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 became this very kind of calculated decision, which is,

What's the amount of kind of, you know, how big is this market still ahead of us?

We thought very large.

Do we like our kind of compounding kind of, you know, approach where we think we're getting better every day, every week, every month at our product and our strategy?

We know that there's going to be a lot of headwinds and a lot of severe competitive pressure that we're going to face.

So it's not going to be easy.

And then it basically just came down to like, you know, the kind of Bezosian regret minimization framework of like, what thing are we going to regret more or less?

And we at least we convinced ourselves that we would more regret not continuing and just seeing the next set of cards and keeping on scaling more than we would regret, you know, sort of turning down this offer and having to start over.

I don't know if it's actually true.

Like, what would we have really regretted more?

But that was the decision.

It was gut-wrenching.

Like, we did an offsite with the four of us.

We were in our mid-20s, so probably two of us were, like, 25, 24, 23.

And we don't really talk specifically about the offer, but, you know, call it, like, in the half a billion range.

Not safety net levels of secondary.

So this was a very different time period in the Valley.

So this was, you know, very early 2010s and secondary was not neither in fashion as much as it is now, nor were the amounts of capital the same level.

So I think it was like, you know, people could, you know, feel better about the apartment they were renting as opposed to like, we're like good on the decision.

Honestly, if there's like any analogy that works for my entrepreneurial life, it would be that.

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