A $3.6B founder's honest take on the software market right now

TL;DR

Aaron Levie, Box founder, recounts the company’s pivot from consumer/agnostic to enterprise-only, a decision he was initially reluctant to accept but now sees as the only path to survival against Google, Apple, and Microsoft.

Key insights

• The enterprise vs. consumer decision was a multi-month “fork in the road” where consumers would pay ~$5/month and require one set of features, while enterprises would pay ~$5M/year and need a complete
• Box chose enterprise because the consumer space was a “death pit” – Google, Apple, and Microsoft would bundle storage for free, making it too competitive and commoditized. Dropbox succeeded despite th
• “Most dollars in AI will eventually be enterprise dollars” because intelligence is valued most where software is valued – in business, not in consumer (except the three ad-driven giants).