Today is WeWork’s IPO, and it’s time for a first-hand account of life under WeWork.
Having been hired by WeWork as Meetup’s CEO exactly three years ago, I gained a keen insider perspective of WeWork under Adam Neumann. The saga was covered for many months ad nauseam, and after a two-year delay, a canceled IPO, then a delayed IPO again, it’s time to get some perspective on life at WeWork from someone who lived it.
- WeWork and Adam Neumann were sincerely focused on making the world a better place. The company and its leader were not the sinister people portrayed by the media.
- WeWork genuinely cared about human connections and community more deeply than many companies and leaders.
- Great people, with an inspiring mission, were undone by incredibly poor decisions, grounded in impossible goals.
- WeWork is a story of how decision-making and the goals that anchored those decisions nearly destroyed a company and its people.
- However, WeWork’s culture was more insane and the stories far crazier than the documentary, books, and endless press had conveyed.
When Meetup was sold out of WeWork at the beginning of the pandemic in March 2020 I was no longer spending 2.5 hours commuting and I decided to reconstruct the story of Meetup’s survival under WeWork (and later during the pandemic) and share a framework for smart decision making. I started writing an article about the experience and it quickly turned into Decide & Conquer, a 256-page book that is being published by HarperCollins Leadership. It’s a story of Meetup’s survival in the face of some pretty stark challenges and the decisions that made that happen. Because, unlike WeWork, while there were exceptional people at both Meetup and WeWork and a deeply impactful mission, Meetup anchored its decisions in the right goals: mission first, expansion later.
In light of WeWork’s IPO announcement, I thought I would share an excerpt from my forthcoming book.
In January 2019 I was summoned from New York to San Francisco to have a one-on-one with Adam at WeWork’s West Coast headquarters in Salesforce Tower. He began the meeting by telling me what Meetup’s expansion strategy should be. There was then a short break where Adam decided to shut the lights off and play The Greatest Showman in surround sound while he, myself, and the general manager from Latin America (I had no idea why he was there) sang along. The meeting was then interrupted by a critical call that Adam needed to make to confirm that the Samurai sword sent by Masayoshi Son (the largest investor in WeWork) had been delivered to Adam’s home. Then his wife, Rebekah, entered the room, promptly took off her shoes, and asked me who I was. Rebekah recently had been promoted to WeWork’s chief brand officer. From my notes, our conversation went something like this:
Rebekah: Who are you?
David: The new CEO of Meetup.
Rebekah: What’s Meetup?
Adam: We acquired Meetup a year ago.
Rebekah: We own Meetup? What do they do?
David (thinking): The chief brand officer of WeWork doesn’t even know they own us. Boy, I feel pretty damn unimportant.
Rebekah: You should change the name of the company. It is terrible.
Adam: Well, they have built a brand for the last eighteen years, but we should definitely talk about changing the name.
David (thinking because he’s speechless): What the hell did I get myself into?!

Here’s what people are saying:
“David’s analysis of the critical decisions he made prior to and then as CEO at Meetup under some very trying circumstances are engaging and thought-provoking, but told with humility and humor. A must-read.” – Sarah Friar, CEO of Nextdoor
“Whether you’re leading a startup, a Fortune 500 company, or a family, making smart decisions is critical for both success and happiness. Reading David Siegel’s Decide and Conquer … will lead to many more wise choices in the future.” – Tal Ben-Shahar, New York Times Best-Selling author of Happier
“A riveting, story-driven page-turner.” – Radha Agrawal, Founder & CEO of Daybreaker and author of Belong
“Decide and Conquer describes his incredible journey while providing a guide to making tough decisions and maintaining your morals in the process.” – Jon Levy, New York Times Best-Selling author of You’re Invited
“ …making values-based decisions—like starting with kindness, prioritizing people first, and playing the long game—are good for people and great for business…” – Erica Keswin, Best-Selling Author of Bring Your Human to Work and Rituals Roadmap
“ …brutally-honest and often humorous.” – Noam Wasserman, Dean, Yeshiva University, Sy Syms School of Business
Book Description:

Success boils down to one thing: making good decisions. That’s easy to say, but what do we do when we are faced with terrible options, deep anxiety, and fear of failure? Learning the right framework now can make all the difference later.
Turn to Decide and Conquer to access the decision framework David Siegel used when he took over as CEO of Meetup, the world’s leading platform for making connections and finding your community. Let David’s success during one of the most tumultuous times in his company’s history help guide you on your own path.
Decide and Conquer helps all leaders navigate the big decisions that will impact their future and make their organizations a success. David outlines the 44 challenges leaders face when starting a new position. He then shows you the decision framework he applied to overcome these challenges as CEO of Meetup. David takes you on an epic journey of corporate and personal survival that includes industry titans like Adam Neumann, Barry Diller, Jack Welch, Bill Ackman, and other leaders. Learn to:
Apply principles like open communication, transparency, and kindness to inform great decision-making.
Set yourself up to succeed, even before you start, by removing potential roadblocks before they become a problem.
Be a bold and decisive leader and not succumb to fear.
When David took over as CEO of Meetup, the road was fraught with obstacles that could have destroyed Meetup and his reputation. By applying the principles he had learned in previous leadership positions, David was able to make the many critical decisions that would mean life or death for Meetup when WeWork decided to sell the company. From deciding to accept the position and negotiating terms to the first 30, 60, and 90 days on the job and managing a seemingly endless series of crises during the sale and global pandemic, Decide and Conquer walks readers through the key decisions they will face with invaluable advice for each one.

The views expressed in this post and book are the personal opinions of David Siegel and do not necessarily reflect the views of Meetup LLC or its affiliated entities or parent company.
Last modified on October 22, 2021
