Maynard Webb ’74 Shares his Entrepreneurial Spirit With Class of 2021

Maynard Webb '74

The Alumni & Development Office officially inducted the Class of 2021 into the Alumni Association at the annual Senior Dinner on May 28. The 87 seniors are the first to be inducted as graduates of The Frederick Gunn School, following the name change last July honoring founder Frederick Gunn, noted Sean Brown P’22, Chief Development Officer. It seemed fitting, then, that Maynard Webb ’74, an alumnus who has modeled Mr. Gunn’s entrepreneurial spirit throughout his career, was selected as the keynote speaker for the event. A 40-year veteran of the technology industry, Webb serves as a board member, investor, philanthropist and mentor to young entrepreneurs. He spoke to the graduating class about his business experience, the importance of mentorship, and taking risks.

The founder of the Webb Investment Network (WIN), a seed investment firm dedicated to nurturing entrepreneurs, Webb has focused on developing and leading high-growth companies. He currently serves on the boards of Salesforce and Visa. Previously, he served as Chairman of the Board of Yahoo!, CEO of LiveOps, COO of eBay, and he held executive roles at Gateway, Bay Networks, and Quantum.

In 2004, Webb and his wife created the Webb Family Foundation, which provides underprivileged, motivated, young individuals access to quality education and supports individuals who are struggling against the odds to make a positive impact on the world through innovation and hard work. Webb is the author of two books, The New York Times best seller, “Rebooting Work,” and the national best seller, “Dear Founder.” He also writes the weekly “Dear Founder” column for Fast Company. He lives in Silicon Valley with his wife, Irene.

Webb arrived at what was then The Gunnery from West Palm Beach, Florida, in 1973 and played football at the school. Described in the Red and Gray as both a versatile player and a strong lineman, he was named “Most Valuable Player,” and received the Gunther Football Award. Although he had planned to attend the U.S. Naval Academy at Annapolis, after graduating from The Gunnery in 1974, he ultimately decided not to go. “What a difference that year made for me,” he told the seniors. Not only did he return home with long hair and a beard, but, he said: “I also gained a lot of perspective and I realized that I didn’t really want to serve back in the Navy for that long a time, and I didn’t go. That devastated my mom, but I had to figure out what I was going to do next.”

He ultimately chose to return to Florida for college. “Coming out of the Navy and Annapolis,” he acknowledged, “your career is on a much better trajectory than coming out of a Florida state school. So it was a risk,” one of several he would take over the next several years.

“My appetite for risk is much higher now,” Webb said. “I always wanted to do things to prove I could do it. I was always happiest pushing boundaries, which sometimes got me in a little bit of trouble, but most of the time, it was alright.”

After college, he moved to San Diego and was working at Gateway when eBay, which at the time was relatively new, was experiencing massive outages. When the company asked Webb to come in and fix the problem, he agreed, taking another risk. “I lot of my peers said, ‘Are you crazy?’  I thought it was very fixable, and if we did it, it would be very cool. It was a lot of hard work before it became a good decision. But, it worked out in the end.”

Brown, who co-taught Entrepreneurship Seminar this year for a class of 16 seniors, asked Webb to share what it means to be an entrepreneur. “The thing that is amazing is when we tap into our potential and it grows,” Webb responded. “When you go to work and challenge yourself and invest in yourself, you can do things that are unimaginable. It came from those small steps and being entrepreneurial and taking those risks.”

"The thing that is amazing is when we tap into our potential and it grows. When you go to work and challenge yourself and invest in yourself, you can do things that are unimaginable."

You don’t need to be the next Elon Musk or Steve Jobs to be an entrepreneur. “It’s your mindset that’s important … how you want to tackle things and be somebody who can make a difference in a big way and way that hasn’t been thought of,” Webb said.

He counts among his greatest mentors Meg Whitman, the former CEO of eBay and Hewlett-Packard, and the current CEO of Quibi, who sits on the boards of Procter & Gamble and Dropbox, and Howard Schultz, former executive chairman and CEO of Starbucks, who wrote the foreword for “Dear Founder.” But Webb added, “I also learned from people who worked for me. Constantly learning is essential to growing and achieving your potential.”

When Webb was first seeking to become a Chief Information Officer, he built a database of 300 CIOs and sought to discover their “secret sauce.” He met about 150 of them, and is still friends with many of them today. Mentorship pays itself forward and builds this virtuous cycle, which is good for everyone, he said.

Brown asked him which three questions entrepreneurs should always be prepared to answer when making their pitch. The first, Webb said, is “‘Why you?’ For me, I’m looking for founders who are very resilient, who can take the body blows with all the pain of founding a startup. Number two is ‘What problem are you trying to solve? And how big is that?’ If you’re solving something that’s not super big, I’m probably not as interested in that, because it’s not a big market. Then, number three: ‘The people you’ve selected to build a team – what have they done so far?’”

Of course, not every risk pays off, and Brown asked Webb how those moments have affected his journey. “I hate to fail, I’ll be honest with you,” he said. “I founded a company called Everwise. It was a wild success for quite a while, and then it didn’t scale. One of the other founders left and it was kind of in the middle of that desert. It should have made the impact,” he said, explaining that some execution issues prevented the company from going the distance, though it is still operating. “I’m happy that it’s still helping people in their careers.”

To the Class of 2021, Webb offered his congratulations and noted that they have already distinguished themselves as the first class to graduate from The Frederick Gunn School. “Now you have to ponder, ‘Now what?’ You’ve gotten all this great education and you’re going off to school. Hopefully you’ll be less distracted than I was,” he said, encouraging the seniors to “pay it forward” to society and the world and to make a difference. “Never be sad that something didn’t happen. You get stronger when you go through the body blows and get to the destiny that you want. Where you go, it’s deep inside of you. You just have to unwrap it.”

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