What if the most successful version of your business is simply the most honest version of you? Akeshi Akinseye, founder and CEO of Kesh Events and a globally recognized wedding planner and designer, joins James and Otto for a conversation about building a career on truth instead of polish.

Raised in Nigeria in a family of hosts, Akeshi traces how her mother shaped the way she creates, and why she believes your origin is your greatest differentiator. She gets honest about stepping out from behind her brand to stand in front of it, designing celebrations that move people through all five senses, and the emotional luxury philosophy at the heart of her work. Along the way she shares the two lessons that changed everything: be willing to fail, and stop trying to be everything to everyone. She also opens up about her new book, The Art of Celebrating, and the surprising way AI is now helping her book clients.

Part masterclass on intentional design, part permission to simply be yourself.

What does it take to stay at the top for thirty years? Melina Glavas and Stewart Mann lead event sales at The Little Nell, Aspen's only five-star, five-diamond hotel, where weddings happen at eleven thousand feet and Forbes has awarded five stars every year since 1996. In this conversation they join James and Otto to talk about the thing that actually drives it all: relationships.

Melina, who has been at the Nell for twenty years, and Stewart, who joined recently and plans never to leave, get honest about how they build partnerships that last, why they believe everyone succeeds or fails together, and how a new planner or photographer can genuinely break into a place like this. Along the way they share the culture behind three decades of five-star service, the story of one of the best wine programs in the world, and what it really takes to pull off a wedding on top of a mountain.

Part masterclass, part love letter to Aspen.

What happens when you lose the legal right to use your own name? Wedding dress designer Hayley Paige spent nearly five years, and every dollar she had ever earned, fighting to win back her name and her right to design. In this conversation she joins James and Otto to trace the whole arc: the identity crisis of asking "who am I if I'm not a designer?", the businesses she built in the wilderness years, and the surreal comeback of seeing one of her dresses on a real bride during the Super Bowl halftime show.

It's an unusually honest look at the machinery behind the beauty. Hayley shares how creatives can protect their work before it's out in the world, why a strong business structure frees your creativity rather than dilutes it, and how to build a brand on trust that can survive almost anything. For any designer, photographer, or small business owner, it's part cautionary tale, part permission slip to begin again.