David Siegel | The Most Important Decisions Every Business Owner Makes

Srini Rao

 David, welcome to the unmistakable creative. Thanks so much for taking the time to join us.

David Siegel

Totally psyched to be here.

Srini Rao

I am psyched to have you here. So I was introduced to you by way of our mutual friend, Michael Shine, who wrote the Hype Handbook, and Michael's book was one of my absolute favorites. So anytime Michael sends a referral, I almost always say yes, because I don't even usually look. I'm like, if Michael referred to this person, then this is definitely a yes. And then he told me you're the CEO of Meetup. So on that note, I thought I would start by asking you one of my favorite questions. That is, what social group were you a part of in high school, and what impact did that end up having?

on what you ended up doing with your life.

David Siegel

Wow, okay. So I was, the group that I was in were the people that were really into sports, following sports, but really only average in sports. So I wasn't in the jock group. I was in kind of the nerd fantasy baseball, fantasy football, people know stratamatic, people that knew every detail about every single sport and was good enough to play with other people but always kind of the worst person on the team. That was me.

Srini Rao

I can relate. I was the most improved player on my 7th grade basketball team, which just means you're the shittiest player on the team. It's not like in the NBA where you're Jimmy Butler.

David Siegel

But the interesting thing about it is I always was obsessed and very into sports. It meant that I always have like a very competitive type streak in me. I was always into like board games and games and I love negotiating, but I was never good enough. So, but I was so surrounded by people. I was always in the honors classes, but kind of the bottom of the honors classes. So I was kind of that person that never thought that I was anything special, frankly, until later on in life.

Srini Rao

Mm-hmm.

David Siegel

because of the fact that I had been surrounded by so many people in a private school who were just incredibly special. I had 100 kids in my graduating class. We had four people who clerked for Supreme Court justices, for example. So it was a pretty elite class. 40% of people going to Ivy League schools, that kind of thing.

Srini Rao

Wow.

Srini Rao

Yeah. Well, you know, it's funny because my group of friends in high school, I always say like the dumbest people in our group of friends went to Berkeley. We were the dumb ones. Yeah. Well, one thing I know that you allude to in the book is having lost a parent at an early age. And you know, you say that when I was 24, my best friend,

David Siegel

That's tough. That's hard.

Srini Rao

Alan Heimerk passed away from shocking brain aneurysm. Two months later, another friend died by suicide. Then my father died. You spend more of your waking hours working than any other activity. You spend more time at a job than with your spouse or kids. My grief showed me that if possible, no one should waste this time on something that didn't make an impact. Um, and numerous questions come from that for me.

I don't think that any of us imagine losing a parent that young and I can't imagine, you know, losing a parent, I'd imagine is painful at any age and I've talked to so many people about this, but I know there's no way I could ever understand it without going through it. And it's literally the thing that I think I dread most. Like I honestly, I'm more scared that one or both of my parents won't be alive when I get married or have kids than I am of being alone.

David Siegel

Whew. I think that losing my best friend, having another friend die by suicide, and then losing a father at a relatively early age had a profound impact on me, like it would have a profound impact on anyone. I've always believed that what makes life the most meaningful and important is actually death.

as odd as that kind of sounds. Meaning, death makes life valuable because it provides a finite amount of time that you're on this earth. And it motivates me personally to try to do as much positive and good with the time that I have. And when I think about the importance of being efficient and productive and organized, for me, all those three words,

really relate directly into how do I have as maximal an impact as possible? Because when you have those kinds of experiences, you learn about the, how quickly people, people can, can leave this earth and that you just want to make the world a better place when you leave than when you started. So it really did have a profound impact on me. And I would say it also helped my approach to management and my approach to people. Which is.

Never be an asshole. No asshole roles. Be kind. Help other people as much as you can. And everything comes back to you. And there's just no reason not to try to be a positive influence on others with all of your time that you have.

Srini Rao

Yeah. Well, I mean, I know you have kids too. And anytime I've talked to somebody about losing a parent in early age, I wonder what impact has that had on you as a father?

David Siegel

Yeah, you know, I think when you have, so my dad is an amazing person, Kenneth Siegel. He started his own neurological practice actually because he never wanted to work for anyone else. So in many ways he was actually an entrepreneur, physician entrepreneur. And I had the opportunity at a young age to visit, I spent a day or two each year going around the hospital, visiting with him, visiting his patients.

and having him walk into the patient and the patient's eyes would just light up and say, Dr. Siegel, you're here. And as a son, eight, nine, 10 years old, and I saw how the positive, amazing influence that he had on his patients, it just made me think, wow, I wanna be able to do that as well. And then, but the negative side to that was that he worked really, really hard.

and he would work 70, 80 hours a week because he was working on his own. He was building a practice. He was building out other areas of practice, research, et cetera. By the time he passed away, he had 40 to 50 people actually working in the largest neurological practice in Connecticut. And I didn't have that much time with him one-on-one. So sometimes you learn from a parent what to do, and sometimes you learn from a parent, I wanna do something different. So for example, with each of my three kids, I do a one-on-one trip with them almost every year.

Now, so it could be just two days, it could be three or four days, but the one-on-one time with a child is something that I put in just incredibly high priority. And there's something special about total family time, but there's also something special about that one-on-one bonding time. And part of it is because I never did that with my dad because he worked so hard that I thought that was important to me. And the other part of it is because I saw him working so hard all the time, I said, there's gotta be a better way. And how do I kind of...

Even though I'm a CEO, I've really focused on work-life balance throughout my career, probably because of the influence from my dad as well. So I think there's much to learn on both sides.

Srini Rao

So one last question about this. I always wonder how the experience changes with each kid and also how those trips have changed as each kid has grown up. Because I always think to myself, when you're a teenager, the last thing you want to do is hang out with your parents. And you're always annoyed by them. You're embarrassed by them. They're the most awful people in the world, even though you're just a gigantic shithead.

David Siegel

You know, at home that's oftentimes the case. And I think one learning for me, I have a 20 year old, I'm only 47 years old, and I have a 20 year old, 17 year old and 14 year old. So I started very young, got married at 24, I'm my first kid at 26. So I really started quite young. And you know, with the first kid, when he was in the moody teenage years, I got very upset, I got frustrated, I thought we were so close, what's happening? But then you start realizing, but the second and third kid,

Space is really what you need to give them and the more space you give them the better. So for example We just went on a family trip. We went to Israel last week and We had the three kids basically spend two days completely by themselves Without us as a family and they love that and when I go on trips with my kids now and they're 14 year old 17 years old I'm like, hey, what are you doing today? What am I doing today? Okay, let's meet up for dinner or Let's meet up at some point in the day. The key is understanding that your kid doesn't want to be smothered with you

give them separation, and then they'll actually wanna hang out with you more. And they're like, hey, wait, actually, can we just meet for lunch and dinner? I'm like, okay, fine if you want to. Really, I'm like, yes.

Srini Rao

Hahaha.

Srini Rao

Yeah, I always joke that basically when you grew up in an immigrant family and maybe this is just true for all people who are firstborns, but you know, the first kid is the experiment and then the parents fix everything they fucked up on the second one.

David Siegel

Well, I was the oldest, so I was my first parents kid experiment. Unfortunately, like what happened to me, so I think that's true.

Srini Rao

Yeah. Well, one thing I want to talk briefly about is education and preparing students for the future. I mean, I think it makes a perfect segue for from talking about kids. But one of the things that you say students are often taught the importance of building a specialty and taking a focused approach in their career choices. But this focus results in fewer and sometimes no choice, no choices, which then limits the likelihood a student will find a role that is the best fit for their specific needs. Besides, how many students even know what they want and what they'll need when they get to college. And

That really struck me because of the fact that, you know, at Berkeley I got there and everybody basically was, were future lawyers, bankers, doctors, and Google employees. There was sort of this really bizarre paradox that here you are surrounded by some of the smartest and most creative people in the world. And yet, I'm guessing like most sort of elite colleges, it was a breeding ground for conformity.

David Siegel

Yes, especially the University of Pennsylvania, which is very impacted by the war on culture. I had absolutely no idea what I wanted to be when I grew up. I still at 47 kind of don't know what I want to be when I grow up. And that's the fun of things actually. I had taken classes in religion and psychology and I probably took my first 20 classes in 20 different topics. And I was like, crap, I have to choose a subject and take 12 classes of that? Damn.

Srini Rao

Yeah.

David Siegel

And then finally, the University of Pennsylvania announces my junior year, like mid-junior year, when everyone had already finished all their core classes. I had no idea when I was gonna major in. There's gonna be a new major, and the major's gonna be Philosophy, Political Science, and Economics. I was like, yes, it's the smorgasbord of majors. Sign me up. Prepares you for nothing. And you have a cocktail party knowledge of lots of different topics that maybe could be helpful. I think David Epstein and Range talked about the power of

Srini Rao

Mm-hmm.

David Siegel

kind of broad knowledge that maybe is a couple of inches deep and not incredibly deep. And for me, as a CEO, where you're general manager of a business, my core role is not to be a specialist in product or engineering or HR or marketing. In fact, to hire the people who are always better than me in all those areas. My job is to find how to weave the relationships between the different disciplines together so that they could all move forward towards one collective whole. And when you have...

only knowledge in one discipline. I've been in sales 25 years and that's it. Your ability to really be successful in running an organization is so much more difficult than if you've overseen revenue and product and all these other different areas. So it speaks to why I started as a consultant because great way to know nothing and pretend like you know a lot of stuff and sets you up for a CEO role perfectly.

Srini Rao

Well, I can relate, given what I do, I mean, I spend all my days talking to people like you from every walk of life imaginable.

And so I have this like encyclopedia of broad knowledge in my head, but I don't know that I'm a specialist at anything, maybe interviewing people.

David Siegel

So far, so good.

Srini Rao

So now if you were to go into a educational institution like the University of Pennsylvania, or for that matter any other college, what would you change?

David Siegel

So number one is I think the greatest benefit that I personally gained from college goes back to the first question that you asked of what my community was like in high school, which is the communities that you surround yourself in and the people and the groups that you surround yourself in within college. I think one of the challenges in college is that there's a communal infrastructure that's very, very strong in many colleges and it's called fraternities and sororities. And I'm not.

opposed to fraternities and sororities. It's a certain communal milieu that can be amazing for different people. But if I ran a university, maybe one day, well, who knows, I would, and I am the Meetup Community guy, so I guess I have to say this, but I really deeply believe it. I would figure out how to build smaller, niche group communities within the college that could be more than just superficial or tangential.

but can be really deep identity building and provide better infrastructure and support around those areas. To me, that education that you could get could be possibly and even probably more impactful than things you could even learn in the classroom. I'd also do it with all the grades, but I'm a maverick, you know? No, sounds like I should.

Srini Rao

Yeah. Did you ever see the movie Van Wilder? Yeah. Did you ever see the movie Van Wilder? Yeah. Well, the thing that I always think back to when I look back at college is this is the ultimate social opportunity. Everybody here is open to meeting people. And I realized at a certain point that I had basically just spent four years hanging out with nothing but Indian people. And it became very apparent to me when this girl that I met,

who was at Stanford doing research for a year, came to Berkeley and she forgot her ID and she said, do you know anybody you could call who would give me theirs? And I looked at her and I said, this is gonna sound horrible but I don't know any white people. Yeah.

David Siegel

Wow. You know, listen, it comes down to when you come into a college, you look for the familiar. And the familiar for me could have been the Jewish background that I personally have or the Northeast New York background that I have or for you the Indian background. And it's such a natural thing to do because of the social pressures that exist. How can a college really find even greater ways? And they do some things.

Srini Rao

Mm-hmm.

David Siegel

to help people, to get people, to meet other people that are totally different, because you know how it works. The friends that you have, like the first two weeks in school, end up being your roommates, your sophomore, junior, and senior, and somehow you're like, wow, it's all because we met during orientation. I mean, it's really powerful, the people that you meet in your first few weeks in college, that for four years oftentimes has an impact. So what can you do in those first few weeks to really expose people to massively different people than who they happen to be today?

Srini Rao

Mm-hmm.

Srini Rao

Yeah. The reason I brought up Ben Wilder is because he basically spent the story about a guy and it's apparently based loosely on a true story about a guy who spent eight years in college. And he literally joins every single club is friends with every group of people regardless of you know whether they're geeks or not. He goes to the Hillel house and like becomes friends with everybody there. He helps you know a nerdy fraternity throw a party. And I remember looking at that thinking

wait a minute, this guy has the smartest strategy ever to meet people in college. Instead of discriminating, he just joins every club and becomes friends with everybody. I'm like, wow, that would be the way to do it.

David Siegel

I love that. Okay, I'm definitely gonna see it tonight and I'll tell you about it afterwards. But that is the, and think about those relationships and what those relationships can do. And think about your world outlook and the lack of being judgmental or the, the reason why I love traveling, for example, so much, been to close to 50 different countries is because it gives you this opportunity to spend time in a country, talking to people, meeting people. And the last thing I try to do when I'm traveling is do touristy things. It's just kind of hang out where people actually live.

Srini Rao

Yeah, we'll have to talk about it.

David Siegel

talk to those people in coffee, over coffee or bars or whatever, and it just gives you a totally different perspective on life and just the way to go.

Srini Rao

Totally. Yeah, I mean, I think if I were to make a list of all the countries that I've visited, I'd probably tell you that I haven't seen any of the major tourist landmarks in any of them.

David Siegel

That's a win, that's a win. I remember I went to Paris with my wife and we like, should we see the Mona Lisa? Nah, forget it, let's hang out at a coffee house instead. It's great.

Srini Rao

Yeah.

Srini Rao

Yeah. Well, let's go through the trajectory of your career that has led to you becoming the CEO of meetup and you know, as a CEO of a company, why spend your time writing a book?

David Siegel

Okay, what do you want me to do first?

Srini Rao

Let's start with a trajectory. I know you started at DoubleClick early on, but what's been the trajectory that led to Meetup?

David Siegel

Yeah, sure. Okay, so I was, sometimes it's luck, and sometimes it's like brains. And of course, all CEOs are the people that are successful. Like it's always luck, it's always luck. But I'm telling you, there's a lot of luck. It's not just like brains. There were also some planful things that I did. But the luckiest thing that happened was that I got to be an early employee at DoubleClick. DoubleClick was this internet company, biggest internet company really in the New York area. There's over 200, kid you not, CEOs that have,

come out of DoubleClick today because people who are, again, my age, 24, 25, 26, learning about the internet and the World Wide Web when no one else, people aren't working in newspapers, whatever the heck they were working at the time, and it became so much more marketable. So I worked at DoubleClick, then I went to Warden for Business School. That was a tough decision for me because I had to go from essentially two salaries for two people to no salary.

for three people for two years, because we had our first kid right before I started business school. After that, I decided to work for the thing that was most opposite of consulting. So you know, sometimes you have a bad experience in consulting, I did that before DoubleClick, and I did that during business school, and I said, what's the opposite of consulting? And the answer, it's retail. Like, get your hands dirty, fingernail, dirt in the fingernails, you know, retail stores. So it's like, that's what I want. So I worked for...

Srini Rao

Wow.

David Siegel

as director of business development for a pharmacy chain called Dwayne Reed, which at the time was the largest pharmacy chain in New York acquired by Walgreens later on. And I built a business there. And I started what I started doing in a lot of companies, which is to be an intrapreneur as opposed to entrepreneur, to build businesses, leveraging the significant assets of a company, rather than having to, you know, lower, lower risk, certainly lower reward. And we built this quite successful.

Srini Rao

Hmm?

David Siegel

pharmacy kiosk business at Dwayne Reed that was quite innovative I would say in the industry. After that I went to 1-800-Flowers and it's a funny story how I got there. We could go through that later if that's of interest. And I worked there for five and a half years. I basically just signed up with no real job, just become the VP of strategy and we'll figure it out. And I love kind of going into jobs where there's no job that exists.

Srini Rao

Yeah.

David Siegel

you create the job and you create the opportunity. And then by the end, I was overseeing all mergers and acquisitions for the company. We acquired a whole bunch of cookie businesses, chocolate businesses, oversaw marketing, business development, international operations, our database of 30 million names, whole bunch of other stuff. Then I became a general manager of the second largest health publisher after WebMD, it's called Everyday Health. After that, I became, I knew I wanted to...

going the CEO route. So general manager was a good path towards that. Then I became president of Seeking Alpha, which is one of the largest financial publishers focused on investing. Then CEO of Investopedia for about four years, grew the company from about $11 million in revenue to over triple that 35 million and sold it. And then Adam Newman came and knocked in and one of his board members and said, hey David, we'd like you to be the first outside CEO of Meetup. And I said, Meetup.

Srini Rao

Now.

David Siegel

I love meetup! Let's do it!

Srini Rao

Very cool. So I wonder, you know, I mean, obviously, the whole book makes a lot more sense now based on your background, because it seems like you drew a lesson from every single experience that you had. And you even mentioned that there's value in every job, regardless of what it is. Believe it or not, one of my most valuable jobs was working at McDonald's in high school, because it taught me not to be a dick to people who serve you food ever. And.

Because of that, I get free drinks often. I remember one night we were waiting for like 25 minutes at this bar here in Boulder, and the waiter came over there and I was like, he was like, you know, he's like, hey, I saw you guys in Wayne, sorry. I was like, you guys are busy. I went, don't worry about it, man. He was like, really? He was like, he's like, what do you guys want? I was like, yeah, and I just talked to him. I was like, you know, I worked at McDonald's and I learned never to be a jerk to people who serve you food. And he was like, yeah, don't worry, the drinks are on me.

David Siegel

It teaches, want to do that again? Cause I'm sorry, I'll just shut my phone off there. I apologize. It teaches empathy. And empathy is probably one of the most important components to being a successful leader. It's amazing to me, the number of CEOs and leaders of companies that I know, who at one point in high school, for example, or college served as waiters and waitresses.

Srini Rao

Then, in other words, we're good.

Srini Rao

Yeah.

David Siegel

the number of people who are successful, I've actually recently said to my kids, I'm like, you need to work as a waiter and waitress and you're gonna be a lot more successful in your future. And the reason for that is because you're juggling multiple tasks. You're focused on service orientation. You're gonna build more empathy because of it. You have to be very organized. There's just a whole lot of things. You have to be able to balance a tray with lots of food on it at the same time. I don't know how applicable that is to lots of things, but those types of experiences are so helpful in just.

building a person into the person that they ultimately wanna become, totally agree.

Srini Rao

Yeah, my sister told me that she worked at a French cafe in college and when she did interviews for residency, nobody asked her anything about medicine. They asked her, she was going to a teaching hospital, they said teach me how to make a cookie.

David Siegel

Ha! That is great. So, I don't have a resume really in a long time, but I kept something on my resume for many years longer than I should have. As 15, I worked for my dad in a summer job as an electroencephalograph technician, also known as an EEG technician. I don't know how he got away with me being 15 and being able to do this. I would hook, I mean, I don't wanna ask, but I would hook up children.

and the elderly to this EEG machine. I do it like on my own, no nurses there. And then I would try to get some kind of, shoot, yeah, this out. What's the thing called that epileptics have? I'm blanking on the word. Seizures, yeah, sorry, thank you. I would hook people up, get that part out. I would hook people up to this EEG machine. I would try to induce seizure activity by shining bright lights on them, by making loud noises.

Srini Rao

Seizures? Yeah.

David Siegel

And that's what I did at 15 years old. And I kept that on my resume as a trained electroencephalograph technician. And I was looking for CEO jobs. And people would ask me about this, what is this electroencephalograph technician thing? And it's so much more interesting than your typical like, oh, you worked as a consultant for Deloitte, who cares?

Srini Rao

Well, speaking of CEO jobs, I feel like there's two paths to getting there. Yours, which is climbing the ladder and going through sort of the trajectory that you did. And the other is to start your own thing. And I feel like the odds of ending up in your position are way lower than, you know, becoming a CEO by starting your own thing. And at the same time, I don't think there's any, you know, question that the experiences you've had have been invaluable in your ability to run a company.

I have a cousin who's literally like one step down from the CEO at her company now. And she started with nothing but a community college computer science degree when she came here from India a couple of years ago and she started her own business recently. Like I was joking with her. I was like, you want to be the CEO, start your own company. Um, but one thing I wonder is for somebody like me who was just a disaster in the corporate world, didn't have the experience that you did. How do I get that same knowledge and insight? I'm very fortunate because I'm in the position where I get to talk to people like you all day.

And that's been invaluable, but I can tell you for sure that if I had your background and your experience, there are probably a lot of things that I would know how to do that I don't.

David Siegel

So the answer is you gotta start a podcast. Obviously not everyone can start a podcast, though I would say it seems like lots of people have, there's a lot of podcasts out there, none as good as yours, that's for sure. But one great thing about the podcast, and I'll say for that broadly, is the ability to build relationships and learn from others. So at the end of the day, if you're a solo entrepreneur and you're looking to grow,

Srini Rao

Hahaha

David Siegel

the absolute best thing you could do is find, not a mentor, but multiple mentors. There's an idea that every person should have their personal board of directors. I talk about that in the book. And that you go to that board of directors and they go back to you and they say, here's where you're failing. You're doing this wrong, this wrong, this wrong, and this wrong. And they're doing it only because they quote unquote, love you, they care about you, they want you to succeed. They're there for your best interests. So cultivating that personal board of directors around you.

Srini Rao

Mm-hmm.

David Siegel

finding those mentors that are willing to tell you it's straight of the things that you may be doing that are mistaken or things that you're doing that are great, that's the best thing that someone could do. For me, I always wanted to work as close to a CEO as possible. And pretty much in every job from business school on, I worked directly for a CEO. And they gave me the opportunity to be part of executive teams, to be meeting with the CEOs one-on-one and learning from them as much as I possibly could. So the answer is just exposure.

to thoughtful people that care about your success and good things will come.

Srini Rao

Mm-hmm.

Srini Rao

Yeah. Well, it's funny. You mentioned working closely to CEO. I had a guy here years ago. This was before we were called unmistakable creative. And I remember coming across his story and he ended up taking a job as the executive assistant to the CEO, even though he was highly overqualified for the job, for the very reason you're talking about. And he learned so much that he ended up starting his own company and selling it to Zynga.

David Siegel

Damn, okay, that's a good basis for that resume. I mean, when I was in business school, the job that I was looking for more than any other job was an executive assistant to the CEO. And I ended up talking to or emailing with Ken Chennault, the CEO of American Express, and David Stern from the National Basketball Association, all these other kind of famous CEOs and people trying to convince them that I should become their executive assistant to the CEO. It is an incredible learning opportunity. So for all those people who are listening, if you have an opportunity to do it,

Srini Rao

Mm-hmm.

David Siegel

then do it. I was actually just talking to a CEO last week, the CEO of Acorns, and he passed me on to the assistant to the CEO and I was talking to her and I said, you have an awesome job. How'd you get that? And she just said, I went after it and I created it and good for her.

Srini Rao

Yeah. Well, it's funny because I remember sometime after my sophomore year in business school, one of our friends was an intern at the Gap and somehow he got on Mickey Drexler's radar and he gets in the helicopter with Mickey Drexler and he had an assistant at the time whose name was Eileen Lee, who I'm sure you probably know, who is now a partner at Clyder Perkins. Like I've seen her name so many times over the last couple of years. Like, wow, okay, that job really launched her into the stratosphere.

David Siegel

Mm-hmm.

David Siegel

It's amazing. It's the relationship that you have, and also the comfort level that you're able to build and talk to very senior people. They're just regular people. And I think too often there's this, you know, deifying perhaps of people, the Adam Newman's of the world or Fred Wilson of the black ones, these very successful people of, I can't push back in this person. I'm not in the same league as this person, the imposter syndrome. But once you kind of get to know a lot of different other CEOs, you realize they're

Fallible just like everyone is fallible and it ends up being able to give you an opportunity to actually disagree. And once you're able to be in a position where you're comfortable disagreeing with senior people well that's a good place to be because senior people don't know most senior people that are most successful don't want just yes people they want people that are going to disagree they're going to push them on the other side too and I think being around that kind of opportunity you know builds those kind of chutzpah shall we say which is you know a Jewish term for just you know.

Srini Rao

Mm-hmm.

David Siegel

You know, balls.

Srini Rao

Yeah, no, I remember, you know, we have a community manager and we pretty much at the previous community manager was one of our listeners. This is a current community manager, one of our listeners. And I told her the reason I want to work with you is because you're the person who will call me on my bullshit.

David Siegel

Nice.

Srini Rao

Yeah. Well, let's get into the book itself. One of the places I think I want to start is with Adam Newman. I didn't even know that I meet up was owned by rework until you read. I read your book. At least, you know, at that point they were really working with somebody like that, especially given the reputation that he has now. What did you learn? Because I'd imagine there are probably some good lessons that came from it, too. I mean, clearly he convinced people to give him a shitload of money.

David Siegel

Who?

David Siegel

Yes. I think Adam gets a bit of a raw deal and he was...

taken by journalists as the amazing hero and people like taking heroes down and then he became the villain. And people oftentimes put people into one category or another category, they're either heroes or they're villains. He's flawed, he definitely made a lot of mistakes but I'll share with some things that I learned from him because I think that's important. So number one, is he, whether it's delusion or not, you could say derisively as delusion or you could say that it's optimism

and ambition for making the world a better place. He deeply believed that he had a God given, truly opportunity to deeply change the face of the world in terms of how people worked, which is what you spent a majority of your time doing like you referenced in a section from the book that you read. And he had an ambition.

greater than anyone I've ever met in my life, that if you work hard at it, you can have a direct and immediate impact on potentially hundreds of millions of people. And that's what he wanted to focus on. He wanted to create community in the workplace. He wanted to change the way that people work to be more interactive and less cubical-ized.

And he did that incredibly well. He is probably the most charismatic person I have ever heard present. He would give these presentations and I was just sitting there lopping it up, frankly. And I've heard lots of great presentations by lots of people. He honestly had me quite mesmerized. Now there's lots of negatives as well. And at some point, if you want to get into that, we could. But his ambition saw no limitations. And I think that's something great to learn.

Srini Rao

Mm-hmm. Yeah.

David Siegel

and he truly did wanna make the world a better place. He didn't know how to do it, but he wanted to make the world a better place.

Srini Rao

Yeah. Well, it's funny. You say in the book, the job of the CEO is to dream big. And while I admire that ambition, the negative consequences are enormous because it impedes realistic planning and financial forecasting, like leaping off a skyscraper and figuring, you know, you'll learn how to fly on the way down. And I wonder how you balance that level of ambition that is absolutely a necessity to build great things and do amazing things in the world.

with the need to be realistic. I have friends who I think are delusional optimists and they think I'm a pessimist. And I remember writing this thing about why cynics and pessimists have a lot in common. I said, because both of them don't plan for, so basically, optimists, irrational optimists, expect nothing bad to happen so they don't make plans for it. And pessimists expect not everything bad to happen so they make no plans to change it. Both of them do nothing to alter the situation.

David Siegel

Right, the goal is to be the realistic optimist somehow, right? That's the golden mean. To me, the answer is, this approach to business is a lean startup methodology, which is continuously being ambitious and not waiting for paralysis analysis and getting stuff out there, even if it's not great, even if it's a problem, even if it's gonna be an embarrassment, quickly getting feedback and then iterating and making it better. It's that focus.

Srini Rao

Yeah.

David Siegel

on not being afraid to have product experiences that are not amazing experiences so that you can learn from them as quickly as possible and iterate and change, iterate and change, iterate and change. So my philosophy generally is be ambitious on what you wanna accomplish, but understand the way you're going to accomplish that is through incremental small changes and small wins that'll keep adding up. 5% here, 10% here, 15% there, 10% there. Could you get to that 200% leap? Yes.

But if you aim for the 200% leap, you're gonna be striking out a hell of a lot. And I'd rather have an 80% certainty of getting this 20% improvement than a half a chance of getting a 200% improvement. And that's kind of always been my philosophy.

Srini Rao

It's funny because when I talk to writers and they come and tell me like, I want to sell a million books. I'm like, how about you start by writing a thousand words a day instead.

David Siegel

It's great advice. It really is about the discipline and writing a book of just getting up at a certain point in time. Actually, let me tell you an analogy to that. One of my favorite meetup events that I've ever been to was when I went to a meetup event of a bunch of 20 or so PhD dissertation students who all got together every single day to hold themselves accountable for their writing.

and they were writing about totally different things. One person wrote a chemistry dissertation, another person, psychology dissertation, totally different disciplines. But the act of being a community and holding each other accountable to write and make certain amount of progress each day and not get distracted and have people say, hey, I haven't noticed you weren't here last week or so, what's going on? Or seems like you hit a block. That type of thing is incredibly powerful and shows the power of community in kind of driving individual goals.

Srini Rao

You mentioned some of the negatives in terms of what you learned from being so close to Adam. What were those?

David Siegel

Yeah, I think that the best form of leadership truly is the Gandhi servant leadership mentality. It's saying my entire job is to enable your success. Like the reverse organizational chart. I'm in the bottom of the organizational chart for a reason. My job is to support the executive team. The executive team's job is to support their managers. Manager's job is to support individual contributors. And Adam didn't see himself as...

you know, the reverse organizational chart. You know, he took certain, he treated himself differently than how he treated other people. And I think that's a problem in leadership. And that's something that I always try not to follow. It's how can I learn from others, put myself in other people's perspectives and not hold myself to kind of a different expectation that I hold to other people. That would say, that would definitely be one major difference.

Srini Rao

Mm-hmm.

Srini Rao

Well, I'm speaking of leadership. You came in to a startup that you are not the founder of, and you say that when you accept a leadership position, the hard work doesn't start day one. It starts the moment you accept the role, because you have an enormous amount of planning to do before you walk in the door. So your first 30 days are really 90 days compressed into 30, perhaps even into one. Tell me about what that experience is like. And for example, let's just say for, you know, by some...

stroke of good luck, you were like, Srini Rao, I'm going to come over and take over as the CEO of unmistakable media because you're good at interviewing people. I would play like, great. And I'm guessing there are probably things that I would hate about it too.

David Siegel

So, Rene, that was the hardest thing I've ever had to do in my career. Taking over for a CEO who's been running the company for 16 years, who knows every little tiny detail about the company, who's forgotten 10 times the amount that I could ever know even in my first year in the job. And coming in your day one, imagine this, to 250 new faces, none of whom know you, and all of them expecting you to be like, to have the 10 tablets on your hand of like, what the future company strategy is, your day one. It's just a great way to fail.

So one of the things that I did that I really try to encourage all leaders to do is even though my first official day was, I made my first official day on the job one week prior to letting any employees or anyone in the company actually know and I spent the first week just meeting with the executive team, just meeting with Scott our founder, the HR team, understanding which people are strong, which people aren't as strong, where we need to improve, where we don't need to improve.

got in front of all employees, I would have a moment to breathe. So I got a full week of just learning information, learning what was working without the distraction of kind of running a company. And that helped tremendously. And then when I joined the company, what I did is I was able to isolate six to eight big areas in the company where there were big problems happening. And I said, I don't know enough to solve these problems. So day one, we created six to eight different what's called work streams.

And each work stream focused on a different challenge that the company was having. And I brought someone in to facilitate the work streams. They had to meet every single day. And then in a two week time period, we were going to get the answers. And then I ended up following the advice, mostly almost all the advice from the work streams in terms of my plan. So if I had come in and decided we need to fire or end up fire, a number of people shut down a couple of businesses, they'd be, people would say, what, what the heck does David know when the work stream.

recommended that we need to shut down a number of different business areas, and I just followed and supported what the workstream's advice was, then it was obvious that it made sense to actually proceed with that. So there are a whole host of things that I tried to do to set ourselves up, set me and the team up for success without necessarily being the person that's the know-it-all that comes in the beginning and tries to make lots of change.

Srini Rao

Right. Well, but you did also make a lot of change. You know, you talk about breaking bad habits, which that struck me. You said, you know, break bad habits fast. One of the primary jobs of a new leader is to understand a company's bad habits. Every company has them and its employees are often too close to the habits to realize it, identify them, kill them, meet up. Leaders often came late to meetings and had meetings with no agenda. These were bad habits and we need to change them fast. Personally, I never will attend a meeting if somebody doesn't give me an agenda. I can't stand meetings like that. But.

David Siegel

Yes.

David Siegel

Well, it's disrespectful. It's disrespectful because you're not respecting the people's time and using people's time inefficiently. And as we talked about earlier, it almost goes down to our own mortality again. Time is our most valuable, precious thing that we have. And if people are gonna come to a meeting with no agenda, without having thought of what we're gonna talk about, without understanding what the goal is, start off a meeting with what is the goal of this conversation and stick to that agenda.

Srini Rao

Go!

Srini Rao

Yeah, I mean, I at this point, like I literally have one agenda item. I very distinctly remember Keith Rabois giving a lecture in this white commentator startup school podcast. It was Sam Altman's class that he taught at Stanford. And he tells this story about working at PayPal in the early days with Peter Teal and Peter had a rule apparently where if that person was working on something and they came to him to talk about something else, he'd like, I'm not going to talk to you about anything other than this one thing.

David Siegel

See, that's just take such discipline. I hold that in such high admiration. One of the areas, one of our six values as a company is focus on impact. And when I joined Meetup, we were doing so many different things, like many entrepreneurial companies do. You know, the famous line that startups die from indigestion much more than starvation, just really rang true with Meetup because we had so many pet projects that my job was how could we...

Srini Rao

Mm-hmm.

David Siegel

end a lot of these pet projects and just refocus the organization to other things. And that's what a new person can come in and do. It's very hard when an old, you know, when a CEO has been doing something for a year, two or three, and it's been a focus and say, now we're going to shut that down. And oh, by the way, that's all my fault for having started in the first place. It's just hard to do.

Srini Rao

Mm-hmm. Well, I'm going back through Ken Segal's book, Insanely Simple, which is all about Apple and how Steve Jobs basically prioritized simplicity. And it was kind of funny. I'm going back, this is the second time, and I remember talking to our community manager, and I told her, it's like, I want to kill a dozen things that we're working on, because they don't make sense, and they're unnecessarily complicated. They're difficult for people to understand. But...

One thing that you say is that founders tend to make decisions on intuition rather than using data. The reason is fairly obvious. They succeeded and built successful businesses initially on their intuition. And it's a success from intuition based decisions that reinforced its greater value over data. And I can tell you, I started this podcast and which ended up raising around a venture funding for because one guy interviewed when I started a blog 10 years ago, said that I was a better interviewer than I am a writer. An hour later, I mocked up the first version of the website and said, when do you want to get started?

David Siegel

Wow, what a moment for you. What an impactful moment.

Srini Rao

And yeah, I mean, that one moment changed the entire trajectory of my life. I actually want to come back to rapid execution and, you know, moving quickly because that is there's another story about that it just reminded me of. But when you come into a situation where somebody like me, for example, has been running on a single creative and you're suddenly the CEO of unmistakable media or meet up where you're taking over for Scott, how do you make sure you don't?

lose the original essence of what that person created ended up in a John Scully situation.

David Siegel

example actually even talk about John Scully in the book. Quincey in my meeting with him so we get into that some other time. So I think the first is we've talked already in the beginning of this podcast about the importance of empathy and you have to start off with empathy you have to say oh my god I am taking over a company which is the baby of this person. If you have three children this is your fourth child that's how much time and energy attention and just

acknowledging that in the beginning, this is this person's baby, helps you to understand that they're gonna have irrational emotional attachments to their baby, just like any parent has irrational emotional attachments to their children in good ways. So first step is just acknowledging that there's going to be both irrational attachments, but also gold. There's gonna be gold that this person can bring to the organization. So it's me sitting down with you, if I was taking over.

or with our previous CEO, and we made Scott the chairman of the company. And we said, Scott, I need you to stay close to what's happening because you are the heart and soul of this organization. And we can't just go to the extreme of going from, you know, CEO Scott to Scott Knot no longer part of the company. We need to find a path to take the great ambition.

and spiritual value, shall we say, in having built the DNA of the company and apply that in healthy ways. So for example, one of the things that he did is every time new employees would start, he would take them on a meetup tour and he'd bring them from meetup to meetup to meetup and help them to understand the essence of the impact that meetup has on people's lives. And that was just a great role for our chairman in terms of understanding the mission of the company. And I would try to channel that in productive ways because

Too often people just jettison that incredible history and their incredible passion, and that's oftentimes a mistake.

Srini Rao

Hmm. Wow. Well, let's talk about one other area of this. You talk about fake companies and that really struck me because I was just going through this and I'm going through a lot of these issues myself right now. And you say a company that doesn't have a clear path to profitability, profitability is fully supported by investors or its parent company is a fake company. Why? Because if the investors or parent company changes its mind, the company would cease to exist. A company that doesn't provide any.

meaningful product differentiation relative to competitors as a fake company because even if it has had historic success in sales or marketing its advantage is not sustainable a company that does not have proper controls processes and reporting in place to ensure appropriate feedback loops and smart decisions of fake company because it cannot maintain its health without the right strategic and financial processes and It's funny because I feel like you summarized Victor Chang's book extremely revenue growth in three sentences

David Siegel

and I haven't even read the book, so that sounds great to me. At the end, what I focus on between fake company and real company, it's all about sustainability. I don't mean from the echo side. I mean, is the thing that you are building right now, can it be sustained or not? If you are simply charging a lower price, for example, for a product that someone could get anywhere, and you don't have a lower cost structure to support that lower price, that's a fake company, because you're gonna go bye-bye very quickly. If you're...

growing at such extreme rates like WeWork did, and doesn't have the infrastructure and reporting and financial discipline in place to support that accelerated growth, you're gonna be a fake company and you're gonna go crashing down as WeWork did. And I think the key is how do you build out, and a lot of entrepreneurs don't understand how important it is to focus on these things, the processes that will ultimately enable and support the growth of a company, because growth for growth sake,

Srini Rao

Uh-huh.

David Siegel

ain't going to result in growth. Growth with process underpinnings will actually result in appropriate growth.

Srini Rao

Trust me, I... yeah.

Srini Rao

Oh, it's funny. I think right before talking here, I was talking to my friend who's the founder and I just looked at the way he works. I was like, this is a disaster. I can fix this in an hour. But, um, and, and a lot of it is driven by my own diagnosing process issues in the way that we run on, on MistakeWall. But the funny thing is we have certain processes so streamlined. So for example, I can go a month without talking to my audio engineer and we'll never miss a publishing date.

David Siegel

Wow.

Srini Rao

And I have a friend who builds air table automations for companies like big companies We're talking big brands that you know, and he told me half the time he goes in these huge companies they don't even know their own process and I started to realize at a certain point like I remember thinking it's like there's all this bureaucratic nonsense in a big company and I finally realized was like

there's a reason for that because there's no way in hell you could scale if there wasn't some level of standardization. So I always come back to the example. Like imagine if Google was hiring, you know, a hundred people a month and every time they hired somebody, they were reinventing the wheel. They would just be chaos.

David Siegel

Yeah, you know, it's so interesting you talk about this because the goal generally is how do you make yourself as unnecessary as possible, right? If you're unnecessary, then what it means is that you develop the processes and everything else that you could just kind of like poof, disappear, and everything is working really well. And when I need to get, let's say, more involved in a certain function, I know there's a problem because that means I'm too necessary. And if I'm necessary, then we have actually a problem going on. So,

Srini Rao

Yeah, exactly.

David Siegel

You know, at the same time, there's this interesting tension in that executives also wanna advance their careers. And they wanna show they're really necessary and really important. So in evaluating executives, wouldn't it be great if the way that a CEO approached it is they said, you have made yourself so unnecessary as a leader that now I have to promote you because of the great job that you did.

Srini Rao

Yeah, yeah, well, I always jokingly say I'm the most useless person, you know, at my company. Even the email that you got that was the invitation to this link that literally was just me pasting and link into a spreadsheet. I didn't send that. It was all set up with systems and processes on the back end. Yeah.

David Siegel

That's the way to do it. It's the way to do it. That's how you scale. And that's also how you could then spend your time in areas that are not just kind of short-term blocking and tackling, but thinking bigger. It's very hard to go from super detailed micro stuff into larger picture type work. And the ability to get the super detailed micro stuff as part of standard processes allows you to then think bigger.

act bigger and then hopefully then end up ultimately succeeding. It's about growth and it's about success. So process drives growth and success.

Srini Rao

Oh yeah. I mean, I, you know, you may have read Scott Belsky's book, making ideas happen and I'm launching a new online course about the, you know, no taking out mem called, uh, maximizer output. And I started to look very closely as I've been going through this. I was like, the reason people have all these problems of time management distractions is because all these things are band-aids on bullet wounds. None of them address the root cause, which is the way that we organize information.

Srini Rao

Yeah. Speaking of, you know, addressing issues. So when you come in, let's just say I said, hey, I want you to come in and do a complete audit on everything we're doing wrong and what we should kill. What would that look like?

David Siegel

So finding all the mistakes in unmistakable.

Srini Rao

Yeah.

David Siegel

What it would look like, here's what I would say is it would be me coming in with as curious a perspective as possible with reserving as much judgment as I could about why you're doing certain things. Oftentimes a consultant comes in and sees something and says, oh, that doesn't make sense. Oh, that also doesn't make sense. What the heck are they doing there? And it's the key question is why did you start doing this?

And is the reason why you started doing this specific thing still true today or is it no longer true anymore and therefore we should get rid of this particular process that you happen to be doing right now. And just keep asking the question, what made you want to start sending up the emails beforehand? What made you want to start finding this specific guest that you wanted to bring in to the podcast? And is it still as relevant now or is there better processes now like

Srini Rao

Mm-hmm.

David Siegel

like getting feedback from other people like Michael Shine of who would be a great person to be part of it. And hopefully I'm not letting you and Michael down as we're speaking right now. But I think the process I would do is ask as many questions as possible, and then ask questions on why you should continue to do the same things or whether you should possibly stop doing the things that you're doing right now.

Srini Rao

Yeah.

Srini Rao

No, not at all.

Srini Rao

Yeah, absolutely. No, it's funny, I kind of have probably some of the most ruthless guest standards around. I've turned down plenty of famous people. Like, what somebody has accomplished is of very little interest to me. Their story is of far more interest to me. And Michael, I know, has sent me nothing but people with really interesting stories. And if you weren't living up to it, I would have cut the interview in the middle. I've done that before.

David Siegel

Pew!

Srini Rao

Yeah, I'm not an easy person to deal with. Wow. Okay, cool. So at this point in your life, I mean, you've accomplished more than a lot of people get to in a lifetime. And I wonder when you think about wealth, money, success, has your definition of what that means changed with time and age?

David Siegel

So from a young age, believe it or not, I always saw wealth as a simply a complete means towards freedom. It's almost like the slaves of the path that are to, this is a terrible analogy, I'm not even actually gonna go there. What I would say is that wealth and building wealth gives you an opportunity to spend your time, which is the most precious thing that you have in the endeavors.

of how you want to be spending your time. So my plan personally is this is my last CEO gig. I hopefully will run Meetup for a meaningful period of time. And then if we ever decide to go public or sell the company, then I don't have an interest in running another company after that. I'm up for my next adventure of whatever that is going to look like. And I've been a corporate person for 25 years. So for me, success.

Sure, here is the text with the timestamps removed:

Srini Rao

Mm-hmm.

David Siegel

was understanding that, to be so cliche about it, but it's true, you work to live, you don't live to work. And what that meant is I was one of the first people to leave the office in my 20s and in my 30s. When people are grinding and looking to how they could become the next CEO, to me the important thing was, how can I get home, how can I have dinner with my family, how can I make sure to put my kids to sleep, how can I be as happy a person as possible?

maximize my happiness, maximize my positive energy, and I'll be successful because I'm a happy, positive, energetic, and hopefully good at what I happen to do. And an extra hour or two in the office is only gonna cause negative emotions, negative feelings, and potentially let pessimism actually creep into my future. So things like prioritizing exercise and working out every single day, it's one of the best investments of time because it gives you more energy.

Srini Rao

Yeah.

David Siegel

to ultimately be successful in the things that you care to spend your time doing. So to me, that's been the priority. How do you live kind of as balanced a life as possible? And when I hear people say things like, well, I just need to put another five or 10 years into working till midnight every night, and then I'm gonna start enjoying myself. No, no. Like, how can you enjoy your day to day while still setting yourself up for a successful future? Joy in the day to day.

Srini Rao

Mm-hmm. Yeah.

David Siegel

and then setting yourself up for the future.

Srini Rao

Yeah, I remember you may have read it. The sky, Bill Perkins wrote a book called die with zero. And he talks about something called the peak utility of money. And he said that there's going to be a certain point at which you're not going to be able to do things with your money that you can, uh, you know, at when you're younger.

David Siegel

Yeah, listen, the happiness curve is real. And the interesting thing about the happiness curve is that, is that the more money you make leads to more happiness up to a certain point, and then actually the curve goes down, believe it or not, that as you start making even more money into the really big numbers, on average, people ended up becoming a little less happier than they are. So, so there's a negative to that. And when people just have an insatiable appetite for multi-generational wealth,

Srini Rao

Mm-hmm.

David Siegel

I tell my kids, I'm like, I am going to die with zero dollars. My goal is not to create this trust fund for you to be able to lackadaisically, just kind of live off of, but you know why? Because I care about their happiness and you're happy when you're creating something and you know that the reason why you have that is because you put the work into it and from that pain and from that work, you end up being

Srini Rao

Mm-hmm.

David Siegel

so much more appreciative for what you were able to build, I wanna give that to my kids. And if they have the trust funds, they don't have that. So, you know, it's gotta spend some money now. That's the goal.

Srini Rao

Yeah.

Srini Rao

Yeah, I remember, like I put this post on Facebook, I said, you know, somebody said, okay, I'll give you $250,000 now, or you can earn $250,000 over the next year by doing the work, which would you take? And I said, the smarter would be to do the latter, because the thing is that you're gonna learn how to do it.

David Siegel

that. I really like that. And then you'll be able to repeat that next time and make more than $250,000 when you do that. It's you know the old adage of teaching people how to fish versus fishing for them and it's just really important. That's what good leaders do, good coaches do. You know they help people to figure things out for themselves as opposed to do things for them. That's what parents do frankly. There's a lot of similarities actually between parenting and kind of leading a company which you know becomes more apparent, pun intended.

Srini Rao

Exactly.

Srini Rao

Yeah.

Srini Rao

Yeah, wow.

Srini Rao

Well, hopefully my experience of running a small team of three to four people is preparing me for being a parent, but I also get to ask people like you for parenting advice. Although rumor has it that regardless of all that, it's still going to be a giant shit show.

David Siegel

No matter what. Man plans, God laughs. There will be always lots of ups and downs with the kids. But hopefully they don't hate you. That's the goal.

Srini Rao

Yeah.

Srini Rao

Yeah, wow. I feel like I could talk to you for three hours. There's just, you seem to be a wealth of knowledge and this seems like it could be a pretty deep rabbit hole. So in the interest of time, I wanna finish with my final question, which is how we finish all of our interviews. What do you think it is that makes somebody or something unmistakable?

David Siegel

You know, I really believe in the energy that people give off. And I'm sorry if it sounds so wishy washy or whatever, but when you meet with someone, like even this exchange that I'm having with you right now, and we're not in person, we're doing this through audio only, you could just feel your energy just pouring out and coming through and just the way in which you're exuding kind of your enthusiasm, you know, for your subject matter.

for what you do every day. And to me, what makes someone unmistakable is that energy that exudes from them when they're talking about the things that they're passionate about. And I love the fact that you have this podcast because it helps people to share their passions with other people and hopefully learn from that and hopefully be a motivation for that as well. So to me, that's the recipe. It's the energy around people.

Srini Rao

Amazing. Well, I can't thank you enough for taking the time to join us and share your story, your wisdom and your insights with us. And I just realized, I don't know if we did mention the title of the book, the entire conversation. No, no, trust me, I always ask people at the very end to let us know where, so on that note, where can people find out more about you, the book, your work, I mean, obviously meet up, but beyond that, where can people find out more about you?

David Siegel

I was thinking that the entire time I was like, no one even knows what the fuck's Dave is. But I didn't want to say it. Ha ha ha.

David Siegel

Okay, so for Meetup, download the app. It's a great experience, find a community, and it's available for everyone in every country, in every city. In terms of me, the book is called Decide and Conquer. You can listen to it, you can read it, you can find it on Amazon, wherever books are sold. You also go to our website, decideandconquerbook.com or Amazon, and I would love any and all feedback. You can even send me an email to davidatmeetup.com, and love to hear your feedback.

Srini Rao

Amazing. And for everybody listening, we will wrap the show with that.