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Maynard Webb on fixing eBay and your career (Q&A)

The man brought in to fix the auction site's network nearly 14 years ago has become one of the most respected voices in Silicon Valley. He has just written a book about taking control of your future.

Jim Kerstetter Staff writer, CNET News
Jim Kerstetter has been writing about the high-tech industry since the 1990s. He has been a senior editor at PC Week and a Silicon Valley correspondent at BusinessWeek. He is now senior executive editor at CNET News. He moved back to Boston because he missed the Red Sox. E-mail Jim.
Jim Kerstetter
12 min read
Maynard Webb

CAMBRIDGE, Mass.--Maynard Webb is a fixer.

When Webb was asked to take control of eBay's failing IT operations in 1999, the company was in full-scale crisis. The then-young, fast-growing site had become the poster child for dot-com instability as it suffered through a series of outages. CNN crews, as Webb remembers, were parked outside eBay's offices, waiting for the next headline-grabbing crash.

Nearly 14 years later, eBay is a mature company (at least by dot-com standards) and Webb is considered one of the elder statesmen of Silicon Valley. He left eBay several years ago and is now a member of the board of directors at big companies such asYahoo and Salesforce.com and small ones such as LiveOps. He is also an angel investor at the Webb Investment Network, and he's still the occasional entrepreneur, now working with his new startup, Outside Counsel.

Last week, Webb was on tour for his latest project, a book he wrote with co-author Carlye Adler called "Rebooting Work." The new book, available this week, is sort of a self-help guide for workers in the age of cloud computing. It asks, simply, what kind of worker are you and what do you want to be? It traces Webb's career from security guard at IBM to the the fix-it guy at eBay to his current role as an eminence grise to younger tech execs. CNET met with Webb at the Charles Hotel in Harvard Square to talk about his career and the book. The following is an edited and condensed version of that interview:

Q: Why did you take that job at eBay and what was the first thing you needed to address there?
Webb: I thought it was a really, really tough problem that really need to be fixed, to be honest with you. I was in a great place at Gateway as the top CIO guy there, with lots of upside, but I was still just the IT guy there. At eBay, technology was going to make or break the company. And they had a massive technology issue. Instead, of being scared of it, I saw it as something that would be massively fun to fix. I thought eBay had good upside as well. But I joined because the problem was big and gnarly and ugly and I thought I would find a way to fix it.

But you could have been a fall guy, too.
Webb: That's always true. The toughest things you do have the most risk in them. But I never think about it that way. I was just like, I want to go do this. I often have had people tell me that I was an idiot, whether it's setting up my investment network or joining eBay, because there are a lot of people who could have solved that problem but ran away from it...I walked in and CNN was getting ready to film in the parking lot every time we had an issue. It was not for the faint of heart. But I thought it was so crucial, that I felt more needed there than anywhere else I've been.

What was the first big challenge?
Webb: How about trying to keep the site up? The first night I was there...(CEO Meg Whitman) wanted to announce me to all the analysts so she could say I was there to fix all the problems. That Friday I was supposed to fly back to San Diego to say goodbye to my team there and fly back Monday morning for analyst day, the site crashed for 10 hours and Meg just said, "Get in there and fix it." Long story on that, but it came back up, and she was going to announce, "Maynard's here and everything is going to get fixed," and I said, "Why don't you say, 'Maynard's here, it will get better.'" And she said, "By the way, you can't go home now."

On Sunday night, we had a big dry run on how to do everything. As we're walking out of the dry run and the next day is analyst day, the site crashed and Meg's like, "Maynard you fix it with the team and guys who know something and need to be fresh tomorrow, you go home." So at 10 o'clock at night, I went back to the NOC (network operating center) and we got the site back up and we crawled out of there at four in the morning. Showed up the next day at analyst day.

So that was the first day of work.

And then?
Webb: Not only did we have system problems keeping the site up. I asked the question, "When do we run out of capacity?" and they said, "What do you mean?" And I said, "Headroom. I know we're growing and I know we can't keep our site up now. But when do we hit the wall?" And they were like, you know, nobody's ever asked us that question. And they came back in three days and said, "We have about three and a half weeks until we run out of capacity." I don't know if you know that or not, but that's not a great answer.

So I would say all year one was getting our arms around making sure eBay could grow as quickly as possible...So we had the SWAT team working on current problems, we had a team working with Sun (Microsystems) on hardware issues, we were upgrading and putting in high-availability clusters on the current architecture, we were developing the next-generation architecture and code base to deploy it, and we were working on a backup plan just in case. The traditional way to solve this is to stop making changes because changes hurt everything. And we just felt with the Internet you can't do that. So we upped the pace of change and development at the same time we were trying to do all of this.

Today, there are a lot of sites dealing with scalability issues.
Webb: The way I look at it is, most sites don't have to deal with this, because very few of them are relevant. If you're relevant, almost all those folks run into scale issues fast. You saw it with Twitter. Salesforce had their own scale issues. It's a sign of success. But it's painful, and you've got to figure out how to fix it fast.

So who's at risk today of having that eBay moment?
Webb: Take a look at Instagram. Look at what happened with Netflix on Christmas Eve. I'm sure nobody at Netflix expected that on Christmas Eve that AWS (Amazon Web Services) would go down and Netflix wasn't able to deliver streaming pictures on the most important day of the year. I would say anybody that has fast, viral adoption on an infrastructure that has single points of failure, whether it's your database, or your servers. I always stressed the importance of getting a distributed architecture so that if something broke not everything broke.

Is it spikes in capacity that companies are unable to plan for?
Webb: Well, I was always thrilled when our marketing group would come with something like, "Let's do a free listing day." And on that day you were like 6x your volume. And that would be like a years' capacity ahead of time. So I would try to build and architect ways to let that happen. And there are ways to handle it; it's just a question of cost. How much capacity do you want to have before you need it? One day at eBay years after everything was fixed, we had a Polish site that was just a small set of servers without a lot of traffic. The Pope's car that he had driven as a college student went for sale. Well, that site had never seen that amount of traffic. Whoom! And it was like, we didn't have that in our model.

Anytime you have a site that's on the consumer side, and you have viral adoption, something can happen. Twitter went through a ton of issues. Now they're far better today, if you think about it. You don't see the Fail Whale all that often, while there's way more volume than there used to be.

I want to turn for a second to the companies you're involved with. You're on the boards of Yahoo and Salesforce. Let's start with the more difficult company, Yahoo. What's been the biggest challenge there?

Webb: You probably are aware that there's been tons of press about what's coming in and out of Yahoo.

I picked up on a bit of that.
Webb: One of the things the board committed to was not to talk to the press about it. We implemented a policy on that. If you want to talk specifically about Yahoo or Marisa, we have to go clear it with them first. They don't want us talk about it as directors...I think it's fair to say; at the back of my book I talk about the next 15 years. I talk about creating your own plan, and I didn't think it was fair to tell people to create a plan that I wasn't willing to do. And I said in there I want to identify and mentor and help grow, two to five more change-the-world companies. I joined the Yahoo board last year because they used to be that and I think that they should be that again. But we have work to do to get there.

What about Salesforce? It's a success story. But what's the biggest challenge there?
Webb: I will say this: When I joined in '06, a lot of people told me that its best days were behind it and that the cloud was overhyped. But (CEO Marc Benioff) has done a good job at staying humble and so has the team there. And as good as things are right now they know that nothing is guaranteed and companies have to be careful that when they are being successful and the wind's at their back that they don't get too far ahead of themselves. Right now, Salesforce is doing really, really well. But that's the time to be even tougher on yourself and make sure you continue to expand your growth and continue to grow.

They always say companies make the mistakes that seed their ruin when they are at their peak. So what are the risks there?
Webb: Things I'd probably talk to Marc about but not you.

In your book, you describe four kinds of workers: The company man, the disenchanted worker, the "CEO of your destiny," and the aspiring entrepreneur. How many times have you been each of those?
Webb: I started my career at IBM and thought I was going to be there for life...loved it and thought I would never go anywhere else. Since I left IBM, I've been living the majority of my time as the CEO of my own destiny, whether I worked for myself or worked for my company, I never ceded control after I left IBM. I would say that the people I worked for would have thought that I was the company man, I just never gave all control to them because I knew I had to build a network...I don't spend a lot of time as a disenchanted employee because that's a scary place to be, to be honest, because it means it gives somebody else control over your destiny and you're feeling like a victim. I spend a lot of time in the book mentoring and talking about how not to be there because that's not good for your career or your enthusiasm.

So how do you get out of that?
Webb: We need to teach people how to take care of themselves and that there's safety in that and not to hook into a model that's dated...Nobody wants to be disenchanted. No. 1, take an honest assessment, take control of the fact that it's your thing to fix, not the company's, including you may need to leave the company if it's not right. Your value system, the company's value system, if their view of your worth isn't aligned -- No. 1, is it fixable? And if it's not, then where do you want to go? And how do you find a way to be engaged and constructive...I just wish people would be aligned with what are their dreams and what are they doing. Where people get into trouble is a lot of people feel stuck with where they are and where they want to be, and you're way more in control of that than we believe we are.

As an investor, what sorts of companies are you looking for?
Webb: I generally am looking for companies that are doing something that I have been exposed to. I'm looking for pattern recognition in cloud or mobile or Internet commerce. I bought a lot of things as a CIO. So I'm looking at the team, the space, how big the space is, and do I know anything at all about it and does it resonate. So it's all about the team, the technology and the space.

So what does an entrepreneur have to do to impress you?
Webb: First, I have to find out what they're motivated by. When somebody just wants to make money, that's not what I'm motivated by. When folks truly want to make an impact in the world, I fall in love pretty quickly with those folks...and how really committed are they? Are they looking to flip the company really quickly or are they going to be upset if somebody takes control. You can build something that's going really well, somebody comes along and offers to buy it, then you gotta go build it again or you have to be part of a big infrastructure. So I look for people who are trying to build something big for a long time. Now the problem is there aren't very many of those that make it all the way.

So you're not interested in people who are looking to flip.
Webb: Well, flip or just want the lifestyle of being cool and being an entrepreneur. I'm looking for people willing to do the 20 hours a day it takes to build something and create something and nurture it into something that gets talked about.

Is the tech industry consumer tech'd out? Are you not looking for the next widget, the next app?
Webb: I think big data holds huge interest. And I think cloud and mobile are also really cool. I'm not as interested in an app as I am a system. It's very seldom that I would do hardware over software because software you can just move faster on.

What was harder, fixing eBay or writing a book?
Webb: Different problems. Fixing eBay was harder but more natural for me. Writing the book was talking about myself in a way...I don't like things to be about me. That was very uncomfortable for me. I got frustrated with the length of the cycle to get the book out so I thought it would be fun to launch a company faster than the book and get the company out...I thought about it and I thought about mentoring...so I found a team and I launched a company called Outside Counsel. It's going to get a new name and we are up and running. And we are up and running and people are happy and we were out before the book was out.

Who should young entrepreneurs model themselves after?
Webb: If they were truly product visionaries, I'd say Steve Jobs or a Benioff. The problem is there are very few of those. And what I worry about is Steve was able to get away with some pretty different behavior because he was so brilliant and I think there are very few people who are that brilliant. I think Zuckerberg has done an amazing job. Maybe Larry at Google. Find a rhythm that works for you. I really would caution people to not just pick one...Find yourself and then look at these icons to see which of these things work for you and then model your own self into your own brand.