Founder Lessons: A Fireside Chat With Maynard Webb, CEO & Co-Founder at Webb Investment Network

Your success depends on your integrity. And hard work.

Spero Ventures
Jan 16 · 5 min read
Maynard Webb at the 2019 Spero Ventures Founder Summit

If you ask tech industry pioneer Maynard Webb what he aspired to achieve in his career, his answer might surprise you. It’s not fame. Or money. Or more influence. He’d tell you that, in retirement, he’d relax on a park bench. More than anything, he hoped someone he’d worked with would walk by. And when they noticed him, they’d want to stop and sit down beside him.

“A lot of times when you’re at the top of the company, people are very deferential, and they think your jokes are funny when they’re really not,” Webb, the former COO of eBay, explained to a group of young leaders. But they really need budget dollars or a promotion. That’s why Webb’s park bench is such a useful benchmark. “Look, I won’t be able to promote you. I won’t be able to give you dollars for your budget. Will you still want to hang with me?’”

Your answer probably depends on whether you’ve built incredible things together; it matters that you’re doing something valuable. So does your integrity, Webb said, because it’s the mortar that binds real, lasting relationships together.

“Integrity builds relationships.”

“Everybody in this room can think about the people they work with, and in a second, you know what you would do when faced with the park bench scenario. Would you want to hang with them? Or will you just walk by and hope they don’t see you?” Webb asked. “All of us need to work harder to continue to be people who are park bench worthy.”

Your talents and values will follow you into leadership, Webb told the roomful of early-stage founders at Spero Founder Summit 2019. In his typically honest, folksy and heartfelt way, Webb shared dozens of hard-won lessons from his own career about how to grow a great company.

These days, Webb mentors many through his successful seed-stage venture capital firm, Webb Investment Network. He also sits on the boards of several public companies, including Visa and Salesforce. From his perch, he’s seen it all.

“Your life changes radically at the top,” Webb said. “And the people who work for you will be impacted in ways you won’t imagine.” Never underestimate how much what you say and what you do matters to those you lead. People are your best asset and your best ally. Treat them that way.

But how? Start by asking yourself: How much input are you getting every day? If you’re not getting a lot of input, you’re probably not as approachable as you need to be, Webb explained. When you’re a leader, you’re not done. Ask for advice — often. Work constantly to grow and learn and listen and watch. You can feel whether folks are resonating with you or tuning you out.

“If you’re not getting a lot of input, you’re probably not as approachable as you need to be.”

Your audience is a lot more likely to keep listening if you’re not afraid to own your mistakes, Webb said. “Admit it and ask for forgiveness. The more vulnerable you are, the more welcoming your team will feel. That feels counterintuitive, but being humble and admitting when you need to do something differently is a good quality to have.”

Hiring the right people, 100% of the time, is impossible when startups are racing to fill their ranks. Webb has hired thousands of people throughout his 40-year career, and his strategy for scaling teams has evolved along the way.

Early on, he recruited folks who could bring many more people with them. That meant they had a network of people they liked and who liked working with them. But over time, Webb discovered that tactic could breed insular company cultures.

He also made the mistake of hiring people who could do the job in the long run— but may not want to do the heavy lifting today’s job demanded. So, he looked inward, instead.

“When I meet with founders now, I always want to know about their life story — what they’ve faced, what didn’t go so well, and how did they get over that,” Webb said. “Because companies and careers are filled with obstacles. And you want people who are resilient.”

Resilient people learn and grow. No wonder Webb found the greatest satisfaction (and success) when he gave capable folks on his own team more to do. “I’d tell them, ‘Okay, I have a problem. Would you like to help me solve it,’” Webb says. “Then people did amazing things.”

“There’s more potential in all of us… and when you tap it, it grows.”

“There’s more potential in all of us… and when you tap it, it grows,” he explained. (It’s not at all like a budget, in which there are only so many dollars.) “With potential, the more you learn, and the more you try, the more capability you have. So, I’d spend my time working with my best people to let them know that they can.”

But what if their next step is a big job they haven’t done before? How do you support them so their teams and your company don’t suffer through their lack of experience — yet? Simple. Good leaders have to develop them.

Encourage them to find and connect with mentors who are rock stars and learn all they can. Make sure they can identify what success looks like. Then expect them to come back and do the hard work.

That includes you, Webb said. “When you’re a CEO, you don’t know everything, either. You’re still learning, and there are things that you haven’t done yet or seen yet that other people have.” Don’t forget, we’re all a work in progress.

If your actions reflect your values, your integrity inspires trust within your team. That’s crucial because you won’t get anything done at the level you expect if people worry that they won’t be treated well or fairly, Webb warned. “I tell people that you’re building credibility or you’re losing credibility, every day.”

“You’re building credibility or you’re losing credibility, every day.”

That’s true for you and for your company. If you have a bad quarter, people are going to feel that. You have to make sure they know you know: It’s not a great day. But there are better days ahead.

“A lot of times people try to hide from problems instead of putting them in context and trying to paint a vision of where things are going,” he went on to explain. Be honest with each other. When you have those days — and you will — you have to talk about why. What did we learn and what are we going to do differently going forward?

Plenty, Webb offered.

“We’re all going to get smarter. We’re going to make mistakes. We’re going to forgive each other. But we’re going to be relentless at making sure all of us can be who we are intended to be.”


Maynard Webb’s fireside chat was part of the 2019 Spero Ventures Founder Summit. Watch the full talk below.

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Spero Ventures is an early-stage venture capital firm driven to deliver value to shareholders and society.

Spero Ventures

News, podcasts, and insights from Spero Ventures.

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