Entrepreneurs

Dropbox's CEO reveals 4 of his favorite books on how to be a successful leader

Drew Houston, co-founder and CEO of Dropbox
Photo by Drew Angerer
Drew Houston, co-founder and CEO of Dropbox

Drew Houston always knew he wanted to run a tech company.

"I really admired all the great tech companies and even as a little kid, I admired the tech entrepreneurs and I always dreamed of having my own company," says Houston, speaking with Fortune in a video posted Wednesday. "So it was something I had been thinking about and studying for a while."

The cloud storage company Houston started, Dropbox, went public in March and had a market capitalization of more than $13.5 billion as of the close of trading Thursday.

Houston, now 35, started Dropbox in 2007 when he was 24 with his classmate from MIT, Arash Ferdowsi.

"Back then, we were just getting the company off the ground. We were coding in the little room," says Houston.

In the past decade, San Francisco-headquartered Dropbox has grown tremendously. At the end of 2017, Dropbox had 1,858 employees in 12 global offices. Houston has had to learn how to become a leader.

"For me, reading was really important," says Houston.

Here are four of his favorite books, as revealed in his interview with Fortune.

1. "High Output Management," by Andy Grove

"Andy Grove is the amazing former CEO of Intel. I really admire everything that he did," says Houston. Grove's book, was first published in 1983 and again reissued in 2015, and shares advice on managing and motivating teams.

Ben Horowitz, the legendary venture capitalist of the firm Andreessen Horowitz, is also a fan of Grove's tome. "I first read 'High Output Management' in 1995. In those days, there were no blogs or TED Talks teaching us about entrepreneurship. In fact, there was almost nothing of use written for people like me who aspired to build and run a company," says Horowitz, in a blog post about the book.

"Against this backdrop, 'High Output Management' had an almost legendary status. All the best managers knew about it. The top venture capitalists gave copies of it to their entrepreneurs, and aspiring leaders in Silicon Valley devoured its contents. It amazed all of us that the CEO of Intel had taken the time to teach us the essential skill of entrepreneurship: how to manage," writes Horowitz.

2. "Only the Paranoid Survive: How to Exploit the Crisis Points That Challenge Every Company," also by Andy Grove

Houston says this book is "very relevant for any tech company." The book was first published in 1996 and talks about how to manage through what he calls a "Strategic Inflection Point," a time when some massive change forces a company to change course immediately.

"'Only the Paranoid Survive' offers practical advice on how to bridge that narrow line between catastrophe and opportunity, and seize the opportunities," the Harvard Business Review said in 1996 when the book first came out. "That's why this book isn't just for managers of high-tech businesses."

3. "Playing to Win: How Strategy Really Works," by A.G. Lafley, and Roger L. Martin

This is a favorite of both Houston and, he says, his board member and the former CEO of Hewlett Packard Meg Whitman.

Of Whitman, Houston says, "she taught me a lot about managing at scale. She has had an unbelievable variety of experiences, right? She has been in consumer companies with eBay, she has been at HP and HP Enterprise. How do you think about strategy and the strategic planning process? We both have a favorite book called 'Playing to Win' by A.G. Lafley, and Roger Martin, so we trade some book recommendations."

"Playing to Win," first published in 2013, is written by Lafley — the CEO, President, and Chairman of Procter & Gamble — and Martin, dean of the University of Toronto's Rotman School of Management and a corporate advisor. In it, Lafley and Martin explain the strategies Lafley used to double Procter & Gamble sales, quadruple profits and increase market value by more than $100 billion in the Lafley's first stint at CEO from 2000 to 2009.

4. "The Score Takes Care of Itself: My Philosophy of Leadership," by Bill Walsh, Steve Jamison and Craig Walsh

"One of my favorite books is by Bill Walsh, who was the head coach of the 49'ers when they went from dead last to winning super bowls," says Houston. "If you just do the right things, the score will take care of itself."

First published in 2010, three years after Walsh died, the book is the result of a series of exclusive interviews writer Jamison did with the coach.

From his reading and his experience, Houston says he has learned that becoming a leader is a process.

Advises Houston, "I would say being curious is really important and then being resilient.

"We have had our share of ups and downs so if you think of it more as an adventure and know that it is going to be kind of a crazy process and not put too much pressure on yourself to have everything be absolutely perfect or be the perfect leader. You are going to make mistakes along the way, it's really how you respond to them that's important," says Houston.

Going forward as the CEO of a public company, Houston says he is going to work to make sure the Dropbox staff doesn't get distracted by the fluctuating stock price.

"A big part of my job is helping everybody stay focused on what I call our inner scorecard, because we are going to get a very loud and blinking outer scorecard with the stock price and so on and that is important but you can't control the markets and there is a lot of elements of that you can't control," says Houston, who attributes his scorecard terminology to Walsh's book. "What you can control is — are you building great products? Are your customers happy? If we take care of our inner scorecard, the outer scorecard will take care of itself."

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