Why This Founder Says You Shouldn't Be Afraid to Go Big

Entrepreneur Staff

Editor’s Note: Entrepreneur’s “20 Questions" series features both established and up-and-coming entrepreneurs and asks them a number of questions about what makes them tick, their everyday success strategies and advice for aspiring founders.

Aaron Levie started Box, his enterprise file-sharing and cloud-storage company in 2005 with three friends from high school when he was just 20 years old. From their first office, a garage in Southern California, the young entrepreneurs captured the attention of investors like Mark Cuban and their startup took off.

Eleven years later, the company, which makes software solutions to help its users and businesses safely and securely share and collaborate on their work has more than 71,000 business customers across the US, Canada, Ireland, Germany, Japan, Australia and Singapore.

Box, which became a publicly traded company in 2015 and is valued at more than $2 billion, also counts nearly 65 percent of the businesses featured on the Fortune 500 list as clients.

As part of his mission to help people communicate on the job more efficiently, his goal is to encourage creativity all over the the country and the world.

“I think that the job of Silicon Valley more and more is that we have to bring both the opportunities and the innovation to throughout the country and not just be isolated in Silicon Valley.”

We caught up with Levie and asked him 20 questions to figure out what makes him tick.

This interview has been edited for clarity and brevity.

1. How do you start your day?
I usually start every day going straight into email. I catch up on what I missed throughout the night and shooting off rapid-fire responses. Eventually I go into work within 45 minutes or an hour of waking up, so no other crazy morning routines.

2. How do you end your day?
I usually end the day by sending more emails. And then for the last  20 or 30 minutes, I am reading a book. The kind of books I choose are always non-fiction business books, so sometimes I can go to bed pretty quickly after reading one.

3. What’s a book that changed your mind and why?
My three favorites, if I was stuck on an island, and had to build a business, I would choose Blue Ocean Strategy by Renée Mauborgne and W. Chan Kim, The Innovator's Dilemma by Clayton M. Christensen and Only The Paranoid Survive by Andrew Grove.

4. What’s a book you always recommend and why?
Those three books, because they have been some of the most influential in shaping my thinking around how businesses scale and how you should respond to change. How do you deal with disruption in your business? How do you know make sure you continue to innovate?

5. What’s a strategy to keep focused?
I’m not the best person to ask that question, because I tend to be pretty scattered. Most things I’m working on, max, I spend 30 to 60 minutes and then move on to the next thing. It’s a strategy that works for me, but it's just not how I define a strategy for staying focused.

Related: This Founder Shares How to Tailor Your Schedule to Fit Your Brain

6. When you were a kid what did you want to be when you grew up?
I wanted to be a magician and a filmmaker -- those were my two big hobbies in middle school and high school. The art of magic is a fun thing because of the mystery behind it and entertainment that goes into it. I did a lot of birthday parties for little kids, and it was fun to see their reaction to it. But after doing it 100 times, it can get tiring. 

And so I decided after 30 to 40 years of doing kid birthday parties, I would get worn down. I opted for a different path.

7. What did you learn from the worst boss you ever had?
I didn’t have any bosses. I had people that managed me during internships, but they wouldn’t qualify as a bad boss.

8. Who has influenced you most when it comes to how you approach your work?
An early investor in the company was Mark Cuban. He had formative feedback for us early on in the business. We were splitting our strategy in two different directions, and he advised us not to hedge our bets as a young startup. We didn’t have the resources, and it gets too distracting. He advised us that we had to just choose one path. We fortunately chose the right direction.

He was also helpful early on about cash flow, and to make sure we have control of our destiny as a business.

9. What’s a trip that changed you?
I do a lot of traveling visiting customers and getting to know the businesses we work with. I tend to go on trips visiting different businesses in a variety of industries in places like Georgia, Indiana, Minnesota, South Carolina, Ohio.

I think there is such an excitement around what the future holds with technology, and what's possible with technology. I think there is kind of universal kind of hope and optimism around what the future looks like.

I think there is more that can be done going forward, at least as it relates to the future of jobs and the future of work.

10. What inspires you?
The thing that most inspires me is when you see an idea or an innovation that completely changes everything you thought was possible. When you look at Airbnb, seven years ago it would be preposterous, but today it is transformative. Or look at Tesla. Ten years ago it is hard to imagine the ripple effect of one company trying to change the car industry. By seeing insanely hard problems get solved through innovation, or when an industry is flipped on its head and rewritten in a way you never would was possible, helps me reflect back on what is possible in our own space.

Related: Tory Burch Says Inspiring Entrepreneurs Share These 3 Qualities

11. What was your first business idea and what did you do with it?
I started a search engine in high school. It was a really bad idea. We randomized the search results, because it was more beneficial to website owners than it was to users. We wanted to give everybody equal placement. What that resulted in was that it was irrelevant content, and we were out of business within six months. Just don’t do bad ideas was my takeaway from the experience. Over time that lesson was fortified; it is one anyone can live by. No matter how hard you try, bad ideas will never work.

12. What was an early job that taught you something important?
I think everything I learned from being a magician when I was younger, and the impact it had on how I see things -- everything from customer service to how to create experiences for people. And all of the early internet ideas we did informed me on what things work, what things don't work and how to solve problems from the ground up. If you aren’t solving a problem in a way that better than how things have been, customers don’t have enough time to care about your product.

13. What’s the best advice you ever took?
Don’t hedge your bets. That has always been something I've reflected on. I make sure any time we need to make a hard decision, it's better to make that hard decision than trying to create a path that lets us optimize for multiple outcomes. It's the only way you can really execute: put all of your resources behind whatever your strategy is. You can't dilute your resources and go in multiple directions.

14. What's the worst piece of advice you ever got?
The worst advice comes when you have a solution that you know is hard and it could work, but is reliant on some kind of long-term trend working in your favor. The advice in those situations is wait before you execute that plan, or maybe the world’s not ready for it. I've always found that I'd rather be too early and continue to iterate than be too late and have missed the trend completely, because somebody else has exploited it before you do. So, I think relying on my gut instinct and making big bets has gone against a lot of advice we've gotten over the years.

15. What’s a productivity tip you swear by?
I make sure that I take a nap once a day. That is probably the single best driver of productivity other than the three cups of coffee I drink.

Related: Why Everyone Can Use Randi Zuckerberg's Number One Focus Tip

16. Is there an app or tool you use in a surprising way to get things done or stay on track?
I live by our our product called Box Notes. I have a list of 200 things I'm trying to track, pay attention to or work on at any given time, so that’s basically how I run my life. Hopefully, you're checking more things off faster than you're putting things on the list.

17. What does work-life balance mean to you?
Not too much. I think in my case work is so exciting that it is life to me; it is what I enjoy doing. Every day I show up to work, I get to work with my best friends. It’s not something that I need to counterbalance with anything.

18. How do you prevent burnout?
It’s not the easiest advice for anybody to take, but I am constantly tracking the things I'm doing that I don't think I am good at. I try to delegate those things as frequently as possible, and get way better people to solve those problems.

I find the times where I'm the closest to burning out is when I'm doing a bunch of work I don't feel I’m well suited for. Also, being surrounded by people you enjoy being with, that you learn from, energize you and push you prevents burnout, too.

19. When you’re faced with a creativity block, what’s your strategy to get innovating?
It’s a combination of music and whiteboard or a notepad. I play some kind of classical music or Bob Dylan to get creative juices flowing, get a clean sheet of paper and brainstorm every possible solution to a problem. I list out new ideas until I’m exhausted and can’t come up with anything else, or when I get to the point where I think I have the answer.

20. What are you learning now?
It’s not so much new as something I’m diving into with more passion. I’m learning about how companies deliver world-class customer service. I’m learning from a range of businesses from Disney to Starbucks, reading a lot of books of those businesses and the founders of those organizations.

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