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 · last 12 months

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

Consumers wanted to pay as little as possible and they wanted a certain set of features that you'd have to go and build.

Enterprises wanted to pay a lot more, but they would need like a hundred times more features.

And

And as we kind of like thought about like, well, who do you focus on?

We did eventually kind of conclude, you know, something really obvious and retrospective.

And I can't like unsee it as they look at other people's strategies over time.

These were just like totally different markets, like the enterprise needing to securely manage their most important data as an organization.

would require just a completely different set of functionality than what a consumer would need to back up their photos and access their music from anywhere.

And those were just different markets.

And there was different business models.

One would pay like $5 a month.

The other would pay maybe $5 million a year.

And like completely different business models, different markets, different teams you'd have to build, different products you'd create.

So we did eventually run into, you know, effectively a fork in the road.

And after a few months of kind of debating it out and assessing the opportunities and, you know, people kind of having, you know, pretty different views on what to do, we eventually pivoted, you know, kind of very forcefully into the enterprise.

We, you know,

almost burned every boat other than a couple that we still wanted a freemium model in the enterprise.

We wanted you to be able to sign up as a kind of knowledge worker, but we very firmly wanted to make it an enterprise-only business model.

And I was actually the most reluctant and the last one to be convinced to pivot.

So kind of credit to the other founders and some early employees that I think had more conviction.

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