The Intersection of AI Innovation and Running with Jason Kuperberg

From pushing 2:46 marathon times to pushing the boundaries of AI, Jason Kuperberg discovered that the secret to both isn't about scale—it's about building exactly what you want to use yourself.

Jason Kuperberg is a tech entrepreneur, marathoner, and the creator behind ‘Roast My Strava’ — the viral website bringing AI to your runs and rides. He is the co-founder of HyperWrite, an AI writing and research platform used by millions, and was named to the Forbes 30 Under 30 list for Consumer Technology. Jason combines his background in AI and tech startups with lifelong experience in endurance sports to explore how endurance entrepreneurs and outdoor brands can operate, innovate, and experiment using AI today.

Jon chats with Jason about:

• how Jason achieved a marathon PR of 2:46

• introduction to generative AI and large language models (LLMs)

• the “Roast My Strava” origin story

• three-phase approach for implementing AI

• prompting and AI Interaction best practices

• angel investing philosophies 

Stay connected:

Follow Jason:

https://www.linkedin.com/in/jasonkuperberg

http://instagram.com/jasonkuperberg

https://www.strava.com/athletes/jasonkuperberg

https://x.com/jasonkuperberg

Roast My Strava:

https://communityhub.strava.com/insider-journal-9/developer-voices-from-weekend-side-project-to-community-sensation-how-i-built-roast-my-strava-12288

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