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


Alan Olsen: Can you tell us a little about your background?

Maynard Webb: I majored in criminal justice in college and was going to go on to law school.  I 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 to 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 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 around that, and then eventually became 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.

Alan Olsen: Along the way you were involved in starting some companies as a founder or early investor. What prompted you to go that direction?

Maynard Webb: I spent most of my time building companies.  I was a CIO for a number of years at places like Bay Networks and Quantum and Gateway, and then became the COO or the head of technology at eBay when they couldn’t keep their side up.  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.

Alan Olsen: You have a gift of helping companies with strategy.

Maynard Webb: 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 did back in my early board career.

Alan Olsen: What was the inspiration behind writing your book, Dear Founder?

Maynard Webb: 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 (his son) 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”.  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 to 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 a 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. 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.

Alan Olsen: What advice do you have for an individual searching for a mentor in their life?

Maynard Webb: 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 it’s going to pay off for you if they do. You’ll find mentorship in unbelievable places, you just have to be open to it.

Alan Olsen: Why is it important for individuals to find and build diverse and inclusive companies where they can thrive?

Maynard Webb: 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 until you’re up to 50 people before you add your first woman or minority, it’s much harder to have that be a natural flow.

Alan Olsen: How should individuals that are in the business world be seeking for counseling and advice?

Maynard Webb: I joined Silicon Valley in 1991 when I became the head of networking at a 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 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-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 invest 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 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 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.  It’s a multi-faceted prospect and there’s no downtime, you’re on 24/7 and tweets, you know we didn’t have tweets, so you could maybe tell a joke sometime back in the past and not get, you know, in a lot of trouble. Today you’ve got to be careful with everything you say.

Alan Olsen: It seems that with the information age, do you agree that it’s a little harder for companies to be stealth today?

Maynard Webb: I think several companies all try to be stealth and 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. But 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.

Alan Olsen: 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 person inspire and help others to become part of their vision?

Maynard Webb: 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 behave, in a good manner, and many of them were 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 are people that are very talented and can get multiple jobs any place. You don’t have jobs for life anymore and you have people trying to take your talent and hire it away.  That pendulum of power has 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 it become your idea that you want to do this.

Alan Olsen: How should a leader give advice?

Maynard Webb: I think you need to be authentic and you need to not be about you. You need to make it all about the person you’re trying to help. 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 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.  I used to talk about at eBay, that integrity really matters and that at the end of my career of 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.

Alan Olsen: What advice do you have on helping leaders managing their egos and shortcomings?

Maynard Webb: I think to become a leader you have to have a little bit of ego, so like early in your career, nobody thinks 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 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?

Alan Olsen: What advice would you give to a person about their legacy?

Maynard Webb: 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. Those 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 we 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 it will be for all of us.

Alan Olsen: So, when you are looking at your legacy, how do you want people to remember you?

Maynard Webb: 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.

Alan Olsen: The Win Network that you developed; give a little bit more information on that.

Maynard Webb: 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.

Alan Olsen: So how would an entrepreneur say, “Hey, Maynard I think I have a lot to offer”, how would they get involved with you?

Maynard Webb: 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



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This transcript was generated by software and may not accurately reflect exactly what was said.

Alan Olsen, is the Host of the American Dreams Show and the Managing Partner of  GROCO is a premier family office and tax advisory firm located in the San Francisco Bay area serving clients all over the world.

Alan Olsen, CPA

Alan L. Olsen, CPA, Wikipedia Bio


    Maynard Webb on Alan Olsen's American Dreams Radio
    Maynard Webb

    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

    Alan Olsen on Alan Olsen's American Dreams Radio
    Alan Olsen

    Alan is managing partner at Greenstein, Rogoff, Olsen & Co., LLP, (GROCO) and is a respected leader in his field. He is also the radio show host to American Dreams. Alan’s CPA firm resides in the San Francisco Bay Area and serves some of the most influential Venture Capitalist in the world. GROCO’s affluent CPA core competency is advising High Net Worth individual clients in tax and financial strategies. Alan is a current member of the Stanford Institute for Economic Policy Research (S.I.E.P.R.) SIEPR’s goal is to improve long-term economic policy. Alan has more than 25 years of experience in public accounting and develops innovative financial strategies for business enterprises. Alan also serves on President Kim Clark’s BYU-Idaho Advancement council. (President Clark lead the Harvard Business School programs for 30 years prior to joining BYU-idaho. As a specialist in income tax, Alan frequently lectures and writes articles about tax issues for professional organizations and community groups. He also teaches accounting as a member of the adjunct faculty at Ohlone College.

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