Before the cloud powered the modern enterprise, it started with a college dorm, a borrowed garage, and a vision to make work simpler.
In this conversation, Aaron Levie, co-founder and CEO of Box, shares how he turned a college project into a billion-dollar SaaS company. From building during the early days of the internet to leading through massive technological shifts, Aaron reveals the lessons behind Box’s evolution from a storage startup to a global platform used by 70% of the Fortune 500.
He reflects on the rise of AI, how it’s reshaping the software industry, and why this moment mirrors the early days of cloud computing. From the changing economics of software to the new era of AI agents, Aaron explains what it takes to stay relevant and keep innovating when the rules of business change overnight.
A masterclass in resilience, adaptability, and leadership from one of Silicon Valley’s most curious minds, proving that innovation is less about technology and more about the people who dare to rethink it.
Follow Aaron - X (Twitter): https://x.com/levie
Follow Derek - X (Twitter): https://twitter.com/derekjandersen
Timestamps:
0:00 – Welcome to Divot: Making Your Mark on the World
0:19 – From College Project to $4 Billion Company
1:31 – Free Rent, Big Dreams & Dropping Out
2:43 – The Birth of Box and the Cloud Idea
3:49 – The Pivot That Changed Everything
6:45 – AI Disruption: Startups vs Incumbents
10:56 – The New Economics of AI and Software
13:07 – What Clay Christensen Still Teaches Us
15:31 – AI Agents and the Future of Work
20:17 – Managing Teams in the AI Era
26:10 – How Box Shifted to an AI-First Company
40:41 – Leadership, Abundance Mindset & Life Lessons
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YouTube: https://www.youtube.com/@Divotpod
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Hashtags:
#AI #FutureOfWork #Leadership #Startups #Entrepreneurship #SaaS #CloudComputing #AIInnovation #AaronLevie #Box #TechLeadership #DivotPodcast
