Betting on the Cloud Before it was Cool: The Rise of Box w/ Aaron Levie

With an insatiable appetite for “what’s the new model,” Aaron Levie, Co-founder and CEO of Box, grew up chasing ideas without hesitation: performing magic at birthday parties, building websites, and making short films. In this episode of HD in HD, he shares how a curious mind from early ages became his greatest strength, and how staying slightly uncomfortable kept him ahead of the biggest tech shifts, from SaaS to AI. Today, Box powers content for 100k+ organizations and 68% of the Fortune 500, and is still driven by the same restless energy Aaron had as a teenager, always chasing what’s next. In this episode, we also get into: overcoming critical challenges when scaling storage capacity the move that set Box apart from Dropbox how AI is becoming the next major accelerator for Box 00:00 Intro 00:57 Brex Sponsorship 01:44 Aaron Levy's Early Years 02:24 High School 13:04 College 17:29 The Early Days of Box 23:17 Technological Shifts and Challenges 29:39 Navigating Competition 30:00 Enterprise Differentiation 32:24 Brex Sponsorship 33:12 AI’s Impact on Software and Work 44:51 AI's Role in Enterprise Knowledge Management 48:07 Future of Organizational Design 55:50 AI's Influence on Sales and Marketing 01:03:50 Reflections on Luck, Strategy, and Mistakes ABOUT US: We’re proudly sponsored by Brex—a brand I co-founded, now supporting over 30,000 businesses like Anthropic, DoorDash, and Scale AI, helping them make every dollar count. I’m grateful for their continued support as I bring you all conversations with some of the most exceptional founders of our generation. For more information, please go to: https://www.brex.com/?ref_code=bmk_audio_HDinHD Connect with us here: 1. Aaron Levie- https://www.linkedin.com/in/boxaaron/ 2. Brex- https://x.com/brexHQ 3. Henrique Dubugras- https://x.com/hdubugras This episode was produced and distributed by our friends at Atomik Growth: https://atomikgrowth.com/