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Retirement 2.0

by Maynard Webb, former COO of eBay, author of Rebooting Work

This article by Maynard Webb, whose writing has been featured in the Harvard Business Review, first appeared on the Web Investing Network

Retirement 1.0:

When I left eBay in the summer of 2006, I had never not worked full time in my adult life. I had options available to me that I could only have imagined when I started my career: a wonderful wife and family who wanted more time with me, good career options (I sat on 5 boards at the time), and the economic freedom to do whatever I wanted with the rest of my life. However, I really struggled to get comfortable in this new situation.

I remember clearly attending an event at our club and sitting next to a gentleman who told me that every day he would come to the club to eat breakfast, read his paper, hit the driving range, then play a round of golf. Good for him, but I told my wife I could never spend my time like that. I also struggled mightily with the concept of taking money from savings as opposed to putting money in. I knew economically that we were covered, but I was unprepared for the emotional struggle of not contributing.

But in less than six months of unemployment (and a few months from our youngest child heading off to college), I returned to work at the end of 2006 as CEO of LiveOps.

Retirement fail.  

Retirement 2.0:

My wife and I agreed that I would commit no more than 5 years to the new company. It is now 2011 and I have recently stepped down from my responsibilities as CEO of LiveOps.

Now that I’m “retired” again, I’m really excited about implementing a plan that has all the elements in it that I want this time. The inspiration came from a few places.  First, when I was at LiveOps, we encouraged our Independent Agents to be CEO’s of their own destiny, where they would work on their own terms, every day. I was inspired by this message and committed to live by it in retirement. Second, I ran into Mitch Kapor.  Mitch created Kapor Enterprises so that he can remain engaged with new startups while working when and how he wants.

I want to spend my time and energy in retirement on things that are highly engaging but not sticky (like being a CEO of a major company for five years)—except for my time with family, which I hope to get much more of. That is, I want to be engaged in things I’m passionate about but I don’t want to run them. I thought long and hard about what stage of company I most enjoyed and realized that helping early stage entrepreneurs is fascinating. I also wanted to stay in close contact with lots of people I had worked with over the years and so around a year ago I created the Webb Investment Network. On top of that, my foundation is up and running, I am in the process of signing a contract to write a book, and I’m looking forward to finally getting to all the travel that my wife and I had hoped to do over the years. First up, Australia and New Zealand early next year.

I am only a few weeks into this new world.  It is less structured, by far, than the world I was just in.  I am squatting in different places for office space, meeting in coffee shops, etc., but so far it has been exhilarating!   I have already been to one getaway in Jackson Hole with my wife and we have others planned soon.

I am totally committed and excited about being in Retirement 2.0, where I felt lost in Retirement 1.0. I have been told that there are a lot of bets out there on how long I remain retired this time. I’ll happily take them up on it though because I don’t think of myself as retired, but as the CEO of my own destiny.  I am spending time on what I want, how I want, and with whom I want.   It is a privilege to have such options and I can’t wait to embrace them.

Wish me luck!


Maynard Webb’s writing has been featured on Harvard Business Review. His best-selling book, Rebooting Work: Transform How You Work in the Age of Entrepreneurship, was released in January 2013.

Webb is the founder of the Webb Investment Network (WIN) and is currently the chairman of LiveOps, a cloud-based call center. He’s a board member at both salesforce.com and Yahoo, and was previously COO of eBay.

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