Aaron Levie on Entrepreneurship, Education, and More

The transcript of my conversation with Aaron

Afraj Gill
12 min readMar 30, 2014

In July of last year, I visited Silicon Valley for a research trip to interview notable technologists and entrepreneurs, including Aaron Levie, Sal Khan, Vivek Wadhwa, Ray Kurzweil, and others. The purpose was to get their take on the future of education. Of course, when you speak with someone like Aaron, you end up learning a lot more.

So, in the spirit of Box’s upcoming IPO and Aaron’s amazing (and humorous) character, I finally decided to publicly post the transcript of a portion of my conversation with Aaron. Some very small excerpts from my conversations with other folks have been published here.

I am posting this with the hope that some people might find Aaron’s insights useful, helpful or inspiring. I have learned a lot from him, and I feel grateful to have had the opportunity to meet him.

(My questions/comments are in italics/bold, and all answers or quotations are Aaron’s.)

With Aaron (and his red Pumas) at Box HQ.

The conversation:

I know you started making websites when you were 14, but what were your learning interests before that?

Well, it’s sort of a hazy memory, but I used to study a lot of illusions and magic. I did that until about 16, but then the Internet sort of took over my life. I’ve always been interested in business, fundamentally.

How much of your formal education has helped you get to where you are today, with Box?

There are a lot of fundamental things you need to learn in school, such as understanding critical thinking or basic math. I probably didn’t apply a whole lot of vocational or applied skills (they didn’t teach cloud computing in high school back then). [Laughs].

Most skills are the fundamental building block skills — which you can then go and apply in unique ways, based on what industry you choose to go in. That’s where the learning really starts. I read lots of books people have written about the industry, and that’s where I get a lot the applicable skills.

So, self-education is more important?

Yes, through reading lots and lots of books, from business school professors and outsiders who have analyzed industries. Other times, just reading biographies and autobiographies of entrepreneurs.

Hypothetically speaking, let’s assume you were finishing high school in the next few days, and you didn’t run Box. So knowing what you know right now (after having run your company for so long), what would you do? Would you still go to school? If yes, what would you study?

I would absolutely go to school. I think that one of the best things about college — and I think that Peter Thiel may have missed this in the Thiel Fellowship — but one of the greatest things about the college environment is that you basically have a 4 year period where you really have no responsibilities, except going to classes. And you’re around some of the smartest people that you’ll ever meet, depending on the school. You also have a 4-year period where you can do whatever you like. I think a far fewer number of people actually take advantage of that than they should. You’re in an environment and around people where you can actually be starting companies/businesses. You can be going after opportunities.

I think going to college is a great decision. Learn as much as you possibly can. Take as much of a varied curriculum as you can possibly go into. I was at USC and they had a lot of entertainment courses, a lot of business courses, and a lot of technology courses that you could [enroll in]. I wanted to learn as many things as I could about a broad variety of subjects and meet a lot of people [who] were going to go off and do a lot of interesting things. I ended up starting the company with my co-founder, who was at Duke (so I ended up starting it with a high school friend). But college is a great 4-year period where you can actually afford to go out and start new things.

Actually, if you think about some of the biggest companies in history, they were started in college. I don’t think that’s an accident. I think it’s because you don’t have to worry about showing up at a job every single day. Of course, a lot of people have to put themselves through college and that does take up a lot of time in other respects, which we should be thoughtful of. But I do think that going to college, making great connections, learning as much as you possibly can, is a good thing.

That’s a separate issue than the cost of education, the quality of education, and all the other issues surrounding the institution of education. That’s a huge issue. But I don’t think that means you shouldn’t go to college.

“Actually, if you think about some of the biggest companies in history, they were started in college. I don’t think that’s an accident.”

Was it tough for you to decide to dropout?

No, it wasn’t tough for me.

Were your parents supportive?

Oh, it was very tough for my parents. It was much harder for them. They thought I was going to dropout and be a drug dealer [laughs].

For me, I was definitely always — at the back of my head — looking for an excuse to dropout, but you don’t want to do that until there’s enough of a significant and substantial reason as to why you would do that. Mark Cuban ended up investing in our company a few months after we started, and that was enough of an impetus to go off and run the business full-time, outside of college.

What’s been the biggest challenge for you at Box?

I would say that the most important challenge is that you have to build the best team that you possibly can. The companies that win are those that have the best possible people lined around the most competitive strategy. So my job and the job of the organization is to bring in those amazing people, and make sure that our strategy is one that is going to be the winning strategy in the industry. I think the challenge of business is to organize all of those variables and get them to work in concert. Also make sure that you are building incredibly innovative products, catching the markets at the right time, bringing together all the right people, and reaching out to all the potential customers. Those are the kinds of things that we do everyday.

“The companies that win are those that have the best possible people lined around the most competitive strategy.”

You put together a pretty talented team. As a young founder of this company in your early 20s, how did you manage to go to some extremely experienced executives who probably had secure jobs and convince them to join you in a risky venture (particularly given the fact that cloud at the time you started wasn’t a hot thing)?

It’s this challenging thing where people tend to not believe in your idea until it’s too late, for it to be useful for them to believe in it. So you spend a lot of time convincing people about your mission and vision, and about what it is that you’re exactly doing. What’s interesting is that you’re at a disadvantage when you’re younger because you don’t have the networks, and you don’t have a lot of credibility in the industry. But actually, you have a great advantage because you end up looking at the industry in a very new way.

Industries are generally changed and revolutionized by people with less of the historical context. That said, it’s much harder for them to gather the people that they need, to go and be successful. We got very lucky early on, where we brought in a chief operating officer; he was able to help us build the company and build the team around us. But the people that joined before him absolutely took a significant bet with their career and with their future by joining a startup run by, you know, people that didn’t have much experience as the founders running the alternative companies they could join.

Silicon Valley is very well suited for people wanting to join risky startups run by young people.

According to a study by McKinsey, half of the youth surveyed worldwide are unsure if their postsecondary education improved their chances of finding a job. And among the youth who actually worked, the study found that only 55 per cent managed to land a job relevant to their field of study. And on top of that, almost 40 per cent of employers say that graduating students lack the skills required for entry-level positions. I understand that you’re involved closely in the hiring process, where you interview candidates yourself. Have you found this to be true in your own experience? How can it be fixed?

Yes, I think the interesting thing is that, again, college primarily serves to give you the core foundational building blocks, and from those building blocks you go and learn new skills. But because you have the basic skills solved, you should be able to learn new things much faster, and you should be able to understand the core concepts and ideas, and apply them much more quickly.

I think it’s a natural expectation that schools are not going to keep up with the rate of change that happens in private industry. The job of the universities, high schools and middle schools should be to give those kind of building blocks: how to work with other people, how to collaborate, how to be creative, how to do math, how to do basic computer science, etc. Then you take those lessons and learn new layers of knowledge and skills on top of those. You will always probably see statistics like that, of people coming out of school into industry because of the rate of change in business is going to change much faster than what curriculums can possibly respond to.

The best thing you can do as a student: on the one hand, learn the core things that are the foundational building blocks and ideas, but on the side you should keep up with whatever industry you’re looking to join or business you’re looking to start. That makes you far more competitive. The graduating students that come to Box are able to instantly accelerate and perform very well because they were already paying attention to the trends in our industry while they were in school. They were already learning about the ecosystem we are surrounded by, and they have more context and visibility into what we’re trying to do, than their peers. The only troubling thing is that not enough people [put adequate time towards self-learning].

Should employers not become a part of this change? Should employers partner up with education providers?

Absolutely. I think the best examples are right here in the Silicon Valley. You have industry so close and so integrated with the university system of Stanford and Berkley and others. If you’re at the Stanford Graduate School of Business, you can have Eric Schmidt come talk to you, or lead a whole class.

So the level of integration or the closeness your curriculum is going to have to what’s going in contemporary industry is incredible.
Versus: You go learn the exact same category of courses, but you’re somewhere else in the country without that integration, it might be a lot harder.

The much bigger problem, though, is computer science and engineering education.

It’s interesting you say that because I just spoke to Google’s Director of Education and University Relations, and she said the exact same thing: computer science needs way more attention.

Totally. Like, order of magnitude more attention. The amount of computer science education and the number of people taking those kinds of courses is surprisingly disconnected with the volume of jobs that are available in the industry. And that sort of defies any type of microeconomic or macroeconomic learning that we have, which is the more demand there is, the more supply should be created. There’s a tremendous amount of demand for amazing computer science and engineering talent, and yet we’re not producing it at the rate we need to stay competitive.

It’s obviously why immigration reform is important to Silicon Valley. So if I were 15, I would probably study way more computer science, because that’s where the biggest opportunity of job growth is going to be in the next decade or two.

What can a country like Canada learn or take away from Silicon Valley? How can we replicate what’s going on here in the Valley?

You know, I think it’s going to be hard to replicate all of the components that you have in the Valley. You have a confluence of a very healthy capital environment, you have a number of universities that are heavily concentrated in one area, and you have a bunch of companies that continue to renew talent and ideas. It’s hard to take all of that and put it anywhere. I mean, there’s a reason why New York is the center for finance, and LA is the center for entertainment, just as Silicon Valley will remain a dominant player in technology.

If you want to work in technology, come work at Silicon Valley. More of the mentors, community, and capital are still going to remain in the Valley. So that’s important to recognize.

“The only way to get innovation is by accepting failure”

But there must be something we can learn.

The things to learn from Silicon Valley that can be applied in any region or any market is obviously risk taking. The only way we’ll get innovation is by taking risk. But by definition, when you take risk, it means that there will be failure. So perhaps the better way for other economies or regions to think about it is: the only way to get innovation is by accepting failure. And markets and regions and communities that don’t understand that are those that don’t thrive and are unable to produce such significant successes.

Don’t forget: it took many, many companies to try out the search engine for Google to be successful. There were many failures.

Every market needs to realize that you will have those kinds of failures, and those kinds of businesses that didn’t succeed. But the result, or the much bigger effect, is that you also get a Google. You have to risk your time, capital, and career decisions. It’s the only way you can make a big impact.

The thing I generally tell entrepreneurs is do something that wasn’t possible just one or two years ago. Because usually every couple of years, there’s a platform change, and if you’re not building technology or products that are being enabled by that platform change, you’re not probably going to have the underlying tectonic shifts that you need to cause your startup to grow and thrive. And I see a lot of businesses that aren’t actually taking advantage of that. They’re building things that are on a decline. Also: surrounding yourself with amazing people who you can work with is really critical.

“You have to risk your time, capital, and career decisions. It’s the only way you can make a big impact.”

In your opinion, what should the future of education look like?

I think there are a lot of opinions on what the future of education looks like. But I think the trends that are going to be most disruptive and take shape to create the most amount of change are those that fundamentally make education more accessible and more available to more people, in smaller and more modular parts.

The fact that you can now pull out an iPad and learn about a specific subject that is not available to you in any other way is an incredible transformation in education. I think when you apply that to all levels of education — whether that’s in kindergarten, all the way up to university, graduate school, or adult/continued education — that’s when you’ll see tremendous transformations in how people learn and what people learn. That’s everything from the online universities to what Sal Khan is doing, to what even educational institutions can do to put their content online and make it available to other people, extend it to new devices and new platforms that people want to be able to learn from.

These are the underlying trends that will make education both cheaper, affordable, and available, but it also means you can learn subjects at your time and at your own pace, [whichever] makes the most of sense for you as an individual. Education can also get much more precise in the relationship between the content and the student, which I think is very important.

--

--