VC Steve Jurvetson: Elon Musk is more capable than Steve Jobs was

Steve Jurvetson is one of the more prescient venture capitalists in the Valley.

His firm — Draper Fisher Jurvetson (or DFJ) — is legendary for its investment prowess and spotting disruptive technology  long before it becomes trendy.  Jurvetson, along with partner Andreas Stavropoulos and DFJ’s entire investment team, have made some serious early bets with Hotmail, Skype, Twitter, Flurry, and Yammer, among dozens more.

Jurvetson invests primarily at the seed and early growth stages in the consumer, enterprise, and disruptive tech sectors. Like Tesla and SpaceX, which he helped seed. He rose to prominence in the mid-1990s by investing $1 million in a startup called Hotmail, which Microsoft later purchased. An avowed tech nerd, Jurvetson understood early that email was a platform that would thrive if it was free and could be accessed from any browser. Jurvetson returned $400 million to investors after its acquisition, and the deal made him tremendously wealthy.

Jurvetson is 47, married, and lives in the Valley. His intelligence is oddly contagious, and he speaks passionately about how disruptive tech is increasingly shaping our lives for the better, often times by gesticulating with his hands. He spends much of his free time launching rockets with his sons and pursuing his keen interest in photography, and he often posts his photos online.

He has a few regrets, like not investing in his friend Elon Musk’s PayPal, which eBay Inc later acquired in 2002 for $1.5 billion. Jurvetson is the son of immigrants from the Baltic states. And he’s busy. He sits on the board of both electric car company Tesla and the civilian space-transport outfit SpaceX, which are both passionate Musk initiatives. And he believes SpaceX will eventually obtain its stated goal of going to Mars. He believes the time is coming, probably, within the next 15 years.

According to DFJ’s website, investors there “specialize in financing emerging companies that enable large businesses to become scalable and more efficient, such as Box and Yammer. … We have the courage to back entrepreneurs with broad visions that disrupt entire industries, like Tesla Motors and SpaceX. We think big about trends before they become mainstream.”

In February, DFJ closed its 11th fund, raising $325 million. Jurvetson was promoted to partner at DFJ based on the success of his Hotmail investment in 1995. Prior to becoming one of the Valley’s most iconic tech investors, Jurvetson worked as a consultant for Bain & Company. He attended Stanford’s business school and today collects space memorabilia, much of which adorns the company office on VC-firm-laden Sand Hill Road in Menlo Park, Calif.

I caught up with Jurvetson and Andreas Stavropoulos recently at their Menlo Park office and later via a lengthy phoner.

VentureBeat: Your early $1 million investment in Hotmail put you on the VC map. DFJ made like $250 million after Microsoft acquired Hotmail in 1998.

Steve Jurvetson: We were rapidly shifting to Internet companies. It became 80 percent of what we did. This was like in 1995. Hotmail was one of those great examples early on that opened our eyes to a lot of other investments that followed like Skype and Tango.

At the time it was called Java Soft, Inc., which was actually a flat file-database tool company, of all things. It was an infrastructure layer for the Web and a set of tools for developers. We met with them because one of our investors had met with them, but they didn’t really know if this was a good idea. So when we met, we had a similar reaction of “Hmm, this idea that database tools for the Internet didn’t seem like a great idea. Why would anyone think of building tools for a website? In other words, what’s your marketing strategy?”

And their answer, after looking at one another for a bit, was to cobble together a Web-based email application available for free on the ‘Net with no intent to make money off it but just to get attention from people who would be marveling at this wonderful Web application. So they did that — and it took off like wildfire.

My partner, Tim [Draper], had this idea of something called viral marketing, which uniquely allowed Hotmail to spread more quickly than any other company prior to it. I should say not only was there a financial return that we made but it was a really important set of learning that allowed us to be better investors.

The thing they thought would be impressive about building an email application was that it would only take three months to build and entire world-class system. And it really did take them only three months with only two programmers to pull that off.

VentureBeat: What was your concept in the mid-90s about email? Did you understand it?

Jurvetson: Oh, yeah. When I started here [DFJ], I became our webmaster. I built our website. I taught myself HTML. I experienced first hand the frustrations that students feel in college when they leave to take a summer job. And then they come back where you have a different email system. Back then, everything was a walled garden. At home you might have had AOL. There was no continuity to your presence, your identity, right?

I also thought as a consultant, where I worked at Bain and Company for three-and-a-half years. You’re working for clients, and oftentimes you’re stationed at the clients’ [location], your customer. So there was no way get my email, no way to do it at the customer site. And Hotmail was so radically liberating. You could actually access your email from anywhere. Just find a browser. So it didn’t matter where you were. You could be at a government site or cafe, and you could actually get your email.

VentureBeat: How much did you guys actually invest in Hotmail at the beginning?

Jurvetson: It was small. I remember exactly. We invested $300,000. We also did the entire Series B round, which was about $700,000. In the end, we invested $1 million for about 25 percent of the company.

VentureBeat: Aftwerward, Microsoft bought Hotmail. How much money did you guys make off your investment?

Jurvetson: A lot. So at the time we gave it back to our investors it was a billion dollars. The acquisition was $400 million. But then, strange as those days were, Microsoft’s stock price went so rapidly up after it. I learned at that time in a Newsweek article that Hotmail represented over half of all revenue Microsoft was making from its online properties. In the year after the acquisition, Hotmail went from a $400 million valuation to $1 billion, which is what we distributed to our investors.

Hotmail went from zero to 12 million users with zero marketing steps. Not a penny was spent on sales and marketing, which was astounding. It showed us the power of the network effect. From an investors point of view fantastic that it takes so little money to build and test these systems.

VentureBeat: When did you become a venture capitalist and come aboard the company that now bears your name?

Jurvetson: I was at Bain before business school [Stanford]. That was 1990 to 1993, the Bain years. I also worked at Apple and Next over the summer to understand both product marketing and see Steve Jobs in action. Steve Jobs was my hero.

So in June 1995, I started here as an associate. I was promoted after the Hotmail story was playing out. My partners told me “Hey, you’re now one of us.” So we changed the name accordingly.

VentureBeat: Were you close to Jobs? What was your relationship like with him? 

Jurvetson: It was never super close. He responded to my emails, and we went for some walks together, and he tried to recruit me to Pixar. The short version is I’m just a total Apple fanboy. I started programming Apples in seventh grade. So while in business school, I invited him to come speak at what was called the high-tech club I ran at campus, where I would bring in tech leaders. So in this particular case, I finagled him to come to my house to speak. And he did. He literally did a fireside chat in front of the fireplace with the geeks and tech-interested people who were at business school. And he spent over three hours with us. Which was amazing. He yanked all the function keys from my MacIntosh keyboard. I also managed to finagle an agreement to study him and his leadership style. I wrote a school paper about him to understand what he does.

Venturebeat: Was Jobs a real visionary? He was worshipped. And feared. 

Jurvetson: Yes. He was a tech visionary but not as the same way Elon Musk was. He was a tech visionary without the engineering mindset unlike Elon. He was more of the marketing-evangelism mindset not surprisingly. But, other than that, there was a lot of similarities. Elon is more diverse. Jobs would never, ever, say something, even internally, something along the lines of “here’s the master plan of what were doing technologically.” It was more of, “here’s what’s beautiful; here’s what’s ugly. Here’s whats simple and I want beautiful products that will be insanely great.” He never, at least in front of me, expressed overt strategy. And every time, when I was at Next (jobs launched the computer after he was fired by the Apple board in 1985), we’d ask him questions like what kind of “CEO at Apple would ever bring you back and expect to keep their job?” He had no answer. You never got him to say why that was the right answer either.

VentureBeat: DFJ  invested early with Tesla and then SpaceX. You now own equity stakes in both companies and Steve sits on the boards there:

Jurvetson: Sure. Happy to. The context was in the arch in the DFJ story is that Elon was the most prolific investor in the clean energy and clean tech wave. We looked around and saw a lot of opportunities in the clean tech. I went on the board on Tesla in 2008 when the company went through a very tough period. It was an incredible story of near death experience. But they made a major comeback. It’s since gone public as you know. It’s been deemed the safest car ever built. We got involved because Elon knew us. And through this, by the way, we came to understand the SpaceX project.

VentureBeat: How much did you invest in Tesla and SpaceX?

Jurvetson: I don’t think we’ve ever disclosed that. I don’t know the exact amount. It was a sizable amount. It was over $10 million. Elon literally went personally into debt to save Tesla. Which was was astounding that they would go net negative. Tesla almost died. Our investment there was our largest investment. He wrote a check to make payroll. Our DFJ Growth Fund put in $20 million for SpaceX. In all millions. It’s much more valuable now then it was then. With SpaceX, the successful launch on Friday to the International Space Station was a watershed moment for humanity.