Ask For An Answer – Details, episodes & analysis

Ryan produced shows for Royal Caribbean, Six Flags and Disney before most people his age had a 401k. He bootstrapped the entire business for over two decades, bought three companies during COVID, then walked into 42 private equity meetings himself with his laptop and a presentation he built from scratch. This is one of the most honest, specific and genuinely inspiring entrepreneurship conversations the show has ever had.

In This Episode:

• Growing up in Greensburg, Pennsylvania with two entrepreneur parents and why that wired Ryan for business
• Quitting his job, setting up a phone line in his apartment and landing a $200,000 Clear Channel contract on his first pitch
• Why creativity and operations have to have equal respect, and what happens when they don't
• The one-stop shop model: how RWS produces original shows, costumes, casting and choreography for one check
• How Ryan bought the legendary Binder Casting agency to preserve a mentor's legacy, and what that unlocked for his talent pipeline
• Bootstrapping for 20 years: why he never took a loan or an outside investor and how operations funded every bit of growth
• Losing himself as a leader after COVID and the moment he reclaimed his identity and culture with "my way or the door"
• Why he pitched 42 private equity firms himself instead of hiring a banker, and what he learned in every room
• The transition from operating CEO to executive chairman: what it feels like to hand off the baby you raised for 23 years
• What leaving space in your morning schedule does to your brain when you stop filling every hour with calls
• Being an out gay CEO in corporate entertainment and why holding your husband's hand in a flyover state is an act of change
• Why visibility in small towns matters more than visibility in New York or LA

Timestamps:

00:01 – Welcome & how Jim and Ryan met through mutual friend Rema Awad

03:05 – Ryan's background: Greensburg, PA, child performer and theme park show obsession 06:12 – Senior year of high school: "Maybe I want to produce this."

07:19 – Writing corporate shows in college as a one-stop shop for hire

09:23 – Quitting his job, setting up a fake phone operation in his apartment and launching RWS at 21

10:59 – Never burn a bridge: the email that launched everything the next morning

12:00 – Walking into Clear Channel in Times Square and winning a $200,000 contract on day one

15:28 – First hire, first office and 23 years of zero outside funding

18:22 – Bootstrapping principle: the money that comes in is the money that goes out

24:00 – The acquisition strategy: buying companies to build the full vertical

27:32 – Buying Binder Casting to save a mentor's legacy and unlocking Broadway and Radio City

29:01 – What a true one-stop shop looks like from a client's perspective

33:26 – "Every dream I had has come true. Now I want to make everyone else's dreams come true."

34:10 – How RWS not only survived COVID but came out stronger through acquisitions

35:52 – Losing himself as a leader post-COVID and reclaiming his culture

38:38 – The decision to bring in private equity and why he did it himself

40:00 – Pitching 42 PE firms solo and getting 13 interested

41:42 – Choosing minority ownership and why the right partner showed up at the last minute

43:53 – 7 global HQs and an office open somewhere in the world around the clock

50:00 – The transition from CEO to Executive Chairman: what changes and what doesn't

54:56 – "It's like being a smoker without cigarettes": the honest truth about stepping back

58:20 – Morning walks in Miami with no phone and what the brain does when you let it rest

59:38 – Control the controllable, but leave space for the possible

01:00:50 – Being an out gay CEO in corporate entertainment and the responsibility that comes with visibility

01:04:53 – Why mentorship is the bridge to the next generation's success

01:06:47 – Happy Pride and what comes next for RWS Global

Mentioned in This Episode:

• RWS Global (rwsglobal.com)
• Binder Casting
• Royal Caribbean, Six Flags, Disney
• Radio City Rockettes
• The Lion King, Chicago the Musical (Broadway)
• Jim Fielding's book: Control the Controllable
• Clear Channel Worldwide

Connect with Ryan Stana:

LinkedIn: Ryan Stana

Website: rwsglobal.com

✨ Follow Jim Fielding & Ask For An Answer:

💼 Instagram: Instagram: https://instagram.com/hijimfielding/

🌐 Podcast: Ask For An Answer

Website: hijimfielding.com

#RyanStana #RWSGlobal #LiveEntertainment #Entrepreneurship #FounderStory #StartupStory #BootstrapBusiness #CEO #PrivateEquity #AskForAnAnswer #JimFielding #LiveEvents #ThemePark #GayCEO #LGBTQLeadership #Pride2026 #BusinessGrowth #Leadership

From the 51% rule that saved their business partnership to the psychology of why LGBTQ people are wired for creativity, from winning the Amazing Race to the real difference between kindness and niceness, Brent and Josh bring equal parts wisdom, warmth and wit to every topic Jim puts in front of them.

In This Episode:

• How Beekman 1802 grew from goat milk soap wrapped by neighbors to a major beauty brand sold at Ulta
• The 51% rule: the surprisingly simple system that ended years of business disagreements between partners
• Why "being nice is a deferred payment plan" and kindness always costs you something upfront
• The theory that LGBTQ creativity is really just lifelong problem solving, and why that's a superpower
• How winning the Amazing Race came down to one rule: no cheerleading, no fighting, just focus
• The unexpected phone call from a CBS executive at a cookbook signing that started it all
• Why Brent and Josh believe the business may have actually saved their relationship
• What it feels like to be a visible gay couple in the South right now and why just going to dinner is an act of activism
• The "boys" problem: why even running a $100M company, language still has the power to diminish
• How to use your privilege well, especially during Pride season when the community needs its elders most
• What cocktail o'clock taught them about protecting their relationship from their business

Timestamps:

00:00 – Welcome back, Brent. And introducing Josh

01:03 – Did the vision for Beekman 1802 ever match the reality?

02:53 – Starting with kindness: "How can we lift as many people as possible?"

06:01 – Do Brent and Josh ever disagree? (Oh, yes.)

08:40 – The 51% rule: how to make decisions as equal partners

10:11 – Why LGBT couple founders may be more successful than straight ones

13:30 – Creativity is problem solving: the LGBTQ superpower

20:09 – 80 employees, Ulta stores and what Beekman looks for in talent

23:34 – "The ultimate act of kindness is transparency"

25:31 – Kind vs. nice: why they are not the same thing

26:46 – "Being kind has an immediate cost. Nice is a deferred payment plan."

29:18 – Josh on the Amazing Race: "It was the hardest thing I've ever done."

30:16 – Why their age and Gen X doubt actually helped them win

35:16 – "The middle-aged gay couple never wins. Our job is to be everyone's friend and gracefully exit."

37:21 – Did the show Hacks owe them royalties? (The goat milking episode)

39:32 – Inside a week at the farm: cocktail o'clock and how they protect their relationship

41:08 – "The business may have saved our relationship."

44:18 – A gay Shark Tank? Jim pitches a TV idea live on air

46:47 – "What do the boys think?" Why that phrase still stings at $100M

51:46 – Safe spaces, moving to Atlanta and what it means to turn your gaydar back on

57:33 – What Jim, Brent and Josh believe it means to be elders in the community right now

Mentioned in This Episode:

• Beekman 1802 (beekman1802.com)
• Beekman 1802 Almanac (their book)
• The Amazing Race, CBS
• The Fabulous Beekman Boys (Planet Green reality series)
• Hacks (HBO Max)
• Schitt's Creek
• QVC / HSN

Connect with Brent Ridge & Josh Kilmer-Purcell:

Website: beekman1802.com

Instagram: @beekman1802

Instagram: @josh.kilmer.purcell

✨ Follow Jim Fielding & Ask For An Answer:

💼 Instagram: Instagram: https://instagram.com/hijimfielding/

🌐 Podcast: Ask For An Answer

Website: hijimfielding.com

#BeekmanBoys #Beekman1802 #BrentRidge #JoshKilmerPurcell #LGBTQEntrepreneurs #Pride2026 #PrideMonth #GayOwned #SmallBusiness #Entrepreneurship #AmazingRace #Kindness #AskForAnAnswer #JimFielding #LGBTQBusiness #BeautyBrand #GayCouple #QueerJoy

In this episode of Ask For An Answer, host Jim Fielding sits down with 20-year unscripted television veteran and creative entrepreneur Liza Keckler. Liza has navigated the complex world of alternative TV, from producing home improvement shows to leading development for major networks and production companies.

Jim and Liza dive deep into their time working together at Archer Gray, where they focused on building "highly repeatable formats" and prestige non-narrative content during a time of extreme industry contraction. Liza shares the inspiration behind her newest venture, Hedyverse, a creative IP studio she co-founded to build content that lives across platforms—including mobile games, tabletop games, and television.

In this conversation, they explore:

• The Shift to Ownership: Why owning your intellectual property is the ultimate goal for creators today.
• Market Trends: What’s working in unscripted media right now, from The Masked Singer to Squid Game: The Challenge.
• Creative Resilience: How to advocate for your creative vision and navigate industry obstacles like mergers and strikes.
• Collaboration: The power of looking at those in your orbit to see what you can build together.

• 03:57 – Meet Liza Keckler: A look into Liza’s 20+ year background in unscripted and alternative TV.
• 06:01 – Franchisable Content: Jim and Liza discuss their partnership at Archer Gray and the goal of creating repeatable, premium content.
• 09:20 – The State of Entertainment: An honest look at the "hard years" of the industry, including COVID impacts and the writer's strikes.
• 12:17 – Adapting Strategy: Why creative pivots are necessary when meeting a changing marketplace.
• 14:15 – Lessons in Leadership: Liza shares her biggest takeaway: the importance of clarity and advocating for the right choices.
• 17:40 – Launching Heady Verse: How a family trip and a conversation with a friend led to the creation of a cross-media studio.
• 19:27 – Owning the IP: Moving from "work for hire" to building equity in your own creations.
• 20:01 – Mood Box Games: Liza shares details on a new partnership with gaming giant ASMODEE.
• 22:40 – The Next Big Hit: A discussion on why fresh ideas like The Masked Singer take time to cut through the noise of legacy shows.
• 25:13 – Current Watchlist: Jim and Liza breakdown the brilliance of Squid Game: The Challenge and the rise of biography documentaries.

• 💼 Follow Jim Fielding on Instagram: @jimfielding
• 🌐 Learn more about Hedyverse: [Hedyverse.com]
• ✨ Guest: Liza Keckler

What does it take to keep chasing your dream — even after setbacks, reinvention, and unexpected career turns?

In this episode of Ask For An Answer, Jim Fielding sits down with Eva Steortz, executive coach, author of From the Outhouse to the Mouse House, and a longtime entertainment marketing leader, for a conversation about bold moves, career growth, resilience, and the relationships that shape our lives.

From leaving West Virginia with a one-way ticket to Los Angeles, to building a 20-year career at Disney, to navigating layoffs, consulting, authorship, and executive coaching, Eva shares what it means to bet on yourself again and again. Together, Jim and Eva explore imposter syndrome, leadership blind spots, the power of coaching, work-life integration, and why relationships remain the most important asset in any career.

This is a conversation about courage, reinvention, and refusing to let your dream go unrealized.

If you are navigating a transition, building your next chapter, or wondering how to lead with more confidence and authenticity, this episode is for you.

• Why bold moves often begin before you feel ready
• How executive coaching can uncover blind spots and accelerate growth
• The role of imposter syndrome in leadership and career transitions
• Why relationships are the foundation of career success and personal well-being
• How to navigate layoffs, reinvention, and change with resilience and gratitude

Episode Highlights

00:00 – Why dreams matter and the courage to chase them

03:20 – Leaving West Virginia for Los Angeles with a one-way ticket

06:45 – The feedback that changed Eva’s leadership career

16:00 – Why relationships are the foundation of success

22:30 – Corporate change, layoffs, and starting over

32:19 – The dream Eva’s father never got to live

41:24 – Work-life balance, empathy, and leadership with heart

47:00 – Imposter syndrome and confidence in leadership

Follow Eva Steortz

Book: From the Outhouse to the Mouse House

Follow Jim Fielding and Ask for an Answer:

Instagram: @jimfielding

Podcast: Ask for an Answer

Website:

Podcast: Ask for an Answer

If this episode sparked something for you, don’t just agree with it, reach out to one person, revive one relationship, or take one bold step toward the dream you’ve been postponing.

What does it take to build a global entertainment brand from scratch and sustain it for over three decades?

In this episode of Ask For An Answer, host Jim Fielding sits down with legendary entertainment executive Luis Balaguer, CEO and founder of Latin World Entertainment (LatinWE). As the longtime business partner of Sofía Vergara, Luis has been the strategic architect behind one of the most successful talent management and brand empires in the world.

Luis pulls back the curtain on the "secret sauce" of their 30-year partnership, sharing the raw, "hungry" early days of selling DIY calendars out of desperation and how they eventually pioneered the "crossover" from Univision to Hollywood. They discuss the evolution of their "Three Buckets" business model, the eight-year struggle to book Modern Family, and the calculated risk of Sofía shedding her comedic persona to become Griselda. This isn't just a Hollywood success story; it’s a masterclass in intuition, brand longevity, and the power of staying true to your audience.

Episode Timestamps & Key Takeaways:

1. 04:11 – The 30-Year Partnership: Luis reflects on his three-decade journey building Latin World Entertainment and the mutual respect that defines his relationship with Sofía.
2. 06:09 – The $10 G-String Calendar: The "desperation-driven" origin story of their first million-dollar venture and learning to do business directly with the audience.
3. 09:48 – The Three Buckets of Business: How a strategic framework—Ownership, Sharing, and Endorsements—transformed their "kitchen-run" company into a high-value global brand.
4. 14:50 – Culture Shock in Hollywood: Navigating the shift from "loud" Latin production meetings to the polished—but often ridiculous—landscape of LA studios.
5. 18:16 – The Eight-Year Climb: A candid look at the resilience required to survive canceled pilots before Modern Family changed the landscape of network television.
6. 21:36 – The Ultimate Creative Risk: Luis reveals why Griselda was the scariest test of Sofía’s career and the necessity of reinventing yourself at the top of your game.
7. 23:13 – The Matriarch: Sofía’s early responsibility for her family and heritage, and why she started being a "boss" at just 22 years old.
8. 25:22 – The Idea Fountain: How Luis translates Sofía’s raw passions—from fashion to home decor—into massive retail wins at Walmart and beyond.

If you’ve ever wondered how celebrity, strategy, and entrepreneurship come together to create a lasting brand, this episode offers a rare inside look into the business of being Sofía Vergara.

✨Follow Jim Fielding & Ask For An Answer:

💼Instagram: jimfielding

🌐Podcast: Ask For An Answer

What happens when storytelling moves beyond the stage and becomes a fully immersive experience?

In this episode of Ask For An Answer, Jim Fielding sits down with Vance Garrett, one of the creative minds behind groundbreaking immersive experiences like Sleep No More, 29Rooms, and the Museum of Ice Cream. Together they explore how experiential storytelling is transforming entertainment, retail, and live culture.

From Shakespeare-inspired immersive theater to Instagram-era experiences and large-scale retail activations, Vance shares what it takes to design moments that bring people together. Jim and Vance also dive into why audiences today crave collective experiences — from Broadway shows to Beyoncé concerts — and how immersive storytelling is reshaping the way brands and creators connect with people.

This conversation is about creativity, culture, and the power of shared joy.

If you believe experiences matter more than ever, this episode is for you.

1. How immersive theater like Sleep No More changed live entertainment
2. tWhy experiential retail became the future of consumer engagement
3. What Beyoncé, Taylor Swift, and Kendrick Lamar understand about immersive storytelling
4. Why audiences crave communal experiences after the pandemic
5. The future of Broadway, live theater, and immersive experiences

Episode Highlights

00:00 – Why storytelling and communal experiences still matter

01:30 – How Jim and Vance first met working on ModelLand

03:00 – Vance’s background in immersive theater and experiential storytelling

04:00 – The phenomenon of Sleep No More and the birth of immersive theater

05:30 – Creating 29Rooms and the rise of Instagram-era experiences

06:20 – Building the Museum of Ice Cream and the explosion of experiential entertainment

07:25 – Bringing immersive experiences into retail with Westfield

10:50 – Why consumers want experiences more than products

13:00 – Beyoncé, Taylor Swift, and the rise of immersive concerts

16:40 – The psychology of collective joy and live entertainment

20:00 – Broadway, theater, and why live performance still moves audiences

28:20 – The business challenges of Broadway and live productions

32:00 – Favorite theater and immersive experiences of all time

Connect with Vance Garrett:

Instagram: @vancegarrett

Email: V@vancegarrett.com

Follow Jim Fielding and Ask for an Answer:

Instagram: @jimfielding

Podcast: Ask for an Answer

Website:

Podcast: Ask for an Answer

If this episode sparked something for you, don’t just agree with it, try it: take one question into your next meeting and see what changes.

What happens when the spotlight fades and the crown comes off?

In this episode of ASK FOR AN ANSWER, host Jim Fielding sits down with former Miss USA Olivia Jordan to discuss the raw reality of life after the title. Known for her grace during one of the most infamous moments in Miss Universe history, Olivia opens up about the "evolution behind the headlines."

From the high-pressure world of pageantry in Los Angeles to finding peace and rebuilding her life in Tulsa, Olivia shares how to navigate identity shifts, personal growth, and the journey of reinvention.

1. Confidence Under Pressure: The surprising mindset lessons learned from the Miss USA stage.
2. The Power of Pivot: Why Olivia left Hollywood to build a new dream in her hometown.
3. Modern Motherhood & Healing: How she is rewriting her identity to become a role model for her daughter.
4. Finding Purpose: Practical advice for anyone asking "what comes next?" in their career or personal life.

This is not just a story about pageants or Hollywood. It is about growth, vulnerability, service, and stepping into your most realized self. If you are in a season of reinvention or asking what comes next, this episode is your invitation.

✨Follow Jim Fielding & Ask For An Answer:

💼Instagram: jimfielding

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What if a school bus could change lives?

On this episode of ASK FOR AN ANSWER, Jim Fielding sits down with Adam Powell, co-founder of the LGBTQ+ book platform Our Story (formerly Shop Queer), to talk about turning a 10-book idea into a thriving national movement. From launching a bookshop out of their apartment in 2022 to building 30+ book clubs and taking the Rainbow Book Bus across the country, Adam shares how he and his partner Eric are amplifying queer voices—especially in places where those stories are being silenced.

They dive into the realities of entrepreneurship as life partners, the power of in-person community, drag as creative liberation, and why “selfish” might be the most important word to reclaim for your mental health.

In this episode, we explore:

1. How Our Story grew from a garage startup to a 30+ club national community
2. The Rainbow Book Bus tour and giving away 8,000 banned books across the U.S.
3. Boundaries, burnout, and building a business with your partner
4. Why storytelling is one of the most powerful tools for connection and resistance

This is a conversation about courage, creativity, and choosing joy—even when the world feels heavy.

If you believe in the power of story to bring people together, this one’s for you.

✨Follow Jim Fielding & Ask For An Answer:

💼Instagram: jimfielding

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What happens when an untold American legacy becomes a modern business movement and a masterclass in leadership, culture, and brand truth?

In this episode of Ask for an Answer, Jim Fielding sits down with Katharine “Kate” Jerkens, Chief Business Officer of Uncle Nearest Premium Whiskey, to explore what it takes to build an iconic brand in uncertain times—without hiding behind “having all the answers.”

Kate shares the inside story of Uncle Nearest’s rise, including the origin of the Nearest Green legacy (the first known African-American master distiller who taught Jack Daniel), the leadership realities of building distribution and culture in a white, male-dominated industry, and how COVID reshaped consumer behavior, team dynamics, and decision-making.

This is a conversation about modern leadership, authentic storytelling, psychological safety, and the kind of long-game thinking that builds trust, not just revenue.

In this episode, you’ll learn:

1. The real origin story behind Uncle Nearest and why legacy-driven brands outperform “marketing-first” brands
2. What it’s like to lead as a woman executive in the spirits industry — and how to keep your edge without losing your humanity
3. How to navigate uncertainty (COVID, shifting consumer trends, cultural change) with curiosity instead of control
4. Why psychological safety is the hidden driver of better decisions and stronger teams
5. A leadership reminder that applies everywhere: you can’t control the world, but you can control how you show up

Mentioned in the episode:

1. The Nearest Green story and the mission behind Uncle Nearest
2. The Nearest Green Foundation and education legacy
3. The “HBCU Cocktail” initiative and HBCU Heroes
4. 
   

Follow Katharine Jerkens / Uncle Nearest

Instagram: @unclenearest

Website: unclenearest.com

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Instagram: @jimfielding

Website:

Podcast: Ask for an Answer

If this episode sparked something for you, don’t just agree with it, try it: take one question into your next meeting and see what changes.

What if success doesn’t arrive all at once, but shows up quietly when you finally stop running from who you are?

Actor Gerardo Celasco opens up about growing up between cultures, being “othered” in El Salvador, chasing an acting dream without a safety net, and enduring years of near-misses before landing career-defining roles like The Waterfront. In a deeply personal conversation with host Jim Fielding, Gerardo reflects on marriage, fatherhood, creative identity, and what it really means to stay the course when doubt never fully disappears.

In this episode, you’ll hear about:

1. Growing up between countries, cultures, and expectations
2. The reality of chasing a creative dream without connections
3. Redefining success, masculinity, and belonging at midlife

If you’ve ever questioned your path, your timing, or whether it’s “too late,” this conversation is a reminder that your story is still unfolding and you’re exactly where you’re meant to be.