Morning Brew founder Alex Lieberman - what B2B marketers get wrong

Alex Lieberman is the co-founder of Morning Brew, a business newsletter with over 4 million subscribers. Alex founded Morning Brew in his dorm room and sold a majority stake to Business Insider for $75 million in 2020. In this episode, Alex and Auren discuss: Why B2B marketing is brokenThe future of influencer marketingFinding purpose after the exitGeneration media consumption Looking for more tech, data and venture capital intel? Head to worldofdaas.com for our podcast, newsletter and ...

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:01Auren Hoffman?

  Hello data nerds. Welcome to World of DAS. I'm your host, Orin Hoffman, CEO of Safegraph and GP of Flex Capital. Discover more episodes, get weekly data as a service news at worldofdaas.com. That's spelled world of D-A-A-S dot com. Hello data nerds. My guest today is Alex Lieberman. Alex is the co-founder of Morning Brew, a newsletter with over 4 million subscribers. Alex founded Morning Brew in his dorm room and sold a majority stake to Business Insider for $75 million in 2020. He also co-founded Story Arb, a content marketing agency, and is the host of the Founder's Journey podcast. Alex, welcome to World of DAS.

• 0:45Speaker 01

  Thanks for having me. Pumped to do this.

• 0:46Auren Hoffman?

  I'm very excited. Now, B2C marketing is super dynamic, but in contrast, B2B marketing just doesn't feel like it's changed nearly as much. Why is that?

• 0:59Speaker 01

  Yeah, it's funny. I can't remember who said this, but I generally believe that people go into B2C to look cool. People go into B2B to make money. B2B marketing has generally lagged B2C in kind of every facet for two reasons. Partially, it's a talent issue. Oftentimes, the best, most creative marketing talent goes to consumer companies because there's a natural incentive of if you're a marketer, you want your work to be seen by as many people as humanly possible.

• 1:30Auren Hoffman?

  You want the Super Bowl ad or something.

• 1:32Speaker 01

  Exactly. So I think partially it's dictated by just talent. The second part of it is that B2B is very driven by herd mentality. It's very driven by the need for attribution. B2B has always been driven by like demand gen and even marketing being so intertwined with your sales org, which that's not how B2C works. The issue is the second that marketing orgs try to

• 2:01Speaker 01

  Do things that are more creative or more top of funnel in B2B attribution gets harder. As attribution gets harder, because B2B CEOs and CFOs are oriented to thinking about things very simply from a return on spend perspective, people very quickly put the kibosh on creative efforts in B2B. So I can only count on one hand, the number of B2B companies that I actually think are pushing the envelope in marketing. My thing is, what are B2B companies that are not just impressive for B2B, but actually B2C companies can learn from? If that was the proxy, I would say there's maybe two companies, definitely one, that are great

• 2:46Speaker 01

  at marketing. Everyone else, I think it's like meh.

• 2:49Auren Hoffman?

  A lot of B2C companies founders were marketers at some point in their career. Whereas in B2B, it's pretty rare for the founder to come out of marketing. Marc Benioff might be like the only exception. Marketing's always been so core for Salesforce from the original no sales software thing to Dreamforce to all the other things. And just, he's got that DNA built in.

• 3:14Speaker 01

  Just to use an example of a similar giant of the industry, which is the example that I was referring to when I said there's one B2B company that I think B2C companies should actually look to for inspirations, it's HubSpot. I think what everyone thinks about when they think of HubSpot marketing is they think about the SEO-driven blog. They were the first to pioneer that. And at a point, it actually became associated with the things people don't like about SEO, which is very lowest common denominator 101 type content. But if I look at what HubSpot's doing today, from a marketing perspective, it's super smart. They bought the hustle for, I think, $22 million. They basically used that as their anchor property to start up their HubSpot creator network.

• 3:58Speaker 01

  And the reason I think it's so smart is because what HubSpot has basically said to itself is, we are a software business. We are not going to be able to have the world's greatest talent for media and content. So instead, let's just build the infrastructure that supports the best creators and content minds in the world. Let's either partner with them deeply or acquire them. So even last week, they acquired another AI newsletter. In their podcast network, they have a dozen podcasts. Some of them they own, some of them they just offer the infrastructure to, to be part of the network, the production capabilities, editing capabilities, monetization, et cetera. I think they're doing it exceptionally well. And I think more and more, as marketing gets more expensive, both in B2B and B2C, companies are going to have to make the decision of,

• 4:44Speaker 01

  do they want to effectively build their own media company and function more like a media company? Or do they want to partner with the best media talent? And to partner with the best media talent, you have to offer them something. You have to give talent something that makes it worth saying you're part of this company's network or you're a creator in residence or whatever. HubSpot is the closest to doing that.

• 5:06Auren Hoffman?

  There are some like VC firms, which are essentially B2B businesses that have a great media arm associated with it. If you think of like Andreessen Horowitz, they do a really good job on the media side.

• 5:17Speaker 01

  I agree. They launched Future a few years ago, which was like their media website. I haven't heard a thing about it in the last year or two.

• 5:25Auren Hoffman?

  That's a good point. They kind of stopped it.

• 5:27Speaker 01

  You know so much more about venture than me, but my general observation has been in venture, you have to have some spiky point of view and your spiky point of view either can be around a brand and content. It can be around your niche. We are the fintech investor. We are the frontier tech investor. Or it can be around stage. Andreessen has done probably the best job. I'm trying to think who else.

• 5:51Auren Hoffman?

  Hacker News is like the Y Combinator. Again, maybe they're not putting out the content, but they've created a media brand there that a lot of people go to.

• 6:00Speaker 01

  I think to that point, YC has been one of the best in creating a content ecosystem. I think First Round has also done a really good job with First Round Review.

• 6:09Auren Hoffman?

  Now, when you're talking to somebody and you're trying to evaluate talent, whether you're trying to hire them, how do you evaluate if someone's good at marketing? I've always had a real tough time there.

• 6:18Speaker 01

  It depends what type of marketer you're looking for, what your needs are, and what stage of business you're at. And how I think about it is, marketing is this thing that lumps together so many different disciplines, from SEO to the paid search, to organic, to event marketing, to content marketing. There's so much. Before you even ask yourself that question, you kind of need to understand, basically, are you at a place as a company where you know what works and you want to go an inch wide and a mile deep? Once we knew at Morning Brew that we were able to get super efficient with paid acquisition to get high-quality newsletter subscribers,

• 7:01Speaker 01

  the marketer that I was looking for was the type of person who I was confident could scale Meta and the different programmatic channels, who could spend $500,000 a month, and they have a proven track record of doing so. Before getting to that point, honestly, what I was looking for was someone who was an entrepreneurially-minded, generalist marketer, who I believed could create enough structure to run tests and see what works, but also had enough of a flexible mind to be able to test hypothetically five to six different strategies across organic and paid. So like, our first person we hired to do marketing at Morning Brew,

• 7:41Speaker 01

  they had done growth at another media company, but they were probably 25 at the time. And honestly, my best proxy for "I think they can do it" is, I believe that they could be a startup founder one day. My view was, I think this person can be a startup founder one day, and they have a marketing orientation to them. And now this person is a startup founder running another business that they started since leaving the brew.

• 8:07Auren Hoffman?

  Influencer marketing is really big already, but there isn't a brand or a huge company around that yet. What is your feeling about where that goes?

• 8:19Speaker 01

  I've kind of had this dream slash view for a while that what William Morris Endeavor has built over the last 30 years, no one's done that in the digital age. Endeavor is a $5 billion publicly traded company that started with their representation business. Their agents were repping influencers at the time, which were actors, producers, directors. And then after they grew up representation, that's when they went into other things like owned IP. So now they own WWE, UFC, PBR. They actually own entertainment technology now and live events. And my whole view is no one has kind of built this three-headed monster for the digital age.

• 9:01Speaker 01

  The ones who have gotten closest to it, I think that Viral Nation is a really big influencer marketing business. They have tens of thousands of consumer influencers. Basically, they help brands allocate dollars to. So they run end-to-end influencer marketing campaigns.

• 9:19Auren Hoffman?

  So some of these might be small influencers that make one to 10 grand a month type of thing?

• 9:24Speaker 01

  Exactly, and they do go up into larger scale influencers as well. I do think one of the difficulties with when you start working with the long tail of influencers and you have thousands of influencers that you're working with is how do you not degrade the quality of your service? It's kind of the negative economies of scale that any agency business has. I don't think anyone's really cracked that. I think the other big thing is that more and more, unlike back in like the 90s with Endeavor, I think creators have more leverage than ever before. I was talking actually to the president of Viral Nation, and he was saying there are 10,000 agents for creators today.

• 10:08Speaker 01

  So there are 10,000 individual, it can be solo agents or companies. The switching costs are actually pretty low. And there's so much choice that creators and influencers have. That's the new thing that people are going to have to figure out. I don't think you can be a general influencer marketing business and succeed today. You have to kind of niche down. Similar to the venture business, you kind of need to be known for one thing. I think there's a huge opportunity in B two B creator marketing right now. More and more B two B companies are realizing that influencer marketing is important. It's funny, they're like five to 10 years late to do this and they're just starting to get interested in it.

• 10:49Speaker 01

  To me, there's no go to household name for B two B creator marketing to help brands do this. I also think you've seen a number of creators launch businesses. That's become a huge thing. The Mr. Beast of the world have launched Feastables. I think the only way it works to partner with creators in some way, whether it's to help them with brand deals or to launch businesses with them, is you need to be known as an expert in your thing. For example, Dwayne The Rock Johnson has Terra Monet Tequila. Conor McGregor has Proper Irish Whiskey. J Lo just launched a spirits brand. All three of them were co-founded with Ken Austin, who has become known as the operator for any celeb who wants to launch a spirits brand.

• 11:32Speaker 01

  More and more, you're going to necessarily need verticalization.

• 11:35Auren Hoffman?

  Obviously, I'm going to go to you right now and say, because you know a lot about newsletters, but you might not know a lot about burger joints. So they should come to you to help you with the newsletter and maybe go somewhere else with the burger joint.

• 11:46Speaker 01

  A hundred percent. If I was trying to build the next gen endeavor, the way I'd think about doing it is how do I create a wedge to help an influencer either work with B two B companies that they don't have access to? And I try to build my wedge in B two B influencer, or I try to help them launch newsletter? And then as we continue to grow relationships with them, I bring in potentially a GM who knows a lot about the next vertical that makes the most sense for the roster we're already working with.

• 12:13Auren Hoffman?

  What do you think of like community products that are out there? Sam Pars community or some of these other community products that are out there?

• 12:20Speaker 01

  You're saying something like Hampton, these next gen YPOs?

• 12:23Auren Hoffman?

  And maybe you can even build it around an influencer, potentially if there's like a CFO influencer, you could build a CFO community.

• 12:30Speaker 01

  I think it also creates an interesting question around where is there the most value to be created? Is it at the software level? Do you want to be Circle or two or three other businesses that allow you to stand up communities? Or do you want to have the niche communities yourself? I do think there's a huge opportunity, specifically again in B2B, to build high dollar price communities that members put on their company's card. Because you look at the state of communities for senior marketers, senior procurement people, senior finance people, it's like these old school trade organizations. And by the way, you're seeing companies start to do this. So obviously you have what Sam is doing, but then you have another business like Workweek.

• 13:12Speaker 01

  Workweek is a media business that is exclusively working with B2B creators. Imagine like the Barstool playbook, but instead of sports personalities, it's B2B personalities. Their personalities are like someone who is a CHRO, who all their content is around HR. Someone who is a marketer and all their content is around marketing. And the way right now they've raised venture money, and I think their big play is not actually their media assets. They're starting to launch community products where people join to be members of a CHRO community, et cetera.

• 13:47Auren Hoffman?

  Most of these trade organizations are horrible. The conferences are just mind-blowingly boring. The content is terrible. It's just a bad experience all around. Anyone who's like redesigning that from scratch is going to come up with something so much better.

• 14:04Speaker 01

  I also like honestly, just playing in spaces where there's a combination of IQ or standard arbitrage. I always say, one of the reasons I was successful in Morning Brew is I went from working on a trading desk at a bank to working in media. There are smart people in both fields, but the average IQ is lower in media than it is on my trading desk at Morgan Stanley.

• 14:26Auren Hoffman?

  And also the number of hours you're willing to put in. So you have like a doubling effect there.

• 14:31Speaker 01

  Exactly. If you want to win as a marketer and your goal is just to like be the most successful in building either marketing programs or growing a marketing org or building a business that helps companies improve their marketing, to me, it's so much easier in B2B than B2C. To stand out in B2C, you actually do probably by nature need to be more skillful because competition is just so much harder.

• 14:57Auren Hoffman?

  And then of course, if you're competing with trade relationships, well, they're usually like nonprofits. They can't always attract the most talented people because they can't pay people. They can't give them stock. People there are like real mission driven. Are you really that mission driven if you're working for the average trade organization? Anyway, you might be clocking it in. You might not be working as hard. And so if you're competing there, you may have a lot of other opportunities to win.

• 15:21Speaker 01

  I'm mind blown that this stuff still works, but I still talk to B2B marketers who say their webinars still drive so many leads. It's mind blowing to me, but I would have to believe at some point when the next generation of management turns over, people are going to be like, this is just dog shit and we need something better.

• 15:40Auren Hoffman?

  There is something in B2C where you would never just completely bore someone in B2C. Imagine going to like a Taylor Swift concert and being like, this sucks. It's so boring. You're just sitting around and it's there's no light show and no nothing. B2B is just like that. They just love boring people.

• 15:59Speaker 01

  It's wild. This was our whole thesis with Morning Brew when we launched our industry newsletters. After our daily newsletter, which was our consumer newsletter, we launched our professional newsletters, which is Retail Brew, Marketing Brew, CFO Brew, HR Brew, et cetera. And the thesis was We think that we can bring the same tone and conversational voice that we did with the daily newsletter to B2Bs. Let's just say the conversational tone on our daily newsletter is like a seven out of 10. Our whole view was we could have it be a five out of 10 in B2Bs, yet the impact to the reader could be even higher than in the consumer because the bar was so low for people before. And that has been true. And actually, if you were

• 16:40Speaker 01

  to ask me, what is a better business long-term? B2B media is a fundamentally better business than B2C media because the bar is lower, because people need it to be successful in their job, and because the average value of a customer is so much higher. CFO Brew, a fintech or like an accounting software, they need to convert one person because their average customer is paying $100,000 a year. And so the math is just easier.

• 17:06Auren Hoffman?

  Learning Brew is kind of like the quintessential millennial brand in a way. You put a lot of stock in the idea of all these generational differences?

• 17:14Speaker 01

  100%. People have been saying for a while, email's gonna die, people aren't gonna use email anymore. And I don't think that's true, but I will say that I think that younger generations are using email less than I am or you are.

• 17:30Auren Hoffman?

  I freaking love email. I think email is the greatest communication mechanism ever invented in history. I love it, but I am somewhat a minority on that one.

• 17:41Speaker 01

  Yeah, it's incredible. But I think for the 13-year-old, again, I don't know that many 13-year-olds. When I've talked to even like my cousin, who she's senior in high school, so she's 17. When I ask her what platforms does she use most, email does not come up. It's YouTube and Snapchat for her.

• 17:59Auren Hoffman?

  Yeah, if they're getting emails, they're getting emails from like their teachers or something.

• 18:03Speaker 01

  Exactly. And so I think of the media business as a hits-based business where every product you come out with has a certain shelf life to it. And if you're really successful with a product, the shelf life is five years. If you're generationally successful, the shelf life of your media format or product is like 10 to 15 years. Talk about Hot Ones or Joe Rogan, they've been around for so long, that is a complete outlier. And I would say for most products, their cycle of relevancy is like one to two years. And so the way I think about how you build a great media business is you basically need the right orientation of talent and the right culture of trying new shit constantly.

• 18:46Speaker 01

  For Morning Brew's daily newsletter, at some point, it's going to exit the window of relevancy. And we're going to need something that is going to be the fast growing follower to pick up growth. In thinking about what that fast growing follower is, if you were to ask me, what is that in Morning Brew's business today? It's our YouTube channels and it's our creators that we're working with to create content for the next generation. And to be totally honest with you, there's a lot of content our creators at Morning Brew create that absolutely crushes on Instagram or TikTok or YouTube. I watch it and I'm like, this is not for me. This does not resonate deeply with me. But then you look at the comments and people absolutely love it.

• 19:27Auren Hoffman?

  These shorts are really engaging. For some people, they just love those shorts. They just watch them while they're in the bathroom or something like that.

• 19:34Speaker 01

  That is a big shift that founders have to go through in various ways, which is when you all of a sudden are no longer your core consumer. When we created Morning Brew in the early days, I was our reader. So I could make recommendations and be like, this is what I want. And I believe if we extrapolate me, the rest of our audience will want that. That doesn't work for a lot of our content anymore.

• 19:55Auren Hoffman?

  You can make an argument then that you should be playing to your core competency and focusing on the folks you know most, which is why like your B to B might be a better play now. Whereas when you're 22, B to B might not have been such a good play.

• 20:09Speaker 01

  A hundred percent. Now, the risky part about that is it's why, when I talked to the Wall Street Journal as we were building Morning Brew, people would tell me, what you guys are doing makes so much sense. We should buy you, but we're not going to because we're focused on the 60 year old who's paying our bills right now. But at some point, that 60 year old is not going to be paying our bills anymore. And we are going to be wishing that we focused on the 22 year old.

• 20:34Auren Hoffman?

  Now, if you went back five years, what other advice would you give yourself in kind of the Morning Brew days?

• 20:40Speaker 01

  I'll go back four years. I believe our hearts and our intuition very often leads our brains. And so I think there was a period of a year where I knew that my energy and my heart was not in morning brew anymore. And I think it took me a year to a year and a half to drop my ego and allow my mind to catch up to it. For me, the reason for that was is I am very much an early-stage builder. I love the zero to one of companies. I love when building a business feels like art and artisanship. The point at which the brew felt less like artisanship, we had 50 people and it was about org building, implementing OKRs or EOS and

• 21:21Speaker 01

  all these things. It felt less fun to me. It took a year for me to accept that and realize that it's okay to not love building your company for 20 years straight. For me, a big reason that I kind of had this ego around it is I admired these career-long entrepreneurs.

• 21:41Auren Hoffman?

  Mark Zuckerberg or something.

• 21:43Speaker 01

  Yeah, those were always the examples that were talked about publicly. Zuck or Evan Spiegel or Elon, all these people who took it from ideation to public.

• 21:52Auren Hoffman?

  Jetzwag, like all these folks.

• 21:54Speaker 01

  Exactly. And so I set the standard for myself. Oh, of course, I both have to love every part of the journey and I have to be exceptional at every part of the journey. And I think entrepreneurs need to feel more permission and actually encouraged to admit to themselves when they no longer getting the same energy, because the second that happens, I think the odds of their business succeeding goes down. And the best thing they could possibly do is to find the right person who gets the energy that they had in the previous five years.

• 22:20Auren Hoffman?

  Finding that person is really hard and it's very, very risky.

• 22:24Speaker 01

  A hundred percent. And by the way, that's why I feel so grateful. We talk about luck in business all the time. The luckiest choice that I made was picking my co-founder. I had good intuition to pick someone who was very smart, had similar values to me, and I felt like he had a totally different brain from mine. That was 10% of the skill. But what I did not at all know was that when I handed the baton to Austin, my co-founder, he felt most in his zone of genius in the org building stage of the company.

• 22:56Auren Hoffman?

  Plus, he's still our founder. She still has the credibility to make the hard changes and do things that are unpopular.

• 23:04Speaker 01

  Exactly. And I do believe a lot of times the best stage two CEO for a startup is someone who is a stage one COO, because I think the skills of a stage two CEO look a lot like a stage one COO.

• 23:18Auren Hoffman?

  Though sometimes it can backfire. Steve Ballmer, I think, did an okay job, but Microsoft's going through a very tough time in the early 2000s. But it probably would have been better to get like a more product oriented CEO than pick the number two. Or if you think of like Zuckerberg and Sheryl Sandberg, if he left, she probably could run Facebook fine, but she would have been maybe better running Goldman Sachs or Citibank or something like that.

• 23:42Speaker 01

  I totally agree with you. It is the riskiest decision you can make. And that's why I feel very grateful I had Austin. It's why, for some people, being a solo founder works just fine. For me, for a variety of reasons, having a great co-founder is really valuable to me. Not even just the accountability and partnership, but also in some ways to know that you have another possible option before having to go look externally.

• 24:08Auren Hoffman?

  Now, a lot of founders go through this post-exit malaise where they're going through, okay, what should I do next? Or should I top the thing that I'm doing? Or Elon Musk put all of his chips back on? How do you think about it?

• 24:20Speaker 01

  I have absolutely experienced post-exit blues, and I've experienced it in different phases. I experienced it a lot right after stepping out of the CEO role at Morning Brew in April of 2021, where I went from working 70 hours a week on Morning Brew to zero hours a week. And all of a sudden, I had an empty calendar. And I was like, what do I do my whole day? For a period of time, I was occupied and let's call it distracted.

• 24:45Auren Hoffman?

  Making all these angel investments or doing all these random things.

• 24:49Speaker 01

  Yeah, exactly. I went into making a bunch of angel investments. Then I stood up a new business, which was Storyarm, that I was very involved in for like 12 months. But then my CEO and co-founder took it over. And I'm back in this place. I have nine hours a day of free time. And I'm like, what the hell do I do other than go on podcasts and tweet? I do think a big thing that shapes my energy and how I spend my time is the fact that I lost my dad in college. He was 47 years old. I was 20. He was perfectly healthy. And one day, he was alive. One day, he wasn't. Everyone talks about the fragility of time, but unfortunately, I believe there's some lessons in life that you just feel more when you experience them.

• 25:29Speaker 01

  I give that context because something I know I can't do is even if there's a huge business opportunity, let's just say I went through the exercise of spending a month finding what is the biggest possible growing market? What's a massive problem? What's something that I could believe could be a $100 billion business? Even if I felt like I was equipped to do it, I couldn't just go build that thing for the goal of building a $100 billion business. That would not be able to keep my energy, like keep the light burning. I need to feel some sort of intrinsic drive in a way that I never did. The other thing is I feel very grateful for having an outcome from the brew where I have financial freedom. I always find it interesting.

• 26:13Speaker 01

  People say financial freedom gives people the freedom to choose how they spend their time or the freedom of time. And I think it's like a misnomer. What you want is not endless time. You want the ability to spend your time exactly what you want it because I can promise to anyone listening, 12 hours a day of not knowing what you want to do. I wouldn't wish that on my worst enemy. You want the ability to spend your time exactly as you want to. Coming out of the brew, I felt less motivation towards things. I felt less identity. I felt less of a sense of purpose. Where I stand today is I have a clearer sense of my identity. My identity was entirely pent up in Morning Brew.

• 26:56Speaker 01

  Today, I feel like my identity really is balanced.

• 26:59Auren Hoffman?

  You got married around that time too?

• 27:01Speaker 01

  I got married just over a year ago.

• 27:03Auren Hoffman?

  So you're probably already in that process when you're sold it and everything.

• 27:06Speaker 01

  Exactly. But I would say around the motivation and purpose piece, I still am lost on that because my general strategy right now is I'm like tinkering with projects and my general thesis is at some point, if I create enough thoughtful surface area, one or two things is going to really speak to me and I want to dive in. But there's always the little birdie in the back of my head that's like, Alex, you need to build something bigger than the brew. Alex, you need to have a huge impact on society.

• 27:36Auren Hoffman?

  You don't want to be like 20 years later, you're Clinton of fame is ex Morning Brew founder.

• 27:42Speaker 01

  The way you even just spoke through that is what I'm trying to figure out. Am I okay with this idea that Morning Brew could potentially be my biggest claim to fame ever professionally? Would I be okay with that if personally in my family life, that's where my next claim to fame is? And I crush it as a father, as a husband, as all of these things. I think what's also hard for me is after you've built a business, you know how fricking hard it is. It's like the famous Jensen Huang interview quote now where the acquired guys asked him, would you do it again? Would you build Nvidia again, knowing what you know now? And he says, no.

• 28:16Auren Hoffman?

  There is some amnesia. It's like when women have kids, they forget how hard giving birth is. That's the only reason you would do it again.

• 28:23Speaker 01

  Totally. Even now, when I'm starting up a new business and like I'm on sales calls after three sales calls, I'm like, this fricking sucks. I could not spend even like a week doing this. Whereas in the early days of Morning Brew, I was on sales calls with advertisers for 10 hours a day for months straight. I find my threshold for like sucky work is so much lower or like my tolerance is so much lower.

• 28:48Auren Hoffman?

  That's tough because you need to do sucky work to build something great.

• 28:52Speaker 01

  If you're going to build something great, you have to. I'm in the market for trying to figure out what it is while also knowing I'm not going to have likely this epiphany. I'm not going to have this vision one day of, oh, I'm going to build this massive company that's going to save the world. It's so interesting because I've talked to now maybe 50 plus post-exit founders that have experienced some permutation of what I'm describing. And when they talk about finding their purpose after it, a lot of them will say it's like still a work in progress. Or a lot of them will say, I didn't have this come to Jesus moment. I just was tinkering around with things. Something really felt right to me and I've just decided to spend time on it.

• 29:34Speaker 01

  And all I know is what I don't want my answer to be is to go build three more companies because that's what I'm supposed to do. That is what I know I don't want to do.

• 29:44Auren Hoffman?

  You mentioned your dad's passing when you were 20. I imagine that had just a massive effect on how you thought about life, how you think about what you want to do in your career. Can you walk us through some of that?

• 29:56Speaker 01

  The most sadness that I hold towards my dad's death is actually not being able to be with him today. Obviously, I have sadness towards that. It's actually sadness for him because my dad was someone who worked his ass off to get to where he was. He worked in finance, but he didn't go to an Ivy League school. So he didn't have this very clear path of going through rotational program and having the next 20 years. He started as like a bank teller in a branch at a bank, and he made his way up to running multiple trading desks at Citigroup by the end of his career, and he worked his ass off to do that.

• 30:35Speaker 01

  I think my sadness I feel is that he didn't get to truly see all the fruits of his labor, both for himself personally and also the time he put into his kids. I feel so much gratitude towards this guy would wake up at 5:00 a.m. every day, get back from work at 7:30. I'm sure he was exhausted and wanted to do anything other than helping my sister and I with our school stuff, yet he would spend the next three hours helping us with our school stuff for like decades. When I reflect on why my dad was such a great man, of course, it was how he was able to get to such a great spot professionally without starting on third base. But it was the amount of effort and true care he put into giving my sister and I

• 31:19Speaker 01

  the foundation that got me to where I am today and got my sister to where she is today. For me, a big thing is I want to figure out when I ultimately figure out some of my professional purpose, how can I do that exceptionally well? How can I also crush my personal and family purpose? When I do ultimately have a family, I want to be an A dad. And is it possible to be an A dad and an A builder of anything professionally?

• 31:48Auren Hoffman?

  And you don't have kids yet. Do you have a thought in your head? I want to have one kid, six kids, 20 kids.

• 31:54Speaker 01

  In my perfect world, three kids. Living in the suburbs of New Jersey, maybe a ski home in Colorado, go on one to two nice family vacations a year and that's it. That is happiness to me.

• 32:07Auren Hoffman?

  That would be happiness to most people.

• 32:09Speaker 01

  Totally. I think the big question in my head is when money is no longer really an object, how do you find the thing that acts as as strong of a motivator as when that was the primary motivator? I've talked about this with my buddy Jesse Pujee, who's an entrepreneur a lot.

• 32:25Auren Hoffman?

  Also a past role of DAS guest.

• 32:28Speaker 01

  Yeah, exactly. And we've talked about this a lot because him and I both are big believers in Conscious Leadership Group and the 15 commitments of conscious leadership. And there's fear-based motivation and growth-based motivation. I think in building Morning Brew, a lot of my motivation was fear-based motivation, which was fear of not having enough money, a fear of not being accepted by people, a fear of not belonging. And those things were such strong motivators.

• 32:52Auren Hoffman?

  Yeah, especially when you're young.

• 32:53Speaker 01

  Exactly. And those are not that strong of motivators anymore. I still care about money. Don't get me wrong. Like, I don't think I could just go start a nonprofit today and feel fully settled. But I know those can't be the only motivators. And so what I'm trying to figure out is how can I find the thing that lights me up in the same way that I was lit up by my old form of motivation in the first five years of Morning Brew?

• 33:16Auren Hoffman?

  And you think your father's passing made you also want to prove something? Like, so many well-known entrepreneurs have had issues with their fathers. Elon Musk, a lot of them have had absent fathers who didn't even know their fathers. Steve Jobs, Jeff Bezos, Larry Ellison. Some of them have had early fathers passing away. Do you think some of that helped your motivation?

• 33:39Speaker 01

  So I think there's two things. One is like adjacent to my dad's passing, which was my mom had worked on Wall Street for 20 years, but she had retired prior to my dad's passing. So after my dad passed away, there was no breadwinner in the Lieberman family anymore. And so I very much had this fear. I'm a very visual person, and so I had this visual constantly of like a pile of money with the name Lieberman on it.

• 34:03Auren Hoffman?

  Just like slowly going down.

• 34:05Speaker 01

  Yeah, exactly. Just slowly going down in like a little vacuum cleaner, sucking it up little by little.

• 34:10Auren Hoffman?

  You say he was 47, so your mom's young at the time.

• 34:13Speaker 01

  Say my mom lives to 90, that's many years of not having income and also having to pay for her kids. That was a huge thing in my head was baseline, I no longer wanted my family to have to pay for anything for me. And also what I promised my dad, when my dad was in the hospital and we knew that he wasn't going to make it anymore. I whispered to him saying that I was going to take care of my family and I literally like in that moment pictured handing checks to my sister, to my mom. I did not grow up really knowing my family's exact financial situation. I knew roughly socioeconomically where we stood.

• 34:55Speaker 01

  We're upper middle class and so I didn't know to what extent it was actually a rational or irrational thought to want to take care of my family. But that was one thing I promised my dad. And so that became something that drove me forward. The other thing is I was bullied a lot growing up from fourth grade to 12th grade. I was bullied. That's why like honestly, everything in my life has felt like a cakewalk since then. Imagine for like nine years, not feeling like you're belonging at school every day and feeling like people are picking on you.

• 35:28Auren Hoffman?

  That's so common for most entrepreneurs. Part of the reason you become an entrepreneur is because you kind of feel like you're not really fitting in and stuff like that. Otherwise you just stay in that job in finance that you had.

• 35:39Speaker 01

  I think a big part of my motivation also was just proving all these people wrong that I felt inferior to for nine years straight. How do you go from like this incredibly powerful form of motivation? Once that form of motivation is gone, where do you conjure up that similar fire in your belly? Or is it not possible and the motivation has to look different? Is it the difference of lust and like passionate love in the beginning of a relationship versus a slow burning love? It's an interesting thing to think about how motivation shifts.

• 36:09Auren Hoffman?

  You've got a podcast called imposters where you and your guests talk about mental health challenges and stuff. What are some of these through lines that you've noticed?

• 36:17Speaker 01

  The best description I've heard of imposter syndrome was by Jay Shetty, who's a friend and he was on the podcast. He has a great podcast called On Purpose. He basically said that imposter syndrome is the gap in your current skills and your ultimate goals and your goals sit above your current skills today. And he's like, when you think about it like that, not only is imposter syndrome something that many people have, but it actually should be the goal because if you don't have your current skill set being lower than the goals you want to achieve for your business, how are you going to grow? How are you going to be ambitious?

• 36:56Auren Hoffman?

  But a lot of people overestimate their current skills. Then you would think, okay, if you're overestimating, you would have less imposter syndrome.

• 37:02Speaker 01

  It is interesting. If you were to ask me like who I would bet on, it's generally the person that doesn't overestimate their skills. It's the person who underestimates their skills, but they don't let that get in the way of them continuing to push forward. I think that imposter syndrome is not only so common, but I also think it is so shaped by people's early life experiences. The reason that I experienced imposter syndrome and other people on the show did is because they had some experiences earlier in life that made them feel that they were lesser than and they were not capable. My hot take is imposter syndrome happens more frequently to people who had

• 37:43Speaker 01

  challenges with self-confidence early in life and they still feel the residue of that today in certain contexts.

• 37:50Auren Hoffman?

  Interesting. They're definitely friends of mine, I think, who've been very successful, have had imposter syndrome. But there's also a lot of successful friends of mine who've never had it. They've always felt that confidence. I don't think like Elon Musk feels imposter syndrome. He may have a lot of other mental health challenges, but he's always confident in himself and that he can do something. There's some sort of continuum of people.

• 38:11Speaker 01

  I also think imposter syndrome is not a global feeling that people have. Our life is full of specific verticals of experiences that we have more or less competencies in. And based on the vertical that you're focused on, you may or may not have imposter syndrome. When it came to like me doing sales calls or anything related to selling or storytelling at Morning Brew, I never felt imposter syndrome. I actually felt irrational confidence. When it came to me thinking about, am I doing a good job as the CEO of the business? I felt wild imposter syndrome. Elon Musk probably, when it relates to like solving really hard engineering problems, does not feel imposter syndrome.

• 38:52Speaker 01

  But maybe as it relates to like dating, he feels a ton of imposter syndrome. So I also think imposter syndrome is not a global thing. It's a vertical specific thing.

• 39:01Auren Hoffman?

  You're kind of a creator of businesses. What is a weird business idea that you think would work?

• 39:06Speaker 01

  Have you ever heard of Garanimals?

• 39:10Auren Hoffman?

  No.

• 39:10Speaker 01

  So Garanimals are mix and match clothing for babies and toddlers. Basically what it is, is if you shop for their stuff, you can buy articles of clothing, tops and bottoms, that are made to go together. And so you basically can buy five tops and five bottoms, and they make certain combinations that all work together. So you don't have to, as a parent, think about what's going to match with what. You have sets of clothing.

• 39:38Auren Hoffman?

  That makes perfect sense.

• 39:39Speaker 01

  I believe that can exist for adults. As adults, oftentimes we want to look good, but we don't want to spend so much time thinking about what we're wearing. It's like the old why Steve Jobs wears turtleneck and jeans all the time. And I guess pre-Zuckerberg being cool and having swag, why he would wear his sweatshirt all the time. I believe there can be basically like a pretty elevated version of Garanimals for adults, where it's like nice clothing for men and women. But there's a system, a number system, that if you buy a one on bottom, you know it goes with a one on top.

• 40:12Auren Hoffman?

  What doesn't go with jeans? If you're just going to wear jeans, what would not go with jeans or something?

• 40:18Speaker 01

  I think for two people that maybe aren't in high fashion, probably everything goes with jeans. My guess, if I was to ask like a fashion influencer, they would be like, oh, that is such a faux pas.

• 40:27Auren Hoffman?

  Yeah, there might be like certain shoes or something.

• 40:29Speaker 01

  You're not thinking about layering at all. I know a big thing in fashion is layering. You wear a t-shirt and then you wear like a button down with it. So I think that's one, basically Garanimals for adults. I'll give you a few others. I am surprised that there is not a Yelp for travel itineraries. Meaning there is no place that if you want to travel to a place that you can go and basically find people's itineraries that have been created of all of the places they went. It's like kind of crazy to me and people can have their itineraries rated. People can make money off their itinerary by getting paid affiliate by the things they list on their itineraries. You can be a power creator.

• 41:10Auren Hoffman?

  My wife spends so much time, she's so good at it. She'll do it at 2am and stuff, but she'll spend so much like finding that perfect guide.

• 41:19Speaker 01

  Exactly. And travel is such a custom experience and personal experience that potentially like me asking one of my friends for a Greece itinerary may not make sense either from a budget perspective or like say, my wife and I are more into adventure and not just sitting at a pool all day. And so you could filter for all of these things on this website.

• 41:39Auren Hoffman?

  Of course, like I don't like golf, so it gets rid of all these things.

• 41:43Speaker 01

  Exactly. So I don't know why that doesn't exist because I would use it every day.

• 41:46Auren Hoffman?

  I love that. That's great. Any others while you're on the roll?

• 41:49Speaker 01

  I have a few ridiculous ones. Okay. So one, this is a fun story. The thing that got me into media is actually ironically, I became like the director of a publication at Michigan's campus. It was totally a resume booster for me. I wasn't thinking about it actually being like an important formative experience for me, but it ended up being the only relevant experience to me building a media company after college. And what the publication was, it was called Consider and it was a two-page magazine, print publication that would do a point and a counterpoint on a hot button issue. So it would be like abortion and you would have someone who is pro-life and pro-choice, super well-educated on the topic and it would basically be a written debate for arguing

• 42:34Speaker 01

  each side. I would love to bring Consider to like everyone. What if there was just a print publication? It also doesn't have to be print. I just think print at a time where everything is digital, there's something special about it of the most hot button topics in society that to be a educated citizen of the world you should know about with really well-educated point and counterpoints on these issues.

• 42:56Auren Hoffman?

  Yeah, that's good. I love it. We ask two questions to everybody before they leave. One is what is a conspiracy theory that you believe?

• 43:05Speaker 01

  So there's two that I was thinking about. One was about the government putting fluoride in our water.

• 43:11Auren Hoffman?

  I've heard about this.

• 43:12Speaker 01

  My understanding of the fluoride thing is that the government puts fluoride in the water. So it was a 1950s conspiracy. And basically, the claim was that fluoridization was a communist plot to undermine American public health and that basically it would be used as a way to hurt health of Americans so that Americans would need to receive more health and it would boost our healthcare system. That was one of the conspiracies.

• 43:41Auren Hoffman?

  It's interesting because my dentist told me I should stop drinking bottled water and drink tap water. He's like, it's so much better for you. And it's like, just drink the tap water.

• 43:49Speaker 01

  I feel like this is like a very hot thing right now because that's what I always understood is fluoride in water was good for your teeth. I think there are recent studies that have come out saying that fluoride is poison for you as a human.

• 44:00Auren Hoffman?

  Oh, interesting. Okay. I'm not going to be brushing my teeth anymore.

• 44:03Speaker 01

  Yeah. The other one is just the whole alien argument around aliens on Earth. Are we in the presence of aliens? If that was a conspiracy, I don't know what that's considered, but I am fully subscribed to the idea that we are on Earth with aliens today.

• 44:20Auren Hoffman?

  You think there's another life form that's super intelligent that is interacting with us in some sort of way, but they're making sure we don't see it?

• 44:30Speaker 01

  I think the most likely scenario is that alien life has experienced our planet and had the observation that we are so dumb and so single minded relative to their capabilities. It would be as if I saw an ant on the floor of my apartment and I explored deep conversations with that ant a little bit further. So that's my belief. It's just we're a waste of time for smarter forms of life.

• 44:56Auren Hoffman?

  I like it.

• 44:57Speaker 01

  Do you have one, by the way?

• 44:58Auren Hoffman?

  Oh, I have so many conspiracy theories.

• 45:01Speaker 01

  Okay, we'll have to spend a whole nother podcast on that.

• 45:03Auren Hoffman?

  We could do like 10 podcasts on all my crazy conspiracy theories.

• 45:06Speaker 01

  Love it.

• 45:07Auren Hoffman?

  Last question we ask all of our guests, what conventional wisdom or advice do you think is generally bad advice?

• 45:13Speaker 01

  This is going to be a very timely one, which is follow your passion is one that's been debunked a lot. I'm going to talk more specifically around like follow your energy. People say as you're thinking about the next business you want to build, figure out what gives you energy. People always talk about like, look at your calendar from the previous week and color code the things that were energy positive versus energy negative. And I think it's a load of bullshit. I think back to my early days of Morning Brew, you were talking about it before, like there's some amnesia, it's hard to remember the exact thing. I do not believe that I was so energized on day one about writing a PDF for myself and for students, feeling like I was changing the world with it and feeling like

• 45:58Speaker 01

  this deep energy around it. I believe energy came later. Whatever the minimum threshold of energy is, I felt just above it to keep me going. And then it was traction and momentum and hearing from students that raised the energy level. And so I have this belief that if you just follow your energy and you kind of expect seven out of 10 energy that you feel in order to start something, you will never end up starting anything worth doing. And I actually believe the amount of energy you need to feel towards a new project is probably lower. It's probably like a four out of 10, but you have to have belief that it's enough to sustain you for a little while. And then when momentum comes, that will take your energy to the next level.

• 46:38Auren Hoffman?

  Let's say you're a professional athlete or something like that. Yeah, I get a lot of energy out of taking that final shot in the game or even being in the game. But all the stuff leading up to the game is just grueling. It is a full on gruel of everything. Exactly what you eat, you have to track, you have to work out in these like crazy ways or think of being a stand up comedian, just the gruel of getting to like that one joke that actually people laugh at is so hard.

• 47:05Speaker 01

  Exactly. And I think it's just really unhealthy when people set this expectation of how they should feel based on their perception of what energy looks like towards most entrepreneurs. Yes, the first five years of Morning Brew were the most energized I've felt holistically in my life. But if you zoomed in, if you did like a zoom in of a week in the life.

• 47:27Auren Hoffman?

  Yeah, any given hour, you're like, cuz it's tough.

• 47:30Speaker 01

  I was like a LinkedIn monkey 10 hours a day for months on end.

• 47:34Auren Hoffman?

  I still am, but like.

• 47:36Speaker 01

  Yeah, exactly. And so I just think it's actually is really dangerous for people to anchor themselves to that perception.

• 47:42Auren Hoffman?

  There's enough of crap work that people have to do. There's a high degree of crap work that everyone has to do. The President of the United States spends so much of their time doing crap work. The President of the United States. You ever like follow around a Senator or Congressman? 90% of their day is absolute crap, maybe even 95% of their day is absolute crap. It is terrible to have that job. If you're CEO of a public company, like there's so much crap work that you have to do.

• 48:10Speaker 01

  And I think, again, we live in a time where now because of social media, people see the best, the 10% that is the enjoyment time for people. And then we also live in a time where in every facet of life and we're talking about over optimization, how do you optimize your calendar? And anything you don't like doing, how do you either teach AI to do it? Or use Zapier or send it to offshore talent in the Philippines or Sri Lanka? And so I think it just creates this unrealistic view for people that you're able to basically delegate anything in life you don't enjoy doing and spend all of your time on things that you absolutely love. And it's just not realistic.

• 48:43Auren Hoffman?

  You're a congressperson, like you literally have to go sit there and some old couple has to like complain to you about the pothole across the street from them. And you just have to like listen attentively for 30 minutes to them. Like that is your job to go do that. And you can't outsource that to the Philippines. You have to be in person doing it.

• 49:01Speaker 01

  Anyone who is in the position to actually be thinking about the energy and enjoyment they get from their work has to realize how incredibly privileged they are. I was thinking the other day, I live in Hoboken and I was at the dry cleaner down the street. This Chinese couple has been running their dry cleaner since 1994 and they're like a super happy couple, but at no point have they, I'm sure, thought to themselves, do I love the work that I'm doing and what are my alternatives? Let me think about doing this other thing. They, very simply, they wanted to build a life for themselves and this is how they've done it.

• 49:34Auren Hoffman?

  How do you think about, there's this trope with that, with optionality? How do you think about that?

• 49:38Speaker 01

  First of all, I think actually to do anything great, you have to cut off your optionality at some point. In order for me to be a media entrepreneur and be known for digital media, I had to basically cut off every other option. And it is why it's a very interesting thing now that I think about where it's like, if I want to build other things, do I do them in the media world? Cause that is the very specific set of skills that I've built up. Or do I do something totally different, but I have to basically start from not having made any of the mistakes and so I have to make all of the mistakes again. But yeah, my general view is to end up senior or successful in anything, you have to cut off your optionality. Elon Musk, what's interesting about him, I would say he's kept the most optionality

• 50:18Speaker 01

  by having four businesses, very disparate companies, but also he's cut off tons of optionality. One option is having a life outside of his four companies.

• 50:28Auren Hoffman?

  True, yeah, or just enjoying himself or something. And of course, you mentioned you recently got married. That's the ultimate elimination of options. That is the thing that people get so much happiness and fulfillment out of.

• 50:40Speaker 01

  Even though you have to cut off optionality, if you've made good choices, you never think about that. I've never thought about cutting off my optionality through marriage, but to your point, it is cutting off basically all of the optionality that existed pre-marriage.

• 50:53Auren Hoffman?

  All right, thank you, Alex Lieberman, for joining us on World of DAS. I follow you at Business Barista on X. I definitely encourage our listeners to engage you there. This has been a ton of fun.

• 51:04Speaker 01

  Love it. Thanks so much for having me.

• 51:07Auren Hoffman?

  If you're a super data nerd, go to worldofdaas.com. That's D-A-A-S, worldofdaas.com, and sign up for our weekly Data as a Service roundup newsletter. Thanks for listening. If you enjoyed the show, consider reading this podcast and leaving a review. For more World of DAS, and DAS is D-A-A-S, you can subscribe on Spotify or Apple Podcasts or anywhere you get your podcasts. And also check out YouTube for videos. You can find me at Twitter at at Auren, that's A-U-R-E-N, Auren, and we'd love to hear from you.

• 51:44Auren Hoffman?

  World of DAS is brought to you by Safegraph. Safegraph is geospatial data for physical places. Check it out at safegraph.com. And by Flex Capital. Flex Capital vests and data companies like those we talk about at World of DAS. Check it out at flexcapital.com.