Rebooting Work: Transform How You Work in the Ageof Entrepreneurship
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More About This Title Rebooting Work: Transform How You Work in the Ageof Entrepreneurship


From Silicon Valley leader Maynard Webb, how we can leverage technology to change how we work

Maynard Webb has always been the go-to guy when Silicon Valley companies have thorny problems. Whether revamping eBay's crashing servers (transforming their technology weaknesses into a competitive strength) or investing in emerging technology start-ups, Webb brings strategic and operational savvy to every issue and venture. In his first book, Webb brings this same focus to tackle outdated models of work, created a century ago, which no longer sync up with either individual or employers' needs.

Through a unique framework, Webb identifies 4 different mindsets around work (the company man, CEO of your own destiny, disenchanted employee, and the aspiring entrepreneur). It organizes those who are self-motivated versus those who are waiting to be discovered and aims to give readers the tools to become more self-actualized, happier, and ultimately more fulfilled in their careers. In identifying a paradigm shift that is already under way, Webb demonstrates clearly how to harness technology to embrace our own personal happiness, allowing people to become more productive at work and also spend more time with their families.

  • Contains a framework that demonstrates how we can leverage technology to create better job opportunities and foster more balanced lives
  • Written by Maynard Webb, chairman of LiveOps, former COO of e-Bay, founder of Webb Investment Network (WIN), and board member of Yahoo! and
  • Includes personalized worksheets and empowering action-oriented advice

Rebooting Work reveals how anyone can take control of his or her own future, finding greater fulfillment, productivity, and happiness.


Maynard Webb is the chairman (and former CEO) of LiveOps and a board member at both and Yahoo! Previously he was the COO of eBay. He is the founder of the Webb Investment Network (WIN) as well as the Webb Family Foundation. He lives with his wife, Irene, in Silicon Valley. For more information, please visit

Carlye Adler is an award-winning journalist and bestselling author. She is co- author, with Marc Benioff, of Behind the Cloud and The Business of Changing the World, as well as coauthor of The Dragonfly Effect. She lives in New York. For more information, please visit


Foreword: The Benchmark of Success ix
by MegWhitman

Preface xiii

Introduction xxv

Part 1 Why Work Isn't Working

1 Changing Work 3

2 Technology: Powering the Future of Work 11

Part 2 Reframing How We Think About Work

3 The Framework 27

4 Frame 1: The Company Man or Woman 41

5 Frame 2: CEO of Your Own Destiny 61

6 Frame 3: The Disenchanted Employee 79

7 Frame 4: The Aspiring Entrepreneur 105

8 The Age of Entrepreneurship 123

Conclusion: Break New Snow 133

Part 3 Getting Started

Appendix A The Worksheet 141

Appendix B Worksheet Examples 147

Appendix C Services You Should Know About 157

Notes 161

Acknowledgments 171

About the Authors 175

Index 177


#3 New York Times Best Seller (Hardcover Advice, How-To, and Miscellaneous)
#6 New York Times Best Seller (Hardcover Business)
#2 Wall Street Journal Best Seller (Hardcover Business)
#9 Publishers Weekly Best Seller (Hardcover Nonfiction)
#9 Entertainment Weekly Best Seller (Hardcover Nonfiction)
#8 Los Angeles Times Best Seller (Hardcover Nonfiction)
#10 Washington Post Best Seller (Nonfiction)

“You can't have everything you want, but you can have the things that really matter to you. Rebooting Work shows you how to make the right changes to get the most out of work—and life.”
—Marissa Mayer, CEO, Yahoo!

“Maynard Webb is one of those rare individuals who sees tremendous possibility where others see problems. In Rebooting Work, he applies to individuals the same intuition and expertise that helped leading companies embrace technology and prosper. This is a terrific guide for anyone who wants not just a fulfilling career, but also a fulfilling life.”
Howard Schultz, chairman, president, and CEO, Starbucks Coffee Company

“The world is changing faster than ever. The social, mobile, and cloud technologies that are being rapidly adopted provide amazing new opportunities to engage with customers and employees, and fundamentally change the way we need to manage our companies. Rebooting Work outlines how tomorrow’s successful companies must completely rethink how they work to engage and motivate people.”
Marc Benioff, chairman and CEO,; author, Behind the Cloud

Rebooting Work covers a fascinating topic—the future of work—and nobody is better
qualified to write about it than legendary Silicon Valley company builder Maynard Webb.”
Marc Andreessen, co-founder and general partner, Andreessen Horowitz; co-founder, Netscape Communications

“Maynard is one of the most effective leaders I have ever worked with. He knows how to blend innovation with execution at scale. Rebooting Work shares the practical insights and lessons from his experience.”
John Donahoe, president and CEO, eBay

“In order to succeed you must have the courage to take risks. Rebooting Work outlines the reasons to choose change and gives readers a foundation for success.”
Brad Smith, president and CEO, Intuit

“Maynard Webb’s old-school belief in working hard and shooting for the stars, combined with his understanding of cutting-edge technology, is the playbook for winning at whatever you do.”
Jed York, CEO, San Francisco 49ers

“People do not like to be managed, but they love to be led. Rebooting Work introduces a new vision for work and Maynard Webb leads readers to a place they want to go, one that has less traffic congestion and a better work-life balance.”
Scott McNealy, co-founder, Sun Microsystems; chairman, Wayin; founder, Curriki

“In every corner of society, there are optimists, agitators, and rabble-rousers—people who have never lost hope that it is possible to create change. Maynard Webb has created economic and technological change through so many companies he’s helped build.  In Rebooting Work, he takes his message of hope to change how the world works.”
Jeffrey Skoll,founder and chairman, Participant Media;founder and chairman, The Skoll Foundation; former president, eBay

“As you go and pursue career goals, it’s important to do something that you love. Rebooting Work acknowledges the importance of putting passion and purpose in work.  Maynard Webb—Silicon Valley’s go-to guy to get stuff done—gives you a framework to help you get there.”
Jeffrey Housenbold, president & CEO, Shutterfly

“Rebooting Work is as profound as it is a pleasure to read. Not only will this book help you achieve the happiness that comes with being fulfilled, itwill also help companies achieve far more by cultivating and supporting motivated and high-spirited people.”
—James M. Citrin, leader, CEO and board practice, Spencer Stuart; author, You Need a Leader, Now What?

“The social and mobile revolution is forcing customer service contact centers to go social or get left behind with decreased customer loyalty and loss of market share. We’re seeing companies transform their businesses and reach new heights of success by integrating social and mobile capabilities in their customer service contact center. Rebooting Work takes a different angle on the revolution—how this positively impacts individuals—and shows anyone how to get on board.”
—Marty Beard, president and CEO, LiveOps

“We are all entrepreneurs, accountable for our own professional destiny—whether we are launching a technology start up or working in a large corporation. This unique and accessible book is one big Silicon Valley mentoring session, delivered by a battle-tested executive with a can-do attitude.”
Thomas J. Tierney, co-founder and chairman, Bridgespan Group; former CEO, Bain & Company; co-author, Aligning the Stars and Give Smart

“Maynard Webb understands the importance of thinking big and starting small. Rebooting Work is an engaging and informative book that helps readers find clarity of purpose. It will influence entrepreneurs for years to come.”
Jim Goetz, general partner, Sequoia Capital 

“Enlightening, entertaining, extremely practical. Maynard Webb has given us the best kind of business book: a treasure-trove of practical wisdom woven into a fascinating story. If you are looking for a highly-readable map to business success in the 21st century, look no further. Maynard Webb helped invent the new technological world we live in, and no one knows better how to channel the power of technology while maintaining the essential heart-connections that allow work to be a source of joy and life-satisfaction. Get this book! Reading Rebooting Work could well be the best investment you make this year.”
Gay Hendricks, Ph.D., author, The Big Leap and The Corporate Mystic

“Seeing trends in technology early is what matters. Maynard Webb sees them early, and Rebooting Work covers what’s next in IT and how to use it to transform work and your life.”
Matt Carey, executive VP and CIO, The Home Depot

“A near perfect storm of digital technologies has enabled the emergence of electronic marketplaces for everything from stocks to antiques. In Rebooting Work, Maynard Webb compellingly illustrates the emergent electronic marketplace for jobs and the profound implications this has for our careers.”
—William A. Thornton, former CTO, Fidelity Investments