A Discussion with Maynard Webb on Rebooting Tech Entrepreneurship in the COVID Era

Michael Osakwe
June 24, 2020
A Discussion with Maynard Webb on Rebooting Tech Entrepreneurship in the COVID EraA Discussion with Maynard Webb on Rebooting Tech Entrepreneurship in the COVID Era
Michael Osakwe
June 24, 2020
On this page

Maynard Webb is a tech industry leader and veteran with a distinguished career. Since joining IBM straight out of college, he’s had a variety of roles—from entry-level to CEO and board member—in some of the tech industry’s most prestigious companies. Maynard’s former roles include being the CEO & Chairman at LiveOps as well as serving as the COO of eBay. He is currently a board member of Salesforce and Visa. He’s also the author of the New York Times bestseller Rebooting Work, which anticipated the working from home trend that has emerged over the past decade.  Today Maynard supports early-stage entrepreneurs through the Webb Investment Network (WIN), as well as through his columns in Fast Company where he provides nuggets of insight addressed to foundersm, which continues to build on the advice he provided in his book Dear Founder. Our discussion with Maynard has been condensed and edited for clarity.

We found it very interesting that your college background was in criminal justice. A lot of people mistakenly believe that your college major is your destiny, and your story is a great counterexample to that. Can you go into your early career and how you got interested in tech?

Sure. The first thing that I'd say is that I wouldn't necessarily advise people to follow my path because it was very untraditional. It’s always a good thing if you know what you want to do, and you get a great degree. But in my case, I actually thought I was going to law school, which is why I did criminal justice. What ended up happening was that I became a co-op at IBM in my senior year in Boca Raton, Florida, which was great. And they told me they were not hiring anybody, so there were no prospects for being a permanent hire. But I got lucky enough that they offered me a job in Rochester, Minnesota.

At first, I thought they meant Rochester, New York. When I graduated, I got to move with a full-time job to IBM in Minnesota. It was nice but to be honest, it was a physical security job; I was a security guard. IBM is an amazing company, and back then they were great at making sure employees could grow and learn. So, I took a number of technical classes and programming classes that they offered. I got promoted very quickly to start doing jobs that involved technology. I took courses at local colleges as well. I was always probing, how could I do more?

Today, everybody wants to do computer security; it's one of the coolest jobs on the planet, but not so much then. None of the system programmers wanted to do it. They thought it was beneath them. But I thought it was very cool, so I would go to my boss every week, during our 1:1, and say, "That job's open, nobody's in it. I'll do it.”

"Well, Webb, you're not qualified to do that job,” my boss replied.

"I'm not asking you to not do my day job. I'm saying, let me also help do the open job for a while until you find somebody, and I might surprise you."

And he was like, "Would you be quiet? Go back to work. Who's going to do two jobs? That's ridiculous."

“I was not ready to accept that answer. I kept pushing, and I had done some other extra credit projects that were going well. Eventually, somebody from corporate came down and said, ‘You should let that Webb kid try that. I bet he'd be pretty good at it.’”

That was my big break. It turns out I was pretty good at breaking things, and it was quite fun. I used to travel around the company, and they'd give me a week to see what I could break. Of course, it was easier back then, but I was able to do a lot. And that led to me doing a lot of the other jobs to fix things that got broken. So, that's how I got started. I’ve been fixing things my whole career.

Can you tell us about your time as a board member of major companies, and then what's your biggest take away for how board members can provide value to companies and ensure that companies continue to provide value to their customers?

Well, our biggest fiduciary obligation is to the shareholders. We're there to be stewards over the company to ensure they're doing things appropriately and legally. But I really think the question has become much broader. We need to take care of all of our stakeholders, our employees, the communities in which we do business, the environment, our suppliers, and our shareholders. And I think the biggest thing that we're responsible for is to ensure that the company is transparent, has values, and lives up to those values. I'm a big believer in saying what you do and doing what you say. I think we need to treat all of our stakeholders well. One of the things that board members are responsible for doing is seeing around the curves a little bit and making sure the company is always thinking about what else could come. For example, on the coronavirus, nobody saw this coming. And we're dealing with a lot of pain because of that in many places.

We're really impressed with your writing. You've written books like Dear Founder and Rebooting Work, you write a weekly feature in Fast Company. How did you get started doing all this writing, and what's your goal in creating these assets?

Thanks for the question. I started blogging when I was the CEO of LiveOps, and I have an amazing writing partner that makes it all super easy for me, Carlye Adler. She's awesome. And she looked me in the eye one week as we were writing blogs, and she said, "This isn't a blog. This is a book." I'm like, "What are you talking about, a book?" And she said, "Yeah, it's a book." I said, "Okay, well, let's make it a book." That turned into Rebooting Work. And it's funny because the book is very timely now with everybody working from home. But we were proselytizing about firing the commute back in 2011. You can dedicate yourself to your career and to those you love; you just have to figure out how to steal from things that don’t add value, like your commute. The pandemic has made believers of a lot of people about the ability to work from home.

I think what we did next though, really captures what I learned most and what I wanted to be doing all along. I love working with founders and I love building companies. My son, Kevin, who at that time was with us at Webb Investment Network (WIN), read a post based on an interesting concept on Medium. It turned out to be fictitious, but it was a good article about a father who was dying and left his son a bunch of letters to read at different stages of his life. "When you're getting married, open this letter, when you have a fight with your mom open this letter." And it says, "Remember, she's hurting too." And the last letter says, "When you're about to die." And you open it, and it says, "I hope you're old. And I look forward to seeing you soon."

It was just a very emotional thing. And he brought it up with the team who agreed it'd be a great idea to write these letters about the stages of a company's growth. So, we wanted to do this, but I didn't want to do another book with all the craziness that goes into the book tour. We ultimately agreed to do it just for our network; we created this little blue book and made 300 copies. I ended up getting frustrated because Kevin would not let me give them out. Like one of the things that's cool about having a book is you get to give them the people, and it's a nice thing. He said, "No, we only have 300. You can't give them out." But the founders who received the book liked it, and they said, "You should do more of these." We went to work, and we made it a book that St. Martin's Press turned into Dear Founder.

It was a lot of fun, but we haven't stopped. We just keep writing these letters. We see things all the time. And so that's what's going on with Fast Company. We're in the process of another a hundred or so letters that we published in the last year or so. But honestly, my goal is to help people, period, and writing is just one of the ways to reach them.

“I've been blessed beyond my imagination, and I certainly can't meet with everybody who would like advice, or needs it. So, I just try to share what I've learned, and hope it's helpful. That's my whole reason for doing it.”

Another question about your writing, we know that you like the themes of resilience and fortitude for founders, as well as responsibility for creating and maintaining excellent products. How did you develop these ideas across your writing career?

My writing career is not my main career. I had an operating career for years, running companies, being in roles, and being in what I call “the fray.” So, what comes from me is not simply what I think should happen. I either saw it, I was living it, or I saw somebody have it.  That's where these ideas come from—the school of hard knocks—is what I'd say. And I always try to figure out, what are the "so what's." A lot of people like to sensationalize things and appoint blame to people. I'm much more interested in asking, what are the learnings? What's the advice we can extract out of all this to help make things better for somebody else? It's all our jobs to make life better for other people. And honestly, I was just very lucky. I had an amazing family and mom, but we did have body blows. I lost my dad when I was seven, similar to the kid in the Medium article that inspired Dear Founder, and that's why Kevin knew it would hit me this way.

I didn't have an easy path. Nobody said, "Oh, that guy is going to be amazing." I had to knock down doors. When I joined eBay to run all of technology, they had camera trucks in the parking lot, because every time they had a glitch, they'd be on the national news. Most technology execs were like, "No, thank you." And I was like, "Hey, that sounds like fun. I'll do it." So, I think most of these themes come from experiences like this.

Oftentimes in Silicon Valley, coaching and mentoring can take a back seat to profits or pursuing company growth. How do you get founders to recognize the power of both mentoring and coaching, and developing strong leaders from that?

Sometimes it's easy and they get it from the beginning. And then sometimes it's something you have to learn. But I really believe in human potential. Our job as leaders is to make sure people go as far in their career as they can, which is often farther than they initially think. When it comes to mentoring and growth, it's not “either or,” it's an “and.” You can't do just the work and not care about people. And the more people know you have their back, the more they'll do for you, too. It’s a little counterintuitive; the more you care about folks, the better they perform. But you shouldn't care for them just because you care about their performance. People can read through that very easily. But if you genuinely care with a big heart for where they're heading, and what's holding them back, they will work very hard for you.

We actually spoke with another Nightfall investor recently, and they said something similar. It’s great to know that our investors are on the same page about that. In terms of building a company culture with true equity & inclusion, we know that's a theme that recurs in your writing. What advice can you give the founders who are trying to bake that into the fabric of their company and make it actionable?

I think the first thing is that everybody who joins your company ought to be a shareholder and own equity. Hopefully they take less in cash than the market would pay because you're trying to be scrappy, but there's big upside rewards when the team wins. You'd like to see everybody win when the company wins.

When it comes to inclusion and diversity, we have so much more to do. There are a number of things in my book—I write about studies that have shown how much better companies are when they are diverse and inclusive. Little things, like you ignore half the workforce if you don't do a good job at the inclusion of women into your application pool, which is pretty easy to understand.

“On diversity, I’ve always worried about hiring people who were my friends or were exactly like me. You don't do your best when you just hire somebody that is exactly like you. You need to hire people who can give you points of view that are different. It's often easy, especially if you have a lot of people you've worked with, and a good following, to bring people with you. That's not horrible, but you just need to make sure you bring a lot of different people from different backgrounds.”

I'm very proud that our first two new investments this year are both led by female CEOs. And they're not announced yet, so we can't talk about them.  I’ve instructed the team to pay special attention to CEOs of diverse backgrounds.

It's very interesting that you put diversity and inclusion in terms of blind spots. A lot of times it's hard to see what you don't know, and obviously capturing diversity means that you are kind of improving your vision around areas that you're less familiar with. It's something that a lot of people overlook.

Oh, the other thing I'm learning is the older I get, the more I’ll need to learn. We live in a world where all the young folks tell us, "OK, boomer." You have to always keep listening and learning. That's what makes life fun, when you realize what you think is true may not be true. It's all about growing your perspective.

Big companies like Facebook and Twitter are now extending remote work as a result of the coronavirus. How do you think the pandemic is shifting priorities in investing & founding companies? And does this change your assessment for the future of work, or does it simply fall in line with what you've been talking about?

First of all, the pandemic has shifted a lot in terms of how companies are performing—it's basically a reset. It's kind of hard to believe, but in our portfolio, we have some companies that are doing amazing. Okta is a security company; it hit an all-time high recently. When March hit and the market reset, its stock was trading at 50% of today’s price. So that's crazy, very amazing. And then we have some companies that are in the sharing economy or the travel space which are in real trouble. Those markets have shifted a lot. I think about it as a spectrum. And then we have some people who have been doing well, but companies are being cautious with their purse strings right now because nobody knows what the impact of this crisis will be.

And so, advice shifts based on where you are, how you assess the situation, and what you want to do. We are continuing to look for investment opportunities that will ride through this. I also think we can't over-index on just the coronavirus. We will survive this. Companies have to make sure they can get through it though, right? It's very frustrating for founders who were doing great. Some were thinking about going public and then this happened. Think of Airbnb.

We also have people losing jobs all over the place, so we're trying to be smart. I keep talking about whenever we invest, we have to have a high bar. We see a lot of companies, for every company we decide to invest in. So, I think you just need an even higher bar in these uncertain times, where the world is still sorting out what it's going to look like post COVID. But I also would say there are a lot of opportunities.

On the future of work, I think this is going to be fascinating. We proved that we have the capability to give people more choices. I think the whole experiment from working from home has gone better than anybody thought it could go. And the question is, will we ever get back to the way we used to work? I don't think so. I think people will have more choices. I think the fear of getting sick on planes, once we have vaccines, will go away. Travel will come back. But the idea of flying overnight to get to a meeting in the afternoon over in Europe somewhere when you can do a Zoom meeting, that idea will seem silly. I mean, think of all the hours you'd save. So, I wonder what impact it will have on business travel, for sure. And I think hopefully people will realize it's not either or, that people can work from home and be productive, and stay out of traffic.

I'm on the Salesforce board, and an employee asked yesterday, "Okay, I know we're going to be safe when you get us to the office. What about mass transit?" We don't control mass transit, and I think a lot more people are going to drive or bike, and so the freeways may become even messier, even with fewer people coming back to work. I think it's going to be an interesting progression, but hopefully people will have better lives and better choices, as companies realize they can make this work now.

What advice do you have for startups in a post-COVID world as they adjust to “the new normal?” What new opportunities exist for entrepreneurs in this world?

Whether you're doing really great, or your market just got obliterated, or people's buying has slowed down, you have to assess where you are. That's the first thing I would say. And then you have to do different things. If you're doing really well, you must double down and capture the opportunity. Don't lose opportunity, even in a crisis. If you're a security company or a collaboration tool like Zoom, make sure you sustain all of this enthusiasm you're experiencing. Grow. Don't hinder your growth. That's where eBay was when I joined. They had all this opportunity, and they were hindering themselves. If you're in the middle of chaos, where people are scared to buy, but your market's still going to be there afterward, then you have to trim expenses enough to ride out the storm. Make sure you're in a position to do better when things loosen up a little bit.

In the instance where the market is gone, things still might be okay. We hosted Geoffrey Moore at an event we did recently. He's the author of Crossing the Chasm. And he said, even if you've made it through the chasm and you've truly built a good company, if that market went away, you’ve got to go back to your value proposition and find somebody who wants to buy what you’re selling. So, you have to go back to being scrappy until you get a new product. One thing that I’ll just share is that it's been amazing to see Salesforce building a product out of scratch that's now serving the public and private sectors while everybody is figuring out how to get back to work. That wasn't in our plans. It wasn't anywhere. And now it's growing legs and getting a lot of attention. That was an opportunity that they saw they needed to solve for themselves.

I would just say keep your eyes open and see where the opportunities are. Also, if you're starting a company, that's way easier than running an established company in a market that dissipated and you have to figure it out again. If you're able to raise money now, by the time you need your next round, this whole issue may be all the way behind you. It's a great time to start a company as counterintuitive as that sounds.

What made WIN want to invest in Nightfall?

That's an easy question. Isaac Madan and Rohan Sathe were part of WIN Labs, and so we knew them well. We’ve known Isaac for even longer. Both are great people, and they made great progress with Nightfall. Being big fans of what’s happening in the security space, we wanted to be a part of what they were building.

Tying into that, what do you think are the big opportunities in cloud security? Are you going to double your investment in the cloud space?

It's one of the toughest spaces. You have the most innovative people in the world attacking businesses. I wish we had all those folks working in our company for the good of the world. As we migrate to the cloud, they attack even more. There are different sides — it's like a war. Every move they make, we have to make another move. It just escalates. There are point solutions that are spread out in different places. Some of our biggest exposures still come from phishing. It doesn't seem like that should be our big exposure, but it is the number one threat. So, the whole spectrum of security is wide open. We're getting better, but the crooks are getting better too. And we know that nation states are interested in cloud security. It's extraordinarily important, and I find it fascinating.

It's going to get even more complicated, too, providing a solid opportunity for great companies to come along and make things easier. Of course, there's no one company that's going to solve it all, because there’s too much innovation happening from all sides.

One more question. Can you recommend any good books or podcasts you've been listening to?

Sure. I just finished rereading the Sixth Extinction by Elizabeth Kolbert, which just reminds me that with all the good intentions or progress we're making, we’ve had a pretty devastating impact on the world. It both saddens me and inspires me to figure out how we're going to do better. I also just finished a biography of Andrew Carnegie, which was fascinating to read how he went from rags to riches in a robber baron kind of way. But later in life he was one of the biggest philanthropists in the world and was fighting for world peace. His transition and journey was quite fascinating to read about.

We have two affiliates in the WIN network who just published books. One is Kevin Scott, the CTO of Microsoft, who wrote Reprogramming the American Dream: From Rural American to Silicon Valley Making AI Serve Us All. And Rob Chestnut, the Former Chief Ethics Officer at Airbnb, who wrote Intentional Integrity: How Smart Companies Can Lead an Ethical Revolution and Why That's Good for All of Us. I’m plugging those books too because they're coming out. Kevin's came out in April, and Rob's comes out in July.

Nightfall Mini Logo

Getting started is easy

Install in minutes to start protecting your sensitive data.

Get a demo