Maynard Webb, Author of Dear Founder: Letters of Advice for Anyone Who Leads, Manages, Or Wants to Start a Business

Bestselling author Maynard Webb is a 40-year veteran of the technology industry. An active leader in the technology and business community, Maynard serves as a board member, investor, philanthropist and mentor to young entrepreneurs.
As the founder of the Webb Investment Network (WIN), a seed investment firm dedicated to nurturing entrepreneurs, Maynard brings his experience developing and leading high-growth companies.
He is a co-founder and board member of Everwise, a talent development startup, and a board member of Visa and Salesforce. Previously, Maynard served as Chairman of the Board of Yahoo!, CEO of LiveOps, COO of eBay, and held executive roles at Gateway, Bay Networks, and Quantum.
Maynard has also served on several public and private boards including Yahoo!, Gartner, Niku, Extensity, Hyperion, Peribit (acquired by Juniper Networks), Baynote, and AdMob (acquired by Google) where he was also one of the first investors.
In 2004, he 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.
Maynard is the co-author of the critically acclaimed book, Rebooting Work: Transform How You Work in the Age of Entrepreneurship (Jossey-Bass, 2013).
His second book, Dear Founder: Letters of Advice for Anyone Who Leads, Manages, or Wants to Start a Business, will be released by St. Martin’s Press on September 11, 2018.
Maynard lives in Silicon Valley with his wife Irene.
Bio Sourced
Question: Can you tell us a little about your background?
Maynard: I majored in criminal justice in college and was going to go on to law school and got hired by IBM my senior year as a co-op student and a security guard and then I was hired permanently by them and shipped from Florida the Minnesota and that’s where I started. IBM was a great place and I was very ambitious and they kept letting me do more things and so I quickly got promoted to supervisor and then I was able to take some programming classes and went back to school for programming and did a number of things in security that eventually a hacker. I got to go all over the country and break systems for IBM and that was quite fun. Then I spent the rest of my career trying to fix things which isn’t nearly as much fun as breaking things. But it’s still fun.
Question: Along the way you were involved in starting some companies as a founder or early investor. What prompted you to go that direction?
Maynard: I spent most of my time building companies and I was a CIO for a number of years at places like Bay Networks and Quantum and Gateway and then became the CIO or the head of technology at eBay when they couldn’t keep their side up but throughout all those jobs I got asked by friends to invest in their companies and so that was a lot of fun and I got asked by VC’s to sit on boards of some of their high-growth companies and then as I stopped operating after LiveOps I promised my wife I wouldn’t run companies anymore I decided to do this Webb Investment Network that I’m doing now and it’s been a blast.
Question: You have a gift and helping compass with strategy.
Maynard: I like to help people achieve their potential. I think I’m known not only for the strategy as much as the heavy lifting of actually fixing things and making things work and scaling, I’m probably even better known for strategy. I was the chairman of Yahoo as they went into the sale to Verizon for five years. I’m on the board of Visa and Salesforce right now and I’m also on the board of a company that I helped create called Everwise. But I’ve been on a bunch of other public company boards and learned a lot and the boards have changed a lot. What’s required today versus what we what we did back in my early board career.
Question: What was the inspiration behind writing your book, Dear Founder?
Maynard: At the Webb Investment Network we’re always trying to figure out how to codify some of the advice that’s given. My son actually saw an article about a father who was dying and left him a bunch of letters for him to read at every stage of his life. The first one was when your mom starts to drive you crazy and you open it and it says, remember she’s hurting too. And then when you’re getting married, when you have children, and the last one is when you’re about to die and you open it up and it says I hope you’re old and then I’ll see you soon and I looked at that and you know we think about the lifecycle of companies from birth you know an idea is easy but getting it to relevance is hard. Getting it the scale is even harder and having it be a legacy company even harder. I said this would be perfect why don’t we go start writing letters at each stage of her company’s growth and so we did and that was what inspired us to do it. We first created a book for our network and had about 32 letters and my son self-published it, a little blue book that we gave to the network. There were only 300 of them so it drove me crazy because people would be like, can I have a book, and I’m not allowed to give any out. There’s only so many and then people from the network said, you know this is really good you should do more of these. So we found a publisher who’s amazing St. Martin’s Press, and we wrote a bunch more and now we have 80 letters and it’s a real book for the world.
Question: What advice do you have for an individual searching for a mentor in their life?
Maynard: I think well I think you should first realize you can learn from all kinds of sources. Stephen Covey helped me in my career. I never met Stephen but I certainly read his books and seven Habits of Highly Effective People was transformational for me. Be constantly seeking to learn to grow to ask questions and so finding people that are going to help you and people love to help you way more than you might think as long as they think the it’s going to pay off for you if they do. You’ll find you’ll find mentorship in unbelievable places you just have to be open to it?
Question: Why is it important for individuals to find to build diverse and inclusive companies where they can thrive?
Maynard: Well the first reason is frankly the population is broad and if you’re missing half the population that’s probably not a great place to ensure that you’re getting the best talent that’s there. We have to let everybody belong and we have to treat people fairly and equitably and the faster you can fix this or try to address it in your company, the better. If you wait till you’re 50 people before you add your first woman or minority it’s much harder to have that be a natural flow.
Question: How should individuals that are in the business world should be seeking for counseling and advice?
Maynard: I joined Silicon Valley in 1991 when I became the head of networking at a district company called quantum and I had read about all the magic here and I’d been in technology companies all my life but it was just amazing to find how close and it closely connected everybody was when you talk about mentoring and somebody is always able to introduce you to somebody else. As a head of technology I would call on the VCS often to try to make sure that I knew some of what their latest technologies were and they were thrilled to have somebody that could be a potential buyer of those technologies so there’s synergy that works everywhere you go in Silicon Valley and that continues to be true. There’s way more money today than there ever was back in the day. There were angels but there weren’t things like- but you could classify what I do maybe as a super angel but there’s lots of regular angels they’re super angels and then at the end there’s all the VCS and then at the upper end of the market you have folks like Softbank doing a hundred billion dollar funds and companies taking longer to get out. It’s way easier to start a company today because you don’t have to best as much and you can do things like use Salesforce or Amazon or Google to get your platform moving from the beginning so that’s easy but it’s really way harder to actually strike magic than it used to be. It’s way harder to have those ideas actually get all the way to scale and become public than it used to. I just think in general running a company whether you’re I you know I’ve helped create companies from scratch and I’ve been in big public companies it’s harder today than it ever was because you’re on you’re on point all the time and you’ve got lots of constituents that want a lot of things from you: your employees your shareholders your customers society… Look how people are responding to some of the tech stuff going on in Washington today so it’s a multi-faceted prospect and there are there’s no downtime you’re on 24/7 and tweets that you know we didn’t have tweets you know so you could maybe tell a joke sometime back in the past and not get you know getting a lot of trouble today that you’ve got to be careful with everything you say.
Question: It seems that with the information age do you agree that it’s a little harder for companies to be that stealth today?
Maynard: I think several companies all try to be stealth. I roll out things with a big bang. I serve on a board with a guy who’s amazing at celebration which is Marc Benioff and you know we have our big show, Dream Force which has a lot of hoopla and attendance in there and we sell out everybody mobs San Francisco for the week and all the hotel rooms are gone. So I think there’s still some of that there. You can’t take days to go address something that starts to go south. Do you remember when Intel had their Pentium chip problem and it took them a while to admit that there was an issue? Well today that would blow up and be all over the place in five minutes. When I was at eBay when the twin towers went down, we got called and we had to have a policy statement within three minutes after the bombing because people were taking debris from the towers and trying to sell it on eBay. Thank goodness we already had our policies in place, which is, we don’t profit from disaster so take those down. That’s the speed at which things happen today.
Question: When we look at the business world today, there’s individuals that will lead through inspiration and others will lead through fear. How does a how does a person inspire and help others to become part of their vision?
Maynard: Well I think we used to live in a more command and control world, we admired hierarchy and anybody that was at the top of the hierarchy got to say whatever they wanted and behaved hopefully they still behaved in a in a good manner and many of them weren’t inspirational. I think that today’s employee wants to be inspired and guided and they have more power today than they ever had. That’s not tops down you know. There’s people that are very talented, people can get multiple jobs any place you don’t have jobs for life anymore and you have people trying to take your talent and fire in a way and so it’s that pendulum of power have shifted a lot and the more you can create a place where people can learn and grow and reach their potential the longer people will stay with you. So I think you have to do a lot to transition to not I’m the boss and you have to do what I say to hey here’s what we’re doing here’s why it makes sense here’s how it’s going to transform you and you’ll be better for this and have you know haven’t become your idea that you want to do this.
Question: How should a leader give advice?
Maynard: I think you need to be authentic and you need to not be all about you. You need to make it all about the person you’re trying to help and I think too often we’re all involved in our life so much that that’s what we want but, when you’re able to actually channel what somebody really needs and you can generally help them you can make a big difference and I think you we need to take the time to do that and be human we can never lose the magic that comes from being human or authentic and I used to talk about at eBay that integrity really matters and that at the end of my career 20 years, after I was done, if I were sitting on a park bench, would people come over and give me a hug or would they walk away and you know intuitively how you feel about somebody when you see him, whether you’d go see him on the park bench whether you’d walk away. So every day we have to do more to have integrity and serve on that park bench.
Question: What advice do you have on helping leaders managing their egos and shortcomings?
Maynard: I think to become a leader you have to have a little bit of ego, so like early in your career, you can do anything. So you have to believe in yourself and prove that you can do things, and then people start believing in you more maybe than they should and you have to get a little more humble and self-aware and make sure that you know your press clippings aren’t what you’re reading and that you go do what you need to do. I think when you’re running an organization you have to be harder on yourself than anybody else can be because they think of you as a boss and a leader and you have to know what they’re thinking of you. What does your boss think of you? Your board? What are your employees thinking of you? You can look everything up on Glassdoor today, that didn’t used to exist and what are you doing to make yourself all you can be and are you continuing to learn and to grow. It’s for me in my life what I have learned every time I think I did something and climbed the hill, I realize there’s a whole set of mountains behind it and it’s way more complicated than what I thought. I’ve got a lot more to learn and I think we do best when we continue to learn and grow and try to stay humble, get excited and celebratory about what you have accomplished. That’s great but that’s history. What are you doing to get voted onto the team the next day?
Question: What advice would you give to a person about their legacy?
Maynard: I think you have to be clear. Why my first book rebooting worked, was I talked about standing on a stage with the people you most admire and telling them honestly what you’ve done the last five years and that people will either be amazed or they’ll be you’re talented that’s what you should do or they’ll be unimpressed. I think too many of us don’t actually stay in touch with what you really want to achieve in life. Life is short, goes fast and the more focus you can be on what you really want your legacy to be I think the more powerful will be for all of us.
Question: So in when you are looking at your legacy how do you want people to remember you?
Maynard: That I helped them achieve more than they ever thought they could achieve, that I was a winner, that I gave back and that the world is a better place because I was in it.
Question: The Win Network that you develop, give a little bit more information on that?
Maynard: I built this, I do it all for free for my friends, so I have 90 amazing individuals then invest by my side and when we find a deal, I offer it to them if they want to come along with me and then they jump in and help my companies grow. so it’s like bringing an army now it’s not just me I have an army to come help you get better and then we have fun and it’s just been one of the neatest things that I’ve ever done and lots of fun lots of impact.
Question: So how would an entrepreneur says they’ve Maynard I think I have a lot to offer how would they get involved with you?
Maynard: Reach out to my team at We get a lot of people that do and we’ll be happy to listen to your idea and if we like it maybe we’ll fund it.
Edited for Concision and Clarity