Cover Page

Table of Contents

Praise for Rebooting Work

Title Page



Foreword: The Benchmark of Success


Breaking Systems


Meritocracy Versus Entitlement and the Age of Entrepreneurship

Part 1: Why Work Isn't Working

Chapter 1: Changing Work

Freelance Nation 2.0

Getting to Green

Chapter 2: Technology: Powering the Future of Work

Innovation Drives Productivity

Harnessing the Power of the Web

The World Goes Mobile

Work Migrates to the Cloud

Powering a Global Community

Work Is the Next Killer App

Part 2: Reframing How We Think About Work

Chapter 3: The Framework

Chapter 4: Frame 1: The Company Man or Woman

The Rise of the Paternalistic Company

Company Freefall

The New Mobile Workforce

Location, Location, Location Is So Yesterday

Chapter 5: Frame 2: CEO of Your Own Destiny

Everyone Has to Get Voted on to the Team Every Day

Chapter 6: Frame 3: The Disenchanted Employee

Work Really Could Be Killing You

The Mentor Mandate

Mentoring in the Modern Age

There's Nothing to Fear (but Fear)

Advice for Powering out of Frame 3

Chapter 7: Frame 4: The Aspiring Entrepreneur

So You Think You Can Be an Entrepreneur?

The Experience Issue

The Path out of Frame 4: Plan Ahead

Chapter 8: The Age of Entrepreneurship

The New New Company

Conclusion: Break New Snow

Part 3: Getting Started

Appendix A: The Worksheet

Appendix B: Worksheet Examples

Appendix C: Services You Should Know


About the Authors


Praise for Rebooting Work


“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, cofounder, 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 and 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, it will 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 startup 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, cofounder and chairman, Bridgespan Group; former CEO, Bain & Company; coauthor, 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, 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

Title Page

To my coaches, who inspired and brought out the best in me, and to the teams that I was privileged to be a part of

Foreword: The Benchmark of Success

By Meg Whitman

There are people you encounter in life who stand out above all others—who teach you, challenge you, and inspire you. In my life, one of those people has been Maynard Webb.

I first met Maynard in 1999, shortly after I became the CEO of eBay. The company was growing very quickly, and it was an incredibly exciting time. But one of the challenges we had to contend with was the stability of the site. Our technology, built when we were a fledgling start-up, just couldn't keep up with the growing transaction volumes. The site was frequently breaking down and disappointing sellers and buyers in the process. One particularly severe outage lasted for twenty-two hours. It attracted enormous national news media attention and nearly cost us all of our customer data.

The outages required me to look for someone strong and smart enough to tackle the problems. We simply didn't have the in-house talent to fix the site. We needed someone to come in and rapidly overhaul the technology while we continued to grow and do business. I described it as changing an airplane's engines in flight without losing altitude or crashing.

As I started my search for a great technologist, I began to hear about Maynard Webb. Maynard was the widely respected chief information officer (CIO) at PC maker Gateway and had previously been at Bay Networks, where he completed a notoriously challenging SAP implementation in a remarkable nine months. This sounded like the guy we needed, but unfortunately for eBay, Maynard wasn't looking for a new job.

After some prodding from our recruiter, Maynard agreed to meet with me in California. True to his nature, Maynard thought the challenges eBay faced were “awesome.” eBay was just the kind of job Maynard loved—a big, hairy problem no one else wanted, but that if solved, would make a huge impact.

About a week after our meeting, Maynard agreed to join eBay. For the next seven years, Maynard solved every problem we threw at him. Maynard rebuilt our technology infrastructure and took what was once a big liability and turned it into an area of strategic strength. Over time, he built a world-class technology team that has, as he likes to say, been “breaking new snow” ever since.

And what Maynard's team created was awe inspiring. The new ultrareliable infrastructure they engineered and the quality measures they put in place helped sustain the company's explosive growth. It enabled the site to scale to handle more than a billion transactions per day and store over two petabytes of data—two hundred times more data than contained in the Library of Congress.

Maynard architected much more than eBay's technology, though. Later, as eBay's COO, Maynard helped introduce the processes and day-to-day operating structures that moved us from a business of 250 employees to a global company of more than 10,000 employees. In his seven-year tenure, Maynard enabled eBay to effectively grow revenue from $140 million to more than $5 billion by the time he left in mid-2006.

In working so closely with Maynard for so long, I noticed how much he enjoyed being a mentor. He always made time for anyone who wanted his advice—and there are many who sought him out. He hosted regular “fireside chats” in eBay's offices, in which he shared his career experiences and insights with intimate groups of twenty people; they became very popular and allowed him to reach more employees.

At one of our annual Leaders' Meetings, Maynard told a story I will never forget. He spoke about sitting on a park bench long after he retired. He was no longer the boss, had no budget, and could no longer hand out a job or a promotion. There was no ulterior motive to be nice to him. Maynard wondered if the people he encountered throughout his life would walk over to say hello or turn and walk away. He then stressed the value of conducting oneself in ways that draw people toward you.

When Maynard left eBay, we dedicated the park benches in our new courtyard to him. We inscribed a quote from Maynard on each one, a piece of wisdom from him that continues to guide us. And when Maynard comes back to visit and sits on one of his benches, I know no one will ever walk by without stopping to say hello.

Though I was sad when Maynard left eBay, I also understood. He had finished what he had come to do. It was time for new challenges.

As CEO of LiveOps, Maynard helped a new generation of workers prosper on their own terms. He also started investing in innovative companies that are leveraging technology to help workers find greater levels of achievement and personal fulfillment. Maynard serves on the boards of and Yahoo!, companies he believes embody his focus on people, success, and a better future.

Rebooting Work takes on a big problem—the broken state of work—and reveals a solution, one that is better for employees and employers. As with every problem Maynard solves, he has ferreted out the answers and made certain that his solutions are easy to understand and possible to implement.

This book is the result of Maynard's journey through an exciting and varied career. It makes Maynard's knowledge and mentorship accessible to everyone. It will help people become the “CEOs of their own destiny” and live happier and more fulfilling lives. And it will help companies operate better as they move forward into the evolving landscape of work in the twenty-first century.


As the chairman of a cloud computing company that creates work opportunities for thousands of people (contractors and employees) each month, I see the world of work as very different from the one that's being reported in the headlines. I'm convinced that this is one of the most exciting times in the history of work—and one of the best times for anyone to enter the workforce. Just as the Industrial Revolution was defined by manufacturing that gave people jobs, today's IT revolution—defined by new technologies—is giving people more flexible and empowering opportunities for work than ever before.

When I started working, I had to leave my home in Florida and take a permanent job with IBM in Minnesota. I've moved nine times for a job, and I moved three times in less than two years. We all know that this model is steeped in the past, but two years ago, as I started to think about what was happening in the world of work—and about writing this book—I realized that even though those IBM days were long behind me, there were other outdated work models that I was perpetuating and that were not right for me or my family. My career was still defined by the limits of working for a company. I was working with assigned teams that were static, and we worked from the same location. I spent set hours in an office building and not enough time with my wife and family.

Once I became involved with LiveOps and became inspired by the twenty thousand independent agents who were truly working on their own, I realized that there was a better model for working. They were paid for performance, but they worked on their own terms and were happy with their freedom. It was great for them and great for our company. It was a win-win for workers and management like nothing I had experienced before. I bought into it so much that I decided that I needed to walk the talk myself. I gave up formal operating roles and began to reframe the way I thought about my career.


In many ways, I've been very blessed—I am married to the love of my life; I have wonderful children and grandchildren. I've enjoyed a career in technology that has inspired me and provided for my family beyond my wildest imagination. I've also had some body blows. The times I've been thrown a curve ball or knocked down have been just as influential—perhaps more influential—in determining the ultimate outcome of my life.

Over my career, I have had the good fortune of being in the right place at the right time in several industries. I was thus able to witness and participate in significant transformations in technology, which gave me good strategic insights into where the world was going. I worked at IBM during the PC revolution, focusing on computer security long before it was “cool” or even possible to be a hacker. During the PC heyday, I was transferred to Boca Raton and put in charge of financial systems integrity, which at the time was in a shambles. I worked at Thomas-Conrad as “networking” began taking off, and at Bay Networks as the Internet exploded. I was at the epicenter of Internet commerce at eBay and in the middle of the revolution in work at LiveOps. My extracurricular activities as a board member at Gartner and at visionary companies including and AdMob allowed me to see such technology trends as cloud computing and mobile long before they were hot.

With the insight that comes from hindsight, I now realize that the most interesting parts of my career happened when there was something that urgently needed fixing, and it was also in an area of nascent strategic importance. I was never interested in just doing something that anyone could do; I was always fascinated by aiming high—shooting for something that would be truly marvelous.


As lucky as my story is, it is also in many ways an unlikely one. I grew up in West Palm Beach, Florida, the third of five kids, and my family was considered upper-middle class. My father was a real estate appraiser and the president of his own company. My mother was a stay-at-home mom who took care of the kids and my father's mother, who lived with us. Life was good: playing outdoors, figuring out ways to finagle out of piano lessons. Then, everything changed dramatically when my father died suddenly from a stroke ten days before my seventh birthday.

My father held no life insurance, and our small savings account quickly ran out. Growing up with little money, we learned to make sacrifices. For several months, we lived without hot water. For a couple of years, we lived without a TV. I couldn't join the Cub Scouts because it required my mom to serve as a den mother, which she didn't have time to do because she was working. Of course, the biggest loss was not getting to live with—or really know—my father.

My mom had a college education and went back to teaching to support the family, first as a boys' physical education teacher, the only opening at the time, then as a science teacher. Two years after my dad died, she decided to pursue her master's degree so that she could make more money. I was nine at the time. That summer, Mom enrolled at San Jose State in California, and with her five children moved into the dorms. There, our after-school fun involved learning to play poker from the other grad students. My mom was incredibly strong, and also industrious. After that summer in California, we moved back to Florida, where she would eventually run the Jupiter Marine Science Center and was voted Teacher of the Year for the State of Florida, one of many accolades she would receive. I had so much love and admiration for her, but was troubled by the position in which my father had left us.

I promised myself then that when I had kids, I would not leave them unprotected as we had been. I also became convinced that I would die at a young age, as my father had. That drove me; I expected life to be short, so I needed to get going at achieving all that I wanted.


I always wanted to work, and when I was ten, I secured a route selling TV guides. (It was small; I had three customers.) By the time I was twelve, I took on a paper route. My mom would wake me before dawn to get to the local gas station and fold the papers before delivering them. I was so exhausted by the end of the day that I'd fall asleep on the floor of the living room.

The thing I loved the most about being a paperboy was the tips I earned around Christmas. One year, I used these funds to buy a Ping-Pong table for my family. I worked several jobs over the next several years: at a gas station, cleaning toilets at Mister Donut, busing tables at the Pancake House, working at an outdoor store, and doing the night shift at a mattress factory.

These were small jobs, but I dreamed big. As a kid, that meant a career as a Major League Baseball player. When I was nine, I was told I shouldn't try out for Little League, as the rest of the new kids were ten. I wanted to anyway. I had my brother's hand-me-down glove, and because he was left-handed, I struggled to catch well as a righty, but I practiced relentlessly and ultimately made the team. I played sports throughout school; our Babe Ruth All-Star team even won a state championship. My athletic career culminated in being recruited for football to the U.S. Naval Academy in Annapolis.

That was 1974, and I had grown long hair and decided I didn't want to go to Annapolis. My mom was very disappointed, as my dad had been a naval officer, and she felt that I was throwing away an opportunity for a great (and paid for) education. I found myself on a different path, though. I went to college in Florida and studied criminal justice. I worked throughout school, even creating a retail business at a local wholesale nursery, and I interned at IBM during my senior year.

Upon graduation, I was offered a full-time job as an entry-level security guard at IBM in Minnesota. Considering my thirty-five-year career in the technology industry, some people assume I mean computer security, but at the time, computer security was in its infancy. (It was a mainframe and minicomputer world.) I worked in physical security, protecting the buildings and its employees.

Every day brought something different. I worked in the lobby of the office building. I also toured through the halls, ensuring that the building was safe and that people got to where they needed to go. No job was too small or too big. I took the flag down at night, assisted with first aid, and one time had to handle a situation where an employee murdered his wife and then killed himself.

Within a year, I was offered a chance to move to a new facility in North Carolina, and shortly thereafter was promoted to become a supervisor of security guards. The physical security work segued into product security—I was in charge of securely administering the most confidential documents at our location and also checking up on how our vendors secured our information.

Then, within five years, as technology evolved, I moved into computer security. Both computer and physical security were becoming hot topics, as we had experienced attacks on our physical premises and had concerns about computer espionage. Although I transitioned from blue collar to white collar, I never gave up my blue-collar approach to work. I continued to understand the value of heavy lifting, and perhaps my willingness to do heavy lifting became my greatest strength.

Breaking Systems

I love new technology, and I'm obsessed with how it makes our lives better, but my role in the technology industry has never been that of the dreamer. I've always been the doer. I've been fortunate enough to work for companies that allowed me to witness the birth of new groundbreaking technologies, but in every company in which I worked, I was brought in because there was a difficulty on the path to growth or advancement. In each job there was a problem, a big issue that seemed insurmountable. While others seemed turned off by these types of challenges, I was really excited by the opportunity to fix something—the chance to make a difference.

Sometimes my job also meant that in trying to fix something, I had to figure out how to break it. At IBM, one of my early jobs in computer security was indeed breaking systems. That was a very cool job. I would be sent to a location, given general access to the systems, and told, “See what you can do.” With that mandate, I was able to confiscate highly confidential documents, take over operating systems, and once even cut a check for a significant amount of money. (I returned it.) It was fun breaking systems, and it gave me insight into how to fix them. Determining what is wrong with something and trying to find a solution has been the thread that has tied my career together.

The truth is, I was unqualified for many of my career roles when I was assigned to them. However, no one else was willing to do them, so I volunteered. Some people called me insane, but in every opportunity that I signed up for, I was very confident that I could do the job well, and tackled the challenges with gusto and no fear. Several times this led to approaches that weren't considered normal practice, but to me they made common sense, and I've always allowed common sense to lead.

For example, when I was doing product security at IBM, vendor security was taken very seriously—vendors were required to log visitors, physically lock documents, and track the removal of files. Amazingly, though, no one thought to lock up the files on the computers. There was no security system in place to protect the digital versions. That was a big gap. The product and security guys had to learn to become more computer literate, and I helped lead that charge. At first this idea was seen as unconventional, but soon, as everything went digital, it became an everyday imperative.

Later, when I was working as a network director at Quantum, a disk drive manufacturer, we had a pressing deadline to get long-distance circuits and technology infrastructure into new factories that were coming on line. Not one telecom vendor said it could meet this deadline. This was not a good outcome; it would delay everything, thus costing us a considerable amount of money. I called a meeting with all the vendor representatives together to address the situation. I explained that the suppliers who were willing to find a way to work with us would build a long and profitable partnership with our company. I then challenged them to find a way to help us. All it took was for one rep to raise his hand and say he could do it. The others followed, all committing to find a way to make an exception. We delivered the project on time.

I went from Quantum to Bay Networks as CIO. The CIO role was very new and was just beginning to be elevated to the executive table. It is actually the only job in my career that I have done multiple times. It is very strategic, very hard, and very risky; at the time, most people said CIO stood for “Career Is Over.” I loved the role and the challenges that came with it.

At Bay Networks we faced very serious issues. We were merging two companies, SynOptics and Wellfleet, onto a common architecture and platform. I agreed to do an aggressive enterprise resource planning (ERP) implementation worldwide, which had been tried several times before and met with failure. I committed to do the implementation in twelve months, and the first step was to ensure that everyone was playing on the same team. I created a mandate that enforced timely decisions (within twenty-four hours) and key executive involvement. I created an untraditional bonus structure that was collaborative with our vendors. For example, our consultants at Accenture were on the same bonus plan as our executive stakeholders, which created a win-win environment. Nobody could go home on Friday unless the week's open issues were rectified. And there were consequences: one factory wouldn't go fast enough, so we pulled it out of the scope. We completed the effort in nine months—at the time it was one of the fastest ERP implementations in the world. We even received a Computerworld Smithsonian IT nomination for the project.

I left Bay Networks after about four years to join Gateway Computers, which was facing many growth challenges. I was hired to significantly improve its web capability, but was surprised to learn upon arrival that although the year 2000 was only two years away, the company was not Y2K ready on its legacy systems. I led a major project to address that, as well as developed a radically different systems architecture.

In 1999, I was heavily recruited by eBay to become its president of technology. The company had some very sizeable technology issues, including one twenty-two-hour outage of its whole service. It was a very public debacle, and unfortunately the site had become the poster child for instability. I found that a crucial part of the solution involved taking a collaborative approach. I encouraged our partners to work with us in a way that they had not in the past. For example, we were using Sun servers, and as a way to motivate our vendor to be a real partner, I suggested that it carry our availability as a metric for executives' bonus plans. This had never been done before, but it worked for both parties, and later Sun adopted this model with its top customers.

The team was fabulous; we worked extremely hard and turned things around. We were growing so fast that we outgrew being able to use one big back-end database server to run our site. We either had to transition to a mainframe system or implement a dramatically different approach. We chose to implement a distributed architecture (what we called a small soldiers approach), which enabled us to achieve scale and stability much more quickly by distributing the database traffic across many different servers as opposed to one. We became world class at innovating on time and at a high velocity without impacting site availability. It was at the time unprecedented to be able to fix the site and keep it running while simultaneously adding new features, functions, and capabilities.

I stayed at eBay for seven years, the last four as chief operating officer. As COO, I helped codify and establish the company's culture, implement decision-making models, and oversee the budget process and corporate initiatives, along with managing all my functional areas (trust and safety, customer support, HR, billing, technology, and product management). I was charged with managing executive staff and helping to administrate the board. I did the same thing for the company that I had done for the technology: implement processes that would ensure that it could scale while facing hyper growth.

Early on in my career, a very seasoned technology veteran at IBM once told me, “What's beautiful about working with you, Maynard, is you haven't been trained on why this is impossible.”

It's true: my training happened on the job, so I didn't know what was deemed unprecedented or insurmountable. I'm grateful for the fresh perspective that inexperience provided; it not only gave me the confidence that I could get the job done but also afforded the most interesting and most rewarding opportunities. I began to become recognized for my willingness to do the jobs no one wanted, and top technology leaders began to rely on me to solve daunting problems. That's how I became known by some as Mr. Fix-It.