As has become a ritual for much of the Silicon Beach community, I headed out to Jason Nazar’s latest Startups Uncensored last night and surprised myself by just how many great insights I took away from his guest, Box CEO Aaron Levie.

Box CEO Aaron Levie

To get an idea of his impact, Aaron co-founded at 19 years old and 8 years later, it’s being used by 92% of Fortune 500 companies (He’s only 27!)   I’ve been often told that I talk fast, but Aaron was going full speed for a solid hour and a half… and I just about blew threw my iphone battery taking notes in evernote!

With that said, I boiled my insights into the top 5 takeaways. Enjoy!

  1. Capitalize on getting lucky.  He mentioned multiple times in multiple ways that he simply got lucky with timing. But the real difference that came through in his talks was that he was always looking to capitalize on inefficiencies and deficiencies in the market.  One example that stuck out was that he was lucky to be at USC in 2005 struggling with a problem (storing files online) that was not only a common problem at universities, but a common problem within the enterprise as well (although he didn’t know the latter issue at the time). By solving this problem and then bringing it to the enterprise first, he has been able to create a business with 700 employees that has raised 300M in funding!
  2. Learn by doing. Although he co-founded at 19, it was far from his first company.  He had been creating websites since a young teenager and had attempted tons of different monetization strategies.  By the time he was ready to solve the online file storage problem, he had the knowledge and skills to bring together services from many different sources allowing him to start the company on the cheap and start charging users on day 1 of launch.
  3. Solve enterprise problems. He’s admittedly  bias towards enterprise software, but genuinely sees so much opportunity there.  One great example he gave is that smartphones (mobile) have been a core part of enterprise for a few years now and yet there are no major new players in the space. Surely some startup can figure out a way to crack the nut and become a major player there.
  4. Listen, listen, listen. His biggest mistakes revolve around not listening to customers soon enough.  He talks about how customers were asking for an enterprise solution early on (back when was consumer-focused), but it took them over a year to start serving this market that has become core to their business.
  5. Ask the right questions when hiring. He mentioned that Box is extremely focused on only hiring incredible candidates… and he said one question that they often ask themselves about a candidate is “what would it be like if we took a drive to LA (from SF) with this person? Would we learn new things? Be engaged? Bored?”   Even better, I’m definitely going to be using this questions during interviews with rockstart candidates:  What was holding you back from accomplishing even more?

Curious to see some insights our team has gained from other Startup Uncensored interviews? Check out:

And if you’re feeling the need to learn even more Aaron Levie, Inc published a great article a few months ago that dives into his business and work habits.