In this episode of Superhuman AI: Decoding the Future, Hassan and Zain are joined by Jesse Middleton, former WeWork executive, early-stage tech investor, and hacker extraordinaire. Jesse shares how his journey from playing with early Apple computers to helping WeWork scale from a small team to a global phenomenon has influenced his unique approach to startup investing and the future of work.

Jesse provides insights into the wild early days of WeWork, how culture and focus built the company, and the lessons learned from its downturn. Jesse also dives into his investment philosophy, the explosive growth of AI, and why he believes the next decade will see AI transforming industries in ways we can hardly imagine.

We also learn about the role of culture in startups and hear Jesse’s predictions for AI’s impact on the regulation space.

What we talk about:

(01:05) Jesse’s journey from hacker to WeWork and beyond
03:42) How Jesse’s love for breaking things led him to the tech world
(05:48) The moment Jesse met Adam Neumann and joined WeWork
(07:06) WeWork Labs: Building a space for tech entrepreneurs
(09:58) How WeWork grew
(12:00) The rise and fall of WeWork from an insider’s perspective
(13:14) Key takeaways from WeWork: Focus and culture
(15:12) Jesse’s philosophy on startup investing and AI’s future
(19:12) AI’s impact on regulated industries and the creative fields
(21:33) The rise of Small Language Models (SLMs) and agentic AI
(25:51) AGI: Will it happen and how it could change everything?
(28:35) How AI is already making a difference in Jesse’s life?

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