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/

This week's episode features a trip down memory lane!

Jim returns to Indiana University to sit down with student Joey Mora live and in front of the next generation of retail and fashion to discuss his journey, but more importantly: his success in the retail industry - how he got involved, and what informed him along the way that he was in the right place.

Jim also dives into the specifics of his early career, including trips to Japan, living with a Danish family, and his big jump into the upper echelons of corporate leadership - and his newest chapter.

Episode Highlights:

(0:00) - Intro

(0:37) - Episode beginning

(2:31) - Meet Joey

(5:45) - Getting into retail

(12:32) - Travelling, fashion, where it takes you

(16:20) - More on Joey and her work on campus

(22:01) - This semester for Joey

(32:54) - Advice you give to students starting their careers

(39:44) - Staying true to yourself

(55:49) - Wrap-up

CONNECT WITH JIM FIELDING

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

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

This week, on Jim Fielding and Friends, Jim is joined by Oana Leonte, the Founder & Editor-in-Chief at unmtchd. Her company is a media platform decoding the business of brand and translating cultural insight into systems that scale.

Oana sits down with Jim to discuss the path less travelled:

Leaving corporate (and your job + safety net).

The reason? To achieve a balance in life that few get. The synchronicity between what you're doing, what you're good at, and what you like.

Episode Highlights:

0:00 – Welcome and introduction to Oana

2:56 – How Jim and Oana met

7:23 – Diving into “the journey”

8:04 – Building your own brand

10:12 – From “different” to Unmatched positioning

13:22 – Hardest part of the transition

16:48 – “Disney deprogramming” & imposter syndrome

24:15 – Growing up (fast) as an entrepreneur

26:39 – Multi-hyphenate authenticity vs titles

35:03 – Biggest surprise of year one

36:30 – Rediscovering self before strategy

42:13 – Bad Bunny case study: roots → global demand

51:30 – Wrapping up + contact Juana

52:17 – Mic-drop advice: be faithful to your unmatched essence

55:02 – Gratitude & sign-off

57:11 – Outro + subscribe/reminder

CONNECT WITH JIM FIELDING

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

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

CONNECT WITH OANA LEONTE

Website: https://theunmtchd.com/

LinkedIn: https://www.linkedin.com/in/oana-leonte

Blake Collazzo is a PR operations and culture lead, community connector, and longtime collaborator on Jim’s book, brand, and podcast.

Jim and Blake trace the genesis of their collaboration and their first intro via Joanne Martino, unpack a wild personal-assistant story that ended at a Ramada, talk vitality vs. stagnation, and get candid about coming out, “inviting in,” and showing up for the LGBTQ+ community.

They also cover a practical mindset that can do wonders for your day to day experience..

Episode Highlights:

0:00 - Welcome and introduction to Blake

2:32 - From book launch to brand and podcast

6:10 - Vitality over stagnation and lessons from Jim’s dad

8:32 - The 1% assistant story and the Ramada pivot

14:17 - The 2015 epiphany and 2016 move to LA

18:23 - Coming out at 19 and “inviting in”

27:40 - Representation, safe spaces, authentic leadership

28:11 - Control the controllable, leave space for the possible

CONNECT WITH JIM FIELDING

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

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

CONNECT WITH BLAKE COLLAZO

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

Brian Tran is a multi-hyphenate founder, designer, and community builder whose journey runs from Houston to Pandora, Kleiner Perkins, and an eight-year startup ride focused on LGBTQ+ connection.

Jim and Brian unpack coming out at 13, landing a first VC check in 15 minutes, surviving pivots (including web3), the painful decision to shut down—and the hopeful next chapter: SE / “sector,” a platform creating intergenerational connections for LGBTQ+ industry leaders.

Episode Highlights:

0:00 - Introduction

0:36 - Meet Brian Tran—founder, designer, connector

2:20 - Houston roots & coming out at 13

6:36 - Why he builds LGBTQ+ community products

7:05 - How Jim & Brian met; authenticity, connection, community

9:13 - College pivots: journalism → film theory → entrepreneurship

14:26 - First roles: Pandora product design → Kleiner Perkins (VC)

16:50 - What VC taught him (scale, stakes, networks)

18:20 - Side app to funded venture

19:52 - The 15-minute pitch that landed the first check

21:29 - Angel investing 101: what investors really back

24:10 - Eight years of pivots

30:13 - Why the web3 chapter was the toughest

31:54 - 2025 return to hospitality; real-estate hurdles

33:34 - Building a membership without a space; sponsor headwinds; shutdown

35:08 - Founder reality: failure, resilience, learning

39:03 - The next chapter: SE/“sector” for LGBTQ+ leaders

41:57 - Mentorship as a two-way street

44:02 - Closing & where to find Brian

CONNECT WITH JIM FIELDING

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

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

Dr. Jon Paul is fighting “the good fight” – which is even more important now, more than ever.

Dr. Paul’s new book, “Black. Fat. Femme: Revealing the Power of Visibly Queer Voices (in Media) and Learning to Love Yourself” is a guide to standing at the intersection of multiple identities, communities, and causes shapes people and how they see the world.

Jim sits down with Dr. Jon to explore his journey in creating this book, the influences he sought and most importantly: his lived experience which informed the book.

Episode Highlights:

0:00 - Introduction

1:20 - The Dr. Jon Paul story

7:58 - What has surprised you the most?

12:30 - Influences in the book and on Jon

18:56 - Sometimes you need to say what needs to be said

29:11 - RuPaul’s Drag Race

44:19 - Final thoughts

CONNECT WITH JIM FIELDING

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

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

CONNECT WITH DR. JON PAUL

Website: https://www.doctorjonpaul.com/

LinkedIn: https://www.instagram.com/doctorjonpaul/?hl=en