Jason Kuperberg is the co-founder of HyperWrite (OthersideAI), an AI writing and research platform with millions of users. Named to the Forbes 30 Under 30 list in 2024 for consumer technology, Jason studied biotechnology at Syracuse University before pivoting to entrepreneurship. Based in New York City, Jason balances his work in AI and innovation with his passion for running, having qualified for the Boston Marathon and holding a USATF marathon specialist coaching certification. Combining his interests in AI and fitness, Jason created Roast My Strava, an app that has been used by thousands of athletes around the world. He continues to develop tools and experiences that enhance creativity, productivity, and wellness through emerging technologies.

0:00 – Intro

1:30 – The Three Buckets of Jason’s Life

2:50 – Early Entry Into AI

3:40 – A Lifelong Runner

5:15 – Where AI Meets Real Life

7:30 – The Power of Online-Offline Connections

10:30 – Agency, Free Will, and the TikTok Moment

13:00 – Taking Initiative IRL

14:30 – Tools That Enable Real-World Connection

18:00 – Friend Curation as a Practice

21:00 – The Uncanny Valley of AI Companions

24:30 – From Glasses to Neuralinks

28:00 – The Small Talk We’re Missing

29:50 – Jason’s Personal Tech Guardrails

33:00 – Friction as a Feature

36:40 – Context-Aware AI Tools

39:00 – The Future of Wellness x Tech

41:15 – Sticky Notes and Side Quests