How This Silicon Valley Legend Achieved Work-Life Balance By Launching His Own Investment Firm
But having a great career often comes at the expense of sacrificing one's life, and that has certainly been the case with Webb as well.
Like, when he had to meet former eBay CEO Meg Whitman in the airport on a Friday night before even taking its COO job. Or the time he had to buy a home without having his family even take a look at it.
In one instance, his wife had to bring him underwear to the office because he had spent all night at work.
So when he left eBay in 2006, after serving over seven years as the company's president and COO, Webb's wife hoped he would take a year off and travel the world with her.
Instead, just three months later, Webb took the CEO position of LiveOps.
"I don't think I communicated everything very well," Webb told Business Insider.
So, as he took the LiveOps job, Webb made a promise to his wife: it would be the last operation role in his career.
That made him think, by the time he left LiveOps in 2011, "What am I going to do for the rest of my career?"
Webb knew he didn't want to just retire. Although he held multiple board seats (he's now Yahoo's chairman and is on the board of Salesforce), Webb still wanted to be pretty involved with companies. After all, Webb has spent almost 30 years just running businesses.
After much pondering, Webb settled with the idea of becoming a full-time investor at his Webb Investment Network (WIN), a VC firm he helped create a year earlier in 2010.
Webb had always been an active angel investor throughout his career, so he knew investing was something he would enjoy doing. Plus, WIN was cofounded by three investment directors that included his son, Kevin, so it wasn't going to be a tough transition, either. Webb wouldn't say it was a compromise, but it was definitely a win-win deal for everyone.
"My wife knew I was going to do something. She just wanted more flexibility for us to have a life and still have me do work. That's what we've set upon - and it's working," Webb says.
But WIN isn't just any kind of VC firm. It takes a slightly more creative approach by running what it calls an "affiliate network." People in the network, all friends and former colleagues of Webb, are basically a group of investors that provide more than just money, such as on-demand advice, counsel, and help with PR.
There are currently almost 80 affiliates, including Blackberry CEO John Chen, former Sun Microsystems CEO Scott McNealy, and even the author/reporter Carlye Adler.
Webb says he doesn't charge any fees to the affiliates, but instead, they're expected to provide hands-on support to all WIN portfolio companies.
"We don't take board seats. We want to be advice on-demand, as opposed to judging our companies," Webb says.
But perhaps the biggest draw may be Webb's role at the firm. He doesn't merely just bring in the affiliates; he's very much involved with the investments. He meets every single CEO and reviews every deal before it goes through. He also makes sure to give advice to the portfolio companies.
Adler, one of the affiliates who's best known for co-authoring books by people like Webb and Salesforce's Marc Benioff, says that's what really makes WIN a special group.
"It really is a tight-knit community," Adler told us. "People are always emailing Maynard for advice, and he seriously writes them back all the time."
And now, WIN is becoming a popular space among Valley insiders. Webb says it's "way oversubscribed" with potential investors, and the community is just continuing to grow, both in size and influence.
"The whole thing was built to do good things and keep me entertained, but now it's much bigger than that," Webb says. "It's so much fun. It's work but it doesn't feel like it."