I am now “retired” for the second time.
The first time happened at the age of 51 when I left my position as the COO of eBay. I spent more time than ever with my wife (and I still didn’t feel it was enough), served on five corporate boards, and also found that I personally missed some of the structure of an executive role. Within months of that “retirement,” an opportunity arrived to become the CEO of LiveOps. I took it, and promised my wife that I would only stay five years.
In 2011, about five years after taking the position at LiveOps, I did leave the CEO role. Unlike the last time, however, I didn’t leave to retire; I left to build the life I really wanted — great experiences with my wife and family, and making meaningful contributions in the world on my terms.
I started my first job at nine years old. During my career, I’ve been a paperboy, delivered mattresses, done landscaping and cleaned toilets. Eventually, a gig as a security guard at IBM led to my first white-collar job, and an opportunity to work with technology. It was a lucky break, but also one I worked hard to get, and it ignited the rest of my career.
Early on, I was mostly focused on earning a paycheck and providing for my family. Later, after I’d had some success, I felt encouraged and inspired to keep taking on tougher challenges. I always felt motivated to work, and rarely thought about what I would want to do if I had the time and resources to do anything.
That opportunity came when I turned 56, an age that some consider ancient in the technology industry. I found myself with a lot of time on my hands, and a strong desire to do something meaningful and that would hopefully have a lasting impact.
I reflected back to a conversation I had with my dear friend Gay Hendricks, who was a trusted advisor and one of my coaches at eBay. Some years before, when I was thinking about leaving eBay, he offered some sage advice: “Your 50s are a decade of creativity or stagnation — so be searching for what you are intended to do.” Gay certainly was a case study of that advice. He was running an organization that helped people have better lives, had written dozens of books with his wife and even appeared on Oprah. Now at 69 years old, he has started writing detective novels and is producing his first movie. Amazing.
I was leaving LiveOps halfway through my decade of creativity. What did I want to do with the rest of it?
I started to search for what would be next. I was already on the saleforce.com board and found myself energized by its leadership and vision and the opportunity to contribute to such a disruptive company. I loved being involved in these transformations and throughout my career I had a solid track record of picking winning companies. I realized maybe I was intended to help companies, big and small. The startups I invested in were doing well and I looked at how I could partner with someone to grow my angel investments and formalize this hobby. This would be my next role, I thought. I identified what I was intended to do, as Gay had urged me long before. Another friend, Mitch Kapor, the founder of Lotus, who had also “retired” to build the career he wanted, offered additional pivotal advice on how to approach this point in my life. “It’s not about you joining someone else’s team,” he said. “It’s doing what you want to do.” That led me to create the Webb Investment Network (WIN) and run it how I envisioned.
WIN is a network of my friends and former colleagues who invest alongside me. They don’t pay anything to join the network, and I don’t charge any fees, but I ask that they make themselves available to help our portfolio companies with their expert advice. And though I didn’t join someone else’s effort, I did receive pivotal guidance from those around me. Super angel Ron Conway told me to treat people with respect all the way through, and to celebrate what they are doing. Entrepreneur Aaron Levie, the CEO of Box, told me to include young people on my team, which I did. They are not only excellent at this work, but they are a lot of fun. They keep me young (and knowledgeable about the need for a better dating site).
Aaron warned me to “be careful as this could be addictive.” He was right. With WIN, my family’s foundation, and my work on boards, I have found what I was intended to do, and I’ve never had a better time or more fulfilling career and life.
Some people fear getting old. My father’s death at 47 made me think that I’d never even see my 50s. Because of this, I never thought I would have enough time. I don’t fear that anymore, and I am making the most of the lifetime I have.
I was recently reminded of an opportunity we all have every day when Jim Harbaugh, the great coach of the San Francisco 49ers said to his players, “You are either getting better or worse every day, there’s no staying the same.” That is critical advice as I inch toward my next decade. We must always move forward. We must always work to get better and always be searching for what we are intended to do with our lives, including with our loved ones. It’s a lesson that’s important at any age. I wake up every day grateful for this time — I would argue the happiest of my life — and I’m inspired by the knowledge that my best years are not behind, but still very much ahead.