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1. I tend to not discriminate when it comes to people I can learn from. Basically, if someone has built a meaningful business in software, technology or media, faced disruption and adversity, and overcame underdog status, I want to know how they did it.
2. My dad is a chemical engineer, and my mom was a teacher. They were pretty serious about education, but I always thought about things a little bit differently.
3. My acronym is WWSJD: What Would Steve Jobs Do?
4. Steve Jobs is the most epic entrepreneur of all time. He served as a guiding light for any emerging businessperson who wanted to learn how things should get done. He’ll be looked at as one of the best business leaders of all time, and certainly one of the best tech entrepreneurs.
5. My downtime tends to resemble my uptime. Weekends are workdays, but toned down. Over the whole weekend, I may have five meetings, as opposed to six on a weekday. I used to play piano for 30 minutes at night, but I had to pull that out of my schedule. I don’t have time for nonwork stuff.
6. I interned at Miramax and subsequently at Paramount because I was really curious about the future of entertainment — how were we going to get films online? While the inspiration for Box didn’t come from that experience directly, it was very obvious that bigger businesses had a lot of slow processes and cumbersome technology.
7. The dynamic with social is you tend not to have products with 30% market share. It’s all or nothing. Email works because we have open standards that let you communicate across any email client.
8. I think people are always able to achieve more than they think they can. While that’s cliche, I don’t know if managers think about that enough. You have to set your sights extremely high.
9. I’m certainly not into money and prestige. For me there is simply nothing more exciting than people involved in the creation of great products. That is what drives me.
10. My mom is proud of me. But she might not be too happy about the hours I keep or how little I eat. I wake up so late that it would be inappropriate to have breakfast. At most, I will have a snack in the day and dinner. I realize that it’s not the healthiest way to live, but it’s all I really have time for.
11. It’s not accidental that products get worse over time; it’s because companies stop paying attention to them. They stop caring as much about maintaining the same quality they did when they were just trying to fight for survival and no one would pay attention unless they had the best technology.
12. If you think about the market that we’re in, and more broadly just the enterprise software market, the kind of transition that’s happening right now from legacy systems to the cloud is literally, by definition, a once-in-a-lifetime opportunity.
13. My workday begins around 11 A.M., with a cup of black coffee in each hand. If I had more hands, there would be more coffee.
14. There’s a lot of pride that business owners have. It’s actually really critical that pride and ownership extends to everyone in the organization. I think of everyone is in the same boat in driving the company forward.
15. I think bad politics are incredibly dangerous, so it’s important to make sure that people are communicating well. Culture and morale are super important. It’s best to not force it, but let it happen organically and genuinely.
16. I think I’m the kind of person who would be very difficult to employ — I’m pretty annoying, but driven.
17. It’s unfortunate biologically we have to sleep.
18. The business models in enterprise have changed pretty dramatically. A huge problem with enterprise software traditionally has been usually you sell to the customer and then they adopt the technology. The great thing about ‘freemium’ and the new way enterprise software is being sold is you get to try it first and then buy it.
19. My co-founder Dylan Smith and I left our junior year of college to move to the Bay Area. To the horror of our friends’ parents, we actually had two other friends drop out of college to work on the product. The four of us were just working non-stop growing Box.
20. All of a sudden, if you think about the entire ecosystem of connected devices that can pull down information, access content and allow me to share and work and communicate, the vast majority now are not Windows computers. They are iPhones. They are iPads. They are Android devices.