Aaron Levie

speaker

468 appearances 1 recordings 1 series first heard Jul 2026 last heard 2 Jul

Aaron Levie’s voice in public audio — every appearance, attributed to the second.

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Recordings per month over the last 12 months — 1 in all, peaking in Jul 2026 with 1.

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My First Million · I dropped out of college and built a $3.6B company from scratch · 2 Jul 2026 podcast

So it's one of these things where it's like, you know, we have turned down offers, but we've also been in situations where we totally would have taken, you know, that very early offer and just taken it off the table.

And then later as we scaled, because we've had every problem thrown at us.

We've had rounds that didn't happen and just like totally busted rounds.

We've had to be bridge loaned by our investors twice.

So there are definitely parts of the journey where we would have, if anybody has shown up with any offer, we would have accepted it probably.

And then it's, you know, as these things go, like when people do actually show up for offers, you're like, your chemicals in your head are totally different.

And you're like, oh my gosh, like, we just got to keep doing this.

And so probably the most classic one that we faced was a very kind of serious interaction where,

where we would have been, I think, quite happy about the outcome on any kind of financial measure, but we looked at the situation and we were maybe our mid-20s, early to mid-20s at the time.

And I think this is now well-documented by a bunch of people, but I think it kind of just happens probably pretty uniformly, which is if you really deeply process it in a very intellectual sense,

And you're like, okay, this much money, this is super interesting, et cetera.

And then you start to play out, what am I gonna do in two years from now or five years from now or 10 years from now?

We basically just processed, we would probably be doing something just to get back to exactly where we are now.

It's unlikely that we're gonna work at this new company for more than five years each.

So that's not gonna happen, because every one of our friends that had gotten acquired had already left their acquired company.

So that was probably not gonna happen.

So then you just look at it and you're like, okay, well, you're probably trying to do everything you can just to get back to this exact situation.

But of course you have more cash, that's obviously positive.

But now we're in this situation, we've already defied all the odds of getting here in the first place and all the things that kind of got in our way.

Like, why don't we just continue to double down on this, given that we still believe the market is still a hundred times larger.

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