You can be on Entrepreneur’s cover!

How Success Happened for Meetup CEO David Siegel David Siegel, CEO of Meetup, discusses his creative and persistent approach to problem-solving.

By Robert Tuchman

entrepreneur daily
David Siegel, CEO of Meetup

I was thrilled to talk with David Siegel, CEO of Meetup, the leading platform for finding and building local communities, for my recent episode of How Success Happens.

Stepping in to take over as the CEO of an established tech company with a presence in 190+ countries takes grit and drive. David has cultivated a lot of both during his 20-year career as an executive at Seeking Alpha, Investopedia, and now Meetup. Despite David's impressive resume, I was surprised to find how easy-going and approachable he was. We talked about his work philosophy: he's comfortable with failure but relentless about trying again until he achieves success.

Related: Why Your Startup Needs an Advisory Board

A significant test of David's grit was his experience leading Meetup through the early stages of the pandemic in March 2020. As a company with a mission of bringing people together at events for shared interests, the COVID-19 outbreak threw a wrench in the company's day-to-day operations—Meetup had to pivot from in-person events if it was going to make it. I realized in our conversation that David has a knack for making decisive calls and leading during a crisis. He talked about the company's quick switch to hosting online events, which still make up 20% of Meetup's events today. That commitment to helping people connect—and thinking creatively about how to do so—got Meetup through uncertain times.

The outbreak of COVID-19 was by no means the only turbulent point in David's tenure at Meetup. If you're a listener of my podcast, odds are good that you're familiar with the details of WeWork's meteoric rise and fall, as well as its infamous co-founder and CEO, Adam Neumann. At the height of WeWork's multibillion-dollar valuation frenzy, it acquired Meetup to bolster its reputation as a tech company.

Related: How to Lead With Transparency In Times of Uncertainty

If you thought the depictions of Adam Neumann and WeWork's corporate culture were exaggerations, David is here to assure you that, if anything, the media has downplayed his former boss' eccentricities. He shares some juicy stories from his days working for Adam Neumann, including a whopper about a WeWork executive who hit his head on a massive gong hard enough to get a concussion. If the WeWork highs were high the lows were even lower, culminating in a failed IPO and the quick sale of its assets. When WeWork tanked, David was tasked with finding a new buyer for Meetup and maintaining staff morale right as the pandemic began to rage across the world.

With these tumultuous changes all taking place in his first few years at the helm of Meetup, it's no surprise that David has a wealth of fascinating examples of making tough calls when the stakes are high. In his book Decide & Conquer, David shares his framework for making decisions to succeed in life and business. We chatted about some of the most common decision-making pitfalls and reasoning biases that lead people astray. It struck me how David's response to a hectic period in his life was to reflect on the events by writing a book. He even describes the process as something akin to therapy. Read it for yourself to become a better leader and a more strategic decision-maker.

Related: 3 Strategies for CEOs to Improve Corporate Culture

Throughout our conversation, I was impressed by David's sincere passion for his work. Meetup's mission to bring people together and end the loneliness epidemic resonates with David on a deeply personal level. I can easily imagine him coming alive at a Meetup event and inspiring everyone there to start mingling and spark real friendships.

Robert Tuchman

Entrepreneur Staff

Host of How Success Happens

Robert Tuchman is the host of Entrepreneur's How Success Happens podcast and founder of Amaze Media Labs the largest business creating podcasts for companies and brands. He built and sold two Inc. 500 companies: TSE Sports and Entertainment and Goviva acquired by Creative Artists Agency (CAA).

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Side Hustle

This Dad Started a Side Hustle to Save for His Daughter's College Fund — Then It Earned $1 Million and Caught Apple's Attention

In 2015, Greg Kerr, now owner of Alchemy Merch, was working as musician when he noticed a lucrative opportunity.

Growing a Business

Bantam Bagels' Founder Fell Into a Mindset Trap 'People Don't Talk About' After Selling the Now-Defunct Business for $34 Million — Here's What Happened

Elyse Oleksak and her husband Nick founded their mini bagel business in 2013 — and it was an instant hit.

Business News

I Designed My Dream Home For Free With an AI Architect — Here's How It Works

The AI architect, Vitruvius, created three designs in minutes, complete with floor plans and pictures of the inside and outside of the house.

Money & Finance

Setting Your Business Up for Success Through the Rest of 2024

CFO's mid-year update: Understanding the latest trends and regulations impacting business finance.

Business News

Yes, You Can Buy a Foldable Tiny Home on Amazon — And Now It's Selling for Less Than $12,000

The waterproof and flameproof house was listed around $35,000 a few months ago.

Thought Leaders

We Live in a Data-Driven World — Here's a Case For Listening to Your Gut Instead

Honing and trusting one's intuition can lead to quicker, more effective decision-making. Here's how to harness the power of listening to your gut to make the best choices.