Box CEO Aaron Levie will be the keynoter at Startup Day on September 22

We always get a kick out of Box CEO Aaron Levie’s musings on Twitter, from his needling of Microsoft to startup lessons to homespun advice. But that’s not the only reason we invited the Mercer Island High School graduate to be the keynote speaker at Saturday’s Startup Day.

Levie, along with co-founder and former Mercer Island high school grad Dylan Smith, have built a popular cloud storage and collaboration platform used by more than 12 million users and over 125,000 businesses. And the company got an extra boost in late July when Levie reeled in $125 million in venture capital, reportedly valuing the 7-year-old startup at over $1 billion.

Levie was our guest on the GeekWire podcast last weekend, and we had fun asking him about business and life in Silicon Valley. Heck, trick-or-treating at Paul Allen’s Mercer Island mansion even came up. Of course, he couldn’t escape the show without at least one Microsoft crack.

“You can almost think about (Box) as SharePoint done right,” said Levie, who frequently skewers Microsoft on Twitter. Later in the show, he discussed how Box is working with Microsoft and how he’s excited about Windows 8.

Oh man. We’re looking forward to our chat with Levie on-stage on Saturday, digging even deeper into his life as a startup entrepreneur. (Editor’s note: Tickets are available for Startup Day here). 

Todd Bishop: You are one of the best people on Twitter that either John or I follow. How much time do you spend crafting the Tweets that you put out?

Aaron Levie: “It is only about 18 hours a day.”

John Cook: How can you be running Box, and doing that?

Aaron Levie: “I am up for 19, so we have enough time. You’ll be in a meeting and somebody will say something, and it will just trigger some advice that you think sounds interesting, when probably isn’t as interesting as you think, and you put it on online, so that’s all I do.”

On Facebook’s IPO and valuations: “Ultimately, I think people are disappointed about the near-term price, and the results of the IPO. But I think that anybody in the Valley that was focused on what the 90-day out price was going to be anyways was probably not in it for the right reasons. I think ultimately that people are still building their businesses, and people are still focused on the long run. And, if you think about it just in absolute terms, not in kind of relative to the IPO terms, Facebook is still a $50 billion company in a matter of eight or nine years. That on its own is pretty spectacular, and I think that’s actually driving a lot of positive value creation, versus just the fact that the IPO is a little bit under water.”

Planning to make the startup plunge, or already in the deep end? Don’t miss Startup Day 2012 — Saturday Sept. 22 in Bellevue, as Box CEO Aaron Levie and other startup vets help you find your roadmap to success. Details and tickets here.

Todd Bishop: You grew up on Mercer Island … and went down there to Silicon Valley to build Box. How would you compare and contrast the two cultures?

Aaron Levie: “I don’t want to get hated by everybody in Seattle…. I am trying to improve relations. And I do think that things have dramatically improved — 2005 is when we started the company and maybe when Seattle was less accommodating to the idea…. The reason why we came to the Valley is that we saw it as an environment that was going to be supportive of our kind of business model, and the fact that we needed to raise venture capital, we needed to hire the right kind of people and bring on the right kind of advisers very early on. Mathematically, there’s just an abundance of that down here, which certainly benefits entrepreneurs. At the same time, fast forward a number of years, I think both ecosystems are thriving and supportive in their own unique ways. Again, if we were to do this situation exactly the same way in 2012, I think the outcome could certainly be pretty different. It was more of Seattle in 2005 at that point…. We talk about Seattle a lot. The first four employees of the company still have their 206 numbers still.”

John Cook: What about an engineering center. We’ve seen all of the Silicon Valley tech titans set up engineering centers here, what about at Box. With the roots here, could you do that?

Aaron Levie: “We absolutely could. I wouldn’t put it past us. It is not something that we’d be announcing in the near run. We have one engineering center, and that’s in Los Altos. As we are expanding out, I think Seattle is a really attractive market for engineering and for a lot of the R&D efforts that we have. But I don’t have a specific date for that.”

Todd Bishop: You are pretty brutal towards Microsoft on your Twitter account… :

Aaron Levie: “Just to be fair, I’ve said plenty of nice things as well, so hopefully we can make this fair and balanced.”

On competing with Microsoft: “We’ve been competing with Microsoft since day one of our existence, and we didn’t intend to compete with them. In fact, when we started the company, and my co-founder and I were in college, we didn’t even really interface with things like SharePoint just in our day-to-day lives, so we were trying to solve a problem that was specific to our environment and it turns out that lots of people in businesses had the exact same problem because a lot of the legacy technology wasn’t helping them share and collaborate and work with their data. It is less of an indictment on a specific company and actually mostly just the paradigm. On-premise infrastructure and software has never had the ability to stay as relevant and up to speed and really solve the most current problems that a cloud solution could. We were fortunate and almost had an unfortunate advantage because we were born into this cloud and Web-based world, and we were always building newer functionality that always responded to the latest problems that our customers were having in a way that you wouldn’t be able to do if you were at a Microsoft, Oracle or an IBM.”

On Windows 8: “We are going to be doing a lot of things to support Microsoft and their platforms. We are pretty excited about what they are doing in Windows, what they are doing on Azure. So, we are going to work with them in some areas, and compete with them in others.”

On competition: “The way that startups have to compete against big companies is by focusing on what are the things that the big companies can’t do. It is never enough that you are just building a better product, or that you put together some different type of optimization on the service. You really fundamentally have to attack dimensions that are almost impossible for an incumbent to be competing on. We think a lot about what are the things that our speed and agility offer as advantages.”

Todd Bishop: What’s it like being someone in your 20s running a $1 billion company in Silicon Valley?

Aaron Levie: “I can’t confirm the valuation part of the question, but I can say what it is like to be 27…. One of the huge benefits, frankly, of growing up in Seattle is that my co-founder, myself, the third and fourth employees of Box, who were basically there on day one, we’ve all been building businesses or Internet services since we were 12 or 13 or what not. So, we’ve been doing this for like 14 or 15 years. It doesn’t really feel like a new thing for us…. That’s one of the advantages of obviously being in Seattle, and growing up around such a deep technology community, we used to trick-or-treat at (Microsoft co-founder) Paul Allen’s house…. You’d go swimming in the lake and you’d see this gigantic sort of Death Star style boat that Paul Allen owned, and obviously all you can think is why not build a technology company. So, we grew up around this, and I think that gave us a really great advantage.”

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