That would be Rich Barton, the startup wunderkind who founded Expedia as a twenty-something Microsoft manager, spun it into the world’s largest travel business and became a serial entrepreneur.
Barton went on to co-found Zillow in 2005 and became a venture partner at Benchmark Capital, the Silicon Valley venture-capital firm that owned 20 percent of Instagram before it was sold earlier this month to Facebook for $1 billion.
From Barton’s perch, at least, it looks like another tech boom is under way and money’s flowing like the old days, back before 2008.
Barton shared this view — and tips on how to start and build big companies — last week with the local chapter of The Indus Entrepreneurs. Here’s my edited trove from the event.
On today’s climate for startups: “It’s pretty frothy. It’s a great funding environment, great for the entrepreneurs. There is a ton of money chasing good people with big ideas. It’s as snap, crackle and poppy as I’ve seen in more than a decade. There are lots of exits happening, there are lots of companies going public right now, there is a reasonable amount of [merger and acquisition] activity that’s going on. If the market holds up, we’re about to enter a phase of serious IPO activity.
On demand for new tech stocks: “The public market, buy-side guys — the guys who run the mutual funds, the technology-oriented mutual funds — are starving. They’ve been starving for a decade for product to buy. It’s kind of been fashionable, if not convenient, for companies to not go public, and all of a sudden everything’s coming public. I think we’re going to see a ton of activity.”
On making mistakes: “I think the great skill of the entrepreneurial mindset is the ability to forget mistakes. Learn the lessons from the mistakes, but forget them and not obsess on them and not let your mistakes undermine the confidence you have around the dreams you have. I think that’s a big thing.”
On spreadsheets: “I tell you, the spreadsheets never work out the way the entrepreneurs and the venture capitalists think they’re going to work out. We all know that. … Rarely does the company end up being what the original idea was anyway. So you’ve got to have people on the boat who can figure out how to change the fly, put something new on there and be creative and figure it out.”
Pitching stories, not numbers: “I’m a PowerPoint guy, not an Excel guy, put it that way. I think people that come in with lots of projections and Excel spreadsheets at very early stages doesn’t necessarily bode well. … It’s very difficult to plan the unplannable, so I look more for passion around a story and idea than I do around a spreadsheet.”
Mobile, mobile, mobile: “If an entrepreneur comes to me these days and gives me a demo of a website and doesn’t demo something on a smartphone, I almost out of hand am not even interested in it, because that shows an unbelievable lack of understanding of how people are actually interacting with the Internet now.”
Traffic before revenue: “All of my businesses — I look for getting a mass-engaged audience first and worrying about a business model second. Expedia was that way, Zillow was certainly that way. … Get the masses in first, then figure out how to monetize.”
On changing course: “Pretty much everything I’ve been involved with had some kind of pivot. Zillow had a really big one. We had raised money — my guess is, we had raised $20 million — before we even figured out what the product was going to be. … We actually thought the way for perfect price discovery in real estate was going to be auctions.”
On raising money: “The whole venture-capital business is one that operates a lot on personal networks that have been established. For people who are trying to get plans in front of me, the best way … is to have somebody who I know really well and think is smart tell me to take a look at something.”
Capital in Seattle vs. Silicon Valley: “There’s plenty of money up here. There’s a lot more down in the Valley. … I find that the Seattle startup ecosystem is a few steps behind but on the same path as the Silicon Valley ecosystem.”
On Gates and Ballmer: “Bill Gates and Steve Ballmer were my venture capitalists at Expedia. I kind of thought of them that way. When I pitched the idea of Expedia to Bill and Steve, I tried to get them to fund me on the outside. Honestly, I said I want to start my own business and said look, this is a travel business, not a Microsoft software business. They kind of laughed at me and said, ‘Who are you going to hire?’ But what they did say is look, you may be right, let’s get this going internally and if it makes sense to spin it out, we’ll think about it.”
On spinning off Expedia: “You know, huge credit to those guys: When it came time … I came to them and said, ‘Look, Expedia is on the brink of becoming something huge and interesting and important. If we stay at Microsoft, it will not be. If we spin it out, it might be.’ And along with that I asked for $100 million to spend in marketing. Steve Ballmer was my boss at the time [early 1999]. … He said, you’re not getting $1 million from me to market. I said, ‘Well, you know what, the public markets will give me $100 million, and they’ll give it to me really cheaply, so let’s go do that — let’s take the public market’s money and turn this thing into something real.’ And he said OK and we did it. It was a grand experiment for Microsoft.
“Microsoft has not done anything like that since but it obviously worked out — it worked out quite well. Expedia was half the size of the largest player in the space when we spun out. Within 18 months, it was twice as big as the No. 2 player.”
What’s needed to take the startup plunge: “Courage. Think of ‘The Wizard of Oz.’ We’ve got the Cowardly Lion, the Scarecrow and the Tin Man. My kind of view of great entrepreneurial leaders is courage for the Cowardly Lion, you’ve got to have brains for the Scarecrow and probably most important is, you’ve got to have a heart because you cannot attract people or capital without a heart. People respond to passion; people respond to real feelings, real emotion, things that really matter.”
His busy schedule: “When you have eight jobs, it turns out nobody knows when you don’t show up to work.”