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Jim Fielding & Friends

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by Jim Fielding

42 episodes

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Podcast Overview

ASK FOR AN ANSWER is more than a podcast—it’s a practice space for real leadership. Hosted by Jim Fielding, each episode features an honest, unscripted conversation with a leader facing a real challenge: a hard transition, a high-stakes decision, or a moment when the answers aren’t clear. Together, they work through it in real time with clarity, candor, and a growth mindset. This isn’t abstract theory or polished performance. It’s leadership as it actually happens: live, thoughtful, and grounded in shared insight. More than anything, ASK FOR AN ANSWER captures what it sounds like when leaders stop performing and start thinking—when they lower the armor, ask for help, and trust the process. If you believe leadership is a practice, not a pose, this podcast is for you.

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Recent Episodes

Episode thumbnail for John Weinstein: The Educator Who Built America's First Queer Leadership Program & Why the LGBTQ Community Needs Intergenerational Mentors Now More Than Ever | #25

June 18, 2026

John Weinstein: The Educator Who Built America's First Queer Leadership Program & Why the LGBTQ Community Needs Intergenerational Mentors Now More Than Ever | #25

What if the future of leadership is being built by people courageous enough to be fully themselves?In this Pride Month conversation, Jim Fielding sits down with educator, scholar, and queer leadership pioneer John Weinstein, Provost of Bard Academy and Simons Rock at Bard College and founder of the Bard Queer Leadership Project. Together they explore how far the LGBTQ+ community has come, why Pride still matters, and what it takes to prepare the next generation of leaders.John shares his personal journey navigating education as an openly gay leader, the lessons he learned about authenticity and code-switching, and how creating spaces of belonging can transform lives. The conversation also dives into mentorship, chosen family, intergenerational learning, and the responsibility we all have to preserve LGBTQ+ history while building a better future.Whether you're part of the LGBTQ+ community or an ally, this conversation is a powerful reminder that progress happens when we honor our history while boldly imagining what's next.Listen in, celebrate Pride, and discover why the leaders of tomorrow are already showing us what's possible today.<h3>In This Episode:</h3><ul><li>Why queer leadership brings unique strengths to the table</li><li>The importance of intergenerational mentorship and chosen family</li><li>How authenticity, visibility, and community shape future leaders</li></ul> <h3>Mentioned in This Episode:</h3><ul><li>Bard Queer Leadership Project (BQLP) at Simon's Rock</li><li>Bard College All Pride</li><li>No Ego by Jim Fielding </li><li>Leading Queer podcast hosted by John Weinstein and Carlos Stevens </li><li>Skylar Baylor, author and queer leader </li><li>The Laramie Project </li><li>Matthew Shepherd </li><li>Sliding Doors (film) </li><li>The Adjustment Bureau (film) </li><li>Robert Frost, "The Road Not Taken" </li><li>Bard Microcolleges</li></ul> <h3>Timestamps:</h3>00:01 – Welcome and how Jim and John met 03:26 – What Pride Month means in 2026 04:16 – Are things really worse for LGBTQ young people now? 08:08 – Out with colleagues, not yet with students 09:28 – The student who thought John was out the whole time 11:15 – What semi-closeted leadership actually looked like 13:58 – Returning to Simon's Rock as a fully out campus leader 20:00 – Code switching: not inauthenticity, wisdom 26:26 – "I'm teaching students to be the kind of leader I have yet to become." 29:26 – How the Bard Queer Leadership Project was born 36:28 – Mixing teenage and adult learners in the same queer leadership room 38:34 – Why intergenerational mentorship is non-negotiable 53:03 – "It took me until my 50s. I want people to get there in their 20s." 56:34 – Reclaiming patriotism as a queer act 01:01:03 – Why there is no silver bullet for fixing education 01:03:17 – Legacy and what comes next for the BQLP✨Connect with John Weinstein: Institution: simons-rock.edu Podcast: Leading Queer LinkedIn: John B. Weinstein✨ Follow Jim Fielding & Ask For An Answer:💼 Instagram: Instagram: https://instagram.com/hijimfielding/🌐 Podcast: Ask For An AnswerWebsite: <a href="http://hijimfielding.com/" rel="noopener noreferrer" target="_blank">hijimfielding.com</a>#JohnWeinstein #BardCollege #SimonsRock #QueerLeadership #LGBTQ #Pride2026 #PrideMonth #QueerEducation #LGBTQLeadership #Intergenerational #AskForAnAnswer #JimFielding #OutLeaders #LGBTQMentorship #QueerHistory #Education #BardQueerLeadershipProject

June 11, 2026

Ryan Stana | From $600 a Week to 7 Global Offices: The RWS Story, Private Equity & Being a Gay CEO in Entertainment | #23

<h2>What does it take to build a global live entertainment company from scratch at age 21, with no investors, no loans and two roommates answering your phones for $3 off the utility bill? In this episode, Jim Fielding sits down with Ryan Stana, founder and CEO of RWS Global, the world's premier one-stop shop for live entertainment, to tell the full founder story from a living room in New York City to seven headquarters across the globe.</h2>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:<ul><li>Growing up in Greensburg, Pennsylvania with two entrepreneur parents and why that wired Ryan for business</li><li>Quitting his job, setting up a phone line in his apartment and landing a $200,000 Clear Channel contract on his first pitch</li><li>Why creativity and operations have to have equal respect, and what happens when they don't</li><li>The one-stop shop model: how RWS produces original shows, costumes, casting and choreography for one check</li><li>How Ryan bought the legendary Binder Casting agency to preserve a mentor's legacy, and what that unlocked for his talent pipeline</li><li>Bootstrapping for 20 years: why he never took a loan or an outside investor and how operations funded every bit of growth</li><li>Losing himself as a leader after COVID and the moment he reclaimed his identity and culture with "my way or the door"</li><li>Why he pitched 42 private equity firms himself instead of hiring a banker, and what he learned in every room</li><li>The transition from operating CEO to executive chairman: what it feels like to hand off the baby you raised for 23 years</li><li>What leaving space in your morning schedule does to your brain when you stop filling every hour with calls</li><li>Being an out gay CEO in corporate entertainment and why holding your husband's hand in a flyover state is an act of change</li><li>Why visibility in small towns matters more than visibility in New York or LA</li></ul> 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 GlobalMentioned in This Episode:<ul><li>RWS Global (rwsglobal.com)</li><li>Binder Casting</li><li>Royal Caribbean, Six Flags, Disney</li><li>Radio City Rockettes</li><li>The Lion King, Chicago the Musical (Broadway)</li><li>Jim Fielding's book: Control the Controllable</li><li>Clear Channel Worldwide</li></ul> Connect with Ryan Stana: LinkedIn: Ryan Stana Website: <a href="http://rwsglobal.com/" rel="noopener noreferrer" target="_blank">rwsglobal.com</a>✨ Follow Jim Fielding & Ask For An Answer:💼 Instagram: Instagram: https://instagram.com/hijimfielding/🌐 Podcast: Ask For An AnswerWebsite: <a href="http://hijimfielding.com/" rel="noopener noreferrer" target="_blank">hijimfielding.com</a>#RyanStana #RWSGlobal #LiveEntertainment #Entrepreneurship #FounderStory #StartupStory #BootstrapBusiness #CEO #PrivateEquity #AskForAnAnswer #JimFielding #LiveEvents #ThemePark #GayCEO #LGBTQLeadership #Pride2026 #BusinessGrowth #Leadership

June 8, 2026

Brent Ridge & Josh Kilmer-Purcell: The Beekman 1802 Boys on Building a $100M Brand From a Bar of Soap, Winning the Amazing Race & What Pride Means in 2026 | #23

<h2>What does it take to build a $100 million beauty brand from a single bar of goat milk soap on a farm in upstate New York? In this special Pride Month episode, Jim Fielding sits down with both halves of the duo behind Beekman 1802, Brent Ridge and Josh Kilmer-Purcell, for one of the most honest, joyful and wide-ranging conversations the show has ever had.</h2>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:<ul><li>How Beekman 1802 grew from goat milk soap wrapped by neighbors to a major beauty brand sold at Ulta</li><li>The 51% rule: the surprisingly simple system that ended years of business disagreements between partners</li><li>Why "being nice is a deferred payment plan" and kindness always costs you something upfront</li><li>The theory that LGBTQ creativity is really just lifelong problem solving, and why that's a superpower</li><li>How winning the Amazing Race came down to one rule: no cheerleading, no fighting, just focus</li><li>The unexpected phone call from a CBS executive at a cookbook signing that started it all</li><li>Why Brent and Josh believe the business may have actually saved their relationship</li><li>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</li><li>The "boys" problem: why even running a $100M company, language still has the power to diminish</li><li>How to use your privilege well, especially during Pride season when the community needs its elders most</li><li>What cocktail o'clock taught them about protecting their relationship from their business</li></ul> Timestamps:00:00 – Welcome back, Brent. And introducing Josh01:03 – 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 thing26:46 – "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 nowMentioned in This Episode:<ul><li>Beekman 1802 (beekman1802.com)</li><li>Beekman 1802 Almanac (their book)</li><li>The Amazing Race, CBS</li><li>The Fabulous Beekman Boys (Planet Green reality series)</li><li>Hacks (HBO Max)</li><li>Schitt's Creek</li><li>QVC / HSN</li></ul> 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 AnswerWebsite: <a href="http://hijimfielding.com/" rel="noopener noreferrer" target="_blank">hijimfielding.com</a>#BeekmanBoys #Beekman1802 #BrentRidge #JoshKilmerPurcell #LGBTQEntrepreneurs #Pride2026 #PrideMonth #GayOwned #SmallBusiness #Entrepreneurship #AmazingRace #Kindness #AskForAnAnswer #JimFielding #LGBTQBusiness #BeautyBrand #GayCouple #QueerJoy

42 total episodes available

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Frequently asked questions

Have a different question and can't find the answer you're looking for? Reach out to our support team by sending us an email and we'll get back to you as soon as we can.

What is Jim Fielding & Friends?: ASK FOR AN ANSWER is more than a podcast—it’s a practice space for real leadership.

Hosted by Jim Fielding, each episode features an honest, unscripted conversation with a leader facing a real challenge: a hard transition, a high-stakes decision, or a moment when the answers aren’t clear. Together, they work through it in real time with clarity, candor, and a growth mindset.

This isn’t abstract theory or polished performance. It’s leadership as it actually happens: live, thoughtful, and grounded in shared insight.

More than anything, ASK FOR AN ANSWER captures what it sounds like when leaders stop performing and start thinking—when they lower the armor, ask for help, and trust the process.

If you believe leadership is a practice, not a pose, this podcast is for you.
How often does this podcast release new episodes?: This podcast updates daily.
Where can I listen to this podcast?: This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
Does this podcast accept guests?: No, this podcast does not typically feature guests.

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