David Siegel - Decide and Conquer: 44 Decisions that will Make or Break All Leaders

Make the decision on your leadership journey to buy this book! Throughout this book, the power of community and how to harness it shines through. David Siegels analysis of the critical decisions he made prior to and then as CEO at Meetup under some very trying circumstances is engaging and thought-provoking but told with humility and humor. A must-read.

Sarah Friar,

CEO of Nextdoor

Whether youre leading a startup, a Fortune 500 company, or a family, making smart decisions is critical for both success and happiness. Reading David Siegels Decide and Conquer is likely to be a very timely and smart decision that will lead to many more wise choices in the future.

Tal Ben-Shahar,

New York Times bestselling author of Happier

David Siegel is the kind of CEO I would want to work for. Understanding how he makes decisions only further shows why. 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 bestselling author of Youre Invited

David Siegels been faced with some tough calls throughout his career, and as a leader you will too. But as he shows us in Decide and Conquer, making values-based decisionslike starting with kindness, prioritizing people first, and playing the long gameare good for people, great for business, and, after the pandemic year weve had, just might change the world.

Erica Keswin,

Workplace strategist and bestselling author of Bring Your Human to Work and Rituals Roadmap

I loved reading David Siegels brutally honest and often humorous romp through the key forks in his career and his reflections on decisions gone right and very wrong. Even though David has had entertaining experiences, he also has a unique ability to apply the lessons to situations we might all find ourselves facing.

Noam Wasserman,

Dean of Yeshiva University, Sy Syms School of Business

In his riveting, story-driven page turner, David Siegel shares ground rules that will change the way you look at leadership and make you rethink how you build your teams from day 0 onward. If youre interested in community architecture and building teams from the inside out with deep intention, thought, and fun, this book is a must-read. Its my new leadership bible.

Radha Agrawal,

CEO and founder of Daybreaker, author of Belong

David Siegels leadership journey is expansive across industries and at some of the most iconic companies that have shaped New York City. Reading this book was a much-needed reminder to me that I can choose to fear making mistakes or have the kindness and confidence in myself to make bold decisions and learn from them. I want to choose the latter every time.

Wendy Tsu,

Early-stage investor and partner at AlleyCorp

2022 David Siegel

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Published by HarperCollins Leadership, an imprint of HarperCollins Focus LLC.

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ISBN 978-1-4002-3088-4 (eBook)

ISBN 978-1-4002-3087-7 (HC)

Epub Edition January 2022 9781400230884

Library of Congress Control Number: 2021952499

Printed in the United States of America

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To Lara, my lifes best decision

Working with Adam Neumann provided all WeWork executives with an abundance of outlandish stories. A traditional pastime during offsites, in fact, was to swap Adam tales. My favorite of many encapsulates not just the man but the challenges I would have under him as chief executive officer of Meetup.

In January 2019, I was summoned from New York to San Francisco to have a one-on-one with Adam at WeWorks West Coast headquarters in Salesforce Tower. He began the meeting by telling me about what Meetup should evolve into. 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 swords sent by Masayoshi Son (the largest investor in WeWork) had been delivered to Adams 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 WeWorks chief brand officer. From my notes, our conversation went something like this:

Rebekah: Who are you?

David: The new CEO of Meetup.

Rebekah: Whats Meetup?

Adam: We acquired Meetup a year ago.

Rebekah: We own Meetup? What do they do?

David (thinking): The chief brand officer of WeWork doesnt 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 hes speechless): What the hell did I get myself into?!

For those of you who are not one of the thirty million people who have attended a Meetup event since our founding in 2002, Meetup is the worlds largest platform for finding and organizing community groups. The companys 300,000 groups in 193 countries create and host about 15,000 events every single day. Groups are organized geographically and meet online or in person around a shared interest, such as hiking, video games, or learning Java, or around a shared identity. Meetup groups are run by an organizer, who is charged a fee, and uses Meetups online tools to set a time and place for the groups events, find new members, charge fees, screen potential members, upload photos, chat online, and more. Some groups are as small as three to five members and some have tens of thousands of members, but every group is its own unique community, with the potential to change the lives of its members. Meetup strives to drive both in-person connections and to use technology to connect people of shared interests and identities from around the world.

Meetup is a true public good and has bettered the lives of millions of its global members, as its founder, Scott Heiferman, intended when he founded the company following 9/11. He said:

I lived on Houston Street, and everything was shut down south of us for a few weeks. People in our apartment building started to make eye contact in a way that they never had before and they would ask you how youre doing. When people said hello to each other, you got this very palpable sense of community.... I had been the last person in the world to think that local community gatherings, or people turning to each other, are important. But this really hit me.... So then I started to read up on the topic. I came across Frances Cairncrosss