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Success Story Podcast

David Siegel – CEO of Meetup | Decisions That Make or Break All Leaders

By April 5, 2022January 18th, 2023No Comments

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About The Guest

David Siegel is the CEO of Meetup, the largest platform for finding and building the 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. David’s book, Decide & Conquer,(HarperCollins) lays out the framework for decision-making that leaders can use to ensure organizational and personal success.

Talking Points

  • 00:00 — Intro
  • 04:02 — David Siegel’s origin story
  • 06:33 — David’s pre-Meetup life
  • 09:36 — Assistant to the CEO
  • 11:27 — Early career struggles
  • 15:10 — The most notable part of David Siegel’s career
  • 19:41 — David’s leadership book
  • 21:55 — The serial CEO
  • 22:26 — What is the definition of a leader?
  • 23:31 — Leadership principles & shareholder expectations
  • 29:11 — Leadership principles
  • 37:00 — Decision-making process
  • 38:46 — How to hire
  • 40:33 — Skills to hire for
  • 44:25 — The importance of de-prioritization
  • 46:15 — Lessons from David’s book
  • 47:34 — Where do people connect with David Siegel?
  • 48:19 — What was the biggest challenge of David’s career?
  • 48:51 — David Siegel’s mentor
  • 49:39 — David Siegel’s book or a podcast recommendation
  • 50:38 — What would David tell his 20-year-old self?
  • 51:04 — What does success mean to David Siegel?

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What is the Success Story Podcast?

On this podcast, you’ll find interviews, Q&A, keynote presentations & conversations on sales, marketing, business, startups, and entrepreneurship.

The podcast is hosted by entrepreneur, business executive, author, educator & speaker, Scott D. Clary.

Scott will discuss some of the lessons he’s learned over his own career, as well as have candid interviews with execs, celebrities, notable figures, and politicians. All who have achieved success through both wins and losses, to learn more about their life, their ideas, and insights.

He sits down with leaders and mentors and unpacks their stories to help pass those lessons onto others through both experiences and tactical strategy for business professionals, entrepreneurs, and everyone in between.









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Machine Generated Transcript


people, ceo, decision, hiring, business, meetup, leader, important, smart, iac, book, company, person, career, executive, biases, spoke, double click, story, role


Scott, Scott D Clary, David Siegel



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Scott D Clary  00:35

Welcome to success story, the most useful podcast in the world. I’m your host Scott D. Clary. The success story podcast is part of the blue wire podcast network as well as the HubSpot Podcast Network. Now, the HubSpot Podcast Network has incredible shows like The Hustle daily. It’s hosted by Zachary Crockett Jacob Cohen, Rob literalist, and Juliette Bennett RYLA. Now the hustle daily brings you a healthy dose of irreverent, offbeat and informative takes on business, tech and news. And it happens daily. So if you want to stay up to date on the latest and greatest, and some of these topics are interesting to you, then you’re going to love the hustle daily topics like Amazon’s grocery strategy. The rise of the ugly shoe economy is AI the secret to love and America’s sleep deficit problem. So if these are topics you want to get into and you love hearing up to date content whenever you wake up in the morning, go listen to the hustle daily wherever you listen to your podcast. today. My guest is David Segal. He is the CEO of meetup. He’s overseeing meetups global business. They have 52 million members they host 15,000 events daily, and 193 countries as a business leader and expert in building personal and professional communities. He also hosts a podcast keep connected and he is the author of the best selling book, decide and conquer 44 decisions that will make or break all leaders he has 20 years experience leading technology and digital media organizations focused on community health care and finance. He has a significant background in innovative product development, rapid revenue growth and digital traffic acceleration. This is evident by his work at meetup. In his first 18 months, he brought the social media platform to its most profitable state in the company’s 18 year history. In March of 2020. He oversaw its acquisition from WeWork that previously acquired meet up to a consortium of investors led by Ali Corp. From 2015 to 2018. He was the CEO of Investopedia, he 5x Their growth, and he led them through a successful merger of Investopedia to dotdash. Previous to that he served as president of Seeking Alpha, a crowdsourced Investment Research business with more than 4 million registered users, between President General Manager or chief executive, he has had five leadership roles Chief Executive Decision Making roles in large organizations. So he’s had an incredible career. What did we speak about? Well, we spoke about lessons in leadership and business that he has learned over his career through stories that he’s experienced some ups and downs, how he’s applied them to the various organizations that he’s worked at, most recently, some very practical stories of how he’s applied some leadership lessons that we discussed, to meet up where he’s obviously currently CEO. We spoke about principles of open communication, radical candor, transparency, kindness to inform great decision making. We spoke about types of biases and how they impacted organization for types in particular, and how to overcome them and how to make sure that your decision making process doesn’t succumb to these biases. We spoke about how to hire executives, he’s done it a lot, the most important and least important things to look for when hiring executives. We spoke about his decision making process to make effective, Speedy, meaningful and hopefully correct decisions. And we also spoke about his prioritization and D prioritization framework, which is ultimately the most important framework that he deploys to be successful and to decide what he should even focus on, let alone make those decisions. So some great business stories, some lessons, some very tactical things based on all these different leadership lessons that he’s learned over his career and how he actually executes them in meetups. So if you want to learn from a really great tenured executive, you want to learn how he operates his business today is a great show. Let’s jump right into it. This is a David Siegel. He is the CEO of meetup


David Siegel  04:38

I was born in a small log cabin in Kentucky. Don’t worry, we’ll get a lot faster now. I’m not born in a log cabin in Kentucky but I was born in Kentucky on an army base in Kentucky. Now let’s fast forward. I’m grew up in the New York metro area. upper middle class, amazing parents incredibly lucky to have the love The household that we grew up in, had really like the standard high school experience, where I was kind of like a little nerdy, but not nerdy enough to be like superduper smart, but nerdy enough to hang out with the people who were really smart and okay in sports, enough to hang out with people who are really, really good at sports, but always like, at the like the lower end of each of those different areas. And maybe that’s why I became like a particularly competitive person. But anyway, I would say the most important, probably professional opportunity that I had in life was, after graduating college, I worked in consulting, and my biggest client was double click. Now double click at the time, most people don’t know this unless they’re like 35, or above double click was the internet website, all advertising, came through double click, most advertising on the Internet came through alchemy, the Internet free, Google acquired double click for like $3 billion. And over 200 different CEOs of internet companies have come from double click. So it was very lucky at about 24 years old to become a director actually, at double click. And I did that. And that one experience when I was really quite young, a couple years out of college had an impact on my life to fast forward. And I can rewind back a little bit to when I became CEO of meetup, and we work was imploding. And we worked on meet up, the person who I went back to 20 years later, after having built the relationship was the CEO of double click at the time to acquire me up out of WeWork. So I can fill in the gaps in the middle. But a lot comes down to kind of those early experiences that I had. And then just, you know, the Quick, quick bio as I was, at one point president of a site called Seeking Alpha, one of the largest financial education sites, and then I became the CEO of Investopedia. But for years, we sold that company. And then Adam Newman came knocking on my door for WeWork. And it was an opportunity I couldn’t refuse. And that’s the origin.


Scott D Clary  07:09

Do that’s an awesome story. And you’ve done a lot too. So where do you want what’s what would be some of the most interesting pre meetup stories, you can pick a few. Some of the I know, there’s I know, there’s a lot Investopedia we weren’t, those are like, those are names that people know. And plus probably some some at some a double click to so pick some fun stories that I would say were like key points, defining points in your career that allowed you to speak to some of the things that you speak to in your book, some of the leadership lessons, those were not just thought thought up overnight. So there’s things that you learn as people you worked with, there’s good times, there’s bad times for sure. So go into some stories.


David Siegel  07:49

We’ll do a good story. And we’ll do a challenging story. So we’ll do both of those. All right. Thank you for that. Good story. So after double click decide to go to business school. And I was in Wharton for business school. And I didn’t want to do the standard, like investment banking consulting thing, because just That’s boring. I had a dream job. My dream job was to become the assistant to a CEO, to be like the right hand person not to get the coffee or whatever it is, but like to work on board decks and work on strategy and just learn from really, really smart people. So one night in business school, a couple months before graduation, I decided I was gonna go on a blitzkrieg of like sending out insane numbers, even emails, I stayed up all night. I kid you not I figured out what the email addresses were for all these different companies like at David’s at DC gol, Dave underscore Segal, whatever the email just happens to be and send about 10,000 emails to every executive for about 100 different companies and said I want to become the assistant to the CEO. Great. I ended up having conversations through that with an end connections with David Stern, the Commissioner of the NBA National Basketball Association at the time. Kentia not the CEO of American Express. All these us like illuminate David Neeleman, the CEO of JetBlue, all these companies that like were amazing companies. And I couldn’t get the role of becoming an assistant. See, I tried, I tried, I tried, didn’t work out. Okay, fast forward. I took another job. Three years later, I also spoke to the CEO of a 100 flowers. Fast forward three years later, there was a posting on the Wharton alumni database, and the posting said, One 100 Flowers looking for an assistant to the CEO. And I was like, Wait, three years ago, I spoke to Jim McCann, a founder and CEO wanted flowers. And I begged him to become the assistant. He’s like, I don’t need an assistant. So I sent him an email. This is three years after graduating from business school. And I said, Hey, we haven’t talked two to three years but I just if I in any way influenced your decision to decide to hire an assistant for CEO then I would love to you know, get together sometime. So it will be back five, like amazing words, five words where I was looking for you.


Scott D Clary  10:10

So it’s like a


David Siegel  10:11

Harry Met Sally kind of thing, you know? Yeah.


Scott  10:14

Yeah. It’s, that’s, that’s a lesson in and of itself, that, you know, like how everybody gets somewhere in life. There’s this, there’s this book by by Alex Banyon. And he and he interviewed a whole bunch of like, executives like he interviewed. On Tour, I’m blanking on the names now. But like very, very notable people. And it’s always like this third door, like there’s like the the front way and the back way that you can get something done. And there’s like, the third third door, like the other opportunity where like people like think outside the box and figure it out. This is what you’re doing is exactly what you’re doing.


David Siegel  10:45

It sounds surprising, but there’s not a single job that I got off at seven jobs that that existed beforehand. I love every job was like a job I created except for a CEO role that kind of had existed before and because companies, right, so but it’s the reason why I think there’s an illustrative comment in terms of decision making is number one. When you’re making decisions, you have to think about how are you creating options for yourself? Are you limiting the number of options for yourself and making a decision? Now you have fewer things that can happen to you in the future? Are you creating options for yourself, that can end up resulting in you just getting lucky at some point in time, and I actually believe as crazy as it sounds, that you can create your own luck by making decisions and having enormous numbers of volumes of conversation. That lucky stuff just ends up kind of like happening to you. And people are like, Oh my God, you’re so lucky. I can’t believe well, am I lucky? Yes. But I also had 10,000 little points out there that would create situations where I could end up becoming lucky. So how do you make decisions that create many different options for yourself? So luck ends up happening to you?


Scott D Clary  12:01

Smart, very smart. Okay, so that was great. That’s, that’s, that’s a good story. So how did that work out? How did that where did that? Where did that place you after the assistant to the CEO did you take


David Siegel  12:12

so it changed my career, honestly. So I met with him. He ended up hiring me not for that role, a made up role called vice president strategic initiatives, which is usually like some person on the way out. Like, we don’t know what to do with you. So you’re gonna be vice president’s condition is Oh, no, what does that mean? But that was like, early day, so. So I did that. And then like, we’ll just figure out what you’re going to do. And by the end of four and a half years, I want to enter flowers. I was running all Mergers Acquisitions, for the company, a lot of shared marketing services, international operations, just a whole bunch of other other things that you know, just kind of took on over time. So it really helped to make my career and was great, great. A great opportunity to learn from some very smart people. Okay, now, I will tell you the I mean, I have so many like crappy stories.


Scott D Clary  12:57

Okay, so the if I have to, I have to just that is the bad story. Oh, we work story, whatever, you know, I got lots I don’t know, because I figured there was the org. I figured there was a story with we weren’t like God, like there’s not not a story.


David Siegel  13:10

No, I got like, I’m just stories we work. Okay, here’s the story of where we work. So this is a crazy story. So I, I was running meet up and we work had been acquired by we work in late 2018. And, and everyone meet up had we worked stock. That’s the only stuff that they had when I came in. And we work stock had gone up to a valuation of $47 billion. And, you know, come 2000, late 2019, early 2020, we start seeing like articles on Wall Street Journal of like, Dow now with 41 or 40 billion. Now we’re 30 billion now worth 20 billion. Now we’re 10 billion. And we’re like, the I don’t know if I can say just for the shits gonna fall down, and it’s gonna fall a little meat out, but we know this is gonna happen. So and I kept being assured Don’t worry, David, it’s not going to impact meet up, it’s, everything’s gonna be fine. I was like, Come on, we know that. Like, it’s not gonna be fine. So I was also coincidentally it’s kind of a random thing for like the death of a company. I was actually visiting my father’s grave once a year, I visit him in cemetery, and I get a call. And the call says, David is about to hit the Wall Street Journal. That Meetup is for sale. Just total surprise, no forewarning no nothing. And I’m like, Oh my God. If our employees or 200 plus employees hear about this for the first time, from the Wall Street Journal and from their friends, well, that’s a great way for me to for them to lose all trust. because they’re not gonna believe that I didn’t know about it, they didn’t think I knew about it, I hid it from them. And every time I tried to convince them of something, you know, they’re gonna be surprised. I hooked it to meet up. I quickly I quickly got a senior person that we work to meet me there. So they knew it was legit. called all of our employees for an emergency meeting. I started telling them that you know, Meetup is about to be for sale within like three minutes of the conversation. Every person’s phone is like buzzing because it hit the wall. So just just caught it and we just caught it in time.



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David Siegel  16:42

unless you know one story but I’ve got many other Adam Newman crazy. No plane ride experiences, whatever that’s out there as well.


Scott D Clary  16:52

Yeah, no, definitely. Okay. So then let’s but that wasn’t that was a difficult situation. What was the most notable, negative or difficult time in your career that shaped Yeah.


David Siegel  17:05

I had an experience in my career, where I was, like semi catatonic in how deeply disturbing it was. So here’s here’s the experience, and it definitely helped to shape me. So prior to meet up, I was the CEO of Investopedia. Okay, and Investopedia is owned by IAC. IAC is the chairman of IAC is a very famous individual. Barry Diller, the CEO of IAC is Joey Levin, and I worked for them. We had an amazing success in investing, VDI joined the company was doing $11 million, and ended up four years later doing $35 million in revenue. So over tripled in size. One day, senior executive, I won’t say who came into my office after four and a half years being there. And he said, David, we just sold Investopedia. And I was like, wait, I’m the CEO. How did you do due diligence without any companies wanting to talk to like the executive team? Who bought us what what happened? And like, Don’t worry, David, we’re going to take care of you. We got a really, really good price for it. And you’re gonna be happy financially. I’m like, forget the financial thing, like what happened here. And basically a sister company of IAC called dotdash. Convinced IAC to acquire WSB they knew our business because it was all part of the same umbrella brand. And, and that was it. It was a I was I was out well, with just a complete and total surprise, and we were just like at the top of a mountain and at the time. And and I think the and they actually IAC to their credit did do above and beyond appropriate things for me and for others. And they also offered me to stay on at IAC corporate, as in another role, and another executive position, but I was so in total shock, and surprised. The reason why that really didn’t impact me is because I swore kind of after that experience that the number one job of a CEO and a leader is not to surprise people. Your job is not to surprise your employees. Your job is not to surprise your board. Because having been surprised actually numerous times in my career. Now. It’s so painful, because it’s not about the experience of being surprised. That’s hard. But it’s about the loss of trust that you haven’t people whom you trusted previously, and they weren’t able to be upfront with you for for whatever reason it happens today. And and I think having a kind of a no surprise leadership philosophy up down and all around is certainly referenced and talked about in the book around how do you make decisions and how to be transparent decision making. But it definitely really impacted me.


Scott D Clary  20:17

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David Siegel  21:53

Great question. The reader is for both leaders and aspiring leaders, is what I would say if you don’t have an interest in ever being a leader, it’s really not a book for you. And what I found is that there’s a number of principles that exist out there, because as a leader, you’re making like hundreds of decisions every single day, even deciding not to make a certain decision, and to empower someone to make a decision is definitely a decision. Right? So you’re making 100 decisions a day. And, and and what I wanted to do is I always wanted to kind of write a book I teach at Columbia. So I love kind of teaching and education. And, and it was always been important to me, but I didn’t want to write in this boring, like, you know, textbook kind of books with just like the five principles, this the sixth principle that whatever kind of stuff, I want it to be a story where that was riveting. And through the storytelling, you end up kind of learning a ton around kind of smart decisions that you could ultimately make to become more successful. So it’s for it’s for that audience, and you know, things like, how do you think about whether decision is a trapdoor decision, meaning you can’t change it, which most people think many decisions are trapped or decisions, when in fact, you could change laws you can change, like whether you’re going after you have a kid, like that’s a chapter decision. But most decisions are incredibly changeable. And people are so fearful of oftentimes making decisions because they think they’re trapdoor decisions when they’re actually not. And just other elements of of decision making. So you know, that’s, that’s what we did. And the story under WeWork was so insane, and such a roller coaster experience, and made for just some pretty crazy material.


Scott D Clary  23:36

I was gonna say so I feel like and like, obviously, you’re on the inside. So I’m just going to speak as a layman. And yes, I feel like we work is not the epitome of great leadership decision making.


David Siegel  23:49

And learn to do just as much as you learn. Yes.


Scott D Clary  23:54

So you’ve been how many? How many, like, chief executive roles have you held over your career?


David Siegel  23:58

This was, I would say this is my third president or CEO or CEO role. And if you include general management positions, then it’s my fifth.


Scott D Clary  24:10

So what is out of obviously, you have some experience. So what is what is what is the definition of a leader in a business context? And what is the most important trait for a leader? Oh, wow.


David Siegel  24:19

Okay. So let’s go backwards. The most important trait for a leader, from my perspective, is understanding that your role is to enable the success of everyone around you is to think about a root the reverse organizational chart, where like the leader is on the bottom of the chart, not at the top. Your role is to support and enable the success of all the executives. And the executives role is to support enable the success of their managers and managers role to enable the success of individuals. My role is not to succeed myself. I don’t need to succeed myself. I need to enable the different people on my team to succeed and guess what that looks like. cede, but that’s my job is to enable everyone else to succeed around me and do whatever is necessary. Sometimes it means letting go of people to enable them to succeed, actually, to me, that is the most important role of a leader support the success of those around you.


Scott D Clary  25:15

Now, I agree with I agree with it, the role of the leader is, and I want to, I want to understand your opinion about how to do this tactically, when there’s interests of other parties that are that maybe prompt different decision making. So for example, when you were acquired at Investopedia, obviously, stakeholders, there were certain stakeholders that were making that decision, because they thought it was for the benefit of those stakeholders or even shareholders. But in a business environment, how do you align that leadership principle, which I agree with, with the expectations of shareholders, for example, or owners or whatnot, because that’s the that’s the fundamental thing that I think I always see, causing conflict. Everybody agrees what a good leader is, but nobody knows how to do it, when they’re bored, and their owners feel the need to do things differently, for example, that obviously drive ROI, or whatever that metric is, right? Good.


David Siegel  26:11

Okay, so to me, the golden rule is all about transparency, meaning, if I am told by my parent company, or by my board, transparently, you’re not doing a good enough job, you need to focus on this not that etc, I transmit that information to someone else, it aligns interests in a lot more effective way than if information is withheld. The biggest challenge oftentimes, and why there’s lots of misalignment like you’re referring to Scott, is because a board will have access to certain information, like, oh, a company wants to go public, or whatever the we want to sell this company, wherever the the incentive is, for the board. And, and the management team, or the employees have a completely different incentive. And then there’s tension. And there’s problems because people have missed this asymmetrical access to information, the more that a leader can ensure that there’s as consistent information as possible, so that the most junior person, and the board member knows the same thing about and could say, Oh, David, that’s unrealistic. We share all of our financials, every employee, our board does not know any information that every single employee does not know and get access to. Is there a risk in doing so? Can that employee take screenshots of like our financials and post them on wherever? Read it? Yeah, they can. And there’s a risk, but the reward of having alignment and incentives and priorities, because you’re brutally transparent is the way to go and it goes with managing someone, you need to be transparent. Someone’s not doing a great job, it’s not nice to them. Not kind to them to like, say, Don’t worry, keep it up, you’ll everything will be okay. And then surprise him later on. Kind of the kindest thing you could do is give very critical, transparent, maybe overly blunt in order to be clear information in as respectful way as possible, so transparent to see to me is like the end all be all.


Scott D Clary  28:22

This is like, this is like radical candor. Yeah, like that’s true. Yeah.


David Siegel  28:27

Our company, we have like a book. We had a book club. Yeah. And Ramakrishna was one of the books in the book club. Yes.


Scott D Clary  28:33

Yeah. I have no doubt it was it’s a it’s a great, it’s a great leadership philosophy. So and this is what you’re doing this is this is one of the principles.


David Siegel  28:41

One of the things about it. Yeah, don’t mind.


Scott D Clary  28:43

Yeah. So just show me say whatever you want


David Siegel  28:46

your show, dude, it’s not my show. But like, I’m still gonna, like say, so go for the there’s one of the most famous managers leaders ever. In fact, he One Time Magazine’s manager of the century, for the 20th century was Jack Welch, the CEO of GE, General Electric for 20 years, at the time that he left the highest market cap company in the world. He was on ICS board, and I got to sit down with him and meet with him one on one. And I said to Jack Welch, you were the manager of like the century, what can you teach me about management, like on one foot, and he’s like, just focus on transparency. Focus on trust. If you build transparency, you’ll have trust. And if you have trust, you can have anything. Make sure you have trust of your employees, trust of your board, trust of your team. That’s all that’s, that’s the most important thing. So that had an impact.


Scott D Clary  29:45

It’s amazing, because it seems like that runs counter to almost every company operating out there that seems to hide everything from their employees. So there’s always like that. There’s like the large companies that have probably been around for a long time that operate the way that they feel like they have to You know, hide everything. And you don’t even you don’t know what the next person in the cubicle beside you is making let alone what the company’s financials are like unless they’re public. But outside of that you also have the startup that’s worried about sharing information, because they may not have a run rate longer than six months. So it’s very, it’s a very, very scary feeling. But go ahead, no, no, go ahead.


David Siegel  30:20

If you’re a startup, and you don’t have a runway more than six months, I know that scary. So you get the team together, and you say, Okay, who do you know, what angels? Do you know? Or let’s be aligned, we got to reduce our costs. Well, how can we focus on our hosting costs? What do we need to do to reduce costs just get everyone aligned? Or else people are like, Why are they asking us to reduce our people just start jumping to conclusions. And frankly, usually those conclusions that they jump to those assumptions that people are far worse than the actual truth that’s actually going on accepting the worst case, the truth was actually worse than we work, but for many companies is not.


Scott D Clary  30:55

Okay, so let’s, let’s talk about some things that you’re doing. So let’s talk about this is an interesting way of doing it. Let’s talk about some of the principles that you speak about in the book outside of trust in communication, not to say those are not like, incredibly important, but there’s other ones in there, there’s like a lot, I think there’s like 40, some 44 is a 44 are a lot of a lot of decisions and concepts in there. So whatever, we won’t be doing 44 Whatever it is today, hope not. Yeah, I know, I gotta have like lunch eventually, and whatnot. But let’s say let’s pick a couple others. And I think that what would be great is if you pick your like your favorites, talk about the concept and why it’s important. And then I think it’s really great if you speak about how you’ve done it in meet up, because there’s the theory. And then there’s the very tactical, and people love the theory, but it’s really good to see it executed in an actual successful company. So that’s great, too. So let’s do that.


David Siegel  31:49

You’ve done  this before I think down it’s good question. Okay, sorry, guys, your crackers, I crack myself up. It’s terrible


Scott D Clary  31:56

. I love my own jokes, sushi.


David Siegel  32:01

Oh, my God. Okay. So I think the one that I also, we talked about a few just to remind people, the ones we’ve talked about so far, and then I’ll share a new one, once we’ve talked about so far are be surprised only about being surprised. That’s kind of one. Another one is focused on being kind not necessarily being nice. A third one is focused on creating options for yourself, rather than limiting options in your decision making. So the next one that I’ll share is around decision making biases. So there are many major biases that we all have, and I’ll name a few of them. And the key is to understand how you are biased because it’s not a question of whether you’re biased or not biased, you’re biased. We are all influenced by these biases. So here’s an example of three or four different biases, and then could choose one out and then we’ll talk about it. So first one, recency bias. So recency bias is, is the concept that if you had 10 data points, is that last data point, that’s usually going to have a way over influence on how you perceive something in decision you end up get you end up making. So the example I like to give around that is, yoga can be exhausting. I love yoga, and you’re stretching all over the place. But at the end, you do a Shavasana. And you’re chill, and you’re relaxed. And that’s it, you remember most that like shavasana feeling. So you want to go back to yoga, because you did that shavasana at the end, you have that recency bias, or the the the work experience I would give to that, because as you had asked for was, oftentimes, there’ll be an executive that’s not working out. And you need to unfortunately, let that executive go, hopefully, you’ve given enough critical feedback during that process. And then executive is too extreme in one direction, the executive is too aggressive or not aggressive enough, or whatever the challenge happens to be, you end up hiring the next person, just as the opposite of the person who just happened to have been there. When in reality, there’s could be 10, different factors that are important in an executive, great communicator, domain knowledge base, great hire of talent, whatever those four or five things happen to be. But because they skew really extreme and a challenge in one way, you go the exact opposite direction because of that recency bias in hiring that next person. And that’s oftentimes a mistake, you have to recognize that you have this recent bias that you’re going to end up trying to overly compensate for, and not let that bias overly influenced the next decision that you’re going to be making. Does that make sense?


Scott D Clary  34:39

That’s 100% that’s smart, very smart. So we have biases, what are so we can go through a few more. I’ll let you I mean, I’ll let you lead you know, which ones you know which ones are sort of like that. That’s a great one, by the way, but you know, which ones are the ones that come up again,


David Siegel  34:56

give  me more biases, that people haven’t decision that’s fair. So The next one I would say is confirmation bias, which is, you know, things are going great. So you’re going to keep looking at the data when as long as it’s going great. And then when things aren’t going so well, you don’t really look at that information, you’re looking for just things that confirm what you want to see, as opposed to it seeking out different opinions of others that can actually help you to make a smarter decision. If you surround yourself with people who are just confirming, confirming, confirming your thinking and making smart decisions, the key to actually great decision making is disagreement and debate. And the more disagreement and debate that you have, the less confirmation bias you’re going to have the better decision ultimately gonna make. So I’ll give you an example of what we do. Actually a bunch of different companies, but certainly a meet up, which is, when we come into a meeting, we don’t just come into the meeting and talk about something prior to the meeting, we have someone create a Google Doc. And in that Google Doc, they’ll put a specific opinion out there. And they’ll share that opinion with everyone in the meeting. And then we expect everyone who’s before the meeting, to give their opinions and disagreements in that document. And then when we have the meeting itself, it’s a discussion of where there’s areas of disagreement in order to then figure out how to align on those and not spending time where already we agree on something and you know, because that’s kind of a waste of time. What it also does, is it gives people are more introverted, an opportunity to really participate as effectively as people are extroverted because this is asynchronous time, where individuals can share their opinions to help to influence decisions, not necessarily in the room, but in a document. And that helps with reducing it with increasing debate and disagreement and reducing confirmation bias.


Scott D Clary  36:52

very smart, very smart. Okay. Do you have do you have two more now?


David Siegel  36:56

Okay, two more, boom, quick. So one a status quo.


Scott D Clary  36:59

You keep pausing. And I’m like, Listen, man, I just didn’t get the smart idea. I’m just taking mental notes. I don’t have anything else to add on to it. You’re the expert here. I’m just gonna do it. In my next meeting. I’m like, Yeah, that’s a pretty damn good idea. Okay,


David Siegel  37:10

you should, it really is very efficient, actually. So status quo bias is the next one, which is this people’s fear of change. And just people are oftentimes prefer to have the status quo, even if it sucks, and it’s terrible, and they’re miserable, and they’re unhappy, then then the fear of the unknown, that could be potentially worse, even though it’s likely going to be better. And kind of helping people to understand that you need to pivot careers, you need to pivot businesses. Pivoting is essential to survival. And status quo is just something that’s incredibly dangerous as part of many people’s biases. And then the last ones, I won’t even give you a chance to comment on. The last one around biases that I find happen oftentimes is around sunk cost fallacy, which on a personal note, for me is things like I go to expensive restaurant, I ordered lots of food, I feel sick, because I ate all the food. But of course, I had to eat all the food, because I paid for it, when in reality, the goal was like, enjoy yourself, and like leave over some food. But a lot of people don’t appreciate that, that if you already did something, it’s a sunk cost. You already invested millions of dollars into a business. Too often people will say, Well, look how much we invested. And it looks so bad. We can’t you know, jettison that business when in reality, it’s gone. It’s over. By by $2 million US invested. What is the right decision at this time? How do you divorce kind of emotional connections to these costs that you will put in so that you make a smarter decision moving forward?


Scott D Clary  38:44

Now you have these biases that you have to be cognizant and aware of which is very smart. Once you’re aware of these, what is your what’s your decision making process, once you are aware of your biases,


David Siegel  38:55

find as many people to disagree. And if you don’t have tension, or disagreement, then you probably haven’t thought about all the different angles and challenges that could be in front of you. And only then


Scott D Clary  39:09

how do you do that? Oh, how do you do that? I’m gonna say, how do you well, especially I was gonna say especially because unless you have an extreme amount of psychological safety in your organization, people are not comfortable.


David Siegel  39:24

But you nailed that all you nailed it right there. And you need to create an environment where people understand that the best thing that they could do to quote unquote, look good. And to help is to actually disagree and people on my team will say things like, I don’t know if I even agree or disagree with my disagreement about to say, but I’m going to disagree now because I know that that’s actually helpful in the decision making process. And, and the key is that when someone does disagree, you have to hold that up to a high. You have to say thank you, you So Right? The moment that eyes a leader become defensive, when someone’s disagreeing is the moment that you’re cabal Xing the ability for people to feel safe, and to disagree, and then what your kibosh saying essentially never said that word twice in whatever sentence, you’re bashing is able to actually make smart decisions, which is a serious problem since kind of life and business are all about kind of one decision after another.


Scott D Clary  40:28

And as a leader, do you hire for that particular personality? Is that something that you look for when you bring a new exam or anybody on


David Siegel  40:36

I can’t say about anybody, I would love to say anybody, I would love to say that. Because I’m not interviewing, I’m interviewing my my reports, or sometimes my reports are direct reports. And we do have values that we do interview for, like embracing change is a value that we interview for. And that’s actually helpful, we have six specific values that meet up that we interview for. But for people that are on my team, I do look for disagreement a lot. And I would say that there is a certain level of self esteem, confidence, but not cockiness. That’s really important for people. Because if you lack self esteem, and you’re scared to share your voice, then it’s harder to disagree. My job is to then figure out how to get that disagreement out of you. Because some people are more introverted and less comfortable doing that. And I’ll then try to talk to people in one on one sessions and invite disagreement if I could, because I know some people in a group setting are less apt to disagree. And my job again is what can I do to help people on my team and others to feel as comfortable as possible. And that’s just creating that kind of environment where you are, you are praised for being being contrary. But you also need to at certain point, obviously, be the appropriate soldier and not just continue to be contrary or contrary sake, either


Scott D Clary  42:05

very smart. And a lot of the things that we just spoke about, there are things that you have to you have to work on internally. But you also mentioned that I thought was a little interesting. You mentioned when you’re hiring a when you’re hiring an executive, and I assume it would be for you as a CEO as well. What are the top skills like the hard skills? So is it? Is it hiring? Is it domain expertise? What is the list of things that you look for in people that you’re looking to bring in at an upper and upper level,


David Siegel  42:37

I’ll say the things that I look for, and also list a couple of things that people look for. But it’s actually I think, less important than people realize. And it’s okay, it’s one of the things I like to talk about is D prioritization is more important than prioritization, you could say like these 10, things are really important, when you’re looking for that, that’s not helpful to hear the things that are not important actually are less important than people realize. So I’ll start with a less important one, actually, you hit on their domain expertise. Now, I’m not saying that our Head of Marketing shouldn’t be very strong and marketing. Obviously, she’s amazing at marketing, and very important. However, I would rather have someone who is an eight and a half or nine out of 10, in eight and a half out of 10, even in domain expertise, and is great at hiring people underneath them is a phenomenal communicator is a strong team player is highly analytical, all those things are much more important than kind of years of experience or having been there done that because you could learn things from other people. And you don’t need to be the absolute experts expert in many things. So that’s something that I think people actually over prioritize, they also prioritize things like what company someone worked at, or, or what school someone went to all that stuff. That’s just such BS and, you know, way over prioritize brand names. The thing that I tend to prioritize the most are trying to understand kind of the level of selfishness versus unselfishness of a potential team member, when someone has a ego driven, deeply selfish approach to the way in which they approach business and you can ascertain that I’ll tell you how I tend to ascertain that you don’t want that person on the team no matter what, no matter what. So what I tend to do, is I do zero reference checking. Zero, you might be like, but how could you not do reference checking? It’s kind of important. Can’t remember us. All I do is back channeling. So I never asked someone for like three, four or five people that I should talk to, because they’re only going to give me like the great people they’re going to tell me feel that like think they’re the bee’s knees or whatever. Bee’s Knees are good. I don’t even know what those are. But instead, I am LinkedIn like 30,000 people so I always find someone so I I find someone else won’t connected to the person. And then I just reach out and I backchannel the heck out of any potential hire. And it’s kind of served me well. And we’ve pulled back from potential hires, based on the back channeling as well, because then you get the unfiltered and transparent truth.


Scott D Clary  45:16

What is what is back channeling? I’m sorry, explained to me


David Siegel  45:18

is basically just. So if I’m thinking of hiring Michael, then I don’t say to Michael, hey, who should I talk to from your past? That is good. I go on LinkedIn, I look who’s connected to Michael, I reach out to those people that have worked with Michael in the past. He just asked him, I say, Hey, did you work with Michael? I don’t work that closely. Okay. Do you? Can you can you refer me to someone who did work closely with Michael in the organization? Oh, yeah, of course. Janine worked really close with Michael. Great. Would you mind making an instruction to Janine shore? And then talk to Janine about Michael?


Scott D Clary  45:56

Can you just see what what the average what the average, you know, the average view of somebody who just, you know, worked a couple hours a day with this person, how they treated other people? What I got it understood, smart, very, very smart. And I’m also curious, this can be like, the, the final question that I like to do is a couple rapid fire. But we’ve been going for a bit now. But I like to I like to understand people’s frameworks for things. So you said you’d like to deprioritize. And that’s more important than prioritizing. So how do you because there’s a million different ways to do that, like the urgent important the Eisenhower matrix, all the different ways to you know, to figure it out? So how do you do it? How do you d prioritize things?


David Siegel  46:35

Yeah, I try to have as objective a basis as possible in D prioritizing opportunities. So the challenge is that many startups and leaders, they die more of, of have of overeating, and then of starvation. You know, they, they, they try on too many different things at the same time, and they can’t prioritize. So I try to quantify as much as possible. So every opportunity, I’ll say, Okay, let’s put an assumption in there. How big is this market? Precisely, we think we get to the market. What are some examples of that? If we move this needle in terms of improving search on meetup, and there was a 3% increase in the number of people who became organizers because we improve search? What’s the dollar value of that? So what I tried to do in prioritization D prioritization is anything that potentially not everything can be, but anything that could potentially be quantifiable, we push hard to make it as quantifiable as possible, and then it’s oftentimes becomes more obvious of like, what I know, you think this would be great. But why would we prioritize this when this other opportunity has like 10x the potential value and it just, it takes things from opinions into a subjective into more objective, which then builds higher levels of alignment? You know, between different different people around resources?


Scott D Clary  47:55

Very smart idea. Okay. In closing, any other points that you want to bring up? floor is yours, but also, if not, it’s okay. If there are but if not, what do you want? What do you want people to take away after they’ve after they’ve read this book? What do you want them to feel? What do you wanted to learn? What’s the what’s the goal?


David Siegel  48:13

I think the number one thing that I want people to take away after reading the book is their careers, their life, their future, is more in their control than they may realize. I think too often people have an external locus of control. And they say these things happen. It’s unfortunate. And they blame kind of outside forces. And I think the book is kind of a story of lots of different experiences, where I and others did things that were seemingly impossible, like getting meet up to be acquired from by someone who I knew from 20 years ago, even though there were 30 other companies that were looking to, you know, acquire meat about if we work and, and persevered. To make it a reality. That would be the greatest thing if people felt more ownership of what happens in their lives. To me, that’s the biggest one.


Scott D Clary  49:17

Amazing, okay. And if people want to get the book connect with you chat with you, where do they go? Social website, all


David Siegel  49:23

that. Okay. So, books coming out March 8, and you get on a little bookseller that some people might have heard of called Amazon as well as any other you know, online book selling place. We have website, it’s called Design and conquer You get a website, you could check out stuff there, you know, just go on to any bookstore also, we’ll have it. And in terms of reaching me, LinkedIn is probably the best ways you can easily find me just David Siegel on meetup. You can send me an email And I’d love to hear from anyone who is interested in the topics we’re talking to About


Scott D Clary  50:01

amazing No, that’s great. Okay, let’s do a couple rapid fire. Biggest challenge you’ve overcome in your life. What was that challenge? How did you overcome it?


David Siegel  50:10

I was deathly afraid of public speaking, sweaty palms really nervous as all hell look, I can I know, right? And overcame his practice. It’s just over and over and over again. And you just get less and less nervous and then it’s just become second nature to you. So now I’m like public speaking in the shower. So you know, it’s really easy.


Scott D Clary  50:35

If you had to choose one person, obviously, there’s been many, but pick one person who’s been highly influential in your life, who was that person? And what did they teach you?


David Siegel  50:42

Okay? So I decided to become sighted. I set ambition for myself to run a company. Because I saw someone who became my mentors name is David Rosenblatt. He is on the, he’s the CEO of first dibs, and he’s on the board of Twitter and IRC and a bunch of other amazing companies. And he just took me under his wing. And I used to meet with him weekly or every other week. And still 20 years later, whenever I have a important career decision to make or like decision to make not just career but life decision to make a kind of he’s always there and he’s always supportive of me. And he’s had a big influence on me and my family.


Scott D Clary  51:22

Amazing, a book, podcast, Audible, something that’s helped you that you’d recommend people to check. Oh, boy,


David Siegel  51:27

okay, it’s an oldie but a goodie. When I say only, I mean, like really only so controversial. But I’m gonna go with Dale Carnegie’s How to Win Friends and Influence People written in like 1930, or something, and I teach a class and I have all my students, they have to read the class and a lot of it is inappropriate, let’s say for our times, and and it’s unfortunately, way, way too white male. However, there is such beautiful learnings in terms of helping to kind of build relationships that can last a lifetime. So if people have not read it, it’s a classic. I always recommend it,


Scott D Clary  52:13

it and candidly, it was written in the 1930s. So understanding the time frame when it was definitely a different time, different time for sure. If you could tell your 20 year old self one thing, what would it be?


David Siegel  52:27

Don’t care about money so much. Money will always come. Focus on what you want to what you feel like you could be great at and good things will come. Don’t put so much pressure on yourself around that. It’s just not that important. It’s important up to a point past a point isn’t that important?


Scott D Clary  52:48

And last question, what does success mean to you?


David Siegel  52:51

Success means happiness. Being happy person, if you have a lot of money and you’re unhappy, that’s your failure. Right? And if you want a family, not everyone necessarily wants one. But if you want a family and you have a wonderful family and you’re happy in that family, and that’s the way that you want to live your life. To me that’s success.


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