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.
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
