Strategy

The CEO of Dropbox shares his best advice for his 24-year-old self

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Drew Houston
No one is born a CEO. Dropbox founder Drew Houston pictured.  Drew Angerer/Getty Images

Drew Houston founded Dropbox when he was 24. 

About 10 years later, the file-sharing service has more than 500 million users, generates $1 billion-plus in annualized revenue, and was valued at about $10 billion in 2014.

In March 2018, Dropbox went public as a $9.2 billion company, and stock surged 44%.

Speaking with Business Insider US editor in chief Alyson Shontell on an episode of Business Insider's podcast "Success! How I Did It," Houston reflected on what he's learned about being CEO, and the advice that would have been a "relief" to his 24-year-old self.

Listen to the full episode here, or listen later with the buttons below:

"First, no one is born a CEO," he told Shontell. "This is an acquired skill set, and, furthermore, it's one that you learn on the job. So everyone is a first-time CEO by definition at some point."

Second, he said, "just about everything is learnable. I started out just on the engineering side. I had no real business experience. I literally went on Amazon and typed in 'sales' or 'marketing' or 'strategy,' and would just buy the couple top-rated books, and that's what I would do on the roof of the fraternity. I would just read."

He continued:

"But whether it's just the fundamentals of business or things like public speaking or being more inspiring or being a better leader, these are all things you can get better at with practice. You should set your sights high in terms of what you aspire to do, but you also have to be patient.
"It's like playing an instrument. You're not going to be great as a public speaker, or you're not going to improve a lot in five days, but in five years, you might be really surprised at how much you can improve."

For that reason, he recommends starting early, and being "systematic" about learning. "So what that means in practice is, I've always found it valuable to ask myself, 'One year from now, two years from now, five years from now, what will I wish I had been learning today?'"

This post was updated after Dropbox went public on March 23, 2018.

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Libby Kane was a personal finance expert who has reported and edited stories about money for more than 10 years. She previously held the Certified Financial Education Instructor (CFEI) certification issued by the National Financial Educators Council.Experience She has written and edited articles on everything from investing tips to model budgets and has interviewed dozens of authors, financial planners, and early retirees to share their advice, experiences, and insights with a global audience. Before joining Business Insider in 2014, she was an associate editor at LearnVest, a personal finance site to help women learn about money. Her work has appeared on sites such as MSN, AOL, Forbes, Slate, and The Street.Her team at Business Insider has tackled projects including:• Women of Means, a series about women taking control of their finances• Inside the Racial Wealth Gap, an exploration of the causes, effects, and potential solutions of the racial wealth gap in the US (finalist, Drum Award, "Editorial Campaign of the Year," 2021)• Strings Attached, a series of essays from people who have left insulated communities and how that journey affected their relationship with money• Master Your Money, a year-long guide for millennials on how to take control of their finances  (first runner up, Drum Award, "Best Use of Social Media," 2022)• The Road to Home, a comprehensive guide to buying your first house (silver award winner, National Association of Real Estate Editors, "Best Multi-Platform Package or Series – Real Estate," 2022)Libby believes in one universal truth about money: Advice is never for everyone. The best strategies, tools, and products depend on your preferences, financial situation, history with money, and goals.ExpertiseHer expertise includes:• Behavioral finance• Early retirement• Budgeting• Saving moneyEducationLibby holds a bachelor's degree from Wellesley College.Outside of personal finance, Libby enjoys reading, baking, and walking her dog.
Alyson is the Editor-in-Chief and CCO at Fortune.  She was previously a co Editor-in-Chief overseeing Business Insider's tech and business coverage.She joined Business Insider in July 2008 as the company's sixth employee. She started as a sales planner before joining the editorial team in 2010, where she became a startup reporter and was first to cover some of today's largest tech companies, including Pinterest, Tinder, Instagram, Uber and Snap. Alyson rose to become a senior correspondent, then Executive Editor.She was appointed Editor-in-Chief of Business Insider in 2016, at which point she became the youngest and only woman to run a global business publication. Under her leadership, the business division has grown to hundreds of  millions of monthly readers.Alyson was a host of  Insider's conferences and launched a podcast, "Success! How I Did It," where she interviewed influencers ranging from Sheryl Sandberg to Steve Ballmer about their career paths (subscribe on iTunes here).She has appeared on ABC, Good Morning America, Al Jazeera, MSNBC, CNBC, CNN, and CBC, and she has interviewed media personalities such as Megyn Kelly, technology leaders like Fred Wilson, political leaders like John Brennan, and sports star LeBron James. She is a judge for the prestigious Gerald Loeb Awards in business journalism, and has been named one of Min's Rising Stars in Media, as well as Folio's 2017 Top Women in Media.She graduated from Syracuse University's Newhouse School of Public Communications, where she majored in psychology and advertising.You can read some of her investigative articles here:— Leaked videos reveal the true founding story of Snapchat— The founder who dumped Jared Kushner: Inside the phone call that left the White House star in a fit of rage— The downfall of billion-dollar startup, Fab— How a startup that raised the largest seed round in Silicon Valley history blew itself up before it even launched— The dark side of Facebook, where people lie, cheat, and make millions— A profile of Uber's controversial CEO, Travis Kalanick— The mystery of Jody Sherman, a founder who was driven to suicide and left behind a shocking business disasterDisclosure: Alyson owns bitcoin and Snap. She is also an investor in The Spun, a sports-media startup founded by her husband.