7 marathons and still building

Last week I launched the first episode of The Kanso Show, where I sit down with some of the brightest founders, executives, scientists, and creatives to explore one big idea:

How can we live alongside technology without losing what makes us human?

For episode two, I was joined by my good friend Jason Kuperberg.

Jason is the co-founder of OthersideAI, the company behind Hyperwrite, a leading AI writing and research assistant with millions of users.

He’s been working on generative AI wayyy before it was cool (seriously, check out our interview from 2020), and he has one of the sharpest instincts for where the puck is heading of anyone I know.

Dude is also a BEAST of a runner, completing 7 marathons and a PR of 2:46.

We cover:

• how early experiments with GPT-2 evolved into building one of the first generative AI writing tools

• why morning walks are essential to his presence

• the surprising way running and marathon training help him stay human while building in tech

• how digital tools like TikTok can both spark and stifle real connection

• why taking initiative with IRL relationships might be the most underrated skill in 2025

…and a lot more

Pumped to hear your feedback.

See you Wednesday,

Randy

p.s. - you can also listen on Spotify & Apple Podcasts if you choose :)