This episode with David Siegel, CEO of Meetup, explores finding your "why" and then the "how" in order to create new career opportunities and engineer serendipity. We also talk about David’s new book, Decide & Conquer, his relationship with WeWork’s Adam Neumann and how growing up in a tight-knit community shaped his career path.
[Ann 00:00:00] Welcome to this week's episode of the Bet On Yourself podcast, where we speak to some of the world's most inspirational people who have all, at some point in their careers, taken a huge bet on themselves, transforming them both personally and professionally. Today I am joined by David Siegel, the CEO of Meetup – the largest platform for finding and building local community. He has over 20 years of experience as a technology and digital media executive, leading organizations through innovative product development, rapid revenue growth and digital traffic acceleration. David is also the author of an incredible book, Decide and Conquer, within which he has shared his stories of success, the framework he uses, and how he's tackled those darker days. David's career path has been varied, and how many people can say that they were once a courier traveller, flying around the world for only $99? I can't wait to share David's story with you all today, and if you love this episode as much as I think you will, then please do let me know in all the usual places, such as a review on Apple Podcasts, Spotify, Youtube or anywhere else you happen to be listening.
[Ann 00:01:08] David Siegel, welcome to the Bet on Yourself podcast. I'm so excited, I just stumbled over the name of my own show. How are you?
[David 00:01:15] That is really excited. Oh my gosh. So I'm excited that you're excited. Let's do this.
[Ann 00:01:21] This is really fun. So we were talking before we started recording how you and I have been ships in the night through so many moments of our career. So this is going to be a fun conversation because I think we know a lot of the same people. We've also seen a lot of the same challenges, having survived the dot com bust and all the lessons learned through that and the many iterations that have since followed. But first, thank you so much for being here.
[David 00:01:47] I'm glad to be here. I guess that's a euphemism for saying like we're both old, So I love being old. It's great! It means have lots of experience we have seen tons of people and inevitably we know lots of people because we're old.
[Ann 00:02:00] We are old now. I feel like when I hear my bio now, does this happen to you? I hear my bio of like her first job out of undergrad was working directly for Jeff Bezos at 2002. People look at me like I'm a dinosaur. I'm like, to me, it wasn't that long ago. I don't know it's all gone so fast.
[David 00:02:17] Yeah. You know, that's that's why we talk about experience.
[Ann 00:02:21] That's right. We're wise. We're wise. So, David, on the Bet on Yourself podcast, we like to start at the very beginning. I'm curious what a young David thought he was going to be when he grew up. Does that in any way resemble the path that you took?
[David 00:02:35] Whoooh! OK. Somewhat. I mean, the super young David Siegel saw Raiders of the Lost Ark and fell in love with like history and wanted to become an archeologist. And I just said, I want to become an archeologist. And that was like my dream job because I always loved history and learn from history and that was the very young David Siegel and then the college David Siegel. Oh, how annoying is it to refer to yourself in the third person! College me - I hate that guy - The college me wanted to change the world and make the world a better place. And my first internship in college was for a nonprofit. And after working in the nonprofit, I was like, I will never work for a nonprofit. And then I spent, and then I worked as a teacher actually, while I was also in school. And after teaching kids, I was like, I will never work as a teacher. So, you know, going to Penn and having more than around me, I unfortunately became this capitalist person. And, you know, Meetup is about making the world a better place, which we'll get into. So it is not dissimilar, just a curvy path to get there.
[Ann 00:03:42] I am definitely going to dive into a lot of these lessons learned in the early career because I - I'm the oldest of seven kids. So my youngest sister is 22, so she's at the very beginning of her journey. And I think having a lot of much older siblings - because she was she was a surprise. So the used to be youngest is 12 years older than her. But I think having so many older siblings, it looks so polished already. Like that's how it should feel at the start of your career and I love I, I wrangled an early release copy of your book and what I loved in that is so much of what you learned in the early parts of your career that you didn't like that you've just highlighted now you, you learned like OK, I don't like this environment, or I do want these people around me. But before I get ahead of myself, I know you referenced several times in your book about how much of your value system and the way you run your life and your company comes from your upbringing. I wonder if you can give us a foundation because that's such a common thread amongst all the lessons that you share in your books. I thought that was an important foundation to establish.
[David 00:04:45] This is so exciting. OK, I grew up with very, very strong family ties and also very strong community ties. So I think people who grew up with, in a religion, whether it's church or mosque or temple or whatever it is, oftentimes tend to have a strong community ties. And that's not the only way to have community through religion, but it is a way to have community. And as we know, people going to church, etc. has decreased significantly. But fortunately, I grew up in an environment where if, God forbid, someone passed away, they would have food served to them. Dinner, lunch, everything for like a month, you know, by just people in the community. So, so for me, the way in which I grew up with this like very, very deep kind of community orientation definitely influenced my like infatuation, shall I say, with Meetup, which is all about a community platform. And, you know, I consider myself so lucky to have grown up that way and and never really feeling the loneliness that so many people feel and, and, and, and being so fortunate that that was the case. And when I hear statistics like 46% of people regularly feel lonely and 25% of people don't have a trusted confidant to go to it like kills me and I just want to help as many of those people as we can. So it definitely had a big influence.
[Ann 00:06:14] And as Steve Jobs famously said in his Stanford commencement, it's only in retrospect that the dots connect because now it sounds so obvious that you would end up as the CEO of Meetup, where building community in a very digital world seems so obvious, is your way of making the world a better place. But it was actually a varied path that led you here. And that is my favorite part of this podcast is all of those unexpected moments where you really had to bet on yourself and create opportunities and engineer your own serendipity. And you, David, my friend, are a gold standard of that. You did that in so many extreme ways, which I think would be really fun to walk through. And one interesting note that I didn't expect...
[David 00:06:54] Sending out , sending out five-ten thousand emails in one night (Literally!) was extreme? Come on!
[Ann 00:07:00] And I love that you got a corresponding number of rejections, right? It's- that was - that part made me laugh in your book. But right before that, I think it's interesting the way that you framed your education and the way it prepared you for the authentic but bold way you've showed up in your approach to your career. In fact, when I was looking at your resume, you have a B.A. from a University of Pennsylvania in philosophy, politics and economics. And I was like, I've never heard of that. I've never heard of that degree. I probably would have done that had that been offered to me in undergrad. But I love the way you describe it. In the book. You said, quote, "The lessons were an inch deep and a mile wide. I had a cocktail party level knowledge of about everything. I would become a specialist in nothing but have basic skills across broad disciplines. And most important, I'd be able to understand the relationship between disciplines, which is often the best approach for tackling problems." This is my favorite part that I highlighted. "Turns out that was the ideal preparation for becoming a CEO." There's so much emphasis on finding your specialty niching down, knowing your avatar. I myself preach that often to my clients, but I think it's this breadth. When I when I read that in your book, it made me pause and think about the very successful people I've worked with and for. And I see upon reflection, that 100% of innovation comes from the space between the verticals. When I look back on these breakthrough moments I witnessed or was a part of it was in those moments in between. I wonder if you can elaborate on that before we move into this crazy like career journey you've had.
[David 00:08:36] No. I will riff on that I mean, when I go to a wedding, I definitely like the smorgasbord a lot more than I like the main course. It makes sense. I mean, you know, a lot of parents are risk averse and people are risk averse and they tell their kids or they tell - people tell themselves, if I become the absolute specialist in this niche area, then I'm always going to have a job and people are going to people are going to always want to hire me. And you're probably right. You will always have a job if you're a niche specialist. But will you be the most effective in your job? And David Epstein, who wrote Range, which is an incredible book, by the way. So good. Not as good as Bet on Yourself (Thank you) but better than my book. And he talks all about like the benefit of being a generalist versus a specialist in terms of the things that you're actually even specializing in. And the you know, the famous example oftentimes is a basketball player who played all these other sports. And then he's amazing at basketball because of the fact that he played all these sports. So speaking of myself, I have seen so many people that have been in sales, let's say, their entire career or been in product their entire career, and they're in sales and they don't understand that the best way to sell most effectively is to have a product understanding and product knowledge. The best way to be a great product person is to have a commercial understanding and a business knowledge of like the revenue and EBITDA and profit aspects of everything you're doing. I basically took jobs all over the place. I was in consulting, I was in business development, I was in marketing. I just had this exposure to to all these different areas. And it does come from a certain confidence and betting on oneself that, that, that, that you enjoy putting yourself in a position of discomfort because you know you're going to grow more from that position and you know it's going to make you better at everything that you're going to do. And and I think you're right, so many of the CEOs that I've always admired in life are people who had a variety of these different experiences and they're able to niche together experience from one place and bring it to bring it to a totally different discipline. And that's how great products oftentimes get built if you think about like whether it's Airbnb leveraging different things from other companies like Uber or et cetera, great things get built through imitation, not necessarily always from innovation. And when you're able to have that discipline, you can do more imitation than innovation in kind of a different way.
[Ann 00:11:02] I, I was sitting here nodding incessantly while you were talking because I've just seen that to be true in so many instances, so many different moments in time across my career, different industries. I really think there's a lot of wisdom to that. And you touched on a little bit of how you prioritize the opportunities while seemingly disjointed in the types of companies, you know, from consulting to smaller companies to big, huge behemoth companies. I loved in the book how you pointed out something that I say until I'm blue in the face the, what you prioritized in choosing it. You didn't prioritize the money or seemingly external prestige. You prioritized what experiences you were going to have there. Can you give us it's really hard to summarize a career as rich as yours, but I find this this decision making train fascinating in your experience, your first job, as you alluded to earlier, how you got that first opportunity out of undergrad by literally like bombarding everyone who seemed fancy and important, then some seemingly unexpected pivots and risk taking of saying no to things that seemed like the obvious safe choice in order to open doors for you, that seemed unexpected. Can you give us the highlight summary of that?
[David 00:12:14] Let's do it. OK, so I think the overriding theme is exactly what you said, which is how can I have maximal exposure to really, really smart people so I can learn as much as possible from them. Like, that's the headline. So when I was in undergrad, I I - actually before - when I was into undergrad, I applied to 50 different companies for summer internship and consulting. I got rejection letters from 50 different companies, put them all on my wall, and that was like plastering my wall with it. It was great. And then I got like a random call from one company called Mercer Management Consulting and said You're the only person that actually we got a resume from. So it's yours if you want it in Philadelphia. So I spent the summer in Philadelphia. I just started going out with someone who became my wife and you know, we were separated when we first started on, That's OK. And so I took that job as a summer intern for Mercer Management Consulting. And then what I did is I ended up after graduating with five job offers, and four of them were from big companies like Deloitte and really impressive names in business school from BCG. And all these like really impressive sounding brands. And ultimately, I chose a place no one would have ever heard of, and the reason for it - called Brecker & Merryman, it was was a 40 person shop - the reason for it was, was that they said to me, You are going to get full exposure to meet with clients all the time, not be the quote unquote, you know, person who is invisible. Just doing PowerPoint decks in the background, like big consulting firms you would do, you're going to go on client meetings, you're going to be expected to even bring in business within a year or two after you're here. And and that's what I wanted. I wanted maximal exposure rather than the brand name or whatever because that maximum exposure. Yeah, sorry.
[Ann 00:14:00] I'm just curious. How did you have that wisdom so young? Like I say, looking back, it seems like I had this master plan of how I worked for three of the most powerful CEOs in the world. I didn't, but I looking back, I can apply some method to the madness, and I did the same priority number one, I want to work with people I not only like, but I want to become like, I want that kind of a leadership that's going to train me to be my future leader self. Second, I want to learn as much as possible, as fast as possible. And third, I want to be in a disruptive industry team, whatever, because I want to disrupt myself. It seems like you had this clear compass at a young age, or is it more like me, where in retrospect you can kind of like decipher the formula, but at the time was it calculated?
[David 00:14:43] Ah totally retrospective. OK, I mean, of course you like calculating, you think you're calculated, but really like your calculations totally messed up in the beginning. Really for me it was I want to work with people that I feel like I can trust and I don't want to feel insignificant. That was my main thing. I don't want to feel replaceable and insignificant and that my time and what I'm doing doesn't matter. That was kind of my main thing. I really want to have a meaningful life and I'm meaningful work life.
[Ann 00:15:09] That gave me a little bit of goosebumps because maybe it's because of recent conversations with my sisters who are participating in the great resignation and really like realigning themselves on switching teams within their companies or their focus. I think a lot of people are having that conversation with themselves, right? They want a life of significance and a third of our life is spent at work. So how can we stick that out? I think that is a nice segue back to your original story flow, which is because you were wise enough to choose to work at Brecker & Merryman, you were able to get a relationship with the DoubleClick CEO Kevin Ryan, at a very critical moment, which, and that kind of changed the course of your life, I would say.
[David 00:15:49] Course of my life. I was 24 years old. I built a real relationship with Kevin Ryan, with the person David Rosenblatt then took over as CEO with the entire executive team. And then at some point they said, Hey, we're paying Brecker & Merryman $200 an hour for your time. You're getting paid like $45,000. Why don't we pay you more we pay less, and everyone wins! It's a win-win. Well, not everyone wins, but like, at least DoubleClick and I win. So I only got that, exactly what you said because of that, like maximal exposure that I was able to get. And then once I went into Brecker - I think it was once I joined DoubleClick, one of my roles was actually in succession, was actually in human resources department and and working on succession planning and working with every executive really closely and every director and manager on who the people would be that would take over for them should they get hurt by the proverbial bus, which hopefully, thank God, never happened. And that gave me this like deep relationships, because when you're working on people teams, you really get to know the people who you're supporting and working with in just a very different way because you're dealing with such sensitive issues that are, that are complicated that managers and leaders all go through. And I was 24 and I'm advising, you know, people that are much later in life and experience than I was. And it ended up that over 200 people have become CEOs of companies through the early days of DoubleClick. It's insane.
[Ann 00:17:15] Wow. I did not know that. So that network -
[David 00:17:18] Yeah. It's really like, you know, everyone knows the PayPal Mafia on the West Coast and eBay. So it's kind of almost like that in the East Coast in terms of kind of because DoubleClick was built Silicon Alley back in like 1996, 1997, 1988, those early days. So because no one knew the internet stuff. So when people were 27 years old and they knew infinitely more than many people who had, you know, decades of experience on the internet, so and just fast forward. Not to be a spoiler, but Kevin Ryan is then the person who ended up acquiring Meetup out of WeWork...
[Ann 00:17:53] The savior returns. So everything goes full circle.
[David 00:17:57] Savior returns. Exactly.
[Ann 00:17:58] Oh your story is just like full of these like surprises these ebbs and flows as these crazy characters come in I can really relate to that. So I've been alluding to the book because I'm a huge fan already. Binge read it in one sitting and you, so your book is about 44 decisions every new leader makes and you structured the book around, you outline kind of your first 30 days, your first quarter, your second quarter, your first year, but you actually start before that. This is a chapter I didn't expect you actually start off in day zero which I think is advice no one talks about, and the second I read it, I was just like, yes, I've seen this in action so many times. So some of the first principles you introduce are maybe a bit of a surprise of what are these 44 like leadership qualities you really wanted to highlight of how you've learned over and over again in your career. And it's one of the most commonly asked questions I get is like, what are the common denominators between Jeff Bezos and Eric Schmidt, Marissa Mayer and all the Elon Musks that were floating around us for 15 years? And my answers usually surprise people, but it's very much your list. So you start off by introducing us with number one, be kind. Number two, be confident. Number three, be bold, and it continues from there. So in this crazy career that you've found yourself in, um, maybe we should highlight that day zero because that for me is so much of the underpinnings of so much of your success is what you actually do before you take the job in the interview process, the way you negotiate for yourself. In fact, I highlighted one of my favorite quotes of the whole book. You say "The best time to negotiate for anything is actually before you accept the job." And that was just like a lightbulb moment for me. I was like, Obviously, can we start there? Can we start with day zero and like choosing the right opportunities? If listeners right now are participating the great resignation, they're asking themselves those big questions of what meaning what contributions do I want with this single precious life of mine? How can they approach that and create opportunities that are going to bring them that satisfaction and significance.
[David 00:20:03] Woo wee! Okay...
[Ann 00:20:04] No softball questions here.
[David 00:20:07] Yeah, well, I love it. So OK, let's talk about Decide and Conquer, the book. So the first piece of advice I would say is even though the job of the organization that you join, their entire job is to set you up for success. Few organizations are great at doing so. You need to put that burden on yourself. So prior to joining, it is so important to take very specific actions and some of them are actually even universal in nature to set yourself up for success. So what does that mean? That means things like, number one, really understanding exactly what the expectations are in your job of what you're going to be doing and what you're not going to be doing prior to starting. And that's true for a CEO as true for the most junior person sitting down with the manager even before you start and going through literally through a job description and saying, OK, you know, sometimes people write job descriptions willy nilly and they don't put as much time into it. And some things. there could be ten things in the job description, but one of them is like 80% important. And the other stuff isn't important at all, like a line on exactly those things that are the most important items. That's number one. Number two, if you think that something about your accepting is going to be frustrating for you in the months and years ahead and in the back of your head, you're going to be like, Damn, I, I'm frustrated that this is the situation whether it's I used to have a bonus, I don't have a performance bonus now. My work isn't tied to, you know, my future or whatever those things are that are very important to someone - who you're reporting directly into, what the what the plan is for when you would get promoted next. Ask for that, like you said in advance. And if the answer is no, that's OK. Ask for the timeline of when it can be reviewed so that the answer could potentially turn into a yes. Because as you said really well, they need you the most before you sign and once you sign, you signed. So so negotiating beforehand is very important. The other thing that I did at Meetup very specifically and I think this is applicable for leadership roles, is I signed. But my first day in the office wasn't - my first day in the office was close to a week after my first official day. Meaning what I did is I took the first week. No one knew that was even my first actual week. And I spent the time meeting with the founder of the company, meeting with the entire executive team, meeting with lots and lots of different people, meeting with board members, meeting with WeWork and putting a plan together and listening and learning as much as I could before day one of actually starting, because on day one, you're barraged. I had 250 people reporting in to me. Everyone thought I was going to be like Moses with Ten Commandments and telling them the new strategy of the company. And that's never the case. You know, you don't know much, but I set myself up for success by having so many meetings prior to starting that it was very valuable - And the crazy thing, Ann, is that before my first job, even in college, I remember - I don't know how I knew this, but like going to the partners that were in charge of the company and meeting with them before I started, and I said to them, what books should I read so that I could be set up for success before I even start? Because that day zero time or that day -20 time, as you could even say, enables you to hit the ground running in a way that if you just, you know, started off immediately, it won't. And last thing I'll say is that one of the messages that I tell all managers in the company is send information to people prior to their starting. Too often then, the manager will respond back. But I don't want to overload someone. I don't want to stress someone out. I don't want them to feel like they have to read it. No problem. Tell them, you don't need to read any of this. I'm just sharing stuff with you. And if you want to read it, then I'm helping you to get up to speed faster if you want it. But it's no negative reflection if you want to go for a two week vacation prior and now look at it all. No problem. But my job as a manager is to make you as successful as possible. So I'm going to give you these pre reads and inevitably you're like, Oh yeah, that makes sense. And then every single time people say, to me, Thank you so much for giving me all that stuff to read. Now, I could be so much more successful when I start. So managers out there help your people to be successful before they start before day one.
[Ann 00:24:27] When you say it out loud like that, it sounds so obvious. Why is not everyone doing this? But as you're describing that I was reflecting back on my favorite hires the people I hired who were like the ten x force multipliers. Right. And both of them, the first two names that came to mind, both of them did what you just described. One was Brian, who I hired from London, sight unseen before this whole, like, Zoom thing was a thing and respectable. I hired him and had him move to California, sight unseen. And he did the same. He was like, send me a Google phone, send me all this. Like, I got it. I'm going to - I've got a long plane ride like, I'm going to get up to speed, huge force multiplier. And then my first employee in the startup, after I left, I quit Google, Becky. Hired her, before she even started she negotiated a salary increase. Like literally we had signed a contract and she's like, actually I've been thinking about this. That's matching my current salary. I'm taking a big risk coming to a startup like, no. And I was like, You're right. And I gave it to her.
[David 00:25:23] And you know what, Becky would have been frustrated. (Yeah!) And even if she - maybe she - it wouldn't have come out in her work, but it would have come out in other ways. (Yes.) And like we don't want Becky to be frustrated!
[Ann 00:25:34] No! She's amazing! We want her to be happy from the start. (Yeah, exactly). OK, I've - it's so hard for me to choose what question asking next. I'm going to ask you an unexpected one, but I don't want to lose track of where I was going to go, which is back to - because I loved what you said about job descriptions. Because I'll tell you right now, based on my CEO clients, they very much are making those up as they go that's one of the things I focus in my consulting work with them is having much more purposeful job descriptions so they get better hires. So I want to come back to that - We should talk. I definitely want to come back to that because I think you have a great example in your experience of when you sought out a job that didn't exist and had to sell it and then sell yourself as the perfect candidate for that. So that's where I want to come back to. But can I ask you, how did you get to the title of the book? Was that the original title Decide and Conquer, or was that because I just love it and it just something clicked in my brain as you were just giving that answer of like, wow, that's the perfect description for your methodology here.
[David 00:26:32] Thank you. It is all my wife. I was talking to her about, you know, we're organizing this around decision making and biases that people have in decisions. And I came up with a whole bunch of terrible names, like Decisionology and like things like that. And then she's like, how about Decide and Conquer? I love it. And I said, Damn, you're good.
[Ann 00:26:53] Oh, she is good because I too went through like 15 titles for my book before I got to Bet on Yourself. The original title was Say Your Name, which I still kind of like, it just didn't test as well. So some are kind - but yeah, Decide and Conquer. One, it sounds like a spy novel, which I think is exciting, and it's so, it's a perfect encapsulation of what you're doing. OK. Sorry, that was an aside, but I want to go back to - Can you tell us the story of when you invented a job that did not exist in 99% of the company, pitched it, and then many years later, they sought you out for that job. I love this story.
[David 00:27:28] Oh, yeah. That's awesome. OK, great. OK, so I was in business school and part of again, my priority was maximal exposure to key decision makers. So I decided my top job I wanted to be was an assistant to the CEO, which meant, you know, I would do PowerPoint decks or board decks, you know, maybe get coffee on occasion, whatever was needed, but do some strategy stuff and also maybe some admin related things. And I'd get like great exposure. So so I sent notes out to like thousands, hundreds and even thousands of people to CEOs and to like Ken- Ken Chenault, who is from the American Express CEO and Jim McCann, who is the CEO of 1-800 flowers and Monster CEO and David Stern, who just passed away. The commissioner of the NBA. All these interesting companies, at least for me. And and then I end up talking to Jim McCann, who was the founder and CEO of 1-800 flowers and I tried to say, hey, I want to be your assistant CEO and he's like assistant? I already have an assistant. I don't need an assistant. Nice talking to you. Whatever. Three years later, I kid you not. I get an email from a buddy of mine and it said, Do you know, 1-800 flowers just posted something on Wharton's alumni database saying they're looking for an assistant to the CEO. I'm like, hot damn. So I sent an email to to Jim McCann saying, I don't know if you remember me, but three years ago, I had - you and I had a conversation for half an hour and, trying to, and I tried to convince you to become the assistant, the CEO and you kind of rejected me. So then he just emailed back five words, and the five words were, I was looking for you. That's - that's five words. I was like, bro, well, if you're looking for me, let's have breakfast. So we had breakfast and and they weren't actually looking for what's called a vice president of strategic initiatives because what the heck is that? It's just basically a made up name, a title. So then we met and I didn't end up becoming the assistant CEO. I just became vice president of strategic operations which basically meant I could create my own role, create my own job, and they're just like, we want you here and we'll figure out what you're going to do. Are you ready to jump in? And I was like, Let's go. How deep? I took the job and it was interesting because the whole executive team I met with, a couple of people were like, what is this young, you know, person who is 28 years old coming in as an executive in the company as like a vice president with some made up job? Like, who does he know? What's that? And there was a little bit of pushback, actually, at times because my job was actually to almost serve as a internal consultant, to meet with the different leaders of different areas. And and and try to help them with any ways in which I had helped other companies, whether it was at DoubleClick or when I was consulting, and help them to become more successful. However, you define success. And what I did, though, is, again, how do you set yourself up for success? So I really made sure that I wasn't just going into these meetings with executives kind of cold. I actually wrote the email, I gave it to the CEO, of 1-800 flowers to introduce me in an appropriate way to them so that they wouldn't feel defensive or worry that I was coming out to meet with them and, and, and, and they would be reluctant to share things with me. So the first thing I did is I said, I need to establish trust because trust is everything. So people will share things with me that would actually benefit the company if I share them with the CEO of 1-800 flowers - 1-800 flowers by the way, owns a cookie company, a chocolate company, a Harry & David, a gift basket company, all these different companies underneath the larger company. And I met with them and and I said and they would share information with me and I wouldn't divulge that information because it was more important to have the relationship and the trust than the one off way. And I would say, hey, you should talk about this with X, Y, Z person rather than me being that like annoying, squealing, whatever type person. So because of those relationships I ended up getting promoted by the end of about four and a half years at 1-800-flowers. I was overseeing, you know, the company's database that has about 30 million names across all these different brands all international operations for the business. A couple of acquisitions I was overseeing mergers and acquisitions and M&A for the company. We acquired a whole bunch of other different companies so I had like five or six different kind of functions that were all reporting in to me. So it definitely succeeded. And I was on the executive team of this publicly traded company and learned both what one should do and what one shouldn't potentially do. You know, you know, at a relatively young age.
[Ann 00:32:04] I just think that's incredible. That's exactly I mean, you're hitting all my like love languages of career aspirations because that's exactly what Bet on Yourself is about, is creating, engineering serendipity. You're going to work your tail off, but you're going to create opportunities and you're going to be playing the long game. That's why your career is like being recruited, recruited, recruited. Once you found your footing is because of that. You thought about playing the long game. I would be remiss. OK, wait.
[David 00:32:32] Before your next question, I have to say something (Yes.) if you don't mind on the thing you just talked about. OK, which is engineering serendipity, which is just like an awesome way to put it. I oftentimes use the term kind of prioritizing optionality and decisions. I love it. Meaning, meaning some people make decisions and it narrows down your opportunities, like having a kid or having a dog. You have less free time and there are certain decisions that are like trap door decisions that are tough to change. But many opportunities, many decisions can open up new opportunities for you and your job in making decisions is to figure out whether it's limiting the number of options you have or maximizing the options. The reason why that's so important is because of what you said, which is serendipity. And luck. You could create your luck and have lots of lucky things end up happening to you. Like, Thank God they've happened to me and they've happened to you also in your career because of the decisions that you make invites luck to happen because of oftentimes relationships that you built or because of experiences that you've had. So figure out how to actually make decisions that open up many different options for yourself and then luck ends up happening. The best thing you could probably do is build relationships with people and and try to do as good a job as you can in those relationships. Good things end up happening from that.
[Ann 00:33:53] I couldn't agree more. And I love how in your book you quoted Good to Great where it's figure out the who first and then the what I think is the quote that has 100% been true for me. That's probably 90 plus percent of the luck that I've had is just the relationships the people who think of me later or recommend me for someone or something or that follows you and that leads I would be remiss if I don't say you have enough time to do justice to your current incredible career move. So one. you are CEO now of Meetup but that was not an easy arrival. So you were taking over from the founder. And I know from experience, I've worked for founders and I work for professional CEOs. They're very different. Founders have some secret sauce, special thing that cannot be replicated. And so when you bring in a professional CEO to replace them, that transition has to be really well managed. You describe so beautifully in the book things that you did to make that successful, but you had the added crazy factor of Adam Newman had bought this company and you came on board as CEO of this subsidiary company immediately before the famous downfall of WeWork. But it was a huge acquisition. I mean, put like what was that 150 something million dollars into acquiring this company. So there's so much we could say about this and I'm happy to talk about any part of this insane journey that you've been on. But one I think is really applicable to our listeners is how do you manage up to difficult people? How do you be seen as a leader when you need to get people to know, like, and trust you very, very fast, which was the scenario you walked into. What are the universal universal applicable things that listeners might be able to adopt right now if they find themselves - hopefully not with an Adam Newman type of personality, but with a challenge that seems a little bit outside of their seniority or control?
[David 00:35:45] Oh, wow. OK. Oh, OK. And we all face that in our lives of working for people that we can't change and we just have to make the best of that situation. And so here's a couple of thoughts. So number one, figure out what kind of relationship you want to have with someone right from the start. In Adam's case, I had decided right upfront that I was - did not want to have a best buddy relationship with him, that if I had a best buddy relationship with him and I divulged everything going on with me, and if I went to him all the time to seek advice because the decision making was so haphazard and he was all over the place, it would end up with me constantly ping ponging back and forth between kind of aberrant behavior that could potentially hurt, hurt, Meetup. So I actually made the decision I'm going to keep him far away. In fact, one of the negotiations that I said right upfront before I started, as I said, I don't want to report to Adam, and that was fine. I reported to an incredible person, the president, the company, Artie Minson. And I also don't want to have Adam constantly calling me up with ideas and suggestions. And one of my like amazing moments was and Adam calls me like a month and a half into starting and he says to me, I know I'm not allowed to talk to you, David. I just have a quick question about someone who used to work for you who I just want to get your quick feedback on. And then, and then I won't ask anything about having to do with Meetup. And I was like Vice. And when Adam Newman actually is listening to someone, that is really remarkable.
[Ann 00:37:21] So for listeners who are not familiar with the WeWork demise and Adam Newman, he's a very unique character. In fact, one of the few Silicon Valley people I've never met in person so I know it just by reputation. There's an amazing podcast, what was it called - We... I'll find It, put it in the show notes, but it's about the demise of WeWork.
[David 00:37:40] Yes. We Crashed is also (WeCrashed!) on Apple. There was a great book called Cult of We, another book called Billion Dollar Loser. Hulu had a documentary series also, I think it was called We Crashed.
[Ann 00:37:50] We Crashed was the podcast I listened to last summer. So good. And I think there's a lot to learn because people ask me - this is an aside, but people ask me all the time. A lot of entrepreneurs see those larger than life personalities, those people who will like, the Travis Kalanick's of the world, who put their head through a brick wall day after day, and they think that's what a CEO is. I think there's a lot to learn about how to - I think through your example is you had a very clear idea of what you were going to change. You had a methodology for when and what to change. Because you weren't going to, you talk about that in the book of not changing it like a core value, core definition. Do the small wins first, learn those trust. There's, oh, everyone just go buy and read the book. It's so good. But I think there's a lot to learn from, you know, the bad the, the, the bad examples out there as well. Sorry, continue.
[David 00:38:41] Sure. So, so number one is determine what kind of relationship you're going to have with the person. It doesn't - you don't have to be best buddies with your manager. You have to do as good a job as possible. And, and that's kind of piece of advice number one. Number - advice number two is figure out how to build a personal relationship with your manager and with your colleagues like we talked about earlier outside of just work related stuff. So too often I have a meeting with, let's say, someone who reports to me and they're like, here's my agenda, blah, blah, blah, blah, blah, blah, blah, blah. And I'm like, OK, could you talk about how you're doing right now? How like, you know, how are you handling everything going on? And and sometimes all of my one on one with someone is just on personal type conversations. When you build that personal relationship, it helps you professionally more than just a purely professional relationship. So that's the second advice. Barriers will break down in a difficult relationship with a boss or with colleagues if you're able to find some commonality in personal relationships as well and people fear doing that, they don't want to be rejected. I had $1,000,000,000 in revenue or I want to have a plan together by a week from now. You need to have the backbone and the and the confidence in your betting on yourself to say, I know that's what you want. That's actually not what's in the best interests of the company. And here's what we need to do that's better. So, for example, I'm not going to give you a strategy plan in a week that you're asking for. I need to take three months. I need to get feedback. And that's what we need to prioritize. I'm not going to just make tons of tech changes and create even more tech debt. Maybe the right thing to do, is to take an entire six months or a year and replatform our business onto a new technology so we could succeed in the future. Be comfortable saying no and with the reason of why you're saying no to your managers and colleagues. Because oftentimes their advice can disenable your success and you feeling like you have to do what you're told to do will also disenable your success.
[Ann 00:41:14] I love that. I think that last bit there is just like like this little mic drop of gold getting into always. Whether you're a decision maker, you may or may not feel like you have the ability to push back in that way, but you do probably more in more ways than you think. Even as a junior, most employee and I found early in my career the way that I could do that in a way that felt non-threatening and comfortable to me was to what you just said is hone in on the why - why is this important, why is this tied to the company or team or my manager success? Because usually that's the first way to get in is like, I want you to be successful and look the best, get that promotion, whatever their driving forces and get that clarifying why? Because in that Why conversation, there's often those moments to be like, oh, well, if we're trying to do that, I would really need to do a good job here or have this foundational understanding or blah, blah, blah. And that helps you reframe that to make sure that everyone's on the same page for how we can approach this most successfully. Because a lot of the time managers are just moving so fast and they're like throwing the what at you, the what they need done, and not the why.
[David 00:42:20] And they don't give the context, not the context of what they're looking for. Pushback is deeply respected by almost every successful person out there because the way that they became successful themselves was that they were able to push back to their superiors and the supervisors and their managers. So when a junior person push it back on me, I'm like, Go you. Yes, thank you. You are totally right. Do it your way. Let's move on. And then they take so much more ownership of it because they feel more pressure to succeed because they did that push back and then are even more motivated than if they did something that they were told. So like everyone wins.
[Ann 00:42:50] I so agree. We could spend like the next 45 hours talking about just, your adventures as CEO there. I'm going to just use that as a teaser for everyone should go buy, Decide and Conquer. But I would be remiss if we didn't talk a little bit about the future because not only are you a CEO, I don't know how you have - do you have more hours in the day than the rest of us? Because you're also an adjunct professor at Columbia University. So you're also on the academic side. You're teaching the next generation of entrepreneurs what excites you the most about them? What are their unique approaches to business and to the future? Because I am obsessed with this space. And I'm curious your take on that.
[David 00:43:31] Oooh, OK. So first of all, my teaching also goes back to my wife because at one point I said to my wife, like ten years ago, when I retire, I think I'm going become a university professor because I love being around young people. I love teaching and she said, why are you waiting? Like, do it now, don't wait. So that's in general a good thing to do. I agree. So I'm teaching at Columbia, and before that I was teaching at Pace is probably one of the most meaningful experiences in my professional career. And the reason for that is because, again, it's the duality of res- of academic and, and professional. I am a better CEO because I'm teaching things at a university. Concepts that are kind of going on in the back of your head are forced to come in the forefront of your head. And a lot of times I'll be teaching something. I'll be like, Wait, I just did the exact opposite oh my God, oh, god, how can I teach this to you all about the Lean Startup methodology and MVPs when we're now doing. This whole approach is totally different, and I literally on my train ride home after teaching, I will send messages to people being like, I'm totally doing things the wrong way. So being a professor helps me be a better CEO and being a CEO definitely helps you to become a better professor because like students yearn for like real practical experience that is based on, you know, not just academic kind of stuff, but but real life stuff. And I'm so excited because today is the first day that I'm going to be teaching in person in two years.
[Ann 00:45:03] Oh, that's exciting. Oh, my God, I'm glad we've had this pump up conversation. Like, get you ready. Yeah. I was laughing really hard about that because I can't tell you how many times I've hit send on a strategy memo to a client and been like, all right, I need to read that to myself. That's like self therapy, right there, like, but I heard another entrepreneur describe it as you can't perform surgery on yourself. So I was like, OK, yeah, that makes me feel better about it.
[David 00:45:27] But it's so true. It's the same reason why all therapists go to go to therapy because it makes them more successful as therapists.
[Ann 00:45:33] But it's really true. It wasn't until I started public speaking or crafting the book that I started really being like, What are the steps like? What are the universal truths? What are the nuggets? And it's- so I love having that academic approach. I want to do that in more areas of my life of sitting down and being very purposeful and thoughtful and doing the math of like this plus this I thought would equal that, like clearly not going to lead to the result I was hoping for.
[David 00:45:58] I got to say one thing I do in the class, you could get any of this out later if you want to. So my first class, what I always do is I say one of the most important ways to build a product or service is to listen and understand the needs of your clients and your customers all comes down to that you, my students, my 70 students are my clients. You are my customers. My job is to help to make you all as successful as possible. So therefore, what we're going to do is I'm going to tear up the curriculum and I literally tear stuff up like in front of them.
[Ann 00:46:27] Like Dead Poets Society style, like...
[David 00:46:30] Yeah, Robin Williams standing on a table, the whole thing. And I tear it up and I say to my students, What do you most want to get out of this class? And we go through the things that they most want to learn. What are you most interested in? And then and then we craft the first third or so of each class - then we do a vote and everyone votes for things they're most interested in. And and then that's what we focus on and learning strategy, entrepreneurship, because then they feel this ownership of what you end up talking about because they're the ones that help to create that syllabus actually in the first place.
[Ann 00:47:04] I OK, a, I have so many questions about what they've chosen to talk about. Can - please send me notes after day one and let me know what your curriculum is because this is the future that's happening right now. B - so many managers should do the same of being like, why did you take this job? What do you want out of this next phase of your career? What does success feel like? I say all the time, my regular listeners have heard me say it a billion times, but I'm a big believer in your job should give as much to you as you give to it. And for me that's a decidedly high bar. So ask for it, be like, I'm here to learn this, I'm here to experience that, I'm here to volunteer for this. And there's always a way to create a win win win between what you want to evolve into in your career and what your manager needs and your company needs. If not, it's time to look for a different challenge. But more people should have those conversations of like, what? Why are you here? What does success look and feel like for you? Can I come to your class? I want to, I feel like I want to be a fly on the wall.
[David 00:47:59] Come, come! You're invited at any point in time. It would be lots of fun. The whole concept that a lot of companies are doing right now Facebook, Google, Apple is these stay interviews do the great resignation. And in these stay interviews, they're doing exactly what you said, which is which is what will keep you excited here, what will motivate you? And they're kind of restarting that whole conversation people had when they started a company six months a year, three years ago and doing it again. And too often it's only done. - it's not done at all. But if it's done, it might be done in the beginning, but certainly not done after people are here for two or three years. It's so important.
[Ann 00:48:34] So true. So true. OK, you've been very generous with your time. I only want more of it, but I'm going to wrap it up with two short questions. One is what excites you about the future? I know that could be a very long answer, but what excites you about the future immediately? And then how can our listeners connect with you and continue to follow you, through your book, your journey, your classwork coursework, your amazing podcast, please share about that. So yes, I will end there.
[David 00:49:03] OK, so the first question is around what I look most forward to. And you know, it's what you said originally, just serendipity. Life, you get one life and one of the great things about life is surprises. Like when the mail comes, even though it's almost always just bills, I get excited pathetically at 47 years old, I'm like, Oh, I'm so excited. I run downstairs, look at the mail. Of course, it's just like garbage and bills, but you just never know that thing that's just going to show up when you get an email. You just never know that. Like, I was just invited to speak in Saudi Arabia yesterday. I'm not going to because I can't. But like, that's cool. That's cool! Just randomly falls in your lap and like there's career exciting things that happen and there's life exciting things that happen and, and, and you're ability to figure out how to create that serendipity for yourself because you can if during the pandemic you decide to spend a year or six months living in a totally different city, you will create those serendipitous moments. If you join Meetup, because I have to put a plug in for that. And because it's true and you come to a new city and you meet a new community and meet new people, then you're going to create serendipitous moments from that as well. You sit around watching TV and playing video games all day. You're probably not going to create that many serendipitous moments. So you can have an impact on all these lucky, exciting, challenging, growing, painful, wonderful things that could happen to you. And that's what I look forward to in life. All those great things.
[Ann 00:50:33] That's so beautiful. And you're so - I love what you said there at the end of like, get out of your comfort zone, get out of that routine, get out of that safety bubble and invite some adventure. Gosh, we didn't even get into that part of the book. I love like the young, crazy person you were, jumping on $99 flights with an hour's notice. I love that story. But invite some adventure because that is where the surprises come when you didn't know you had the strength or you didn't know how funny that could be or how rich a new cultural experience could be, but inviting new things that allow the world to surprise you again.
[David 00:51:08] Life is full of good surprises and bad surprises and bad surprises are scary. But they also can be the greatest growth opportunities in the world as well. You just don't know. Invite those surprises and and you'll hopefully live a more meaningful life. In terms of the second question...
[Ann 00:51:25] How can we get more of you?
[David 00:51:27] Oh, here's my cell number. Just kidding. So what I would say is feel free to LinkedIn with me, you know, David Siegel, can find me on LinkedIn. My podcast is called Keep Connected. It's all about interviewing people who are experts in community and people. who are meet up leaders who change people's lives and it can be quite motivational. I'll have to have you on it sometime, Ann. The other way is, you know, buy the book and, you know, you learn a little more about me and even the book. You could send me an email, what the heck, [email protected]. Let's do it.
[Ann 00:51:59] David, you've been so generous with your time and your wisdom. I am a huge fan. I'm definitely going to be cyberstalking all of those places you just mentioned, you're going to be an avatar mentor of mine for sure. I'm going to watch this space. But listeners, I hope you will take advantage of those incredible resources and go out there, enjoy Decide and Conquer today. I certainly have. Thank you, David, for being with us today. This was amazing.
[David 00:52:22] You rock. Thank you.
About my guest
David Siegel, CEO of Meetup

David Siegel

David Siegel is the CEO of Meetup, the largest platform for finding and building local community. He has over 20 years of experience as a technology and digital media executive leading organizations through innovative product development, rapid revenue growth, and digital traffic acceleration. Prior to joining Meetup, David was CEO of Investopedia and before that, President of Seeking Alpha. David holds a BA in Philosophy, Politics & Economics and an MBA from the University of Pennsylvania. He is an adjunct professor at Columbia University where he teaches strategic planning and entrepreneurship. He hosts the podcast Keep Connected which is dedicated to the power of community.