpose thing is really interesting and I think you learned it so young and I had a similar experience when I got injured and I liked that you brought up athletes but when I was a sophomore in college I tore my ACL again for the second time and I had to step away from sports. And I was 15 years old and for those 15 years of my life, except for when I was like a baby and toddler, I was an athlete and that was my identity and I wanted to go to college for it just like my brothers did and all of that totally. And that felt like my purpose so much. And then when that ended it was like I had to figure out okay, what is my purpose without that sport. And I think the beautiful thing about life is understanding and knowing that there’s going to be different stages of your life and you’re going to find purpose in different ways. And it’s kind of an experience you were going through.
Alex Lieberman: And you know there’s an interesting, I forgot who posted it the other day but there was like this interesting study done around how one of the bit the biggest drivers of positive mental health is working towards something like we as people. I really think like it’s like in our reptile brains we, we are built to work towards things and that could be professional, personal or whatever. We’re not reptiles. But I, I don’t know our monkey brain or reptile brain.
Kate Mackz: Our reptile, the reptilians are going to.
Alex Lieberman: Be like news flash, you’re cold blooded. But I in our reptile brains, so in, deep in our reptile brains I like, I do think we, we have a need to work towards things. And so I think one of the hardest parts about stepping out of the brew is like I did not know, I did, I wasn’t working towards anything anymore. I didn’t know what I wanted to work towards. And so I like, I think when you feel like you are not moving forward it is especially for a certain type of mentality, a certain Type of brain like it is now. I’m saying reptile brain. In my mind, it is a really difficult thing.
Kate Mackz: We talked a little bit about life after work and, you know, stepping away from morning brew. I find it really interesting that you are in this network of founders. How did you find, you know, becoming friends with other founders that were in similar positions helped you?
Alex Lieberman: Yeah. So I would say actually probably the most valuable community that I’m in is. It’s literally called post Exit Founders, and it’s a group of 3,000 founders that sold their businesses that was started by my buddy Barack a few years ago. And I would say, like, the telltale sign of any really quality community is two things that the founders of the community don’t have to be engaged in discussion for a week, but discussion goes off without a hitch. Like, the community is the driving force of engagement that happens. And the second is that a very high percentage of all conversations that happen in the community feel relevant to you. And that was the thing with Post Exit founders is, like, 80% of all topics that are discussed in this community feel relevant to me. And so it’s like, there just were so many things after selling a business that I had never thought about before that I can’t talk to most people about, but that this community talks about. So it’s everything like finding purpose after selling your business. And also, it feels like a really douchey thing to talk about with other people. Like, you sold your company, you make money. Like, it feels like, oh, you’re gonna complain about the most first world problem of, like, not having purpose.
Kate Mackz: So it’s like, I don’t think it’s douchey at all. I think any experience that you go through in life, you deserve to have people around you that have experienced that too. And was there any perspective that somebody gave you that really shifted something in your mind that you were like, oh, that’s a good way to think about it.
Alex Lieberman: I think after you sell it, this is a very niche thing, but after you sell a company, like everyone says, like, get a great tax person. You have to, like, make sure you optimize every part of your taxes. And. And I’ve seen, like, founders go to the most extreme lengths to optimize their taxes, like moving to Dubai where there’s zero taxes. And I just think, like, some perspective that a founder gave me at some point is like, look, at the end of the day, sure, you can optimize your taxes, but, like, your money is supposed to work for you to, like, live your, like, happiest and most fulfilling life. And if like you optimizing your taxes takes you away halfway around the world to a place where you’re not around your people, then what was the point of it in the first place?
Kate Mackz: Completely.
Alex Lieberman: So I would say I’m like very tax aware, but like not trying to optimize to the last dollar because to me like the marginal benefit of that in my happiness is actually it, it creates less happiness. And then I would say the second thing that I haven’t done yet, but I’ve thought a lot about is a lot of founders have, in this group have taken sabbaticals where they very explicitly, for a period of time, don’t work on companies where they just take time off. There’s no end goal in mind. They, they live in California, they go surfing every day, they take their kids to school, they sit at coffee shops, they listen to podcasts, and every founder I’ve talked to got something of value out of their sabbaticals. I can’t bring myself to do it yet because at least the story in my head is I’d go crazy. Like I’m too restless. But it is an interesting thing that I’ve thought about. Like at some point I think I’m going to try it out. Like I’m actually close with the, the founder of Butcherbox and he’s like taking a three month sabbatical while he’s the CEO of the business right now. So he like literally handed over the business to his execs, taking a three month, doing I think like a silent meditation retreat. And so I do think there is something really valuable in boredom. Like I think we, I’m really bad at boredom. A lot of people are. But I think in boredom and in kind of like getting rid of the chatter that’s in your head, it creates space for like really interesting thoughts you’ll never have while you’re in kind of like the constant motion of needing to do things in life.
Kate Mackz: Right. I mean, yeah, there’s Beauty in silence 100 and you need to have those outlets to turn your brain off.
Alex Lieberman: Yeah, I think in a lot of ways we distract ourselves from like the harder, deeper, more provoking thoughts in life. And so I think a sabbatical or anything that resembles that removes the distraction of, of reconciling these harder conversations in your head.
Kate Mackz: Speaking of silence, let’s talk about working in silence with strangers on the Internet.
Alex Lieberman: Great transition. So Focus Mate is probably my favorite productivity hack. It’s basically a website where you get paired with some stranger around the world to co work with them. And so like literally what I do is I go to Focus Mate. I start a session, it can be 30 minutes, 50 minutes, or an hour or 90 minutes. We get on the camera and I will go on our mics and basically share what is our goal for our, our session, set our intention, then we mute ourselves and we work in silence for the entirety of the session. At the end of the session, we go back on Mike and we say how the session went and if we accomplished our goals. And sometimes I and people on Focus Me will actually share screen share so that the other person can see whether you’re actually doing the work you said you would do. And it just is all this. It follows this concept of body doubling, which is you’re more likely to be productive and do work if the person across from you that you see is also doing work and is being productive. A lot of people call me crazy for it, but I love doing it. Whether it’s for staying productive and focused or just if you work from home and you love the feeling of working in an office, but you don’t have that feeling anymore. So for anyone as crazy as me, I highly recommend Focus Mate. And it’s like 20 something bucks a month. I’m not affiliated at all, but I love it.
Kate Mackz: I think it’s great. I feel like you know so many niche businesses.
Alex Lieberman: I do. Speaking of niche businesses, this morning I’m walking in Hoboken and I see one of our friends in Hoboken and this is a true story. So this dog, Simba, great name for a dog. So yeah, Simba’s a great dog. And he was recently attacked by a dog at a dog park. And it’s so sad. Like there are pictures of him with stitches in his head, all these things. Simba is great though. He’s a resilient little guy. And we were talking to the owner of Simba and. And the person was like, wait, we didn’t tell you about this, this thing we recently did. And we’re like, no. They’re like, we brought Simba to a psychic. And so Simba went and saw a psychic to see if there was any unresolved trauma from his attack that he needed to work through as he came out on the other side of this attack. And I just thought to myself, one, that is absurd. Two, but put it, put aside the absurdity. It is unbelievable how many niches and ways there are to make money on the Internet. And if someone can convince people that they will do tarot readings and Psychic work on dogs. There really are endless ways that you can make a living.
Kate Mackz: I mean that is wild. I, I love that though.
Alex Lieberman: Yeah.
Kate Mackz: Little Simba.
Alex Lieberman: People will do anything for their pets.
Kate Mackz: Yeah, they really will. Yeah, they really, really. Well, I would do anything for little Jean Pierre.
Alex Lieberman: Exactly.
Kate Mackz: What’s your dog’s name?
Alex Lieberman: Rambo.
Kate Mackz: Oh, that’s a good dog name.
Alex Lieberman: Yeah.
Kate Mackz: So how long did it take for you post leaving the Morning Brew? How much time did you take between starting something new?
Alex Lieberman: About a year.
Kate Mackz: Okay. What did you do during that year besides like having all these thoughts and stuff, which is very normal.
Alex Lieberman: So one, I started a plunger game.
Kate Mackz: Okay. What is that?
Alex Lieberman: So, and this is crazy, honestly, I’m so glad that I started it, but basically we were talking about creator led businesses before. There was a period of time where I wanted to build like a holding company of creator co founded businesses where I would, I would basically help big YouTubers launch a business. I’d be their co founder and we’d use obviously their, their channel as distribution to drive sales for the, the business. And so what ended up happening was I was watching a Dude Perfect video.
Kate Mackz: Love dude perfect.
Alex Lieberman: And their second or third most watched video ever is plunger trick shots. That is, that’s like one of the most watched videos ever. And basically it’s them in their old space taking toilet plungers and throwing them at plexiglass and getting them to stick. And so I saw this video and I was like holy. Like that looks like ax throwing. Is this like a safe way way to build axe throwing like an a back to a backyard ax throwing game. So I literally saw this video. I immediately, because I had way too much free time, I immediately drove to Home Depot and I went to the plunger aisle and I started throwing plungers in Home Depot. And that took me on a.
Kate Mackz: This is what, this is what 28 year old people that have sold their companies do for everybody listening.
Alex Lieberman: And, and so I literally. So I literally spent the next four months manufacturing a backyard game with a manufacturer in China. And I built the plunge like it was ready to go. We had a Kickstarter campaign set up. I still have a set in my garage.
Kate Mackz: I love this.
Alex Lieberman: And I ended up. The long story short is I ended up hanging up the plunger. But it was incredibly fun to do something that honestly was never really going to be a viable business to build something with like my bare hands. Like I think there’s just something really satisfying about building something physical. And, and I think part of the reason I needed to do it is. I had this fear. After selling the brew and thinking about what was next, I had this fear that I was going to be kind of like the cliche serial entrepreneur that just keeps building businesses forever trying to chase the high of making more money or building a bigger business. They get to be 75 years old, they have a shit ton of money, but they’re unhappy and unfulfilled in life. Like, that was my biggest fear because I did not want that to happen. And so I think, like, the plunge was like, me basically moving the exact opposite direction, building something that felt so silly and so absurd that of course it wasn’t gonna be a big business, which meant the only reason I was doing it was out of pure, like, love for the game and love for building. So that’s part of what I did.
Kate Mackz: Which is so cool. You’re exploring another side of you. You know, what I think is so interesting is so many things, but I feel like you grew up in this household that was pushing finance, and you probably always thought that, like, finance was gonna be the thing that you went into and you were gonna be like, you know, you are super analytical, but you were gonna be. And you working in finance, working on Wall street, doing, like, the daily grind of that, and then building this successful company, you found out how creative you are.
Alex Lieberman: And I. I do think it’s like. I also think based on the job you do, it like, pulls. It either pulls creativity out of you, or it, like, puts it into hibernation for a period of time. So basically, I was working. I did the plunge for four or five months, then I ended up getting married. And then I got to some level of clarity of, like, what I wanted to do. Like, basically, I got to kind of my. My North Star, that had, like, two key pillars that I knew I wanted to, like, build towards for the next many years. One pillar was, I realized in kind of examining my whole journey with Morning Brew and what I loved about it that I loved, like, the negative one to one. So going from not having an idea to what that idea is, creating that idea, putting it into the world, seeing success with it, and turning it into a business. Like the negative one to one of business is where I get the most joy. And the way I came to that conclusion was there is this really cool exercise called the Best Stuff Exercise. It’s by the Conscious Leadership group, which, if you’re an entrepreneur, honestly, just like a person who wants to think more deeply about yourself. Like, the probably the best book I’ve read in kind of Growth Leadership business is 15 commitments of conscious Leadership. It’s by the Conscious Leadership group. But anyway, there’s an exercise in the book called the Best Stuff Exercise and it helps you understand what your zone of genius is. And the way it does it is it has you list out eight experiences from your life that you felt successful at, that you got a lot of energy from, and that you like time felt like it melted away while you were doing it. You list those eight experiences and then you find in those experiences common themes of like, what are similar types of things you were doing in all eight that maybe start to hone in on what is your zone of genius. And basically my zone of genius was like basically invention, storytelling and relationship building. Like, those are my three things. And by the way, this is a great way that I use Chachi PT also is I basically uploaded the exercise into ChatGPT and I said, prompt me to like, prompt me through the exercise. So I give my experiences, it asked me for the next one, and then at the end it outputs what it thinks my zone of genius is by feeding it these exercises. But anyway, going through this, going through this exercise, I came to the realization that I love the early stage of business. And I asked myself, how can I set up my life in a way that I focus most of my time on the early stages of companies? The second like thing that became really important to me was I wanted to prove to myself that I could be an A plus entrepreneur and also an A plus family person. And the reason that became really important is one, like, family has always been my number one value. But also I think there’s so many entrepreneurs that I look up to, like several of the entrepreneurs that I shared with you earlier that are unbelievable business people, but I am not necessarily trying to emulate them in life. And so my kind of my thing became there need to be more role models of super successful entrepreneurs who also are as successful with their families. And so that’s like my whole Mount Rushmore of entrepreneurs has completely changed from what I shared before to be people who more emulate that style of person that I’m describing who’s like killer family person and killer entrepreneur. So those became my two pillars. And so like, I started orienting my whole life of like, okay, in order to do this, I’m going to incubate businesses, I’m going to bring on a co founder and CEO as early as possible and I’m going to set the expectation with them that I’m going to be really involved in the business for probably the first 12 to 24 months, my goal is to use my distribution, my network, and my knowledge from Morning Brew to increase the odds of success and getting a product market fit by a ton of. And then my goal is once we have product market fit, once we have revenue coming in the door, and once we have a core team, I’m going to roll off to incubate my next business. And I set that expectation from day one. And basically I started building, like, building towards that. And this was probably 2024. And then because life hits you in the face, my wife was actually pregnant and we had to end a pregnancy. And I went from being like, finally getting to a place where I was really, like, professionally clear again, to having no professional clarity. Because when all that happened, I couldn’t care less about my work. And so there was probably like a six to eight month period of work could not have mattered less. We came out of that whole experience, which I’m, I’m happy to talk about. And I would say a few things became clear to me. One is like, it’s an obvious thing, but the person you choose to be your partner in life is the most important decision and it’s not even close to any other decision. It’s also like how hard moments really reveal people’s character. And it just re solidified for me, like my North Star of being really like having more professional ambition than ever before, but never doing it at the expense of being the family person I want to be is going to be core to me for the rest of my life.
Kate Mackz: Yeah, it’s so important. And for everybody listening, Alex is going to be a new dad in about a month, which is so exciting. So congratulations because that’s so hard going through a loss of a pregnancy, but it’s such a miracle now. This is like your miracle baby.
Alex Lieberman: 100%. Yeah. No, we’re so excited. And yeah, I always say we didn’t need this to happen for me to feel so rock solid with my wife. But moments like that just make you realize, like how having kind of like your ride or die, who is like your center of gravity in life is. It’s such a gift when you have it.
Kate Mackz: It’s the hard moments that make you realize how important it is to have that person in your life. Whether it’s a partner or a friend or mom, dad, brother, sister, whatever it is for you, it is so important to have that person.
Alex Lieberman: And one other interesting learning I had from it is like, like, again, we were talking about it on the run, but like, I’ve always viewed myself as like a very distracted person. But what is interesting is when we were going through everything and we were getting this, all this like scary information from doctors. It’s very interesting how quickly, because it was such a priority, I became incredibly focused and for 48 hours straight I did nothing but basically become world class in understanding genetic abnormalities in babies. And it just made me realize like, maybe one of the reasons that I get distracted with a lot of things is like maybe one, maybe that’s like a feature of me in my life and not a bug. And maybe it’s just the fact that like most things are not that important in life, but when the really important things happen, if you can get laser focused on those things and you absolutely grind towards them, that’s actually the true measure of your abilities. And so yeah, it just made, it gave me more grace in realizing that like, I don’t know, my distractibility, I think I wouldn’t be kind of creative and like this idea machine that I am without it. And it showed me that like when push comes to shove and the really important presents itself, I can get laser focused. And so it was just an interesting learning for myself.
Kate Mackz: When you say you became an expert in genetic abnormalities with birth, I mean I’m somebody that wants to have kids soon. So I, I’m just curious like what did you learn? And we if us asking what happened?
Alex Lieberman: Yeah, so Basically there’s like two major scans in a pregnancy. There’s the 12 week scan and then there’s the 20 week scan. The 20 week scan is the, the anatomy scan. So that’s where you like actually get the first 3D picture. And so at the 20 week scan basically there were abnormalities where you know, the, the, the doctor who looked at everything was like, I don’t know what this is, but you need to, to talk to someone effectively like a specialist. So I would say like probably like the most painful period for us was like the two weeks of not knowing what was going to happen. Because it’s not like you have any answers, you just have doubts, which is like there’s something wrong. We don’t know what it is. You need to get more answers. So for basically two weeks we didn’t know what was going to happen. With my wife’s pregnancy so awful. And so we went to like chop, which is a children’s hospital of Philadelphia. It’s like the, the best children’s hospital in the world. And it’s where basically every kind of crazy case is sent to. And basically the abnormality that was found in our baby. When we were talking to the doctor, they had only seen that combination of abnormalities once in their career. But you know, just as a specific example, like the abnormality that was found, which was basically just like a deformity in the chest of the baby, I ended up going down a rabbit hole of reading every piece of scientific research that had been done in history on this abnormality. So much so that like I was reciting studies better than the CHOP children’s doctor was because, well, which makes sense. Like they’re focusing on so many babies. I went down the rabbit hole. But I basically learned everything humanly possible about this abnormality as well as, like, because I was just trying to understand what are the odds that things are okay versus not okay. And the short answer is the unfortunate thing is as you get into things related to like health and science is there is so much unknown. And so we ended up having to make like the heartbreaking decision to end the pregnancy because the odds that things were going to be bad was very high.
Kate Mackz: Oh, and five months. And it is so heartbreaking because that’s at the point where you’re getting excited. Your bump is totally showing.
Alex Lieberman: Yeah, my, my wife’s body was changing. You know, we already had a name in our head. We had done. And this, the hardest part is like we had done a gender reveal. It was on Instagram.
Kate Mackz: I was going to ask, had you done?
Alex Lieberman: Yeah. And so like, you know, people still saying congratulations to my wife and, and then for me, like, I’ve always, I’ve always wanted to be a dad. And so like I already in my head was like taking on this like my, this role of like, I can’t wait to be a dad and like, like planning my head what it’s going to look like to be a great dad. And so yeah, it’s like it is very much. It’s, it’s a death quite literally, but also like the death of a dream for a period of time.
Kate Mackz: Absolutely. I mean pregnancies are so scary and anything can happen. It really, it really is so freaky. It’s like one of. I feel like it’s every couples like biggest fear.
Alex Lieberman: It is. And, and I think what I will say is, and this is talked about a lot but like there’s unfortunately so much stuff that goes wrong with pregnancies and they don’t get talked about a lot. And so it’s like after this all happened, we found out about more and more people who experienced things at the 20 week scan and, but like never knew about it before. And I’d say on one side it was like consoling because, you know, you’re not the only one going through it. But on the other side, it’s like for this pregnancy with my wife, we were absolutely like anxiety ridden until getting through the 20 week scan this time because we had no clarity on if things were going to be any better.
Kate Mackz: It’s so true. I feel like everything you see online with pregnancies is like, yeah, people excited about their pregnancy, one month, two month, three month, whatever. And you never hear about the things that go wrong. It’s like you just hear about the perfect pregnancies, but always are some issues.
Alex Lieberman: And it’s like, you know, this is why you understand when people are asked like, do you want, you know, do you want a boy or a girl? And people say, I just want a healthy baby.
Kate Mackz: Like, so true.
Alex Lieberman: This is why.
Kate Mackz: Yeah.
Alex Lieberman: Yeah.
Kate Mackz: I feel like it’s something that you don’t understand until you’re at that point.
Alex Lieberman: Exactly.
Kate Mackz: I think about that all the time. It’s literally in one month. So we’re getting you at the perfect.
Alex Lieberman: Time because it’s insane. Yeah.
Kate Mackz: Alex is about to go full dad mode.
Alex Lieberman: It is wild. And, and to be honest, like, that’s why.
Kate Mackz: Perfect timing too.
Alex Lieberman: Summer it is.
Kate Mackz: It’s gonna be so nice.
Alex Lieberman: Summer babies are the best. I’m a July birthday. My grandpa is, my mom is like. But yeah, I’m, I’m super excited. But that’s like why I’ve set up my life now with like, I have these four businesses, but I have co founders for all of them. They are the CEOs of these businesses and why I set the expectation up of like I, you are going to my co founders, you are going to be the operational leader of this business. Because I can’t predict what my life is going to look like after having a child and I can’t predict like how long I’m gonna wanna not focus on work for. And so I just knew I needed to set my life up in a way where I had the flexibility to make that choice because I just knew I would have the biggest regret if I was completely sunk into my work. And then I wasn’t able to be present to the moments that only. You only get once in life.
Kate Mackz: Even outside of that, you’re doing what makes you happy, which is being somebody that starts a business and helps it grow. And then once it’s at a certain point you can say, okay, go do your thing. 100, you know, so it’s like learning how to build a thing successful business and then let it go 100 and I think that’s so cool. One of the things that I think is so impressive about you is all while building these incredible brands and businesses, you’ve also been a content creator yourself. So I’m curious, was that something that you always did when you were working at the morning brew or did becoming a content creator kind of start afterwards because you are such a thought leader online?
Alex Lieberman: Yeah, I think it started on the, in the back half of the brew because honestly in the early days of the brew I just, I couldn’t find the time to create content. And so I think that’s just like an important thing to point out because I’m sure like a lot of early stage founders are like, I see like Alex or other people creating content. It feels like they have so much time to do this, I can’t find it time to create a single post. And I would just say like for the first three or four years of building the brew, I did not have a presence online and then I started building presence once I had any semblance of time. I mean, for me, the reason it became important for two reasons. One is because actually three reasons. One is it’s the best way for me to refine my ideas. Like I, I think there are people who are internal thinkers and external thinkers, so people who process their ideas by thinking to themselves. Other people who process ideas by talking things out. I am an external thinker and so it’s also why I love ChatGPT so much because I just have conversations with it now. But like posting on social became my external processing tool for refining ideas that I’ve been thinking about and I just knew I would get better at refining them by sharing them with the world. The second is, is like I just view the Internet is a magnet for attracting like minded people who are interested in what you have to say. And so like the network that I started having access to through posting on Twitter and posting on LinkedIn or posting on Instagram, it kind of became addictive because I was like, this is like a, a CEO or like an artist or someone I should have no access to, yet I somehow have access to. Like this is the coolest thing. And the third is, is like, I think as I thought about where the world is going and where business is going, having unfair distribution is such an important thing. Like I think as software becomes more commoditized, as I think like there’s more businesses than ever before, people have more choice than ever before. One of the biggest advantages you can have as a business is having trusted distribution with an audience. Because otherwise if you don’t have that, you’re gonna have to spend so much money on marketing as marketing channels become less. And so over time, the way I started viewing myself is like, okay, I’m a media company. How do I create content that attracts the right end customer? And then how do I launch businesses that sell really valuable products to that end customer? And so the way I view myself is like I have basically two end customers right now. It’s entrepreneurs like founders and CMOs or heads of marketing. And so every business like in my portfolio basically is built to solve a problem for either founders or for heads of marketing. And so then my whole content strategy is just in service of helping these people. And I just also generally have a rule where 80% of the time I’m adding value, 20% of the time is when I’m natively working in the things I’m doing with my businesses. And the best analogy I could use for that as other creators think about how much content should be about like, not about my businesses or about like things I’m being paid for versus not is I. My analogy is like, imagine you’re driving down the PCH in California and you’re looking at the ocean. The way I would describe it is like you, your content as a creator, your really good content is the ocean. Every time you promote one of your businesses, you’re putting a billboard on the highway and it blocks the view of the ocean. If you do it once every few miles, it’s totally fine. It’s still worth it for the driver to drive down the highway to see the beautiful view. But all of a sudden every 10 seconds you’re seeing a billboard and it’s impeding your view of the ocean. You may start to think like, am I going to still drive down the highway? To me, that’s ultimately how a creator should think about the balance of truly value add content with asking for nothing in return versus promoting the things that actually drive revenue or equity value for the businesses you have.
Kate Mackz: And I think one of the things too that I loved what you said is like, you know your audience so well and I think that’s one of the things that a lot of content creators, you know, have a hard time figuring out. I think that’s the hardest thing about being an early stage content creator is finding those people, especially with algorithms now sending your videos out to such like mass ranges of people. What would be your tips for creators now that are trying to find their audience.
Alex Lieberman: Yeah, I think there’s small things and big things you can do. The small things are like any creator, no matter what platform you’re on, you can have conversations with your audience. Like, like even say Instagram where like the analytics on your audience are relatively broad strokes. Like it gives you age buckets, it gives you gender buckets, it gives you geo buckets. You could very easily just like post a story saying you want to get to know your community and then you hop on 15 minute calls with 10 people and like you will learn a lot in those conversations, who your people are, why they consume your content and what they want more of from you. So like, to me that’s a very actionable thing. As and as simple as it it sounds, I would argue most creators don’t do that.
Kate Mackz: I love that idea. I mean it is so true because the people that respond to that inquiry query are the ones that want to get to know you. Exactly. Are the most passionate about you.
Alex Lieberman: Exactly. And at the end of the, you know, I forgot who wrote this essay. I think it’s Kevin Kelly. But it’s, it’s basically a thousand true fans, which is this idea of like, don’t worry about building an audience of a million people, worry about building an audience of a thousand die hards and then learn everything you can about those diehards. By posting a story that asks people to like opt into a conversation with you. You are just like getting that like the, the biggest die hard of die hards to opt in because it’s someone who saw story saw that they have to take time out of their day to talk with you. They opted into that like, like you’re talking to your not even 1,000 true fans. You’re talking to your like a hundred true fans. So that’s the first. The second is there’s certain platforms that just give you more information about the people that you’re creating for. So like in my mind, the two that can give you the most are either newsletter or LinkedIn. LinkedIn is one of my and, and I have a lot of thoughts on LinkedIn as a platform. But one of the beautiful things about LinkedIn is that I can see who views my profile every single day. So I know like I know the exact people who are viewing my profile. It also makes marketing my companies a lot easier because as an example, let’s just see, say I see a head of marketing from like a B2B software company viewed my profile and I know that my business story arb is A perfect offer for them. I can do an incredibly targeted and custom DM to them, knowing they already have some level of interest in what I’m involved in. The other one is newsletter. Like, the way we always learned about people at the Brew through newsletter is we just put out a survey once a quarter. We’d give away like 500 bucks that you, like, earn a chance to win if you complete the survey. And the survey would get to know people like, you know, age geo. Why do you read the Brew? What’s one idea you have for us to add? What’s your seniority professionally? What industry are you in? And it’s like, you also don’t need infinite information. Like, you can learn a lot about your audience through 10 conversations or from 100 people filling out a survey. So I actually think this stuff, like, is way simpler than it seems. I just think most people don’t end up pulling the trigger and undoing it. And then once they do it, I think people aren’t. Don’t necessarily know what to do with the information. Like, once I know that my audience is xyz, what do I do with that information? I think a lot of creators stop there, 100%.
Kate Mackz: Yeah. I’ve been thinking about it a lot recently. We were talking about this kind of before I started, but just to give everybody listening a little bit of context into my brain and how I’m thinking about my audiences. I did a video the other week with John Gray, and it was one of my most viewed videos and most engaged videos in a while.
Alex Lieberman: What I’m even curious about with the John Gray episode is, like, for people. For people who. Who enjoyed it and engaged with it. Like, what I’d probably do is, like, for people who commented on the video and it’s something of an interesting comment, is like, replying to them, asking them if they’d be down to chat for a second about the interview and why it was so valuable to them.
Kate Mackz: Yeah, no, that’s such a good idea. And I definitely will do that.
Alex Lieberman: Yeah. And you’re gonna get so many people interested because, again, like, it may not feel this, but, like, from people’s perspective who watch your show like you’re a celebrity to them, and people are like, wow, I have the opportunity to talk with someone I idolize. Like, you will just. You have as many conversations as you.
Kate Mackz: Want to have, and it’s fun showing people that you’re just a human.
Alex Lieberman: Exactly. 100.
Kate Mackz: Yeah. And that you’re always down to chat. There’s this article that just came out in Forbes and it’s called the rise of the creator CEO movement and it’s about how a lot of creators are launching businesses. Where do you think the creator industry is going?
Alex Lieberman: Yeah.
Kate Mackz: And what do you think about?
Alex Lieberman: I have a lot of thoughts. I think that. So I think the creator economy as a like, as a business it has gone through a rough patch over the last like year to two years because for a few reasons. One is there are a lot of creator co founded businesses that have not necessarily done as well as people would have assumed. There’s all the other reason is there’s a number of businesses that raised a lot of money to serve creators and they haven’t done as well. And I think these hit on two different reasons. One is if you are raising venture capital money and trying to be a massive startup up, you have to build like a multi billion dollar company. And even though the creator economy is big and getting bigger, I would argue that most money in the creator economy is being sucked up by the platforms. Like the biggest creator economy businesses are TikTok, Meta, you know, IG, X et cetera. And so I think the pie is actually way smaller for businesses outside of these platforms to build really big businesses on the side of like creators who have launched businesses. I think at the end of the day it is just really, really hard to build a great creator economy business. And I think there’s a few common pitfalls that I see. One is creators who launch launch products that are just not truly great products. It’s like creators who just like want kind of quick wins financially. They launch something that’s like kind of a commodity and they wonder why there’s an initial spike in the beginning because they market the product. But then retention is horrible because people aren’t buying the product over and over. So I think that’s the first thing that happens with a lot of creator businesses is a creator wants to launch a company. But they’re more excited by the idea of building like launching a company, announcing it to their audience than the actual like work that has to go into building a company for a long time. So that’s the first and so like what’s the learning there? The learning is like, like a creator should only launch a business if one, they have an appreciation for the fact that building a business is just like building your creator career. Like it, it’s going to take seven to 10 years. The second is the humility to know that being a creator is very different from being an entrepreneur. And either you as the creator need to evolve into entrepreneur. Or you need to surround yourself with the right people who are the operators of the business. And the third is you have to build a product that’s truly differentiated. That solves a very real need for your audience. And I think, by the way, the reason that a lot of creators have launched kind of shitty products is because they saw what happened in alcohol and assumed you could do that everywhere else. Like the first big space that creator businesses were launched was in like tequila and vodka. And so you look at like, you know, avion, which is. What’s his name, the actor, I can’t remember from Oceans 11. Or you look at, you know, like the rock has teremana tequila. Like it became the classic a less a list celebrity thing to launch a. An alcohol brand. And by definition, most alcohol is commodity. Like, the product isn’t actually different. All that matters is brand and distribution. And so I think a lot of creators assumed, hey, I can just do the same model in like other forms of beverage or snacks, but it doesn’t work the same way. So that’s the first thing I’ll share. I think the second thing is what’s interesting is like creator businesses started with like the most obvious categories. So they started again with like, alcohol. Then it went to like, you know, let’s look at like Mr. Beast businesses with like food or like candy CPG. The other next obvious place was like apparel. Like tons of creators launched apparel brands.
Kate Mackz: I tried that and I failed.
Alex Lieberman: It’s incredible. I mean, I invested in one that like, I invested in something. Navy’s apparel brand.
Kate Mackz: Oh yeah.
Alex Lieberman: It just. It’s really hard. I think there’s going to be, I actually think the most valuable creator businesses to launch, depending on the type of creator you are, are like, way more niche. So I’ll even just give you an example. One of my favorite creators is Epic Gardening. Epic Gardening. It’s this guy, Kevin Espiritu. He has the largest gardening channel on YouTube. 3 million subscribers. And they’re so their business. I think it does like 60 or 70 million dollars a year. Half of that is in brand deals. Half of it is they bought a seed company.
Kate Mackz: Wow.
Alex Lieberman: And now they sell seeds direct to consumer and through nurseries. Like they sell wholesale to nurseries.
Kate Mackz: I do love that. I love a niche thing. It makes me think of ballerina farms, who also is making niche products. That makes so much sense for her audience.
Alex Lieberman: Exactly. And so I actually think, like, people just. I think creators, and it’s possibly because they want to shortcut it or they don’t Know the right steps. But to me, like if I’m a creator who wants to launch a business, like my order of operations would be step one, understand my audience. Step two, talk to my audience. Understand what are the products they’re using constantly, what are the pain points they’re experiencing with those products. Where is there, what, what is a product they’re wishing would be better, that isn’t better? Start to form an opinion on a product or a need that you’ve heard over and over from your audience and start to think through whether by yourself or with the team, what does a really novel solution look like for that audience. Come up with like an mvp. Whether it’s a physical product or a digital product, an MVP to solve that problem in a novel and elegant way way. Take kind of like your 50 die hards, get them in a WhatsApp group, send them the product, get their feedback on it, iterate on it. Once you feel really good about it, launch it to your audience. And like that’s how I’d approach things. But I think oftentimes like creators end up landing on product before they go through this entire thing. And like to me oftentimes people find solutions in search of problems. And the best way to build a great business is to find a problem and then find a solution that elegantly solves the problem. And so what I guess all this to say is like I think they’re going to be huge creator co founded businesses. I just think like, well and the other thing I’ll say is like they.
Kate Mackz: Just have to be the right ones.
Alex Lieberman: You have to be the right ones and there’s going to be a lot that won’t work. But that doesn’t mean that there isn’t a lot of opportunity. Just like if you look at the stats on what percentage of startups fail, the answer is 80% of startups fail. So even if the stats are similar for the creator economy, that means 8 out of every 10 creator businesses is going to fail. Because like that’s building successful companies is just hard but you are going to have huge successes. I also think just more than ever before, it just like the other thing that’s most important about creator businesses is like do you actually have an audience that really gives a shit and trusts you deeply and is willing to pull out their wallet it kind of in support of you and the solution you have because again it’s like you could have the greatest product in the world, but if you don’t have a deeply trusting audience, then you, you don’t actually.
Kate Mackz: Have influence and I think sometimes there’s also benefits into in not being the public face of the brand and just having the product. I interviewed a founder recently who just now is and she has a very successful brand that’s like a consumer good for women, goods for women.
Alex Lieberman: Yeah.
Kate Mackz: She was saying that it wasn’t until she reached a certain level of success that she was comfortable being like the face of the brand.
Alex Lieberman: Totally.
Kate Mackz: And that’s not to say she went into hiding with the brand. Like I mean her face was on the about page and all of that but she wasn’t really outwardly doing content. And it’s kind of interesting.
Alex Lieberman: Yeah. And what I would say it’s interesting like in some ways having a heart loyal audience is a huge advantage because you have built in marketing. You don’t have to pay for marketing in other ways. It’s a crutch because if you truly have a deeply trusting audience you can promote anything and it’ll probably sell for a period of time. So it takes you longer to learn is the, are you getting revenue because people love the product or because they’re just going to say yes to anything that you promote in the world? So I would say that’s actually one of the tricky parts of being a creator who has trusting audience is it may take longer than someone who doesn’t have audience to figure out is the thing actually working for the right reasons.
Kate Mackz: I think one of the things that you do that is one of my favorite content series where on LinkedIn and across platforms where you have people pitch you their business in 60 seconds. I love it.
Alex Lieberman: Thank you.
Kate Mackz: How often do you film that?
Alex Lieberman: So I, I took a little bit of a hiatus. Okay. I’m, I’m going to bring it back.
Kate Mackz: You have to bring it back.
Alex Lieberman: I’m also, you guys will be able to help me with this. But I’d like, I’m trying to test other formats of founder type style interviews and like competitions. So if you guys have ideas, I.
Kate Mackz: Mean to test it out. I feel like everybody listening has this thought in their head too. But you would be the perfect person for like a Shark Tank.
Alex Lieberman: And that was the, the original idea for 60 second startup was I was like I love Shark Tank. People love Shark Tank. But there has not been a Shark Tank created for the platforms of today because Shark Tank was never brought to like social platforms. That’s why I created 60C startups up. But I, I, I always thought there was a way to like take it a step further and I couldn’t figure out how to do it, but I. I love doing it.
Kate Mackz: You will. You’re gonna figure it out.
Alex Lieberman: Yeah.
Kate Mackz: I’m so excited. I do love when people bring nostalgic shows, and obviously Shark Tank is still going on, but I love when people bring those shows that have been around for a while onto social media in some way. Like, my show was very in. In a lot of ways was inspired by carpool, karaoke, totally doing it on the run. And I love Caleb Simpson’s apartment tours.
Alex Lieberman: Yeah. Yeah, I. I’ve always thought, like, if you bring back MTV Cribs and you reboot it, it would be sick. Or like, I just think of, like, Dirty Jobs. Like, if you look at what Cody Sanchez does with her content on YouTube, she basically recreated Dirty Jobs. And so, yeah, I think one of the best ways to actually think of content series is to just go, literally, if you don’t have a cable TV box, go to someone who does. Go and look at the programing for, like, cnbc, cbs, whatever, and just ask if this, if there was a rebooted version of this on social platforms, what would that look like?
Kate Mackz: I totally agree. Honestly, I think that’s a really good idea and we might have to do that. Well, you’ve got so much going on. You’re running four companies, you’ve got a baby girl on the way due in a month. So what are you currently excited about? What are you focused on and what’s next?
Alex Lieberman: Well, I’m very excited about starting a family. Probably the thing. Not probably. Definitely the thing I’m most excited about. And it’s been very fun to design a nursery and use ChatGPT to create a nursery. Unbelievable tool for that.
Kate Mackz: Also, my favorite thing is uploading a picture of the room and saying, design it for me.
Alex Lieberman: Exactly. So good at it. And honestly, it’s like, just been really cool to figure out to finally get into a rhythm where I feel like I can spend enough time to add a ton of value to each one of these businesses and just feel like I’m working with amazing, like, co founders and. And for me, the most important thing is, like, I’m just learning a ton right now. I feel like, like building business feels like a game right now. And when building business feels like I’m playing this, like, fun Internet game, life just feels like easy and in flow. And so, yeah, I’m just excited to see what’s ahead for the four businesses. And I’m excited to kind of prove to myself and also to the world that, you know, you can be a really successful entrepreneur. But also be as successful, if not more successful, of a dad, a parent, and a family person.
Kate Mackz: I’m so excited for you. This conversation was amazing. You are amazing. I just can’t wait to see what you continue to do.
Alex Lieberman: Thanks so much for having me.