If you were to look at my cheat sheet, there wouldn’t be a lot on it. There would be a tennis ball, a circle, and the number 30,000. 

Drew Houston of Dropbox is one of my favorite silicon valley entrepreneur; he attributes a lot of his success to his belief that everything is figouratable. In the early days of starting dropbox, when he needed to figure something out, he went to amazon.com and bought the top-rated books on the subject, he read the books, and he then tried to apply the principles to his business.

Andrew Houston is an American Internet entrepreneur, and the co-founder and CEO of Dropbox, an online backup and storage service. According to Forbes, his net worth is about $2.2 billion. He attended Acton-Boxborough Regional High School in the 1990s. He later graduated with a degree in Computer Science from the Massachusetts Institute of Technology (MIT), where he was a member of the Phi Delta Theta fraternity. It was there that he met Arash Ferdowsi who would later go on to be co-founder and CTO of Dropbox.

During his time in college, Houston co-founded a SAT prep company. Houston and Ferdowsi co-founded Dropbox in 2007. Houston currently is CEO and 25% owner of Dropbox. In February 2020, Houston joined the board of directors of Facebook, replacing Netflix CEO Reed Hastings, who left in May 2019.

Some top insights from Drew Houston

• No one is born a CEO – continuously improve yourself: There’s no beginner’s guide for CEOs
• Study Excellence
• Surround yourself with like-minded people.
• Have thick skin (naysayers) and thin skin (customers)
• Beware of your mortality

According to Drew, in an MIT Speech he gave in April 2018 : The best way to learn is to read

To learn how to run a business, Houston initially set out to meet as many successful entrepreneurs as he could. He said he quickly realized that there was only so much that they could cover in a 15-minute coffee meeting — and that, after a while, it all started to sound the same.

Instead, Houston took to reading. To learn about sales, he bought the three highest-rated books on Amazon about the sales process.

“This doesn’t make you great, but it helps you learn what to look for next,” he said.

Being so systematic about learning also helps you approach topics or tasks that are unlikely to be enjoyable at first, Houston said. In his case, as an engineer, it was public speaking and management. “It’s like learning to ride a bike,” he said. “You can’t be discouraged and stop when you get scraped up — and then it becomes super easy later on.”

Take on Goliath — and win, w/Dropbox’s Drew Houston Masters of Scale with Reid Hoffman

HOUSTON: I’ve always found it incredibly helpful to be systematic about training yourself, because no one’s going to do it for you. I had everything down when it came to building the product – or at least the engineering and getting something basic out to market. But then I realized that I did not know anything about sales or marketing or financing a company or managing people. And the list gets pretty long pretty quick – and not a lot of time to learn it.

HOFFMAN: It’s a feeling every founder knows. Drew initially took a brute force approach to learning how to run a company, like a student trying to cram for their SATs the night before the exam.

HOUSTON: I’d go on Amazon, I’d type in “sales marketing strategy”, all these things, and just buy the top one or two rated books, and just crank through them.

In her book, Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity, Kim Scott, writes:

Drew Houston, cofounder and CEO of Dropbox, is the most committed and humble learner I’ve ever encountered in my career. The reason why Dropbox has hundreds of millions of users is because the company, led by Drew, has been relentless in making the product intuitive and easy to use.

Drew has been singularly willing to try things, admit they didn’t work as well as he’d hoped, and pivot. Hard as it is to launch and iterate with your company’s products, though, it’s much harder to do the same with one’s self. But what really impressed me about Drew was that he is even more relentless in reshaping himself as CEO than he is in improving upon the product his company builds. Drew has probably read and reread every book on management ever written. He has thought extremely deeply about what kind of company he wants to build, and what kind of leader he wants to be.

The Tim Ferriss Show (#334): Drew Houston

Tim Ferriss: I was doing homework for this, which I always enjoy doing when it’s someone I know because I dig up all these bits and pieces that I then want to ferret out and explore a bit. I came across this line that described a folding chair on top of a fraternity at MIT and that you would go up there with piles of books and read these books. So, can you place us when that was in your undergrad career and how you chose the books and why you did that?

Drew Houston: Yeah. So, it was about my junior of undergrad. I took a leave of absence because I had an idea for a startup that I wanted to pursue. So, I took a year off to do that. This was back in 2004. I was maybe 21, and the SAT was changing. I started an online SAT prep company because the opportunity was the SAT was changing in 2004, 2005 from 1600 to 2400 points. So, suddenly, all of the course material overnight was gonna be obsolete.

I saw an opportunity to maybe develop not just a course for the new SAT but an online course, and I teamed up with a former teacher from my high school who had his own little cottage SAT prep company. And I’m like, hey, if we come together, we can put this thing online, and we’ll be on an even playing field because all those 800-page books that have been printed about it are now obsolete. And who really wants to go to some classroom at 8:00 on Saturday anyway? We can build a much better experience if we do it online.

I was really excited about starting a company, and we jumped into it. And I think we met in a Chili’s and were planning world domination and figuring out, okay, how do you incorporate a company? And so it was a really great introduction to the world of starting companies. And then the more I learned about the mechanics of starting a company, the more I realized I didn’t know about business. And I knew a lot about engineering and programming, and I had worked at startups. But there was a fog beyond just like building the product. And so I was like, all right, I know sales and marketing strategy.

These are all things, and all I know is I don’t know a lot about them. So, I had the highly scientific method of I’m just going to go on Amazon, type in sales, buy the top three or four books, and just do that for every category. And then I had a couple book recommendations from one of the founders of one of the companies where I worked as well.

But it was great, and it was an important combination. One was actually starting the company gave me motivation to really learn the stuff because I think a lot of times when you’re reading it can just be like entertainment basically. It’s like where you just read the book. You’re like that’s interesting but then don’t use the knowledge. But when you’re actually starting a company, then you really have an excuse to internalize and really study the material.

So, there’s a big difference between reading the material and studying it, but I was pretty systematic about it. I’m like, okay, here’s all the stuff that I don’t know, and then reading’s going to be a good way to get me introduced to all these topics.

Maybe the first instance of that was when I went through my high school, and there are a lot of great books that you read as part of your high school curriculum. Then I stumbled across a book, Emotional Intelligence, by Daniel Goleman, and I was like, oh my god. I mean, it’s nonfiction, but it spelled out something that I just didn’t know you could kind of break down in a logical way.

And, suddenly, I had this understanding about the world that I didn’t have before, and so that was important because it was sort of one of a bunch of early examples that anything is trainable. It got me on a path to developing what we’d now call a growth mindset and realizing that it’s possible to learn about these things where you have no experience or where it’ easy to be like, oh, I don’t know about that, or I’m just the engineer. I’m not a business person and kind of shatter that misconception.

Tim Ferriss: Do you think that you were open to all these different categories of learning because of the necessity vis a vis starting the company? The reason I ask that is that it’s not across the board, but some people with engineering chops seem to have a learned or intrinsic disdain for sales, marketing, these different bits and pieces of businesses that are a little softer, let’s say, less quantifiable in some respects.

Was it simply the motivation in building this company where you had to wear all those hats that kind of drove you into these different categories? Or were you intrinsically – using that word quite a bit – interested in learning more about these different buckets through these different books?

Drew Houston: I think it was a little of both. So, certainly, starting the company made it a necessity and created a lot of additional motivation, but I also found these other topics just as interesting as the engineering. And I think it’s a big cultural thing when engineers start off by being dismissive or defensive about, oh, the technology is all that matters or if it doesn’t have a triple integral and Greek letters, it doesn’t count. That’d certainly be like a cultural meme at MIT, and I think it just creates a huge blind spot for people both because it makes them less effective but the stuff is actually really interesting. But I kept having experiences like that, and that Emotional Intelligence was just one example. But I took a class on negotiation at MIT, which sort of opened my eyes a notch further on this kind of thing where I’m like, all right, negotiation.

I go into that class. I don’t know a lot about it. I’m like whoever yells louder, lies more, smacks the table harder, I guess that’s what makes you a good negotiator. And then this class, I mean, those are tactics, but the class has these frameworks where like, okay, smart people have thought about this. And they have broken it down, and it turns out that there’s a whole process of uncovering mutual interests and figuring out what your leverage is and your best alternative, da-da-da, and spelling it out in a way where I was like, actually, this is a lot more straightforward than some of the theoretical math classes I have to take. And it’s a lot more applicable to my daily life. So, I really appreciated learning a little bit about a lot of different disciplines and just putting up a folding chair on my roof was the first thing that came to mind as far as how I could actually do that.

Drew Houston’s 2013 MIT Commencement Address

• I lived in my fraternity house every summer, and up on the fifth floor there’s a ladder that goes up to the roof. I had this green nylon folding chair that I’d drag up there along with armfuls of business books I bought off Amazon and I’d spend every weekend reading about marketing, sales, management and all these other things I knew nothing about. I wasn’t planning to get my MBA on the roof of Phi Delta Theta, but that’s what happened.
• It took me a while to get it, but the hardest-working people don’t work hard because they’re disciplined. They work hard because working on an exciting problem is fun. So after today, it’s not about pushing yourself; it’s about finding your tennis ball, the thing that pulls you. It might take a while, but until you find it, keep listening for that little voice.
• They say that you’re the average of the 5 people you spend the most time with. Think about that for a minute: who would be in your circle of 5? I have some good news: MIT is one of the best places in the world to start building that circle. If I hadn’t come here, I wouldn’t have met Adam, I wouldn’t have met my amazing cofounder, Arash, and there would be no Dropbox
• The last trap you might fall into after school is “getting ready.” Don’t get me wrong: learning is your top priority, but now the fastest way to learn is by doing. If you have a dream, you can spend a lifetime studying and planning and getting ready for it. What you should be doing is getting started.

The last trap you might fall into after school is “getting ready.” Don’t get me wrong: learning is your top priority, but now the fastest way to learn is by doing.

Drew Houston’s most Recommended Books

• High Output Management by Andrew S. Grove 
• Poor Charlie’s Almanack by Charlie Munger
• The Effective Executive, by Peter Drucker
• The Hard Thing About Hard Things, by Ben Horowitz
• Competing Against Luck, by Clay Christensen and Karen Dillon
• Only the Paranoid Survive: How to Exploit the Crisis Points That Challenge Every Company by Andrew S. Grove 
• Becoming Steve Jobs, by Brent Schlender and Rick Tetzeli
• Emotional Intelligence, by Daniel Goleman,
• Hard Drive: Bill Gates and the Making of the Microsoft Empire, by James Wallace and Jim Erickson
• Founders at Work, by Jessica Livingston
• Guerrilla Marketing: Easy and Inexpensive Strategies for Making Big Profits from Your Small Business by Jay Conrad 

All the best in your quest to get better. Don’t Settle: Live with Passion.