My guest today is someone who's been designing her own path since she was a teenager, and is now helping a whole new generation do the same. Calypso Rose is a British entrepreneur and founder of OffScript, a summit and platform helping young people and their parents navigate a future of non-linear careers, entrepreneurship, and AI.

Calypso describes herself as an accidental entrepreneur. At 22 she created Clippykit, those transparent, customizable photo handbags that grew from a small first order into a full blown brand, with celebrity fans and major retail partnerships. She then cofounded the Indytute, an experience company built around experiences (not things), running everything from ukulele classes to pop-up workshops in places like Selfridges, literally filling department stores with live experiences. Now with OffScript, she's taking everything she's learned—the wins, the loses, the pivots—and turning it into practical guidance: how to think like an entrepreneur, how to build resilience, and how to find your place in a world where AI and creativity collide.

So grab a cup of tea, and join me for a conversation with the wonderful Calypso Rose!

—

If you're in a position to make a donation, your contribution will go directly towards helping young people who couldn't otherwise afford to attend the 2026 OffScript Summit on the 24th & 25th of January, 2026. Every small amount can make the difference between watching from the sidelines and being in the room.

Donate here.

In partnership with 20/20 Levels

https://2020levels.org/

Instagram:

@iamcalypsorose

@offscriptgen

Website:

www.offscriptgen.com

Support the show

Instagram: @standingoutstandingstrong