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- [00:00]
Austin Hankwitz
This message is brought to you by Abercrombie and Fitch. I've been ready for summer for a.
- [00:04]
Robert Kroke
While and now it's finally time for summer outfits.
- [00:07]
Austin Hankwitz
With a trip coming up, the A and F Vacation Shop has me covered. Abercrombie really knows how to do a lightweight outfit. Their tees, sweater, polos and linen blend shorts never miss. I wear Abercrombie denim year round. Their shorts are no different and have the comfort I need for summer. Prep for your next trip with the A and F Vacation Shop, get their newest arrivals in store, online and in the app.
- [00:31]
Robert Kroke
This episode is brought to you by by State Farm. Knowing you could be saving money for the things you really want is a great feeling. Talk to a State Farm agent today to learn how you can choose to bundle and save with a personal price plan. Like a good neighbor, State Farm is there. Prices are based on rating plans that vary by state. Coverage options are selected by the customer. Availability, amount of discounts and savings and eligibility vary by state.
- [00:56]
Austin Hankwitz
Hey everyone and welcome back to the Rich Habits podcast, a top 10 business podcast on Spotify. My name is Austin Hankwitz and I'm joined by my co host, host Robert Kroke. Robert is a seasoned entrepreneur in his 50s with lifetime revenues of over 300 million and I'm an entrepreneur in my late 20s with a background in finance and economics. Since quitting my full time job in corporate finance a few years ago, I've built a seven figure media business and actively advise some of the most well known fintech companies around the world. As the show name might suggest, every episode we talk about Rich Habits as they relate to business, finance and mindset. However, we try and bring you two unique perspectives, one from an industry veteran, which is Robert and and the other myself, someone who's still in the process of building wealth and figuring it all out. Robert, we have a very special guest today. So what are we going to be talking about in today's episode?
- [01:44]
Alex Lieberman
Yeah, I'm super excited. In this week's episode of the Rich Habits podcast, we're joined by Alex Lieberman. He's the co founder of Morning Brew, a wildly successful daily business newsletter that has become a must read for millions of young professionals. Alex and his team have scaled Morning Brew from a college side hustle into a media empire, selling a majority stake to Insider Inc. In 2020 for a reported $75 million valuation. And since then he's launched Story ARB, which is a storytelling consultancy and continues to shape the media landscape as an entrepreneur and an investor. Alex we're thrilled to have you. Maybe spend a few minutes introducing yourself, sharing where you started, where you're at now, and then we can get into it.
- [02:30]
Robert Kroke
Thank you guys so much for having me pumped to be here. I'll try to do the abridged version of kind of, I guess, 31 years of my life. I grew up in the suburbs of New Jersey. I grew up in a Wall street family. My entire life I anticipated that I was going to work on Wall Street. My dad was a mortgage trader at Citigroup. My mom ran the repo desk at Nomura. My grandpa ran fixed income at Prudential. So like, I was, you know, bred from a young age to only think about being in finance. My junior year after college, I was at the University of Michigan. I had my internship at Morgan Stanley where I was trading agency mortgages. I return offer to be there full time. Had free time my senior year because I didn't have to re recruit for jobs. So I was helping students prepare for job interviews. During these conversations, I would ask students, how do you keep up with the business world? Every student gave me the same kind of choreographed answer of my parents told me to read the Wall Street Journal, but it's dense, it's dry, I can't get through the whole thing. I started writing a daily business newsletter after I kept hearing this. At the time it was called Market Corner, not Morning Brew. Also important detail to share is that I was an exceptionally shitty writer. For basically my entire childhood into my early adult years, I wrote this newsletter. It started as a Microsoft Word template that I would convert to a PDF. I would attach it to an email that I would send to a listserv on campus. The listserv was marketcornermich.edu and that was the origin story of Morning Brew. My co founder I met at Michigan because he was one of my early readers. His name's Austin Reif. I was a senior at Michigan at the time. He was a sophomore and you know, fast forward graduated from Michigan. We didn't have enough readership yet that I just wanted to automatically not go work at Morgan Stanley. I couldn't imagine telling my mom, who knew that I was planning on working in on Wall street my whole career, telling her that I was rejecting this job to do my dream job to work on a newsletter that hadn't made a dollar yet and had 10,000 subscribers. So I went, worked at Morgan Stanley, was on the agency mortgage trading desk for a year, quit my job in September of 2016, went all in on Morning Brew, ended up Building the thing to Exit in October of 2020 we sold the business to Axel Springer. April of 2021 stepped out of the CEO role and Bec and 2021 was probably the most confused year of my life. I had this post exit founder malaise of no motivation, no sense of direction, no sense of identity. Took me about a year to a year and a half to get some semblance of North Star. Today what I do is I have a personal venture studio where I incubate businesses. I parachute into the 0 to 1 to help companies get from ideation or idea to product market fit, build a core team, drive revenue and then I have a co founder for all these businesses who are the operator of the business, who run the thing and step out of the day to day. So that's where I'm at today. Calling from Hoboken, New Jersey, excited to chat with you guys.
- [05:16]
Austin Hankwitz
What a awesome breakdown dude. Thank you so much for giving us all that detail. I I think that really does a wonderful job of setting the table for our listeners as to like what your expectations were from your parents, kind of how you bucked the system there, started your company, scaled it into what was a $75 million valuation when you sold a majority of it to Axel Springer, which I think is Business Insider, Right? It's like the parent company.
- [05:39]
Robert Kroke
Yeah. So basically Axel Axel owns ins. They own Politico. Emarketer was a business that was rolled into Insider. Axel owns Morning Brew now and then they owned a bunch of European media businesses as well.
- [05:52]
Austin Hankwitz
Very cool. So let's take a step back though, right back to the early days of Morning Brew. What tactical advice can you give our listeners that are trying to turn their online side hustle into a seven figure empire?
- [06:04]
Robert Kroke
Yeah, I mean I would say the first thing is I highly encourage people to start businesses in college because the cost of failure is so low. Like what is the worst case scenario? The worst case scenario is your business doesn't work out, but you've learned so many applicable lessons you've taken in that bat that will likely make you more skillful at the next business you start. But in the case of Morning Brew, what it did for us is basically we had a year and a half of not having to worry about the cost of our life while building a business. For a lot of people who are mid career and potentially have a family, a mortgage, all of these financial obligations, the bar is just a lot higher to make the choice to quit your job and go work full time on your company. That likely, even if you raise money, you're not going to be making as much as you were in your corporate role. So would say in college, if you have any idea, it is worth taking the at bat of building a business. The other part about it is if you go to any university that has an alumni base, alumni love helping students and they love helping student entrepreneurs. And so every time we would reach out to a well known alum or a successful alum of Michigan, the answer was always yes, how can I help? And so you just have so many resources around you in a university environment. The second thing I would say is like, you know, there's this old adage about like work on things that you're passionate about. And I think it's kind of bullshit because what I found with Morning Brew is I don't know that I was passionate about writing a daily email newsletter from the jump. I think I was curious and my curiosity was I found to be addicting. I think what I found to be the thing that made me passionate about Morning Brew was momentum. As I was starting to get responses from our readers and people were saying, hey, this is so much better than what I read right now. I think understanding our humanity that like we are all driven by some combination of intrinsic and extrinsic validation and like the validation from other students loving what we were putting out, that is what made me ultimately passionate about building my business was the feeling of momentum. And momentum is the lifeblood of any company.
- [08:01]
Austin Hankwitz
You know, I learned about Morning brew back in 2017 when I was in college and one of my friends actually emailed you directly and was like, hey, I love your newsletter and you sent her a T shirt. And she was like thrilled about it. And I'll never forget that as a. I'm sure that you were able to really build that, that listener base. And to the point though, of the alumni, I could not agree more with that tip because as someone who gradu from the University of Tennessee, Go Vols. Anytime I get a LinkedIn message or an email or whatever else from someone saying, you know, University of Tennessee student looking for some advice, I'm always, always responding to it.
- [08:34]
Robert Kroke
One thing that you just reminded me of, by the way with the T shirt thing is one, I'm glad that you said I sent the person a T shirt and I that I didn't totally ignore their email because the point wouldn't land right now. But basically, like, you know, there's the, the old adage about like do things that don't scale. There's the well known Paul Graham essay about do things that don't scale in the early days. And I genuinely believe that actually a very scalable marketing strategy in the early days of businesses is just stringing together a lot of things that don't scale. And we were the definition of doing unscalable things with Morning Brew because again, we didn't raise venture funding. We raised 750k from 28 investors, check sizes ranging from $2,500 to $100,000, and we never raised another dollar. So we didn't have the luxury of a war chest to spend on marketing or team. And so as I think back to like, what are the things that we did to grow of Morning Brew? Like, we were just like ruthless and gritty and we were just like in the fricking arena doing anything necessary to build the business. And so just a few thoughts come to mind. One is the early way we grew Morning Brew is myself and my co founder, Austin. We go to every single business class and business club on campus. We'd go up to the professor or the president of the club and be like, hey, we're students at Michigan. We started this newsletter. We think it's a shit ton better than the Wall Street Journal. It's free, so there's no downside for your students or your club members to sign up. Can we talk to your group for 60 second, I'd go into a class of, let's say 70 to 300 people. I'd give my spiel for 60 seconds, my co founder, Austin would pass around a sheet of paper. Every student would write down their email address. By the way, fun fact, passing around a sheet of paper and asking people to write down their email address was way higher converting than asking people to go on their computer, go to Morning Bukom and type in their email address. We take that sheet of paper at the end of the class, Austin, I would go sit at a table in the main area and we'd manually type in every single email address. That's the first. The second example is basically for the first five years of the business, we reply to every single email that landed in Morning Brew's inbox that started with, let's just say, maybe one email a day if we were lucky. By the end of this practice, it was 200 to 300 emails a day that our team was manually responding to. Some may say that's idiotic. Why are you using people's time in this way? Our view is one, it was a great way to train our writers because it was a low stakes. Way to get our writers to practice the voice of Morning Brew in a low stakes fashion with our most engaged people. But also, even though it will never be measurable, I believe someone that gets a reply from Morning Brew, a newsletter that you know a lot of people as a recipient, idolize or celebritize. I believe people are way more likely to share the newsletter via word of mouth after they've gotten a response from us.
- [11:10]
Austin Hankwitz
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- [11:42]
Alex Lieberman
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- [12:12]
Austin Hankwitz
Right, let's now jump back to our interview.
- [12:14]
Alex Lieberman
Wow. Yeah, I love this. And I want to linger on this for a little bit longer because it really brings me back to I think one of the reasons that I've been so successful in my career is just having the tenacity to stay at it, get out there and do the hard things that you may not know the outcome now, but at the end of the day, if you believe in what you're doing and what the outcome can be, I think it is just where all the magic is. And you mentioned bootstrapping and tenacity and all of these things. And I think it's so important for everyone to understand that because I see so many founders nowadays, as soon as they raise capital, they want to go get a fancy office and fancy desks and a ping pong table and all this stuff. I would rather invest in founders that are tenacious, that are in the woods doing these things like you discussed. So I want to go see what they have. If they already have an office. And if they have all this fancy stuff, they're more concerned of the show than they are building the business. So I really appreciate this coming from you, Alex, because, you know, scaling Morning Brew to millions of readers was no small feat at all. And as we all know and have learned through our careers, entrepreneurship is hard, it's lonely, and it comes with endless no's. So were there any moments along the way for you where you almost gave up and what encouraged you to keep going? Because I'd like you to share that advice with our listeners who might be struggling right now to get started or in their own small businesses.
- [13:39]
Robert Kroke
Yeah, three thoughts here. I'm going to name them out loud or else my monkey brain is going to forget the three points by the time I get to the second point. So, first point, Mark Cuban. Second point is the decision to go full time on Morning Brew. The third is my dad dying. All of those great hooks, by the way. First one, Mark Cuban. Two weeks into working on Morning Brew, I reached out to Mark Cuban because why not? We only had 130 subscribers, yet somehow I decided it was a good idea to reach out to him. I got his email online and I sent him an email basically saying, hey, we're building Morning Brew. Actually at the time, no, sorry, it was still Market Corner. We're building Market Corner. Basically we're building a better version of the Wall Street Journal. It's a daily email newsletter. And he just responds, first of all, I want to give him so much credit that he responded. And Mark Cuban was known for this. This is actually one of the reasons I reached out to him. He responds to everyone's pitches for businesses. He responded to me and he was basically like, I don't get it. There are lots of business newslet. How is yours any different? I responded with some long reply, which by the way, it was my first lesson in like, busy people don't read long emails. But he ended up getting back to it and being like, I still don't get it. And while I wasn't considering quitting in that moment, I think it was a kind of very valuable, low stakes way to get punched in the gut to have someone who I deem to be really intelligent, at least immediately. My emotion was like, oh, he doesn't believe in my idea. That means my idea must not be good. And then kind of me wrestling with that for a day and being like, it's okay, I still can have conviction in this idea and not everyone will agree with me. So that was like the first Experience. The second experience was basically I'd been working at Morgan Stanley for around a year and Austin, my co founder again, he was two years younger, he had to make a decision. And the reason he had to make a decision is he got a full time offer to work in banking for Molis. And if he went full time into that job, I would have never seen Austin again and he would not have been able to work on Morning Brew. And so we had to make a very big decision of like it was very much, I stay at Morgan Stanley, he goes to Molis and Morning Brew becomes effectively nothing. It probably fizzles out or we go full time on Morning Brew. And just for context, like the stakes were high for me. Like I was I think at the time making 85k at Morgan Stanley. I was in my quote unquote dream job for Austin. The stakes were even higher because he hadn't graduated yet. So not only would if Morning Brew failed, he would have not had anything on his resume, but also his job out of school. I think he was going to make year one, 175, 285K. And so we ended up, obviously, you guys know the choice we made, but it was not an easy decision at all because of what the opportunity cost felt like. But that leads number three. And it, you know, it gets to your question, Robert, which was like, did I ever think about quitting? The short answer is I never thought about quitting. That doesn't mean that there weren't times where I wasn't like existentially questioning everything we've done in the business. That happened constantly. But the reason I never thought about quitting is, you know, my story is once steeped in some level of adversity and loss in kind of the first half of my life. So I would say there's two big moments that drove my motivation for Morning Brew. The first is my dad passed away suddenly when he was 46 years old. It was a week before my junior year of college. He was perfectly healthy, in great shape, dropped dead from a stroke one day. He had been working in finance for the last 20 years. And even though no one would ever tell me this, my story at the time was 20 years of compounding stress and cortisol is what led to him having a stroke. When he was on his deathbed, I promised to him that I would take care of my family. I visualized giving a chance check to my mom and my sister and also me not being a financial burden on my family anymore because by the time he passed away, my mom had already retired, so he was the sole breadwinner in my family. I had no cognizance of actually how much money we had in our family at the time, but it didn't matter to me. I just knew that I was putting financial strain on my family. And all I could visualize was dollars, like literal bills flying off the Lieberman money pile and no bills coming onto the money pile. And so after that happened, to me, Morning Brew being a success was an inevitability. I knew that I was going to stop at nothing to make the business success. It was a matter of time, not if it was going to happen. And that if that wasn't motivating enough. The second piece of this is from 5th grade to 12th grade, I was bullied. I went to a small private school. Never felt belonging, never felt smart, never felt attractive, never felt like I was part of something. And Morning Brew ended up becoming my vehicle where I had a massive chip on my shoulder and I wanted to prove that I was actually capable. Those two things basically, like, they locked me in. In for 10 years.
- [18:02]
Austin Hankwitz
What a story. Alex. Oh, my goodness. You know, I think one of my favorite phrases, and it really goes back to really what happened to you, right? Which is like, there's nothing more dangerous than someone who's got their back against the wall and has got nothing to lose. And there's. There's no excuses, right? I remember back in the day, half a decade ago, when I convinced my co founder to quit his job making 150,000 a year on Wall Street. Or actually he was doing management consulting, but he was in New York making all this money. And I was like, dude, similar to what you and Austin kind of had to do. I was already about 2 my career, and I quit and did all this stuff. But, you know, he was like, what if this doesn't work? And I was like, christian, there was never a plan B. It has to work. It's inevitable. Like, it's going to work. We're going to make it work. Like, that doesn't even enter my mind. Right? And so, like, dude, I. I really, really empathize with what you went through and how you so masterfully created a wonderful company that has helped millions of people learn more about business for the first time and become so curious about something that is so important to everyone's daily life. It's. It's. It's incredible, man. It seriously is.
- [19:02]
Robert Kroke
Yeah, no, I apprec. And it's been a really fun journey. I'm super grateful for. I always say that like being a founder and an entrepreneur is personal growth disguised as professional growth. Like I've grown so much more as a person actually than I have grown as a business person because of this journey.
- [19:19]
Alex Lieberman
Yeah, I love it. And I think it's really important because we talk about mindset all the time and a lot of this conversation is really based on what we all go through. And we can't change what we go through, we can just change how we react to it. And you know, and I grew up in a really rough childhood and all of that, and I knew there was no world where I wouldn't grow up successful and rich just because where I came from I wanted to get out of as soon as possible. So I love hearing other stories like yours Alex, about, you know, overcoming adversity and using that that scorn as your energy to make sure that you're the winner in the end and then be able to give back and teach others how to do it. So that's why I love this podcast so much.
- [20:01]
Robert Kroke
100%. I appreciate that. And one thing I would just say, and we we can talk about it in a bit if you guys want to, is I think the interesting thing for me has been post sale of Morning Brew where I derive motivation has changed because once I no longer felt like I had to prove myself, once I no longer felt like I need to make money for my family, those things become a hole in kind of like the well that is motivation. And so I think refinding motivation is a really interesting thing as well.
- [20:26]
Austin Hankwitz
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- [21:00]
Alex Lieberman
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- [21:47]
Austin Hankwitz
Don't you love a good disclosure, Robert? All right, let's jump back to that interview. Well, let's talk about that because that leads to my next question here. I think there's a lot of listeners right now that are in the solopreneurship sort of stage of their business, right. They're getting ready to graduate hopefully into being a small business owner with co owners and employees and things of that nature. So when you sold a majority stake of Morning Brew to Axel Springer in 2020 at this 70 million valuation, obviously you talked about money's taken care of, looking at motivation, things like that. But I guess my question was more around the idea of like, how did you know it was the right time to sell and what was it like transitioning from founder in the trenches, getting it done, doing things that didn't scale to now more of a strategic role.
- [22:30]
Robert Kroke
A few things I would say. The first is basically we went in eyes wide open to what selling a business entails because we had talked to a lot of friends and founders who had sold their businesses what it was like. And I think first of all, for anyone who thinks about selling their business, it's just really important to just be clear eyed to what may or may not happen. And I would say if you sell your company, you should just have an assumption, whether it proves true or not, of a few things. One is that you go from the possibility of feeling complete freedom and autonomy to build in the way you want to build, to feeling less freedom and autonomy. The second is there's the possibility when you move on from your business that the business ends up not kind of being kind of what you envisioned it to be. Like it ends up being someone else's vision. And I would say the third, third is that there's a high likelihood that you end up spending a fair bit of your career after that trying to kind of refine the joy that you felt while you were in control of your business. And I've just, you know, I've talked to hundreds of founders about their sale process and it looks something like this. So those are the trade offs. There were two main reasons that I personally felt it was the right time. One is you know, I just kind of looked at the math and at the time when we sold our business, I was, let's just call it 28 years old. And I just looked at the math and said if we sell our business now, and I just compound this for the rest of my life. It is the definition of a life changing outcome. And I thought about like, what level of regret would I have if I kept this thing running and that opportunity was no longer an option down the road. Because the reality about media is there aren't that many buyers of media companies. And so like you do have a limited set of options. The second part of this was actually my level of energy at the time in which we sold the business. Something that I've just realized about myself is I love the 0 to 1 of businesses. I love coming up with business ideas, I love invention, I love wrestling the business into the world, like kind of forcing it into existence, proving that there's product market fit, building a core team that feels like family. Once the job of a CEO goes from like product builder in chief who's running what I would call like a family, a town or a village to company builder in chief where you're really building like a city, a state or a nation. And it becomes about scaling the organizational machine. I have found myself to lose energy. And so around when we were selling the business, I didn't know what it was at the time. Like I've only realized this upon reflection, but I was starting to lose energy in building the company. And so I think actually in some ways selling the business was kind of like my survival mechanism of being like, I don't know if I can run this thing for the next year to two years. And it's really scary to have all of my net worth tied up in this thing that potentially I'm not going to be running a year or two years from now. So those are the two main reasons I made the decision. So first of all, I would say the phrase executive chairman means something different at every company. I would say in the context of Morning Brew, what it really meant for me was kind of being a champion and evangelist of the brand online. Like, you know, a big part of kind of. I would say my unique differentiator as an entrepreneur has been the, the distribution I've built online. So a lot of it was just meat going from like operator to like creator and evangelist of the business. A lot of times executive chairman roles are focused on M and A and like interfacing with the board because we weren't doing M and A at Morning Brew. That really wasn't a part of my role. I. Because of that, what ended up happening is I went from spending, let's just say 70 hours a week operating as the CEO of the business to a lot less than 70 hours a week. What that created was space. What that space created was my mind racing. What my mind racing created was me worrying about why am I not motivated anymore? Who am I outside of the CEO of Morning Brew. And I'm 28 now. What am I going to do with the rest of my life? Shit, I'm worried that I've peaked and the remainder of my life is going to be post peak. And so that's why April 21, when I stepped down as CEO into the chairman role, the next year was so difficult for me because I was mentally spiraling around who am I outside of basically the thing I've been doing for my entire adult life.
- [26:24]
Austin Hankwitz
I could not empathize with that more. You know, I think as someone who again, I didn't create a Morning Brew, right? But for the last half decade I've been, you know, in, in a similar situation in my 20s, building a online, you know, business and you know, sort of conglomerate of businesses and things like that. And if there ever was a time where I would experience an exit, I 100% would also experience one of those things that's like, well, what am I now, right? For the last, you know, 5, 10, 15 years, I've been thing. But now I am not that anymore. And I think also to your point of stepping down from CEO to chairman, you know, I think Austin Reef, your, your co founder, he recently moved away from CEO and now I think he's also in the more strategic role. So it's really interesting and I want Robert to talk about this because I think he, he has a great amount of experience around this. But I would also agree, I am someone who likes to go from zero to one, taking an idea to just absolutely doing everything you can to turn that idea into something that is actually, you know, it works. It makes money, it's profitable, and it can make a couple million dollars a year. To your point though, like, it's a completely different person though, that can take a couple million $, your business and turn it to a $30 million or $100 million your business. And I'm not that person. I don't find joy in doing that. So it's so interesting though to, to get your perspective on that maybe. Robert, do you have any, any perspective to share as well on that, yeah.
- [27:38]
Alex Lieberman
I went through this exactly with Silly Bands and it's great to hear someone else feel exactly what I felt in different eras. When Silly Bands had all these acquisition offers of 35 million, 65 million, all in that range. I was like, no, this is my baby. I'm going to grow it to 100 million, then I'm going to exit it at 300 million. And at the end of the day, and now as an educator, I tell everyone that'll listen, if you have an exit opportunity that can change you and your family's life forever, take it. Because at any given moment you could lose it and go backwards, then you're just operating a business that may never see that opportunity again. So with Silly Bands, I didn't exit and I should have because I had a feeling that we were at the top. We had had a good two and a half year run. We had made millions and millions and millions of dollars. And I was like, I should just take this, go get a lake house, ride off into the sunset and do my thing. But I didn't exit. And then the business died off and I had all this infrastructure, I had thousands of employees all around the country. So then I had to scale down, down to become profitable again. And then when Silly Bands fell off a cliff, let's say the fourth year, because it was a trending product, then I had all of this remorse and I kept trying and trying and trying. I could recreate this. I can do it with another product. And lightning doesn't strike twice very often for most people. Jack Dorsey's probably one of the only ones that I ever have known to create two meaningful multi billion dollar businesses. But in most instances is if you have the bird in hand, take it and move on. But I went through those same feelings of you, like, is this it? Am I going to always be known as the Silly Bands guy? And it took me years to lose that moniker and now people actually question me, like, why don't you say you're the Silly Band's founder? You should lead with that. That's an incredible feat to have created such a company. And I'm like, because I don't want to be known as a one trick pony. So I love this conversation and I think it's going to help tens of thousands of lists listeners that follow along in the podcast to understand we're all figuring it out on the way up and on the way down. So many people that are well known entrepreneurs or influencers, they have this way of portraying it like it's all Rainbows and unicorns. Nobody has it all figured out. And that's why podcast episodes like this, I think, are so meaningful, to help people really understand from the top to the bottom, bottom, what can happen, what to look for, and how to deal with all the strife that comes with it.
- [30:21]
Robert Kroke
Yeah, so many thoughts there, but I'll share two. The first is if you're a listener and you're thinking to yourself, but Robert Mark Zuckerberg, he had an offer to sell Facebook for Meta for a billion dollars and you know, he would have made a horrible choice. My honest response is, you are probably not Mark Zuckerberg. And that's okay. The second thing I would say is I would actually say a lot. A large part of my motivation post Morning Brew, at least for the first business that I built, speaks to the fear you had right after your first business, which is, am I a one trick pony? Was I lucky? Can I do this again? I've thought a lot about motivation and I think that question really is like it is fear based motivation. And I felt every form of fear based motivation. I don't have enough money, I'm not cool enough, I'm not smart enough. I'm actually lucky. I'm not actually good at building business. And so I think fear based motivation, and there's a great book that, one of my favorite books on entrepreneurship talks a lot about this, of being above the line versus below the line. It's called 15 Commitments of Conscious Leadership. But the the beauty of fear based motivation is it's highly motivating. If you look at your motivation like the burner on a stove, it turns your burner up to the max. But I would say the the trade off of fear based motivation is one, long term happiness, can it create long term happiness? Is it sustainable? And two, the gas in the stove is limited. Once you kind of fill in whatever that fear is, you potentially lose the motivation. And that's what I found happened with me. So the same thing like the next business I built after Morning Brew, which was Story Arb, we stand up marketing content motions for high growth businesses. That was basically my attempt to do three things. One was replace my salary from Morning Brew because there's this very funny thing when even if you make life changing money, you love the idea of driving income in your life and me losing my salary, I felt the need to drive income in my life. The second was given I love the zero to one I was testing with Story Arb, this studio model of can I incubate a business? Can I bring on a co founder and CEO as close to day one as possible. And can I fire myself from the operations within 12 months? And the third reason I did it was can I prove to myself that I'm actually decent at business? And Morning Brew wasn't just luck. Once Story Arb succeeded, it checked off that box. But then that was no longer a motivator. So then I almost had to rethink the whole motivation thing again. After Story Arb, talk a little bit.
- [32:34]
Austin Hankwitz
More about your journey starting Story Arb, where the idea came from and like, you know, I think it's about two years old at this point. So like what is it and how is it continually helping you stay motivated? How have you been able to build a team around yourself? You got some crazy traction in the beginning. So like walk us through some of that as well.
- [32:52]
Robert Kroke
So I would say the first big learning with Arb was that I was spoiled with Morning Brew. And the odds that the first product you launch with a business is going to end up being the product that actually works and drives your success is almost zero. And the odds that you actually have to pivot your product at some point is almost 100%. And I say that I was spoiled because Morning Brew as a newsletter really didn't change from when we launched as a proper newsletter my senior year at Michigan to what it is today. It's better designed as better writing, but like it's kind of the same thing. And that is, I would say, the outlier. So the original, original thesis of storyard was as building businesses becomes lower cost and easier than ever before, there is going to be more competition than ever before for customers. Marketing costs are going to go up, which means having an owned and unfair distribution becomes more and more important. I had realized the benefit of building an audience on Twitter and LinkedIn for my businesses. And I had realized a lot of founders and executives wanted to do the same thing, but they couldn't find the time. So the original idea for Story Arb was how do we help founders and execs build their brand on LinkedIn and Twitter? That idea failed miserably is the punchline. So we ended up pivoting a year in to basically Story Arb is effectively the B2B company's head of content marketing. We stand up a content motion that builds trust with your customers and ultimately drives pipeline of customers. We do long form playbooks on your website, an editorial newsletter that's sent weekly, and then social content from your company as well as your executives. And all this works together to build up actual pipeline like dollar pipeline and instead of it being founders are our customers. It's heads of marketing at companies our customers. A few big learnings from this experience is one what I said is pivoting is usually inevitable. The second is startups are horrible customers 99% of the time. I love building startups. Startups are the worst fricking customers in the world. So every service business has a natural incentive to move up market if they can. It's like our threshold is if a company is not doing at least $10 million in revenue or have 10 million DOL in venture funding, we don't talk to them. It's not because we hate those other businesses, but history has proven they're just more price sensitive, more demanding and churn faster. The third is everything takes longer than you would expect. I wanted to fire myself from Storyard within 12 months. I ended up having to stay operationally involved for 16 to 18 months. And the fourth is every business, if you really deeply understand your customers and the operations of your business, give you 10 more business ideas. So one of my other businesses that I'm working on right now came from the insight that founders and executives want to create content on social they're having trouble with it. And even though Story Arb as an agency was not the best business model to help founders and executives create content online, I spun out a software business called Distro that is the first AI content strategist where you put in what you want to talk about. It interviews you like a world class podcast host. It takes that conversation and turns it into content for you to post from any platform on the Internet.
- [35:43]
Austin Hankwitz
Whoa. That's awesome. Now before we ask Alex our last question in the interview, let's take a moment to hear from this episode sponsor Blossom Investing is more fun when you're doing it alongside like minded people. From dividends to growth stocks. There's a community for everyone on Blossom. And remember, Blossom is not an online broker. They're a social investing app built around transparency, essentially a social media platform built specifically for investors.
- [36:07]
Alex Lieberman
And transparency is key when it comes to investing. You all know just how important that is because you listen to our podcast. I've already connected my personal accounts to Blossom and I enjoy seeing how everything is divided by up and performing on a daily basis. Additionally, they offer duolingo style educational video content for those of you still learning.
- [36:27]
Austin Hankwitz
They were just recognized as a Top 25 app for 2025 by the Apple App Store and for good reason. I love tracking my investments on there so if you're not yet joined Blossom and using them, you really need to check them out. They have over 250,000 users, and it's an easy way to both find your community as well as manage and analyze your portfolio in a very clean and efficient way. So click the link in the show notes below to sign up for Blossom or typ Blossom in on the App Store. All right, let's now ask Alex our last question.
- [36:54]
Alex Lieberman
Yeah, I think it's important you mentioned throughout that, and that was a great breakdown, that you're not always going to get it right on the first try. You might not have product market fit, the business model might not resonate correctly. The pricing model might not work right. And I love the fact that when you see really good entrepreneurs that can work on their feet and learn the workarounds and what to do, they can really make that pivot kind of seamlessly. So you're just moving forward in a better direction, but maybe a completely different direction without having to start over from scratch. And that kind of leads me to my last question, because now, looking back, you're not just a founder, but you're also an investor and an advisor. And I really like this because you're growing in your experiences, in your successes and in your failures. So what would you say is your key approach to spotting promising opportunities, whether it's a startup or a personal investment? And are there any recent investments that you're particularly excited about? Because Austin and I are always looking for new opportunities for ourselves and our community. So walk us through that of how you spot promising opportunities and how you flush them out.
- [38:03]
Robert Kroke
Yeah, lots of thoughts here, but I'm going to be a little bit of maybe the contrarian of startup founders, because what I will say is the typical trajectory for a startup founder is they sell their business and then one or two things happens. They either become a chronic angel investor deploying their own capital, or they go and join or start their own vc. I'll tell a little story, which is, after selling the brew, I was like, I'm going to be one of those chronic angel investors. And so basically, for 12 months straight, I wrote 15 checks and let's just say, like, invested $250,000 across these companies. And at the end, I did a little bit of reflection on that process. And what did I learn from that process? I learned I really did not enjoy angel investing. And the reason I say that is there's a few things. One is, I think in this weird, ironic way, like, you become an entrepreneur to carve your own path. But then some ways the startup journey post exit becomes kind of this corporate defined path which is so obviously antithetical to why you did the thing. So first is like if any an entrepreneur and they have some excess cash flow, do not feel the obligation to go angel invest for two reasons. One is like, you should do whatever makes you happy. But also two, angel investing is really hard. Three of you don't enjoy it. There's a lot of people who love it and you're at a competitive disadvantage if you're trying to compete against them. What I ended up deciding is very simple. I am actually the contrarian in my friends. Most of my startup founder friends who have had exits do not have their money managed by financial advisors. They think financial advisors are stupid. I don't think they're stupid. And I've heard all of the counterpoints on exercise fas. I have a financial team that manages my money. Why do I do that? I don't necessarily think they're going to get better deal flow for me, which is one of like the biggest, you know, pitches of FAs. I think that I don't like spending all day long thinking about my money. I like the idea that I have someone working for me to be a great custodian of my money and just make sure I don't mess up compounding at basically the rate of the market for the next 40 years. So like that's my goal. You know, I could just compound at basically the interest rate adjusted return of the S and P for the next 40 years. Life is golden. And so I would say a big chunk of my money is in the S and P or something called parametric, which is this tax harvesting strategy that mimics the S and P. I have some portion of money that is in alternatives like private credit, private real estate, private equity. And then there is some amount of cash that is my investment money. But I am not investing it in angel investing. I am using it to invest in my own businesses that I'm building. So this personal venture studio that I have, if they ever require capital to get the business going, that is my form of angel investing because I love working, working with founders. But in terms of betting my own cash, I am just going to bet on myself every single day of the week.
- [40:34]
Austin Hankwitz
I really like that because you're totally correct, right? I mean like at the end of the day, we are the biggest believers in investing early and often, right? We want everyone to be participating in American capitalism. That is the S&P 500, the NASDAQ 100. And if you can do it in a Roth IRA or a bridge account on public.com or a tax loss harvesting account, whatever.
- [40:53]
Alex Lieberman
Right.
- [40:54]
Austin Hankwitz
But like, get invested. We are big believers in that. But to your point of, oh, I don't really enjoy or I learned that I really enjoy angel investing, I would argue, as a fellow angel investor, to your point there, right. It's like there's a lot less control whenever you're an angel investor that if you are taking that same amount of money and investing it into something, you can have an impact on the outcome. Which means to your point, whenever you guys come up with these ideas for businesses, if it's distro or if it's story armor, things like that, you then can take the 20, 30, 50, $100,000 that you would have originally written to a startup. You can now take that money and invest it in yourself, having a clear impact on what the outcome could be because you can work longer hours, hire the right people, you know, everything.
- [41:35]
Robert Kroke
Yeah, one other thing I would just say is like, you know, they generally say, like, when you're earlier in life, you can take more risk from like a portfolio perspective. But I would just say I have a different perspective, which is because I feel so grateful to have kind of financial freedom in my life. The marginal benefit of making an extra dollar is way lower than the marginal cost and emotional cost of losing a dollar. And so to me, I just think about that relationship all the time. And that's why I'm totally fine just matching the market for the next 30 years. I'm happy to be boring.
- [42:03]
Austin Hankwitz
Good for you, man. That's awesome.
- [42:05]
Alex Lieberman
That's a great outtake. Because so many people, Alex, that Austin and I talk to on a daily basis in the Rich Habits Network and through the Rich Habits Podcast, they think that becoming wealthy and creating financial freedom is supposed to be this action movie with a lot of different moving parts and there's all of this adrenaline and crazy things happening, and that's how you build wealth. And it's actually, actually the opposite if you do exactly what you've laid out, and that is keep it simple, let compounding do the work and be consistent. You will build wealth. It's inevitable to build wealth. And it's just really good to hear it from other people besides Austin and myself. So we really appreciate having you on as a guest. This has been very, very insightful and just awesome to hear your stories and how you got here today and built such an incredible company and more companies on the way. So we Appreciate you stopping by 100%.
- [42:56]
Robert Kroke
Thank you guys so much for having me.
- [42:57]
Austin Hankwitz
Now, before you leave Ale, where can the people find you if they want to reach out to Story Ar? If they want to use Distro, maybe they want to sub to Morning Brew. What's going on over there?
- [43:05]
Robert Kroke
You can find me on Twitter at business barista on LinkedIn. My name, I wasn't allowed to create a LinkedIn account at business Barista. And then Story Arb, you can go to story ar.com distro you. Distro.com distro.com was too expensive. Yeah, those are the two you can go to. And then, of course, always sending people to Morning Brew. We do a lot of amazing content on YouTube now as well, so definitely check out our YouTube channel. Channels.
- [43:25]
Austin Hankwitz
Alex, thank you so much, my friend.
- [43:26]
Robert Kroke
Thanks, guys.
- [43:27]
Austin Hankwitz
Robert, what an awesome interview we just had with Alex Lieberman. He is such a nice guy, so accomplished, very well spoken, a great storyteller. Hence Story Arb. Right. Any just big takeaways to share before we jump into the Q and A section of this episode?
- [43:42]
Alex Lieberman
Yeah, for me, it was just a very emotional episode. And I love hearing from someone as successful as he's been about the ups and downs, the trials and tribulations, and all the emotion that comes with building a big company, exiting a big company. And I think this episode will really tug on a lot of heartstrings for people that are out there grinding, building, and trying to find their way to financial freedom. So it's in a really, really great interview, and I'm excited for this episode.
- [44:11]
Austin Hankwitz
I totally agree. I think one of the bigger takeaways for me were one, when you're in college or you're young, you have very little to lose, Right? So go take those big shots to Sometimes the first idea, right? So the first idea was Story. I was do like ghostwriting and stuff. Sometimes the first idea doesn't work. And what ends up working is an idea that came after. Right? So it's like you want to just start, get some reps in, and then you'll figure out what actually works. And then once you figure that out, you find that product market fit and you double down on the idea or the business or the service or whatever it is you're offering. And then the last part about it is, I love how he said, he's like, listen, you're right, Investing isn't an action movie. I've got a financial advisor, they're doing my thing, and if I just compound with the markets, I'll be fine. I'm gonna go find motivation elsewhere and I think that's really important to us, especially when it comes to like putting money in perspective. Right? Talk about this all the time. Money only solves money problems. You can become a multi millionaire and if you have a bad relationship with your children, you're still going to have a bad relationship with your children until you like go work on that. You can be a multimillionaire. And if you don't go to the gym or you're not healthy, like you're still not going to be healthy despite having money. Right. So money solves money problems. And I think Alex's take on that was great.
- [45:19]
Alex Lieberman
Absolutely.
- [45:20]
Austin Hankwitz
So our first question here is coming from Michael S. On Instagram. Remember, if you want to ask us a question on the show, DM us at Rich Habits podcast on Instagram or email us at rich habits podcastmail.com so Mike says, my wife and I are raising a toddler. We both work full time jobs in accounting and finance. We've recently made adjustments to our budget to open up some cash flow to allow for more investing outside of our 401ks 529s and money market cash reserves. But we're trying to further create more cash flow in our limited free time with outside sources of incomes or more effective budgeting or maybe a side hustle. What are some creative ways to accomplish this without taking away from our family time without with our toddler? Thank you guys so much for all you do. So I'll take a first stab at this the easiest way and shout out to one of our advertisers NEOS funds that anyone can begin to generate passive income inside of their investment portfolio is to buy SPYI QQQI I Y R I btci right. Any NEOS fund, they're all going to pay about a one to one and a half percent monthly yield on your investment tax efficiently every single month. So maybe learn more about NEOS funds. Mike could be a really good place to start.
- [46:31]
Alex Lieberman
Also I that I think Mike is on the right track. Think about that side hustle. You could go out and pick up five clients at $500 a month to do some bookkeeping for them. It could be really simple stuff. You can do it in your sleep. Take that $2,500 a month, invest that directly into the markets, maybe into, you know, one of your traditional brokerage or your Roth ira if you don't have that yet and let that money just continue to compound for years and years. I think that's a Great thing. But also just keep adding, adding diversity. I can't speak on this enough, especially during tumultuous markets. Get that diversity, get some money into cryptocurrency, get some money working into maybe individual stocks, into the ETFs we talk about all the time and just really continue to do what you're doing. And we appreciate you asking these types of questions because it helps so many other people as well who maybe are good earners but are not sure how to build more wealth along the way. So that. Thank you for the question.
- [47:27]
Austin Hankwitz
And I will add too, you know, maybe there's a world where, I mean you truly could do this passively. You start house hacking, right? Maybe you, you live in a duplex, triplex or quadplex and your tenants are beginning to help you cash flow against your mortgage and your expenses. Obviously there's a little bit of property management that has to be assumed with that, but it's very passive, right? You're just living there, right? There's nothing out of the ordinary that you're doing. And then something else to check out is. And I can link this out in the show notes below for you. Robert and I hosted a covered call webinar about a year and a half ago where I walked through how I generated thousand dollars in 2023. I think it was using covered calls with Tesla stock. So I went out about a hundred shares of Tesla stock, wanted to own the stock of course in perpetuity. So I sold some covered calls around that above my cost basis and was able to generate thousands of dollars. So maybe there's a way that you could learn more about call options and put options and sort of, you know, cash secured puts, covered calls, things like that. But really good question, Mike. We appreciate you listening to the show. Our next question comes comes from Jordan J. On Instagram. Jordan says I love your episodes. I wanted to give you guys a quick shout out here. I've been able to help my sister set up her Roth IRA and three of my friends because of your show. And my mom has completely changed her holdings in her brokerage account because she's lost money so much by listening to the wrong people. So thank you. My question is very short. What do you guys think about crypto credit cards? I was planning on signing up for the Gemini MasterCard as it seems to have some great rewards. But what are your all thoughts on crypto credit cards?
- [48:52]
Alex Lieberman
Well, I'll take this one first. I think they can have advantages as long as you understand kind of the pros and cons. So make sure you read up. You know, they do have really good potential for high rewards. As crypto is get more and more involved in our daily lives, you're going to have some increased flexibility having these cards. And there's just a lot of upside mostly in the rewards part of it. So I do like that. But just make sure you read up on this because with continued volatility, you have to understand that volatility is going to provide havoc on your rewards. Because there's a big difference between bitcoin being at 100,000 and bitcoin being at 50,000 and what the rewards will be.
- [49:33]
Austin Hankwitz
Yeah, to that point. Right. So it's like if you're a credit card person because you want cash back, you get the cash back. Like that's your thing. Right. I've got the M1 credit card and I use it for my 10%, 5%, 3%, 1% cash back. It's super great. I love that. And then I also have another credit card that's more focused on points. Right. So I use it whenever I go eat out to eat, whenever I travel, things like that. I get, you know, travel points and miles from that. So if you're saying you're someone that specifically wants to get bitcoin back or you know, whatever your crypto is that Gemini has at a 1, 2, 3 or 4% bitcoin back, every time you swipe, like, that's cool. Just make sure that you are denominating your rewards in satoshis. Right. In bitcoin versus in the dollar amount because the dollar amount is going to change all the time. So if you're someone who's spending, call it 10, 20, $30,000 a year and you're able to get, I don't know, a blended rate of 2 1/2% bitcoin back on your $30,000 a year, that's about $750 worth of bitcoin at a level price. But if it goes up a whole bunch, it could mean more. If it goes down a whole bunch, it can mean less. Just make sure that you are looking at this as maybe a way to get more crypto exposure passively than a way to actually invest in cryptocurrency. If you want to actually invest in crypto, go open an account on public.com, buy some Bitcoin, buy some Ethereum, buy some Solana, something of that nature, and own it as a part of your portfolio. Don't use this as a workaround to invest.
- [50:57]
Alex Lieberman
Yeah. When people ask questions about stuff like this. Sometimes I feel like they're just trying to get a little too fancy for things. Just make sure everyone listening if you're considering getting a crypto credit card, understand why do you need it? What are the benefits? What are the cons? Because there's always going to be the benefits of something, but also the bad side of it. So just make sure you understand both.
- [51:17]
Austin Hankwitz
So our last question comes from fp. They wanted to stay pretty anonymous here, so FP emailed us. They said hi Austin and Robert, longtime listener and note taker of the show. In episode 96, Building Generational wealth, you talk about investing in your 40s and 50s and you said your largest growing audience for the podcast is actually 55 and up. Which is true. Could you please elaborate on Investing in your 60s and up? I'm 62, live in New Jersey. I have my emergency fund and I've got about a million dollars invested right now between my 401k, my traditional IRA, my HSA and my Roth IRA. I have no plans on retiring quite yet due to a divorce that took place five years ago after 40 years together, my dream retirement was shattered because of that. So I had to start over. Never really having anything now on my own. But I took my half of the settlement, bought a townhouse in cash back during and then after about a year of getting my life together, I went in with a business partner and bought the manufacturing company that I worked for for the last 30 years. It's doing wonderful, but I'd like to slowly start to cut back from 10 hours a day, five days a week to something a little bit more manageable. But I could still continue to build wealth with I have no debt and would like to know how to safely keep investing at this age. I'd love to hear more Q&As from other older folks once in a while on your show, but I'm happy to hear about all the young people excited about learning and investing. I also have three grandchildren that I'd like to on how I could best set them up for their own wealth building journey as well. Thank you guys so much in advance. So I will take the first sort of bit of this, which is the grandchildren. The best thing you want to do here is open up those 529 accounts, right? Go to vanguard.com you can open up a 529 account for each one of your grandchildren. Put in their Social Security number, their date of birth, things like that. They'll be the beneficiaries of this account. Start investing 100, 200, 300, $500 a month into these accounts and allow them to grow. These accounts are specifically used a way to pay for college related or education related expenses. Essentially what what happens here is let's say you've got $30,000 of profit from investing the money through this account for each child. You don't have to pay any taxes on that $30,000 of profit assuming you spend that profit on an education related expense. And if your kids don't go to college or you just have a ton of money in here, starting at the age of 18, you can begin to use the money in this account and roll it over into the kid's Roth IRA at that $7,000 a year. So two, three, four, five, six years they'll have now, I think up to $35,000 rolled over into their Roth IRAs at a very early 20s. And that money will grow for them into millions of dollars over their life, assuming you don't even add more to it. So to the perspective of setting them up for their own wealth building journey, the best thing you can do is open up those 529 accounts and then once they turn 18, start rolling money out of the 529 into the Roth IRA on their behalf. Make sure that you consult with the CPA on that. I know there's some stipulations here and there around that strategy, so talk to someone about it. But that is a wonderful answer and solution here for you. FP.
- [54:17]
Alex Lieberman
Yeah, and my take would be at 62 years old, you own a business, you're still making income and you have almost a million dollars invested. I would keep that train rolling, cut the hours back, start having some fun, but keep some income to live off of. Because if you can let that almost million dollars compound at 8, 10% a year for 3, 4, 5 more years, you could really get that up to a really nice retirement savings plan. And then you the option to sell your portion of the business at some point or step aside, retire from the business, take your profits, keep living on those and keep letting your retirement grow. But to learn more, I'd really like it if you're in the Rich Habits Network, DM Austin or myself, tell us more about your situation because we'd love to unpack. Maybe there's some things you could be doing to diversify the money now a little bit more to get you more gains, some other things you could be looking at to add more income with your retirement savings and your accounts, but you're crushing it. You're doing really? Well, sorry to hear about the divorce. That's a terrible thing. But we love the fact that at least you're at that million dollar mark, plus you're still earning income. But definitely don't let your dreams sit on the sideline while you're working. Cut those hours back, take up those hobbies and start enjoying yourself.
- [55:36]
Austin Hankwitz
I would agree. I think the biggest thing for you here to understand around. And you asked this in your question, right? How do I invest safely? Right. All investing involves risk. I think that's just like we need to keep that in mind. But the people hurt on a roller coaster are the ones that try and get off in the middle of the ride. And that's the same thing with investing, right? Obviously in the month of April, we saw a crazy drop in the markets, but now we're back up and in the green. So like if you were someone who panic sold after everything was down 20% because you were scared of the Trump tariff tantrum and what that was going to do to your portfolio, now you are looking back at like, dang it, why did I sell? I should have just held on tight like Austin and Robert tell me to. So I think like, that's what's really important here to understand. It's not about specifically like what you're investing into. I'm sure you're investing invested into bonds and, you know, some REITs and some stocks and like all the ETFs we talk about. You're probably very well diversified and invested correctly. But I think beyond what you're invested into, you need to have someone in your corner that's going to be able to really make sure you understand that during times of volatility and uncertainty in the markets, just ride the wave, follow the 4% rule, take your distributions like you should work with people that can help you optimize for taxes, things of that nature, and you're going to be just fine.
- [56:48]
Alex Lieberman
I love it. Well, this was an incredible episode. We thank each and every one of you. Every week that shares the podcast, shares it with a friend, gives us those five star reviews and we just love doing this and providing as much value as we can week in and week out in these episodes. And we couldn't be happier to do it.
- [57:06]
Austin Hankwitz
That's right. We love your feedback in the comment section on Spotify. So if you've not yet left us a comment below about what you thought about this episode, please do. As well as vote in the poll. We try and have some funny polls here and there on Spotify. And if you enjoyed this interview or someone sent this to you or you just enjoy the show, please consider giving us a five star star review. It really helps get our show in front of more people that can learn about personal finance and investing. Thank you everyone for tuning in and have a great rest of your week.