Aaron Levie is the founder and CEO of Box, the cloud content management and file sharing service for businesses. If you work in the modern business world, then you have almost certainly used Box to save and share documents. In this episode, Byron and Aaron talk about how he and his co-founders first built the company in 2004, why they decided to serve enterprises over consumers, and insights on building an a C-Suite, culture, and transitioning into being a CEO of a public company.

Top highlights from this episode include:

How Aaron and his founding team approached their pivot to the enterprise: “By ‘06 and ‘07, we asked ourselves: ‘What if we let an enterprise deploy a hundred or a thousand users and we’ll just charge per seat? It’ll be a monthly recurring business model and we’ll have all the IT and the security features that they need?” Aaron said. “We’ll sell this as an enterprise software product with a bottoms-up distribution motion with a sales team that works off of those customers. And so in a matter of a few weeks, maybe to a month or two, we designed the business model that has stuck with us to this day. In ‘06 and ‘07, this model pivoted the company, and made sure that we had a kind of a modern enterprise software model that was bottoms-up, consumer-driven, but also focused on selling to large enterprises and to the Fortune 500.”
Why all feedback is always useful to consider: “I can look back now with the benefit of hindsight and I’d say 95% of the feedback that we got from the investors that turned us down was actually correct,” said Aaron. “Either it took us longer to realize it, we didn’t get it, maybe we didn’t answer in real time in the right way. Maybe we didn’t portray actually why we agreed because we were taken aback by the feedback. Take feedback from everybody you can, because oftentimes you can synthesize it and take just the bits and pieces across all of the people that will give you constructive or critical feedback.”
The importance of finding a great COO: “COO has become obviously quite a catch all term in the Valley and I think one company’s COO doesn’t look like another company’s COO. That’s because the role is usually a way of complimenting and balancing out the skills or the gaps of the CEO,” said Aaron. “For me, I’m very product oriented. I tend to lean more toward thinking about the strategy, our customers, the culture, and not necessarily the entire day measuring the pipeline, building out the salesforce, and coordinating the end-to-end go-to-market execution.”
The power of achieving positive cash flow early on: “Ultimately the reason why cash flow early in a business matters is because it gets you in a mindset of having to build a business that is a real business that’s going to scale,” said Aaron. “When you’re thinking about scaling a company early on, this mindset ensures that you’re not burning lots of money, the model works, and you don’t need to raise an unbelievable amount of capital to keep the business going.”
Why an IPO exit is just the beginning for a company: “For the entrepreneurs and for the team going public is truly when the clock starts and it’s really game time. I think too many startups, too many founders, too many people, they think of the exit or the IPO as some sort of flag in the ground moment,” said Aaron. “All I can tell you is it only gets way harder and so going public at the right time, going public with the right team, with the right business model, both are really, really important because nothing will get easier about your company once you go public. It will only get harder. It’ll only get more stressful. It’ll get more gratifying for sure, but nothing gets easier.”

Dan Springer, CEO of DocuSign

Cloud GiantsBy Bessemer Venture PartnersApr 28, 2020