Hightail

10 Questions: Brad Garlinghouse, CEO, Hightail

March 25, 2014: 5:56 PM ET

On embracing risk, the challenges of the cloud computing market, and his Kansas Jayhawks obsession.

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FORTUNE -- Brad Garlinghouse grew up in the American Midwest -- Kansas, to be exact. His interest in technology first began when his dad brought home a TRS 80 computer. After obtaining a bachelor's degree in economics from the University of Kansas, he went on to earn his MBA from the Harvard School of Business and eventually moved to Silicon Valley.

He spent the early days of his career working at startups, and then he eventually moved on to to senior positions at AOL and Yahoo (where he famously wrote his "Peanut Butter Manifesto," a philosophy of efficiency that he has since brought to his other companies). His current company is Hightail, the cloud storage service formerly known as YouSendIt. Garlinghouse, 43, spoke with Fortune.

1. Who in technology do you admire most? Why?

The person who stands out in my mind is Reed Hastings. One of the things that happens in Silicon Valley, and more broadly as a public company, is that you have a lot of infrastructure and a lot of pieces in place that mitigate and reduce risk. Reed has embraced risk.

He's reinvented the company multiple times. When I think back to when I first became a Netflix subscriber and how I think about Netflix today, as an addict of House of Cards, it's a completely different animal. It's so difficult to reinvent a company and reinvent a product, and Reed has done it, sometimes facing significant headwinds. He has been open enough to acknowledge when he's made a mistake. He stepped back and said, "Hey, we launched this thing called Qwikster, and we shouldn't have done it, so we're going to reverse that decision." I think that takes incredible leadership, confidence, and fortitude, so I give him a ton of credit for what they have built and continue to build.

2. Which companies do you admire? Why?

I'm a big fan of what Salesforce has achieved. Having been around the Valley 17 years, you've seen that many companies have had a bigger impact than they get credit for. Salesforce, in some ways, can be credited with having defined cloud computing. There was a billboard on 101 for Salesforce that effectively said, "Say no to software." The idea being, why, in a world of connected technologies, do we not run software in the cloud? This year they'll do over $5 billion in revenue. I think people thought that Salesforce was a stale CRM [customer relationship management] tool, but they have continued to seek out expansion.

3. Which area of technology excites you most?

I think many people would talk about how health care is so problematic, and I think the intersection of health care and technology is becoming a more and more interesting area. There are two particular parts that I find interesting. Data collection and data infrastructure can improve health care outcomes. I'm an amateur angel investor, and I've invested in a small company called Tonic for Health. The whole premise is that if doctors do a better job of collecting data and understanding the patient, they're going to do a better job of treating you.

The second "kissing cousin" to that answer is genomics and DNA analysis. The idea that genetic engineering could eradicate inherited disorders is a sign that society is changing. There are obviously risks and social impact, but I think it could be really dramatic if, 30 years from now, we can look back and think, "Holy cow, we are so much smarter about how DNA and tech intersect."

4. What is the best advice you ever received?

One of the things my dad told me was, "Take the professor, not the class." The idea was that the subject wasn't as important as the person who's teaching it because if the person who is teaching is incredibly engaging and passionate about what they're doing, then they'll be a better teacher and you'll learn more. I saw that in spades in school, and I certainly see it professionally as well.

I think that's one of the mistakes that many people in Silicon Valley make. When you see the latest cool company, you may end up going to work for someone who has never managed anyone, and so you don't learn much from that person about how to grow your career. So I think if you go work for someone who's great regardless of the company, that's a much more important step, at least earlier in your career.

5. What challenges are facing your business right now?

Hightail's in the midst of a booming market. There are many companies entering the space on a daily basis, which is in part because people see the opportunity ahead. [Market research company] Gartner has said that in 2014 the cloud market will reach $155 billion, and that means other people are flocking to it. Even Duracell has entered the cloud storage market. The challenge for us is to continue to invest and continue to take risks and focus on our core areas of differentiation around security and professional use cases and not get distracted by "the latest and greatest" of other companies. We're going to stay the course and execute our own strategy.

6. If you could have done anything differently in your career, what would it have been?

To be candid, I think in retrospect, it was a mistake to work at AOL when I did. I think I had rose-colored glasses about the opportunity to reinvent AOL. There's a Warren Buffett expression that "Most turnarounds don't turn." I don't think I fully appreciated how difficult the task there was. The good news was that I got to work with some phenomenal people and definitely learned a bunch. There were a number of opportunities in that time frame and I look back and think that turnarounds are very difficult.

7. What is one goal -- either personal or professional -- that you would like to accomplish during your lifetime?

I have never run a marathon, and even though I'm not exactly as young as I used to be, I intend to run a marathon. It's one of those things where if you focus, it can happen.

8. What do you do for fun?

Family is my fun. I've got three amazing kids, and it's really been a joy. My oldest is 11, and my youngest is turning 7 in a couple of weeks. I have found that my weekends are all about sports and engaging with the kids, and I really wouldn't want it any other way. The only addition to that is that I love watching movies.

9. What was the last book you read?

The most interesting recent book I read was The Lean Startup [by Eric Ries]. It has been a great lesson about risk-taking and the art of putting science into the process around something. So I think it's a fabulous book for anyone in Silicon Valley thinking about technology and how user feedback can be incorporated rapidly into development.

10. What is one unique or quirky habit that you have?

People who know me know that I'm a rabid fan of the Kansas Jayhawks. My quirky habit is that every Kansas game is on my calendar and more often than not, I will plan and schedule flights around them so that I can engage and watch. I have already brainwashed my family to be Jayhawks fans.

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