Aaron Levie, CEO of Box

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.”