How Success Happened for Meetup CEO David Siegel

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.

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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.

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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.

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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.