Maynard Webb offers advice for startups in new Dear Founder book

When Maynard Webb first met the founders of GOAT— an online shoe marketplace valued around $200 million — he wasn’t going to invest. Daishin Sugano and Eddy Lu were raising funds for a platform called Grubwith.us, which linked strangers together for meals, and Webb wasn’t a fan of the idea.

He was, however, a fan of Sugano and Lu. “I fell in love with the entrepreneur,” Webb told Business Insider. So when Grubwith.us failed, Webb decided to stand by his investment.

“They went through four years of nothing, and then they found a business model and an idea, and now they’re unbelievably successful,” Webb said. “That was not predictable. What was predictable was that they were scrappy and they were going to be willing to take body blows and live to tell about it and wouldn’t quit.”

Staying scrappy, taking body blows and investing in people are just some of the big ideas Webb explores in his latest book Dear Founder, which went on sale September 11.

Written with ghostwriter Carlye Adler, Webb shares 80 intimate letters of advice to startup founders in a way that is sympathetic and sentimental, but also deeply practical.

Each letter anticipates a different founder-specific event, like, “When a co-founder isn’t pulling their weight,” and “When you need to manage the lawsuit filed against your company.” But Webb is also concerned with company culture and recruiting, and wants the founders under his wing to achieve the success and emotional gratification that comes from building something great for the world.

Webb shares lessons from eBay, Yahoo and Salesforce

Webb, who now runs a venture capital firm called the Webb Investment Network and sits on boards at Salesforce and Visa, was once one of the most influential operators in Silicon Valley.

He joined CEO Meg Whitman’s eBay back in 1999 to help the drive the company though major infrastructure and scaling issues, and took over as chairman at Yahoo in 2012 to help CEO Marissa Mayer right the ship after a series of executive departures.

Those decades of experience gave him a lot of anecdotes to choose from. And while he never throws anyone under the bus in the book, many readers will connect the dots.

In person, Webb described his time at eBay as “cleaning up some of the mess from the early days,” and one could see Dear Founder as an attempt at preventing that mess in the first place.

“Meg used to say every once in a while that somebody had phoned in rich because they wouldn’t show up anymore. But that went away pretty quickly,” Webb said. “I ‘ve been in several other companies that have gone IPO and I don’t see that as much anymore; I think you’ll see a lot of new cars, but they’re still in there working.”

Absentee Ferrari owners aside, Webb said that he worries “deeply” about the people who stick around companies who do OK but don’t have the “impact in the world that they are shooting for.” He calls these less fortunate companies “tweeners” (see the letter: “When you’re afraid you might be a ‘tweener'”).

“There’s this big, ugly middle where people are doing good but they’re not doing great, and I hate that,” Webb said. “In most startups you have some of the most energetic, excited people on the planet,” he said. “Most of them in their prime earning years. And you can spend five or seven years somewhere and burn a lot of time and not see a return.”

But ultimately, Webb said, it’s not about a high valuation or a big exit. The most important question at any startup is “did we deliver on the promise, and have you spent all of those years on something that you’re proud of and that mattered,” he added. “Maybe what I feel more, as a more experienced person, is how fast the years go by,” Webb said. “I just want everybody to work on things that they love and that will help them achieve their dreams.”