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3.4.22   9:37 PM

For Meetup, a social network based on in-person events, the onset of the coronavirus pandemic in early 2020 could have easily been the end of the road. The company, founded in 2002, makes money by charging organizers a fee to run their groups through its site. Overnight, the vast majority of events hosted through the company were canceled, and business “cratered,” its CEO David Siegel told us.

But in a testament to its resilience, Meetup survived. Sensing that people were desperate for social interaction as lockdowns wore on, the company made an aggressive shift into facilitating online groups. The move paid off — business not only recovered, it thrived. Before long, the company went from hosting zero online events to several million, and became “more cash-flow positive than at any point in the company’s history,” according to Siegel.

The challenges of the pandemic followed on the heels of another rocky period for Meetup, which Siegel also managed to steer the New York-based social platform through with a deft touch. From 2017 until March 2020, when it was spun off and acquired by AlleyCorp, the platform was owned by high-flying coworking startup WeWork. During that time, Siegel had to stay in the good graces of the wildly eccentric founder and former CEO of WeWork Adam Neumann, whose leadership style has often been described as “cult-like.” 

In the interest of full disclosure, we should add that The Business of Business’s parent company Thinknum Alternative Data was ousted from a WeWork in 2016, just a half-hour after publishing a blog post that showed the now-tarnished unicorn wasn’t quite living up to its hype. Thinknum co-founder Justin Zhen discussed the incident in a documentary on WeWork on Hulu.

Siegel has also gone public about his experiences with WeWork and Neumann, as well as lessons he learned from running Meetup through the pandemic. These experiences are highlighted in his book Decide and Conquer: 44 Decisions that will Make or Break All Leaders, set to be released March 8.

We caught up with Siegel and he talked to us about his book, his past few years at the helm of Meetup, and why the company has proven to have such strong staying power.

This transcript has been condensed and edited for clarity.

  • Meeting Adam Neumann; managers vs. eccentric founders; getting through the pandemic; writing the book


    Business of Business: First of all, can you tell me, David, why did you decide to write this book?

    David Siegel: So I teach at [Columbia University] and I've been obsessed with education my whole life. And when you're a teacher, or a professor, and you have like 70 students in your class, you help them and guide them. And it's wonderful. But you know, if you want to reach a larger audience, a book is the way to go. I've always wanted to write a book. And I've been obsessed with the fact that people don't realize that we made thousands of decisions every day. And we don't necessarily have good frameworks for decision-making. We do pro/cons list or some very basic analysis based on urgency, importance, metrics, matrices. But you know, the science around making smart decisions, both personally and professionally, is really important.

    But I didn't want to have the standard boring textbook type of thing, like most business books tend to be. I wanted it to be a crazy roller coaster story with intrigue and suspense. And WeWork made that all happen, being part of WeWork, getting hired by Adam Neumann. We kind of descended from $47 billion [valuation of WeWork] down, down, down during the interview process. Also having Meetup get sold out of WeWork, and the entire process around that. And then running Meetup during the pandemic, when you can’t actually meet up in person, IRL, which is exactly what we've been doing for 18 years. And then having a company go from an 18 million loss in 2019, to making $3 million in 2020, during the pandemic.

    “I didn't want to have the standard boring textbook type of thing, like most business books tend to be. I wanted it to be a crazy roller coaster story with intrigue and suspense. And WeWork made that all happen."

    In two months, I just wrote 75,000 words, and then we cleaned it up afterwards. And that's what the book is about. It's kind of like crisis management of one crisis after another crisis after another crisis, and kind of the decisions that you make and a framework for decision-making during that time.

    One of the things that kind of sticks out right away [in the book] is your experience meeting Adam Neumann and that sort of brush with, I don't know if you call it stardom or what it is. But okay, it's clear that he's kind of the poster child for eccentric millennial founder CEOs who do their own weird thing and make everybody else do the weird thing with them. What does that do to a company? Is that good or bad for a company? 

    Let’s take Apple, for example, right? Steve Jobs was an eccentric cult-like figure. And that cult-like figure was probably critical to Apple’s success. Adam Neumann is a cult-like figure who was critical to WeWork’s success, and also was critical to WeWork’s failure. So the answer to your question is, yes, it was absolutely critical. And I'm happy to share if you'd like, you know, a couple of examples, or stories around that criticality. 

    I think what people don't understand, oftentimes, of Adam, and I want to give him credit for this, is that Adam genuinely wanted to make the world and still wants to make the world a better place. He understands that there's a tremendous amount of loneliness in the world, and his vision of WeWork helping to drive down loneliness that exists when people are working, and build community for people in offices was like a beautiful, beautiful thing. And he really had his heart in the right places. How he executed against it, and how he let his own personal incentives get in the way of it was always kind of a challenge. The culture that he built at WeWork was really a culture of chaos, where multiple people will have the exact same job and they didn't even realize that they were doing the exact same thing. And where someone like me had 27 interviews to become the CEO of Meetup before I actually got the job. That just tells you how kind of dysfunctional it is because dating is a good prerequisite for marriage. If you have 27 interviews, during the interview process that tells you a lot about what's going to happen. And, you know, I could share a couple stories if you like, if that's helpful.

    Sure, go ahead. 

    Okay, so one would be that when you're interviewing with someone like Adam, you understand that because Adam has such a craziness about him that the best way to get a job yourself is to act crazy. And I understood that. So one of the times I came to meet with Adam, before our vegan lunch with lots of hummus, which was how Adam ate, I walked in, I was wearing my white button down shirt and a pair of jeans. And I saw in the corner of my eye that no one was wearing white shirts and jeans. So I saw someone wearing a T-shirt that said, “Meetup + WeWork,” because we were just acquired by WeWork. And I said, “Okay, what would Adam do? How do I channel my inner Adam here so that he would be excited about hiring me as the CEO of Meetup?” And I pulled the guy over and I said, “Let's go into the closet over there. I'll give you my $100 shirt. You give me your T-shirt. And let's walk into Adams office, and I'm going to wear my 'Meetup and WeWork' shirt."

    So I walked in. And Adam said, “Where did you get this?” So I said, “Oh, I was able to get the shirt off that guy's back.” And he's like, “Oh, my God, so he got the shirt off of someone's back. That’s someone I want to hire.” So the interview process was kind of like, not your typical interview. There was storytelling and talking about our families and things like that. And then there were, of course, different times where Adam pulled me into his office. And we spent potentially hours trying to figure out what the company's strategy was. 

    “When you're interviewing with someone like Adam, you understand that because Adam has such a craziness about him that the best way to get a job yourself is to act crazy.”

    And, you know, there's some funny moments where he wanted me to take a plane. And, I wasn't able to do that because I had a personal commitment. And I told him, “I'm not taking a plane with you.” And he was very, very upset about me not taking a plane with him. And, and he basically said, like, “how could you turn me down from taking a plane with me?” And after that, we really didn't talk anymore. He was quite surprised about the fact that I wouldn’t take a long plane ride with him just to get stranded in San Francisco. And you know, find my way back.

    I think to any armchair psychologist that sounds narcissistic. There does seem to be a sweet spot, like you're saying, with Steve Jobs, for having a very egocentric, quasi-narcissistic leader who’s kind of eccentric. But where is it just enough? And where is it too much? 

    I think over time, it started to become too much. I think that's the real truth. And there were metrics at Meetup when I joined, where the No. 1 metric was how many employees you could hire was like the goal. That's not a goal of a typical company. The goal of a company are driving profit, and having great member experiences, not “hire as many people as possible.” When I joined, the [Meetup] ballooned from about 130 people to over 250 people. And it was really unsustainable, and we were losing 10s of millions of dollars. And that's not a sustainable situation. 

    One of the things that occurred to me when I was looking over your LinkedIn profile in your past experience, it seems like you have perspective to bring to this because you weren't a founder CEO. You were kind of always a management guy. Like you've had a lot of different roles at a lot of different companies. But you've always been in senior management. Do you feel that gives you a different perspective that a person doesn't have if they're coming up as a CEO starting their own company or coming up from the ground? And do you think you're missing some of that perspective?

    I hate to give the wimpy answer, but it’s both and I'll just explain. When you're a founder/CEO, you have such a deep emotional connection to your company. That it can be inspiring for you and give you the ability to inspire others, but it also can be incredibly clouding in terms of your judgment. And the danger of many founder/CEOs is that the reason why they founded the company and the success that they had when first found in the company, might be because of personal charisma, or a partnership that they happen to negotiate in the beginning, or someone that they hired in the early, early stages. But that doesn't actually translate to being effective later on, in building sustainable processes, building infrastructure, getting rid of tech debt that had been accumulated over 20 years to be able to iterate quickly, not doing 1,000,001 different things. 

    Many founders and startups die of more of indigestion than they die of starvation, because they're doing too many different things at the same time, and they're trying all these different things, because typically, that's why they succeed. In the beginning, they did lots of different things, threw a lot of stuff against the wall. And so it worked. So I think when a person comes in, like me, what I did is I said, “Okay, we're doing a lot of different things, how many of those things that we're doing, have a strong ROI attached to it, and how many of them are really pet projects, or Hail Marys, that don't necessarily make sense? And how many of them are we doing just because WeWork happens to be our corporate owner?” 

    So for example, we were investing millions of dollars at Meetup integrating with WeWork systems to have Meetup events be in WeWork offices, rather than probably the money into better member and organizer experiences. That didn't make so much sense. We were developing a new, completely separate app, kind of outside of the traditional Meetup app, rather than focusing on making the actual current app much better, because it's more fun to do a startup type of thing. 

    So I came in. And what I did is, rather than saying, “These are the things we have to change,” I got the whole company together for them to identify what we need to stop doing. And when we needed to deprioritize. They then put a recommendation together for me, they said “shut this down, shut this down, shut this down, shut this down.” And then within two weeks, we were able to shut down five or six major projects, that everyone in the company knew we shouldn't be doing, and that we're tying up resources. But no one had the guts to be able to say we have to stop it. And a part of that is because of the sunk cost fallacy. Meaning people put so much time and energy into it. They knew it would look bad if we pulled back from it. But when a new person comes in, you could kind of attack it with a completely different perspective. 

    “Many founders and startups die of more of indigestion than they die of starvation, because they're doing too many different things at the same time.”

    Yeah, so you kind of need both, I guess you really do need both. With that said, sometimes you can be overly heartless, shall I say, overly rational. And that's dangerous too. And that's why, what we did is we made Scott Heiferman, the founder of the company whom I took over from, the chairman of the company. So at the heart and the soul of Meetup we still have the Meetup culture. And our 20th anniversary is coming up actually in a few months, and Scott is going to be speaking at the 20th anniversary. So finding ways of keeping the soul of the company through the founder is very important. But removing the founder from the day to day operations and decision making is probably even more important.

    Interesting. So let's talk about Meetup. I am amazed and impressed you guys survived the pandemic. Tell me tell me how that happened. 

    Okay, so picture this, it's early March, late February 2020. We're looking at China. And we're like, “What is going on in China? Our events just got canceled.” We thought, “Oh, this is just like another swine flu. We don’t need to worry about it. “ And then we see what’s happening in Italy, and think, “this is odd.” Then, “Look, suddenly everything's getting canceled.” 

    And then within a week, as we all remember, it hit the U.S. by storm. All of our metrics went down [not] by 5% or 10%, but by 70% or 80%. And we're like overnight, for [a] 20-year company, our events just cratered. We got the whole company together. And by the way, we were in the middle of terms for selling the company at this particular time. And in March of 2020, you have an idea. So a lot of things were happening at the same time.

    Yeah, so the whole company got together. And we said, “What's our mission? Is the mission of the company about IRL, in person? Or is the mission of the company about real connections?” And the answer is, “real connections.” And even though beforehand, we never allowed Zoom-only type groups, we got all our engineers together, and we made a whole bunch of changes to our technology extremely quickly, and we rolled out a new version. We brought in the head of Zoom for training for all of our organizers, hundreds of thousands of organizers. We reached out to all of our organizers, and we said “now you can do online live events, people need you more than ever.”

    And we start seeing the number of online events going up. Since the pandemic, in the two years, we've gone from zero to over 5 million, or 6 million online meetup events, and over 30 million people are participating in online events. It’s kind of both now. So today as we stand literally this week, where it's 68% in person, and 32% online. And it varies dramatically. So like Texas, and Florida, are like, you know, 80% plus or 90% in person because, well, you know, it's Texas and Florida, Australia, same thing. Very, very high percentage in person. 

    But everything is trending to more and more in person, but now we're going to be online and in person. And what we see is this kind of like the roaring ‘20s over again, from 100 years ago. here was the dual threats of the Spanish Influenza, and World War I. They were keeping people in their homes, and then people emerged and the ‘20s happened from that. So our expectation is that and we're already starting to see it is that people have such pent up need to get back out and do things that were you know, every single week we're seeing it. We've been more cash-flow positive, believe it or not, during the pandemic, then, at any point in the company's history.

    That's amazing. Even before the pandemic, it's been a long journey for Meetup. What do you think its staying power is all about?

    Yeah, I don't know if you know the story. I’ve got to quickly tell you the founding story, because it's kind of cool, Christie. So the founding story of the founder, his name is Scott Heiferman, is he was living downtown during 9/11. And when the towers were hit, he went down to his lobby, and he saw most of his apartment building, people were hanging and loitering around the lobby not knowing what to do, but knowing they needed to be around people. He saw people that lived on this floor for like multiple years that he had never met. And he said, “It shouldn't take a tragedy to get people to build community”. And he decided to build a platform, Meetup at that time. On June 14, 2002, he launched the website. And he launched the website, and it started picking up steam very, very quickly, because there was nothing else like it helping to build community.

    “What keeps Meetup going is the human condition...Meetup is the cure for the loneliness epidemic.”

    Then it really hit its crescendo from politics, moving out with Howard Dean in 2004, who at the end of every single rally, encouraged people to go to Meetup. And then a little-known Senator named Barack Obama said,“Anyone that gets at least 100 people to come to my Meetup event, I’ll show up.” And he started using Meetup and all these other politicians started using it. And then companies started using Meetup. And then today we have 57 million members, worldwide in 190 countries and you know, and in about 200,000 different communities. 

    So that's the start. To answer your question very directly — what keeps Meetup going is the human condition. Back in the day, all the way back to Paleolithic, Neolithic man, hunter gatherers, they survived only because of a community. They needed to be around people. It's in our DNA, to build community to be around people. And when you don't have that, if you have a loneliness epidemic. Meetup is the cure for the loneliness epidemic. We see it time and time again, the depression that people have from loneliness, God forbid the suicides and other things that have increased during the pandemic. And what keeps me going is just the innate need of humans to get together and be with other people.

    And just to bring it back to your book — so you have 40-something decisions or lessons that you talk about. If you had to just pick one, one really major one that you want people to come away with, what is it?

    Okay, it’s this. Here's an example of one of them when making a decision. One of the most important things that people don't account for enough is the importance of optionality in the decision making process. What I mean by that is whether or not a decision creates significant options for yourself, or whether it is a trapdoor and minimizes the number of options that you can have.

    So for example, let's say you're great in finance, and you're not sure what you want to do in your career, you could become a trader. And you could do commodities trading. And you don't have that many different options that are available to you. Or you can become an investment banker. And then the number of options that you have available to you are so many. The result of that [is that] lucky things end up somehow happening to you.

    People have always said to me, “David, you got so lucky.” I've never applied for a job in my career, besides my first job, like lucky things kind of keep happening. And what I found is that the reason why lucky things happen is because you work hard to create your own luck. And you can make decisions that enable you to end up having lucky things end up kind of happening to you over and over again. And there's kind of a methodology around creating luck that can happen through decision making.

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