In October 2020, Business Insider bought a majority stake in Morning Brew—a popular business newsletter with over 2.5 million subscribers—for a reported $75 million. At the time, Morning Brew cofounder Alex Lieberman was just a few years out of college. In this Taboo Tuesday, Alex talks to Dr. Emily about his complicated relationship with money and the growing anxiety it caused him following the successful deal with Business Insider. 

Staying emotionally fit takes work and repetition. That's why the Emotionally Fit podcast with psychologist Dr. Emily Anhalt delivers short, actionable Emotional Push-Ups every Monday and Thursday to help you build a better practice of mental health, and surprising, funny, and shocking conversations on Taboo Tuesdays - because the things we’re most hesitant to talk about are also the most normal. Join us to kickstart your emotional fitness. Let's flex those feels and do some reps together!

EPISODE RESOURCES:

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The Emotionally Fit podcast is produced by Coa, your gym for mental health. Katie Sunku Wood is the show’s producer from StudioPod Media with additional editing and sound design by nodalab, and featuring music by Milano. Special thanks to the entire Coa crew!

JUMP STRAIGHT INTO:

(2:09) - Alex’s background and Morning Brew as a side hustle - “At first, I didn't feel like we had enough attraction and I was worried that my overprotective Jewish mom would be pissed that I had left my dream job to go do the Brew.”

 (7:30) -  A complicated relationship with money - “I formed a money obsession. I don't know if it came because I had questions about how well off or not well off are we? Or if it just came because my parents worked on Wall Street, and so business was always talked about.” 

(10:22) - What happened to Alex after Business Insider acquired Morning Brew for $75 million - “I had all this money in the bank, but I wasn't doing anything. My behaviors didn't change and I didn't feel any happier.”

(16:35) - Money doesn’t solve every problem - “Selling the company actually didn't change my level of money anxiety at all. If anything, it actually exaggerated it.”

(18:10) - Finding new ways to stay motivated - “Money is not going to be the primary driver of my motivation moving forward.”

(20:21) - Searching for purpose - “I can get very high level and in my head around these very philosophical questions like, ‘What is my purpose? Am I enjoying the work I'm doing? Do I feel fulfilled right now in this work?’ And it actually creates a lot of stress for me.”

I do believe up to a certain point, money does bring you happiness at the point for whatever your life needs are, you're no longer worried about money, but I think that was far less than what I had made from this deal. And so, yeah, it was basically what do I do now? I don't have money as a crutch. That can't be a motivator for me anymore. I don't have the day-to-day of Morning Brew to distract me. Like, what am I doing for hopefully the next 60 years of my life?

Welcome to Taboo Tuesday on the Emotionally Fit podcast. I'm Dr. Emily Anhalt and I've always loved talking about taboo subjects: sex, money, drugs, death. Because being a therapist has taught me that the feelings we're most hesitant to talk about are also the most normal. So join me as we flex our feels by diving into things you might not say out loud, but you're definitely not the only one thinking.

Quick disclaimer that nothing in this podcast should be taken as professional advice, diagnosis, or treatment. Because while I am a therapist, I'm not your therapist, and I'm not my guest's therapist. So this is intended only to spark interesting conversation. Thanks for tuning in.

Hey, there Fit fans. Today, I am speaking with Alex Lieberman, the co-founder and executive chairman of Morning Brew, which is a media brand that empowers modern business leaders with need to know content. Since its founding in 2015, Morning Brew has provided millions of users with the most important news from Wall Street to Silicon Valley. And in October of 2020, Alex and his co-founder, Austin sold a majority stake of Morning Brew to Business Insider for a reported $75 million.

Alex. Now hosts an amazing podcast called Founder's Journal. And today I'm so excited to be talking to him about a fascinating taboo topic, which is the complicated side of making a large sum of money. He'll share his experience around losing motivation and searching for purpose. Alex, thank you so much for being here with me today.

Thanks so much for having me, pumped to do this.

I'm really excited about it. So maybe you can start by telling us a little bit about yourself. Maybe introduce yourself beyond what I've just shared.

Yeah. I am originally from Livingston, New Jersey, which is a suburb that's about 40 minutes outside of New York City. I grew up in a family of four, have a younger sister, and both of my parents growing up worked on Wall Street. My dad worked as a trader at Citigroup. My mom worked as a salesperson at [inaudible 00:02:36]. I come from a Wall Street family, not just my parents, but my grandparents also worked on Wall Street. And so that was my dream from a young age was to work on Wall Street because that's what my role models did.

Family was the most important thing and so I couldn't imagine doing anything other than what my role models did. You know, fast forward, I went to the University of Michigan.

Go blue.

Go blue. From 2011 to 2015, I was in the business program there. Did the classic thing that you do when you want to end up working in finance. So I did internships on Wall Street and ended up getting a job offer to work full-time at Morgan Stanley in sales and trading after my junior year. Which again, like that was the dream given my background. And during senior year, my co-founder Austin and I started Morning Brew as just this rinky-dinky newsletter that we sent to students in the business school at Michigan. And I guess to round out the story when I graduated from Michigan, I didn't go full-time on the Brew at first.

I didn't feel like we had enough traction and I was worried that my overprotected Jewish mom would be that I had left Morgan Stanley, my dream job, to go do the Brew. And so I went to Morgan Stanley to start. This was in July of 2015. I worked there for just over a year, quit my job in finance in September of 2016, and went full-time on the Brew at that point, and have been working on and around the business for around seven years.

That's an amazing story. And you told us a little bit about your early life, but I know you had mentioned when we were speaking that your experience in middle and high school had a really big impact on who you are today, and what you became, tell us a little bit about that.

Yeah. I would say probably from grades five until 12 were really difficult for me. I never felt like I was enough. I think that was a combination of, one, I was one of the younger people in my grade. I also didn't have like an older sibling to show me the ropes. And so I think part of it was just I was less mature. I think part of it was, it was incredibly competitive school. So I both felt lesser than, it just I didn't feel like I was as smart as everyone. I didn't feel like I was as athletic as everyone.

And then socially, I found it to be very difficult as well. I never felt like I was a part of the group for whatever reason, I always felt like I had to be a part of the cool group, but I never felt belonging to that group. I absolutely experienced times, especially in high school where I was bullied, people would call me names. And also the hardest thing was like it would get to me and I would show that it would get to me, which always would lead to me being bullied more and more because I was giving a reaction in a way that was satisfying the bullier.

And so all of that to say, yeah, middle school and high school was really difficult. I did not have a sense of confidence in myself. I did not believe that I was cool. I didn't feel like I belonged. I didn't feel attractive. Like I didn't feel any of the things that give you a sense of security in yourself.

When would you say that shifted or how has that shifted?

I would say the first shift was probably during my freshman year of college. Once I ended up at Michigan, which again, I think in a lot of ways going to Michigan for me was an escape from high school. Everything about Michigan was so different from my high school, huge school, like well-rounded, kind of academic, sports, social, geographically far away from my school. And also I was the first person in six years from my college to go to Michigan.

And so I think quite literally I was keeping myself in a surround that gave me basically a few reminders as possible of my high school. So I think it was the combination of feeling like I had a fresh start made me feel confident. And I got a few friends early on that made me feel, okay, that's a win under my belt that I can actually make friends that I like, and I feel a part of a community.

Then I would say it's when I started dating my ex-girlfriend now. That was the first time in my life I had basically proven to myself that I can attract a girl. Like I had zero confidence in myself that I could do that in middle school and high school. And so I think that gave me confidence as well. And so I would say the first stage for me was in the early years of college because I proved myself socially, as well as kind of attracting a partner.

And then I would say the second step happened, call it when I quit my job at Morgan Stanley, and there was traction with Morning Brew because all of a sudden I felt like kind of this level of importance and success as an entrepreneur.

You know, your story mirrors mine a lot, including going to Michigan to get far away from the environment that I was used to. So I really resonate with a lot of that. And today specifically, we're talking about the taboo topic of money. So one thing I'm curious about when you talk about your early life, you come from this Wall Street family, what was your financial situation like growing up and pre-Morning Brew?

Yeah. I always knew my family had some means. I had no idea what those means were because we never spoke about money in the sense, like I still to this day have no idea how much money my parents had, my grandparents had basically. Kind of my mental model was we were doing fine, but we were not super rich. Like we lived in this suburb called Livingston, which I just knew like you had to have some money to live in, but we lived in a three-bedroom ranch.

I knew my parents worked on Wall Street. I generally associated Wall Street with being high-paying. Actually kind of my mental model was like my parents were doing fine. My grandpa had a lot of money and he helped us in some ways, I didn't know how much, but that was kind of the relationship because I knew like he had paid for our sleepaway camp. He paid for my first car that I got from college. So that was kind of like those were the reference points.

But yeah, it's interesting. I formed kind of like a money obsession that I don't know if it came because I had questions about how well off or not well off our way or if it just came because my parents worked on Wall Street and so business was always talked about. And so I would say that was a piece of it, but I would say my relationship with money also got more complicated my junior year of college because a week before junior year of college, my dad passed away. He passed away suddenly from a stroke. He was 49 years old, perfectly good health, completely unexpected.

And the way that changed my relationship with money is I couldn't help but feel this kind of sadness and guilt in a way. My mom, she had worked on Wall Street for 20 years, but she had retired at this point. And so all I could visualize was, "Okay, I know like we are in a fine financial situation," but my dad at that point in time was the one making the money for the household. He passed away. Now, all I could visualize was no money coming into the Lieberman household, money only going out to pay for college, to pay for all the things that I wasn't paying of, my sister wasn't paying for, and the cost of my mom living.

And so I started almost kind of like getting an obsession around I need to get to a place where I, first of all, am paying for myself as soon as humanly possible. But also after he passed away, I very much took on the responsibility. I would argue like irrationally, but I created this story that it was now my responsibility to take care of my family.

I mean, it feels like you're speaking to how money is often such a metaphor. Like I would imagine that maybe what you were really worrying about was just, "Will I be taking care of, will I have the resources that I need?" The person who brought a particular kind of security in my life is gone and money sort of stood in for that. Would you agree with that?

Yeah, I would say it was for me I was just trying to make sure that everyone in the family felt security and I felt like it was my responsibility for people to feel security.

Yeah, absolutely. So then you do this venture Morning Brew, it is wildly successful. And I'm curious, what did it initially feel like to come into such a significant sum of money after you had spent this time really feeling worried about money, and the security it would bring?

Yeah, I would say on the day that we sold our business, I was at my mom's place. She has a townhouse in New Jersey. I was there with my now fiancee, who was my girlfriend at the time in our house. And it was kind of like we had a calendar invite to do kind of like the final wire transfer with our partner where it was like a Zoom call set up with my co-founder Austin, and myself, and folks from Axel Springer, which is the German conglomerate that owns Business Insider.

Some folks from Insider and my mom and fiance had gotten like champagne and balloons. I think they were happier than I was. For me, there's a lot of things going on there. One is that I'd kind of known for some time prior to the final deal happening like the financial situation was going to work itself out. The business had a lot of traction. We were doing a lot in profit so even if we didn't sell our business, we knew we could always take distributions from the business and it would be a significant sum of money. So I think I'd kind of been emotionally in this place of money has worked itself out or will work itself out even without a deal.

I think the second part is kind of what I would argue is like one of my best coping mechanisms, but also kind of creates blind spots for me is I think I'm very good at keeping my emotions in like a very narrow band where I never get too sad or frustrated or stressed, and I never get too exuberant. And I think that has been an adaptive thing for me for a lot of reasons. For how I deal with things like bullying or being broken up with. How I've been taught through learned behavior from never seeing my parents really emote a lot.

And I think it was really adaptive to run a business successfully because by being level-headed, nothing would ever rock me. And that was a story I told myself that was really important. And so that was a piece of it as well was just like me training myself to not emote, me already knowing that my financial situation was going to be okay. And the fact that, honestly, the best part of the entrepreneurial journey was these cool wins throughout the process.

Yeah, I just didn't feel, honestly, a whole lot. I didn't feel a whole lot and I became less happy over the next kind of year to year and a half once kind of the let's call it like the money had hit the bank account.

Well, I mean, you're speaking to something that I think we know intellectually, but it's hard to embody, which is when we close ourself off to the negative section of the emotional range, we are also going to close ourself off to the more positive section. So I hear you sort of caught in this middle. So tell me more about what changed afterwards in both positive and negative ways once that money hit the bank.

Yeah. Well, I would say the first thing is my behaviors didn't really change as in like it's not my way, it's not my value to go out and buy a massive house or a big car. And I don't think I even do that from like kind of the I would say what is a very popular story of like you don't want to come off as like braggadocios or superficial. To me, it's just like I don't think I get personal joy from buying a lot of material things.

I still drive my 2011 Volvo. At some point I'd like to buy a better car, but it's still driving fine. But I think it was like my behavior didn't change at all. I was still living life in the exact same way as I was before the money landed in the bank account. The only big purchase I made was our dog and I would've made that anyway. And then what I think ended up happening was so we sold the business in October of 2020. I want to say in March of 2021 is when I stepped out of the CEO role into the executive chairman role. And that was a very provoking experience for me as well after basically having my whole identity pent-up into a title and a position for the prior six years.

But I think what happened was I ended up being pretty like unhappy and lost. I made a good amount of money. I thought that money would bring me a level of happiness because I thought part of one of my goals in doing a business was to get to a point where I could "take care of my family." And I ended up in this position where I was now executive chairman. I had a lot more free time. So let's say before I was spending 80 hours on the business, now I was spending 30 hours of the business.

I had all this money in the bank, but I wasn't doing anything. My behaviors didn't change and I didn't feel any happier. And so I think I just felt lost because I was just like, "Shit, what do I do now?" I'm 28. The only thing I've known professionally is Morning Brew. And now I'm not in the day-to-day of that. I don't know what fills me up or gives me purpose. For a while, I thought money could help in some regard like even though intellectually I always knew and said to myself, "Money doesn't buy you happiness."

I think it's hard to truly appreciate that until you experience it. And I do believe up to a certain point, money does bring you happiness where at the point for whatever your life needs are, you're no longer worried about money, but I think that was far less than what I had made from this deal. And so, yeah, it was basically what do I do now? I don't have money as a crutch. That can't be a motivator for me anymore. I don't have the day-to-day of Morning Brew to distract me. Like what am I doing for hopefully the next 60 years of my life?

And it was a really empty feeling because the thing that I was planning on being part of my chase for my whole career, it's done in 28. And to be honest with you, it's not something I speak about a lot because it feels like a really douchey problem to talk about. I kind of always feel allergic to bragging about money or things that I have, but I think it would also be disingenuous because it very much was my experience where for like six to 12 months, I really felt lost in directionless, and would kind of wake up every day telling my fiance like, "I really don't know what I'm doing."

Well, I'm glad you are talking about it. I mean, that's why this is a taboo topic. It's a problem of privilege certainly. It's a champagne problem, but it's still a problem. And I actually have seen it a lot because I work with a lot of founders and a lot of people who think that there's a particular success they can reach that will fulfill them, that will make them feel something that they really want to feel, and they get there and they don't feel that thing.

And it's very hopeless because if this success isn't going to get it, then what does? So I actually think it's something a lot of people experience, but don't talk much about for worry of sounding ungrateful.

Yeah. And I think there's two other interesting kind of byproducts that have come out of me feeling lost, me doing a lot of work to "find myself." I've realized two things. One is that I still have money anxieties today, even with everything that happened with selling the company. Like selling the company actually didn't change my level of money anxiety at all, if anything, it actually exaggerated it.

Huh. It feels like such an important thing to sit with as someone who is striving and I have my own ideas about what achieving a particular kind of success will get. I think it's actually really helpful for people in that position to say, "You know what? This doesn't actually fix all of the problems."

Totally. Yeah, it's like something I'm actively trying to think about right now is like, "How do I give myself more permission to spend? How do I kind of give myself the feeling of feeling safe within the money that I have?" Because I think it comes from like, "Why do I have money anxiety?" For whatever reason, I have a money hoarding mentality. I don't know if that is a generational mentality. I don't know if it's a cultural mentality, but it's like something that I'm trying to explore.

And then I think the second piece that we can also get to is, yeah, I very much have a fear around like how am I possibly going to have as much motivation moving forward in any sort of career or business endeavor when like the hunt for a really strong form of motivation for a lot of people, which is money or success, that's been hit. I literally have the fear of like being lazy in kind of any of my future professional endeavors.

And so how are you exploring or confronting that?

The way that I'm thinking about it is I think there's a lot of different forms of motivation. Money is one. Fear of failures one. Chip on to shoulders is another. Learning and growth is another. I'm trying to reorient myself to say, "Okay, well, money is not going to be the primary driver of my motivation moving forward." But something that actually seems really exciting to me is there's like two motivations that I think feel exciting to me.

One is the ability to learn and grow. I am a very curious person. I like when I feel like I'm growing. So something that can constantly give me that dopamine hit of growth feels both satisfying, but also it potentially can allow for some balance in life. And I would say the second is being helpful to others. And I feel like that this is kind of like a generational thing. When I read books, people talk about like human beings want to grow and human beings want to be helpful to others.

To be honest with you, I've still not felt this like burning passion to be helpful to others. And again, I feel like that's a taboo topic on its own because it's like we are taught the importance of being charitable and philanthropic. And so it almost at times I'll feel bad if I don't feel a deep desire to be charitable or philanthropic. And I think rather than put that pressure on myself, know that that is a motivation that is there when kind of something speaks to me that I would like to be helpful with, that's great. That can act as a form of motivation.

But I think at the meantime, finding something where I feel like I can learn and grow on the things where I want to grow and get better is kind of like the core motivation that is driving me. And I'm kind of in call it this like search process for finding what that thing is.

Yeah. So you've talked about this idea of searching for purpose. How is that search going for you?

Ongoing. I can get very high level and in my head around these like very philosophical questions. Like, "What is my purpose? Am I enjoying the work I'm doing? Do I feel fulfilled right now in this work?" And it actually creates a lot of stress for me because it creates a lot of gravity, and like importance to the work that I'm doing I think too much where it actually loses its fun. And so to answer your question, have I found my purpose? No, I have not.

I've started to triangulate on the things that bring me a level of joy in the things that I'm good at. I genuinely love understanding people's stories. I genuinely love building relationships with people and I genuinely love teaching people. And so it's something I've spent a lot of time thinking about is how can I use my experience in entrepreneurship to teach people? And there are different ways that can manifest. That can be, how do I teach underprivileged teenagers, high schoolers, et cetera, how to start their first business and think about entrepreneurship?

How can I teach people via career coaching or executive coaching? How can I teach startup founders by investing in being an active participant in them? I haven't figured out the how yet of how am I going to do that, but I know those are things that are important to me.

So what advice would you give to someone who is really resonating with this around like, "Okay, yeah, I've achieved success that I know my younger self would have thought would've brought me all of the purpose and motivation I needed. Here I am, I'm not necessarily feeling all the things I thought I would feel." What advice might you give to someone in that position?

My advice would be a combination of try not to put so much pressure on yourself, but also I don't think you can start self-discovery and development work too early. I think a lot of the work that I'm doing today, basically better understanding how I think what gives me good energy, what doesn't. I think the issue is in a lot of ways it's either felt very prescriptive to people, or it's in a way that doesn't feel approachable, or it's felt very fufu in a way that people are like, "Oh no, that's like spiritual shit. That's not for me." But I actually think there's so much value in kind of the work of understanding how all of us think because we're not very unique.

And then also kind of how I personally think and the thing that drives me, energy and joy and being aware of that, like having an awareness of my emotions, it's been largely helpful for me. And I think there's no regrets, but I would just say if I understood the power of having tools to understand what lands for me, what doesn't. Like knowing that following things that give me good energy is generally a good path and having an understanding of what those things are. If I knew the importance of that, I would've just started it earlier.

Mm, for sure. Well, obviously, I'm big fan of growing our self-awareness as early as possible. And I really appreciate you talking to us about these things because you are far from being the only one who has grappled with this. And I think the more people are honest about their experience, especially people in positions of privilege can be honest about their experiences, the better it is for everyone.

So what I'm going to end with is what we end every Taboo Tuesday with is I'm going to show you a list of taboo questions about all kinds of different topics, read through them, pick whichever one is your favorite, read it out loud, and then answer it for us.

Okay. I'm going to answer what is one trait that you find yourself being envious of in other people?

Great.

So one thing that I'm envious of in other people and I think about this in the context of business, but I think it happens in other areas of life also. When something really good happens to someone, and people I know just genuinely feel great for them, and feel happy for them. Unfortunately, the way that I am wired, especially in business when something good happens to someone, I would be lying to myself if my first emotional reaction actually didn't feel threatened and insecurity because of my competitive nature. And I hate that about myself.

Oh my gosh, that's so common though. Envy is such a taboo stigmatized feeling, but it is a rare, rare person who does not feel a little bit threatened by other people's success. So let me just normalize that a little bit.

Yeah. And it's just something I feel guilty about because I would love to feel super happy for everyone. But also, again, I try not to judge it.

Those aren't mutually exclusive though. I feel like that's my big thought around envies. You can feel threatened, you can feel jealous, you can feel upset, and be happy for them, and want their success. I mean, those things can coexist.

Yep. And I think that's an important point because I think if people aren't aware that kind of both can be true, people will feel almost like they're being inauthentic if they try to be happy for someone because they have the first feeling of envy. So I think that's a good point. And then I'm going to answer with two things. I'm sorry, I'm breaking the rules.

The second thing is because I naturally see myself as kind of like a, let's say, creative founder who I am very much like an idea person, am a relationship builder, kind of like those qualities. I am envious of people who I view as like super focused, super linear thinkers, super analytical. Because at the end of the day, I think we feel envy towards things that we feel like we are lacking and that's kind of one of my areas where I feel insecurity.

Yeah, I resonate with that also. For me, people who can just do the work for hours on end instead of just wanting to think about the work, I think that's an amazing superpower.

Totally.

Well, Alex, I can't thank you enough for this amazing conversation I could go on and on with you about this. Thank you for coming on for sharing all of this experience and I look forward to more conversations soon.

Thanks so much having me.

Thanks for listening to Emotionally Fit hosted by me, Dr. Emily Anhalt. New Taboo Tuesdays drop every other week. How did today's taboo subject land with you? Tweet your experience with the hashtag #emotionallyfit and follow me @dremilyanhalt.

Please rate, review, follow, and share the show wherever you listen to podcasts. This podcast is produced by Coa, your gym for mental health where you can take live therapist-led classes online. From group sessions to therapist matchmaking, Coa will help you build your emotional fitness routine. Head to joincoa.com, that's join C-O-A.com to learn more and follow us on Twitter and Instagram at @joincoa.

From StudioPod Media in San Francisco, our producer is Katie Sunku Wood. Music is by Milano. Special thanks to the entire Coa crew.