David Siegel is the CEO of Meetup, the largest platform for finding and building local communities. He has 25 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 is the author of Decide & Conquer: 44 Decisions That Make or Break All Leaders and hosts the podcast Keep Connected, which is dedicated to the power of community.


Q: Start by telling us a little bit about your background.

  • My career really started after graduating college. I didn’t know what I wanted to do. I actually went into human resources which is pretty uncommon for someone to go from HR to becoming a CEO. HR focuses on recruiting, managing, motivating people, hiring top talent and aligning strategy. Those are a lot of things a CEO ends up doing.
  • I also was really lucky in my career in the late 1990s for this thing that started called the internet. My first client out of school was Double Click. I ended up being in Silicon Alley, New York in a digital company driving advertising. That’s when I met Kevin Ryan who became my lifelong mentor.
  • I went through a series of roles in different industries and companies. Going from a Vice President to a Sr. Vice President to becoming President of a company named Seeking Alpha and then became CEO of the world’s largest financial education site Investopedia.
  • I then became CEO of MeetUp 3 ½ years later. MeetUp is the world’s largest platform for finding and building community.
  • Besides that, I also teach entrepreneurship and strategy at Columbia.
  • Most importantly, I have an amazing wife and 3 awesome children, teenagers. I’m very lucky from that perspective.


Q: You grew up in NYC, still live in NYC?

  • I was actually born in Fort Campbell, Kentucky.
  • My father was a neurologist and opened up a practice in Connecticut. It ultimately became the largest neurological practice in Connecticut. He was a real entrepreneur as a physician.
  • I live in the New York Metro area in a place called Westchester County.

Q: For schooling, you went to U Penn, then continued to Wharton, right?

  • After deciding I wanted to go for HR, becoming a CEO, I knew I had to get a business school pedigree. I got something of a strong financial background at Wharton.

Q: You’ve had this wealth of experiences in your career. You’ve moved in and out of 10 different companies in a relatively short period of time in your career. What do you feel like you’ve learned or gained by taking on multiple new challenges like that?

  • I’m a really big believer in the fact that problems are multifaceted.
  • When you’re able to work for a variety of different companies and industries, it allows you to take a very different approach to a problem and see things not just from a sales, marketing or product perspective, but see the relationship between different industries or challenges and come up with an authentic solution.

Q: What do you feel like has been your most transformational experience in leadership?

  • I would say Investopedia; my first CEO gig.
  • When I first started, the company was really nascent. It had 25 employees, we grew it to 150. It made $11 million in revenue, we grew it to $35-$36 million.
  • We also grew the culture of the company. What I love doing in leadership, leading communities of teams is helping build culture. If you have the right culture, you end up creating an environment where smarter decisions are made. Where people can thrive and feel empowered.

Q: There’s a distinct company culture in Cutco/Vector. Each individual manager begins building their own team when they start. So they have the opportunity to create their own culture or piggyback the company culture or a combination of both. What would be your perspective on how somebody could best create culture on a new Cutco/Vector team?

  • It’s usually in the combination.
  • The most important thing in building culture is for it to represent who you are as a leader. You can’t fake it. People will know.A leader at Cutco/Vector would be well suited to look at the company values and ask themselves, if someone described me, would they use these words to describe me or not.
  • Leverage all the same words and terms that Cutco/Vector has as part of your business. But if there’s anything that doesn’t represent who you are, be comfortable with taking one or two away, and then add one or two that really represent who you are.

Q: I’d like to hear about the toughest times.  You’ve gone through different roles. You’ve had success at some, some weren’t successful as I read in your book. I think that’s shaped you into who you are and the strengths you have now as a leader. What have been your biggest challenges?

  • Coincidentally, Forbes published an article about the book and highlighted the biggest failure, biggest mistake I made in my career. I shared it with the world and people say, aren’t you upset that that’s the one thing Forbes wrote about? I told them no. The bigger the failure, the bigger the opportunity of learning.
  • When I came up to MeetUp, the business was losing $18 million in profits. If you don’t have profits, you don’t have sustainability and there’s a risk of shutting down. My priority was to make MeetUp succeed and I had to reduce some costs.
  • There was so much stress and antagonism after a layoff. I truly believe we wouldn’t have another one and told my team so, yet one year later, we had to take action again. That was a huge mistake.
  • The #1 thing you could do is build trust. If you don’t have the trust of your people, you’ve lost any semblance of relationship.

Q: What advice would you give young entrepreneurs about facing failure in their first business?

  • First thing is context. The vast majority of people fail. You’re an exception to the rule if you succeed. Once you understand that, you’re in an enormously great company.
  • If you fail, take a step back and ask yourself, what can I learn from this experience? What should I have done differently? Am I the right fit for this role?
  • The sooner you’re able to acknowledge the fact that it’s okay to fail, the better. It’s better to fail because you learn more from failures, the more that will open up opportunities to be vulnerable which will help you be more successful or fail a little bit less next time.

Q: Let’s talk about MeetUp. Tell us how it works.

  • MeetUp is the world’s largest platform for finding and building community.
  • We have 57 million members in 193 countries. We have 300,000 different groups which could be everything from a hiking group, bowling group, learning Spanish or Swahili group or even a Cutco/Vector group.
  • One thing I love about MeetUp is the overlap of the personal and the professional. Community is about people who could be very different from each other, helping to support each other and showing up for each other.

Q: How does someone jump in and get started?

  • If you’re technology-forward, download the app and check out the groups and see which ones you like.

Q: Do events happen live and on Zoom?

  • 72% is in-person, and 28% is Zoom.

Q: I’d love to get your insights on what you feel helps people establish powerful connections with the people they meet in these ways?

  • I would say start attending and then if you really want to get the most from the platform, become an organizer. Do something you’re passionate about and organize in that group.
  • The beauty of it is you could build the culture of the group. Schedule your first event. Don’t aim for perfection, don’t wait until you have 100 people showing up.

Q: You’ve referenced in your role as CEO, you’re using a lot of skills gained throughout your wide range of experiences including being a HR. I really want to talk about this idea of establishing culture and core values and how you’ve done that at MeetUp. How do you do that?

  • Core values cannot be a top-down thing.
  • We set up a cross-functional group without me. They talked about what are the attributes that make working at MeetUp a different experience. They presented me with some ideas.
  • The concepts were incredibly consistent between what was suggested and what we ended up rolling out.We use them for recruiting, performance management, 360o feedback and more.
  • We use them as an anchor in so many company decisions. We give awards based on achieving certain values.

Q: What are these core values?

  • Trust and transparency.
  • Focus on impact.
  • Invite change.
  • Stepping up.
  • Elevating people.
  • Leading with integrity.

Q: You’ve got a new book. It’s coming out in March 8th and is called Decide and Conquer. What motivated you to write it?

  • I’ve always been obsessed with decision-making.
  • We all have biases, best practices and values when it comes to making smart decisions.

Q: in the book, you’ve referenced 44 challenges that have come up in the course of your career and what you did and how that worked in those instances.  You’ve described a decision-making framework. I want to ask you about a few of those. The first is the concept of “be kind”. Why is that the first in the framework?

  • People don’t often understand the difference between being nice and being kind.
  • It isn’t nice to hurt someone’s feelings and tell them they aren’t doing a good job or they’re making mistakes or failing.
  • But sometimes, the kindest thing you could do is tell someone this might not be for you.

Q: The other framework is “work for your employees”. Tell us about that.

  • I like to talk about the organizational chart.
  • The CEO and leader is at the bottom of the chart. Our job is to support and enable the success of those that report to us.
  • Their job is to do likewise to those who report to them.
  • Don’t focus on yourself, but how you can support and enable the success of everyone around you.

Q: Sometimes, does that mean making decisions that aren’t in your best interest in the short-term?

  • If something is going to hurt you and be truly negative for you, ask am I going to feel resentful if I make this decision? If you aren’t going to be resentful, don’t do it.

Q: What do you mean in your framework by “be surprised only by being surprised”?

  • People are complex.
  • You’re going to be dealing with people with agendas different than your own, they might have grey lines when it comes to integrity and that might end up surprising you.
  • Surprises can and will happen to you. As long as you have that context, if it does happen you aren’t going to fall apart.

Q: How have you taken all the things you learned in your career and applied it to your personal life?

  • I have a belief you work to live not vice versa.
  • Until COVID-19, half the time when I came home, I’d leave my phone in the car because I didn’t want to be distracted.
  • Vacations, taking care of yourself, exercises. If you don’t take care of yourself, you can’t take care of others.

Q: The podcast theme is changing lives. As you look into your own future, how do you aspire to change people’s lives through the influence you have?

  • The main reason I wrote the book was to impact positively as many people as I can in this world.
  • When I’m teaching my students, it’s the same thing.
  • The most selfless thing I could do is truly help others and I try to really do that. The purpose of giving personally provides a tremendous amount of gratification.


  • The range of experiences David has had over the course of his career and how it has provided him with additional perspective and created solutions for the challenges that come up in his current role.
  • I think about the opportunity young Cutco/Vector people have to take as much responsibility as possible. You have a chance to do so many things that are beyond the scope of what most young people have a chance to do very early in life.
  • Of course, at times there will be failure. David shared that failure must be viewed in context. The context that most people do fail when they’re taking on challenges. If you aren’t failing, you aren’t stretching yourself enough. Mistakes can provide you with the opportunity to have more confidence in the future because you’ve learned how to overcome those things.



Show Notes for this episode provided by Brian Njenga.


To get access to all episodes and free resources, visit our podcast page!



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