Some years give us answers — but as Chris Glass reminds us, some years ask questions that transform who we become.

In this conversation, Jim Fielding sits down with Chris Glass, Global Director of Diversity, Equity & Inclusion at Soho House, to explore the humanity behind leadership, identity, and personal evolution. From navigating DEI in a shifting global landscape to returning to the U.S. after decades abroad, Chris shares how curiosity, humility, and service shape the way he moves through the world. Together, they unpack the idea of “asking for an answer” — a grounded practice of stepping back, seeking perspective, and letting growth lead.

Key Themes:

1. Why leaders don’t need all the answers — and shouldn’t pretend to
2. How living abroad reshapes identity, belonging, and the idea of “home”
3. The changing DEI landscape and how to lead with agility and humanity
4. Turning challenges into lessons instead of failures

Chris’s story is an invitation to slow down, stay curious, and trust that every chapter — even the messy ones — is here to teach us something meaningful.

Connect with Chris Glass

Instagram: Herrglass

Connect with Jim Fielding

Instagram: jimfieldingofficial

LinkedIn: jimfielding

It's the one thing on everybody's mind:

A.I.

Is it here to help? To destroy? With so many opinions and so much complexity, it can be hard to understand where this technology is going and what it actually does to help.

Jim is joined this week by AI pioneer Scott Clendaniel to discuss this topic and better understand the opportunity it presents, and the drawbacks it may bring.

Episode Highlights:

0:00 - Intro

0:34 - Episode beginning

1:11 - Meet Scott Clendaniel

5:52 - Scott’s journey, AI’s history

14:47 - Generative AI’s future

19:07 - Microsoft Co-Pilot and the problem it reveals

24:58 - Should we be afraid?

30:48 - The “return to office” push + AI

34:30 - Anyone can use AI

40:13 - Different tools and the problem w/ software

50:31 - Scott's wisdom-drop

53:31 - Episode wrap-up

CONNECT WITH JIM FIELDING

LinkedIn: https://www.linkedin.com/in/jimfielding/

Website: https://www.hijimfielding.com/

CONNECT WITH SCOTT CLENDANIEL

LinkedIn: https://www.linkedin.com/in/tscottclendaniel/

Jim sits down with Brent Ridge (Beekman 1802 co-founder and author of Goat Wisdom) for a heart-forward chat about building a legacy brand, leading with kindness, and turning real community into real company culture.

They get into the Beekman origin story (yes, the goats), why “kindness” became the brand’s north star, and practical lessons on partnerships, hiring, and storytelling in a three-second world.

Episode Highlights:

0:00 - Welcome and introduction to Brent

3:25 - Why the book, why now?

8:35 - Have you ever felt like you “arrived”?

12:41 - Kindness, building brand

14:41 - Brent’s first big order

19:50 - What the firm (and product) has grown into now

23:36 - Disney, company culture

28:10 - Culture and attention in the era of social media

36:19 - “Two heads are better than one”

40:36 - 51% rule

47:28 - Need for nature

53:06 - Empathy

54:13 - “What would you tell 25-year old Brent?”

55:42 - Episode wrap-up

CONNECT WITH JIM FIELDING

LinkedIn: https://www.linkedin.com/in/jimfielding/

Website: https://www.hijimfielding.com/

CONNECT WITH BRENT RIDGE

Website: https://beekman1802.com/

LinkedIn: https://www.linkedin.com/in/brent-ridge-md-0641791/