Why I Stepped Down As CEO

Alex: What's up, everyone? Welcome back to another episode of Founder’s Journal. I'm your host, Alex Lieberman, co-founder and executive chairman of Morning Brew. Founder’s Journal is my personal audio diary made public for the world. Quick housekeeping: The month of April, we're doing Founder’s Journal once per week, and each episode is about a key inflection point in my entrepreneurial journey. The first week was about growing Morning Brew from zero to 10,000 subscribers. It's not just great for newsletter operators and entrepreneurs, but honestly any entrepreneur who wants to grow their business organically on a shoestring budget. The second episode of the month was about our decision to sell the business. What the leading up to the decision was, why we made the decision, how I'm feeling about the decision today. And today's episode is about my decision to step down as CEO of Morning Brew, why I made the decision, how I felt about it, and how I've navigated those emotions since. 

Just as a reminder, we'll have one more episode after this one in April to round out the April episodes, and then in May we will be announcing a new format that we are working on in the background. And it is going to be absolutely perfect for this audience and it is something that is different from every startup podcast that exists on the market today. So get excited for it. 

Now let's hop into the episode about my decision to step down as CEO. 

Okay, this is going to be a fun/emotion-provoking episode because I am going to talk about the decision to step down as CEO of Morning Brew in April of 2021, which was about five and a half months after we sold the business in October of 2020. I want to preface this by saying that the decision to step down from running the company that I had started while a student at the University of Michigan in 2015 was probably the hardest decision of my life. The months after the decision were probably the hardest months of my life, but also some of the greatest learnings about myself as a person and an entrepreneur happened during those periods of, you know, deep emotional, both distress and just heightened emotions in general. So I wanna walk you through why I made the decision, what the emotions were after, and how I navigated them.

I want to start by saying that although the actual act of stepping down happened in April of 2021, I really had been out of the CEO role for many months prior. And the best way to describe this is to describe how the business changed materially in 2019 going into 2020, I wanna say in like the fourth quarter of 2019. It was the month in which my co-founder and Austin and I really started to realize that Morning Brew was going from a chapter one business, where the goal was to take kind of a specific insight you have about the world, turn that insight into a product that solves a problem, make sure that product is received by the world in a way that leads to product-market fit, and build a sustainable business out of that product, right? It very much is what is described as the zero to one. It is the period of being an entrepreneur or a CEO where product-market fit is your only goal. And so I would say from 2015 to 2019, that was the stage we were in. Middle to end of 2019, we get to a place where Morning Brew has gotten to a level of scale. We have, you know, 1.5 million subscribers roughly at that point. The business is doing eight figures in revenue. We have probably 20 plus team members, very profitable, and my co-founder Austin and I start to get this feeling that we need to figure out a way to get out of the business, because we were working in the business, we were working in the day-to-day, we were still in the weeds, we were doing the jobs, and that was preventing us from working on the business, being strategic about it, setting goals, hiring the right people that allow us to execute on those goals, like really being proactive and forward-thinking.

Up to that point, we were still very much in reactive mode. Everything we were doing was just to keep the business running for tomorrow, and we wanted to get to a place where everything we were working on was in service of goals we had three, six, nine months down the road. And so I remember the moment that kind of changed everything that got us started down this track of entering, let's call it chapter two of building a business, which goes from the job of being a CEO is achieving product-market fit to the job of being a CEO is building a company, like actually building an organization that allows you to grow beyond a single product and be around for a long time.

And so I remember getting a Slack message from my co-founder, Austin, and he told me how he had messaged one of our early investors who actually was the inventor of the Snuggie, and he had explained to this investor that we're kind of dealing with this challenge of working on the business, basically just kind of triaging issues, only working on things that would benefit us tomorrow, not months in the future. And he basically was like, Austin, you have to read this book. It is the best book I've ever written. It's how I run all of my companies, and I would not be where I am without this book. So he gives Austin this book, Austin reads the book, Austin messages me on Slack, and he says, “Alex, you have to read this book. This book is gonna change our business. It's gonna get us outta the weeds, it's gonna allow us to plan ahead, and it's going to take us from working in the business to working on the business and being proactive versus reactive. The book is called Traction. It's by Gino Wickman. It is part of the entrepreneurial operating system. If you have consumed my content either via Founder’s Journal or on Twitter or LinkedIn for a while, you've heard me mention Traction and EOS before, but think of EOS as basically a system similar to OKRs, if you've heard of OKRs, where basically it starts at the very top and has you define your vision for the business, your 10-year goals, your five-year goals, your three-year goals, your one-year goals, all the way laddered down to the shortest-term goals, which are your 90-day goals, which EOS calls Rocks. 90-day goals then informs, basically it acts as like the heartbeat for your business. So every weekly meeting you have is around checking if you're on track or off track for your 90 day goals. And as a company, you have three to seven of these rocks and then your leaders can have their own three to seven rocks. So anyway, Austin tells me to read this book, and I so vividly remember, 24 hours, I tell him I'm gonna read it. I wanna say three days later, he's like, “Have you read the book?” And I'm like, “No.” And very rarely in the early days of the business did Austin and I ever really argue. I think in a lot of ways we were too nice to each other and too afraid of confrontation to argue. But in this moment I remember he was like, he's like, what are you doing? This is our way to actually build a successful business. It's the only thing that matters right now. Why aren't you reading the book? And I was like, you're right. And I remember that day going to the upstairs cafe area of the WeWork we were working in, and I just pounded through the book. I read it in one full day. So I read the book, made sense to me, we're gonna implement this thing. Traction really is an integrator's dream, and an integrator as described in Traction is like the person who loves really taking the vision of the business and implementing it in a way that it leads to success. 

And so Austin kind of takes the reins of implementing the whole EOS process in our business, right? Setting our vision, our mission, our values, assessing, there's something called the People Analyzer where you can see if all your people are the right people in the right seats, creating our 90-day goals, creating our weekly meeting pulse. The other thing that Traction has you do is establish a leadership team, which leads to establishing weekly leadership meetings. And so, you know, in so many ways this was the best thing that could have happened for the business, because it turned us into a true company and it was like the best force function to go from startup to company. But I think what I've realized in retrospect is through the implementation of Traction, what it really did, and this isn't a good or bad thing, I think it's just a fact, is it had Austin take on the responsibilities of a chapter two CEO. All of the things that Traction mapped out in the book, and the things that Austin took the initiative to implement because we needed to do those things, those are the things that a stage two CEO needs to do and needs to focus their time on in order to build a business. Things like building a leadership team, things like setting goals, things like annual planning, things like quarterly offsites, like these are all very important main responsibilities of a CEO. 

And so I didn't even realize this until years later, but I think from 2019 to through 2020, Austin had very much taken on the responsibilities that were necessary for a CEO who was now in kind of the company building mode and no longer in the startup building mode. And so all of this to say, you know, we end up in October of 2020 selling Morning Brew. And during that year, I would say as Austin is very much CEOing the company, I'm spending my time on new products within the business. Like I think in a lot of ways, if you were to look at what I was spending my time on in that year, you would've been like, Alex seems more like a chief innovation officer than a CEO of the business. You know, I was standing up our new education business that we had started, I was working on our new podcast franchise, like any new product in the business, that's where I was focusing my time. And I was really focusing my time there because one, I didn't know where else I should focus my time. I didn't have the awareness to know how my job was supposed to evolve, and it was just focusing on new products is what gave me the most energy. But so that's how I was spending my time. 

We sell the business and then basically in the, let's call it like around New Year's of 2021, it's like December of 2020 into January of 2021. I remember, you know, Austin approached me to have a conversation and the conversation he wanted to have was, what do our jobs look like moving forward? And you know, basically I think from his perspective, he wanted to understand how I envisioned my role evolving, what his role would look like, and I think in the nicest way possible, what he was basically saying to me without saying it is like, I'm running the day-to-day of the business. You're still the CEO of the company. There's like a mismatch here. What are we gonna do about it? 

And so we have this conversation, and you know, what I realize in this conversation is Austin is very much running the business, right? He is managing our leadership team, he's running our leadership meetings, he's setting our quarterly goals, he's setting our annual goals, he's deciding how he's setting our budget, right? Like all of the things that are required of a CEO to run the company. And so I think in that moment when we were discussing what are our roles, there were two decisions I could make. I could either say, I still want to be the CEO of this company, and if I make that decision, that would also be me saying, I want to take back some of the responsibilities that you've taken on because those responsibilities should be my responsibility.

Or the alternative is, I could step into a different position and allow Austin to do what he's doing. And I decided to do the second thing. And the reason I decided to do the second thing is because I felt at the time if I made the choice to stay in the CEO role, it was going to be entirely for ego reasons and not for the right reasons. And what I would say were the right reasons at the time would've been if either, one, I thought I was better suited to do those jobs than Austin was, which I didn't believe at the time. I believed that Austin was a better stage two CEO at the time than I was.

And the only other reason would've been if I genuinely wanted to do those things, like if my energy was pulling me so much to those responsibilities where even if I thought Austin was better than me at the time at those things, if those were things, like the responsibilities of a stage two CEO were things that I was so energized by and so drawn to, and I had the belief that because I was so energized by them, I would become obsessed with them and I'd get really good at them really quickly, then maybe that would've been a reason for me to stay in the role and take back those responsibilities. But neither of those things was true, which to me meant that the only reason that I would be taking back the CEO role right now is because I have an attachment to what that title represents, and kind of the feeling of importance that it gives me more than anything else. And to me, that was not a reason to stay in the role, no matter how hard of a decision it was. 

So I decided to step out of the CEO role and become chairman of the business. And I won't bore you with the details about what it looked like to kind of craft what the chairman role looked like and what I would spend my time on. Because, you know, to be totally frank, I think being a chairman of a company really doesn't mean anything. Meaning there are so many flavors of what being a chairman could look like. For some chairmen, it's literally being a mouthpiece for the business, being out in market, constantly telling the story of the business, and creating brand awareness for the business, basically being like the living, breathing embodiment of the brand and acting as the highest level brand marketer for the business. For other executive chairmen, there's actually more of like an operational focus on managing the board, you know, being involved in M&A or any sort of deals that the business does. And then for other chairmen it looks totally different. 

But what I do want to talk about is what my emotional state was after stepping out of the CEO role. So I stepped out in April of 2021, and to give you a quick window, I would say I still feel emotional unease in the fact of not knowing what I want to be when I grow up since stepping out of the CEO role, because I think one of the beautiful things about when you're running a business and you're the CEO, you don't have to think about what your purpose is or, you know, what your kind of calling is in life or what you're gonna do next. Because one of the beautiful sides of having to be all in on a business is there's no time or mental surface area to think about anything outside of it. And so I never had to kind of ask myself these questions of like, what do I want for my life? Like, you know, what are my values? What do I want to contribute? You know, what are my ultimate goals? None of those things were ever questions, largely because I didn't have the space to ask those questions while I was running the business. 

And so I stepped out of the CEO role, I became chairman, and I probably went through a six to 12 month period of something that I think would look like kind of someone who was in a depressed state. Even though at the time I never thought I was depressed. You know, I never went to a therapist and was like, am I clinically depressed? But basically for six to 12 months, I felt really shitty. And the reason I felt shitty is because I felt like I'd lost all motivation. So for the vast majority of my time building Morning Brew, especially from 2015 to 2019, I felt like a 12 outta 10 on the motivation scale. Like I only had one speed. And that speed was to constantly think about my business and work on my business. And for the first time ever, I felt like a three outta 10, where I kind of didn't wanna do anything. And that felt…there was the shittiness of not feeling motivated. And then there was the shittiness of the thoughts I had around not feeling motivated, because that felt so unnatural and new to me. Then there was the identity piece as CEO of Morning Brew that became my identity from when I was 21 years old in 2015 in college until 2021. Alex Lieberman was the co-founder and CEO of Morning Brew. Like that is how I viewed myself in the world. 

And the unfortunate part about that is, of course, like the reality is that I am and was so many more things outside of that. But I think a lot of the reason I just viewed myself in that way is partially because so much of my mental space and time was spent on Morning Brew, but also because we all want to feel special and loved and belonging in life. And I think that identity specifically made me feel the most special and the most loved and the most belonging and the most important because during that period of time, Morning Brew had been growing a lot. We had received press on Good Morning America and all of these things, and you know, there was so much love being given by the world. And so I think it is so easy to want more and more of your identity to be tied up in something, tied up in an identity that gives so much to you.

Now add on top of that the fact that, you know, I've shared before, part of my story is the fact that I didn't feel belonging or did not feel loved growing up. You know, from fourth grade to 12th grade, I was at a school where I was bullied. I never felt belonging. I was picked on. I always felt like I wanted to be in the cool group, but I was never in the cool group. So I never felt like I was accepted. And so to have kind of this juxtaposition where I felt super accepted and I felt super loved, I think it only reiterated the importance of this identity to me. 

And then the third part about why I think this was exceptionally difficult was, let's call it the skill and capability part. As I mentioned, part of the reason I stepped out of the CEO role is because I realized that I did not enjoy/I was not as good at the chapter two CEO stuff as my co-founder was. And that made me feel really mediocre. It made me feel less than. I was very self-deprecating during these first six to 12 months, blaming myself for not being the CEO role anymore, blaming myself for not evolving quickly enough and learning quickly enough what it meant to grow as a CEO. And during that period of time, I forgot about all the things that I was really good and capable at. So my only thoughts that I had were kind of these thoughts around, you're not good enough. You weren't a good entrepreneur, you got lucky. The only reason your company has had success is because your co-founder dragged you along. You don't have the ability to take a business to the finish line. It really was, you know, if someone could have cracked open my brain and looked at my brain at my thoughts during that period of time, I think they would've really felt bad for me because of how negative my thought pattern had gotten. And I mention this because also what I found is, this thought pattern, as much as I believed that I was special or not special at the time, because I had all these thoughts and fears and feelings of inadequacy, what I've learned is this is extremely commonplace for entrepreneurs. And you know, in my 50-plus conversations with post-exit founders, I have kind of heard this same story over and over and over. And so my hope is whether you're a founder who will sell your business in the future, and you unfortunately have some of these feelings in the future, try to remember this episode and listen back to this when that event happens. Or for founders who have gone through an exit and you're listening to this, hopefully this provides you some comfort and makes you realize you're not special at all, in the best way. 

Now, one more thing I wanna talk about is how I navigated this process. How did I get out of the kind of the trough of negative emotion in the six to 12 months after stepping out of the CEO role? I think there's a few things that happened. The first is that I just mentioned this post-exit founder group that I'm a part of. So I'm in this text group, it has about a thousand founders who have sold their businesses. And I think being exposed to this group at the right time and having conversations with lots of entrepreneurs who have sold their businesses and have a similar story to tell, it made the experience that I was going through feel way less isolating. So it didn't take away the emotions, but it took away my judgment of the emotions, because oftentimes you judge emotions when you feel like you are the only one experiencing those emotions. As I found out that I was not the only one experiencing those emotions, my judgment of those feelings started to dissipate. 

The other thing that I really started to do during this time, other than do the cliche things of lots of long walks, reading books on stoicism, listening to Jay Shetty's podcast and other things that actually, honestly, like up to that point, I had never really committed myself to consuming self-help content. I've kind of like, I've always been really curious about emotions and understanding yourself, but more in kind of like a practical way, where I just like learn through doing and having conversations with people. But I actually think a really nice part of this whole part of my life was just consuming a shit ton of self-help content. And I thought there was a lot of value to be had there. 

But during this period of time, one of the things that I did is I asked myself, in the Morning Brew journey, if I had to pick out moments where I was most excited or most energized, what are those moments and when did they occur? And I started answering that question, and the answers to that question…so I'll give you a few of the examples. I was incredibly energized when I went to pitch Morning Brew at a JPMorgan media day alongside a lot of other media companies. And when I walked out of the pitch, one of the most senior marketers at JPMorgan told me that my pitch blew away every other media company.

I was super energized when I was building and running the ambassador program in the early years of the business. I was super energized when I was hiring our early employees. I was super energized when I was talking through referral rewards with Tyler, who was our first engineering and growth hire. And I don't know if you noticed the pattern, but all of these moments are kind of like firsts. Like they're the first time I did something, and they all occurred in the startup phase of the business, in the first three to four years of the business. And I think it makes sense, because the type of brain that you use to get a business off the ground is so different than the type of brain that you use when you are taking a business that's off the ground and putting the right framing around it so that it can grow beyond just a single product, and so it can be around for a long time. I very much think of the early days of a business more like art. It feels far more creative to me. And the later days of a business far more like science; it feels kind of more analytical. It's, you know, it's way more of a process, a procedure, a grouping of frameworks. 

And so as I thought about that, I was like, hmm, you know, first of all, I don't have to, I started to change the story from, oh, I needed to be the guy who had the idea, created the product, built a business around the product, built a company around the business, scaled the business, took the business public, right? And I think that was largely defined by who my mentors were when I was getting involved in startups in the first place. And my mentors were like, you know, Elon, Mark Zuckerberg, Jeff Bezos, right? The top 0.1% who are the edge cases to most entrepreneurs. Most entrepreneurs don't run their businesses for 25 years. Those people who were on my Mount Rushmore were literally the exceptions to the rule, not the rule. And so I think as I started seeing that most of my most pleasurable experiences in building companies were in the early days, I started to break this story that I had to be this entrepreneur that did everything forever. And I think as soon as that story broke, I actually got way more motivated and excited again because my story started to become, how do I spend as much time as I possibly can in the stages of business where I am most excited and energized?

And so I think that was a huge thing for me is, as you can tell, so much of my negative experiences after stepping out of the CEO role are all emotions I had toward a story that I had, right? And that's most of our emotions in life are not connected to facts. They're connected to stories, right? I felt lesser than because I had a story that I failed as a CEO, I felt like I was no longer cool or important, because I had a story that being CEO of Morning Brew is what made me important and valuable to the world. These are stories, they're not facts. And so I think as I start to separate my stories from my facts, and my facts started becoming that at this point in the history of Morning Brew, I felt really good. At this point in the history of Morning Brew, I felt really good. At this point in the history of Morning Brew, I felt less good. I started to, I think, have a far more objective view of how I wanted to spend my time and actually see the world for what it was. 

And so, you know, just to fast forward, it's three years since I stepped out of the CEO role. The first thing I'll say is I still haven't fully figured it out. I still have questions of purpose every single day. As a 30-year-old, I still deeply fear that my best work is behind me, whatever that means, right? That's a story. But I have a fear that my best work is behind me. I have a fear that I'm not gonna create anything of value again for the rest of my career. I have a fear that I'm too young to retire at 30.

But I will say, on the whole, I am 90% better. I'm spending my time in the earliest stages of business when I am most energized. I have spun up a few businesses that allow me to do that. I'm also spending my time on things outside of business that just fill me up, that have no professional value, don't build any social currency for me, don't make me feel more important or powerful. Literally just make me feel like a child who's playing things like Legos, things like learning the piano, things like playing golf. And I think what's beautiful about these things is they give me a great reference point to know if the energy I'm feeling while building startups is an authentically, intrinsically driven energy, similar to when I'm playing the piano or building Legos.

And the other thing that I'm doing that I'm really excited about is starting to do things that are of service to the world. I think what you realize, and this is talked about in the book Second Mountain, your first mountain in life is doing things for yourself, achieving for yourself, making money for yourself. Your second mountain in life, it starts to become about how can you be in service to others? And so as a way to start dabbling in kind of this desire to be in service of others, and when I say dabbling, the reason I say dabbling is because I still think there's so much more of me to give to startups and entrepreneurship. There's so much more of me that I want to get better at as an entrepreneur, to continue to push myself to be better and more skillful and grow. But there's also a part of me that really wants to use what I've learned these last 10 years and do it purely in service of others where there is no benefit to me. And so I recently joined the board of a nonprofit called Experience Camps. It is an organization that helps grieving children navigate the grieving process. These are for children who have lost a parent or a sibling. It's something that I feel incredibly connected to because I lost my dad when I was a junior in college. And I so wish that I had this as a resource when I was going through the grieving process. Right now, Experience Camps is a collection of sleepaway camps that are week-long during the summer across the country. But the goal is to really meet any grieving child and person where they are when they need it physically or digitally. And so I'm really excited to see kind of the way in which serving others fills me up in this next stage of life. 

So that is a long, long, long-winded way of saying that stepping out of the CEO role of Morning Brew was probably the best decision I could have ever made, but it was also the hardest decision I have probably ever made. But I think it made me grow up and learn more about myself in a way faster period of time than if I stayed CEO of Morning Brew and just learned these lessons the hard way a lot later. 

And so I hope that there's at least one thing that you've gotten from this episode, even if you haven't gone through this exact journey yourself. You know, I think there's still a lot of lessons to learn about the weight we put on stories and how stories aren't fact. They're just these creations that help us make sense of the world. And when we detach from stories, there's a lot of good that can be done for our emotional state. 

And so with that, we are three episodes into our April Founder’s Journal specials. We have one more episode for the month before we officially come out with an update on the show that, again, I think you're gonna be super excited about. It is going to be such a high value podcast for entrepreneurs or entrepreneurial minds. But stay tuned for next week's episode. And as always, thank you so much for listening to Founder’s Journal and I'll catch you next episode.