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!

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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/

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For today's episode, I'm talking to Donna Lamar, an award-winning creative and production leader with more than twenty years of experience shaping culture for some of the worlds biggest brands. She's now a Senior Creative Leader at Spotify, working where music, entertainment and marketing meet. Before that, she helped lead the Twitter re-brand as Global Executive Creative Director, headed production at Wieden + Kennedy/Amsterdam, and was a Creative Director on Gatorade at TBWA/Chiet Day, helping reinvent the brand for a new generation. Donna's a writer, producer, and trans-media story teller who's worked with Nike, Adidas, and Apple, always looking for new ways to connect stories, platforms and people. She also brings that same energy to causes like Heal the Bay, and to championing diversity in surf and board sports.

So grab a cup of tea, and join me for my conversation with the multi-talented Donna Lamar!

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I'm excited to welcome a very special guest this week: the fabulous Lalita Koehler. Lali's career is anything but traditional. She started out in tech at Yahoo, and found her way into advertising almost by accident. But from that unexpected beginning, she went on to lead production at agencies like Martin Agency, Omelette, Saatchi & Saatchi, the Publicis Group, and most recently she served as Global President at Craft Worldwide. She's a passionate mentor and a leader who proves that resilience, reinvention and curiosity can take you anywhere.

Since recording this conversation, Lali has moved on from her role at Craft, but rather than remove parts of our discussion that reflect her leadership in tech and production over the last few years, I wanted to keep them in, because they capture an important part of her story. Lali blends tech, creative vision, and human connection in a way that truly stands out, and I can't wait to see what she does next.

So grab a cup of tea, and join me for a wonderful conversation with Lali Koehler!.

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