How Success Happened for Meetup CEO David Siegel


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



David Siegel, CEO of Meetup

Going on to take over as CEO of a well-established technology company with a presence in more than 190 countries requires strength and drive. David has grown a lot during his 20-year career as an executive at Seeking Alpha, Investopedia and now Meetup. Despite David’s impressive resume, I was surprised to see how easy and accessible it was. We’ve talked about his work philosophy: he feels comfortable with failure, but relentless in trying again until he achieves success.

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An important test of David’s strength was his Leadup Meetup experience during the early stages of the pandemic in March 2020. As a company with a mission to bring people together in events for shared interests, the COVID-19 epidemic threw a key on company day. -daily operations: Meetup had to change face-to-face events if it was going to do so. In our conversation, I realized that David has an ability to make decisive calls and lead during a crisis. He talked about the company’s rapid shift to online event hosting, which still accounts for 20% of Meetup events today. This commitment to helping people connect and think creatively about how to do that made Meetup going 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 to my podcast, chances are you’ll know 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 multimillion-dollar valuation frenzy, it acquired Meetup to bolster its reputation as a technology company.

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If you think Adam Neumann and WeWork’s representations of corporate culture were exaggerations, David is here to make sure that, in any case, the media has downplayed the eccentricities of his former boss. He shares some juicy stories from his days working for Adam Neumann, including a whore about a WeWork executive who hit him in the head with a massive gong hard enough to have a concussion. If WeWork’s highs were high, the lows were even lower, culminating in a failed IPO and the quick sale of its assets. When WeWork sank, David was tasked with finding a new buyer for Meetup and maintaining staff morale as the pandemic began to wreak havoc around the world.

With these tumultuous changes that have taken place during his early years at the helm of Meetup, it’s no wonder David has a plethora of fascinating examples of making difficult calls when there’s so much at stake. In his book Decide and conquer, David shares his framework for making decisions to succeed in life and business. We talked about some of the most common pitfalls in decision making and the reasoning biases that cause people to stray. I was amazed at how David’s response to a hectic period of his life was to reflect on 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 to life at a Meetup event and inspiring everyone to start mixing up and building real friendships.



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