Inside the Speakeasy Podcast - Your Key to Hidden Strategies & Success Stories from Top Entrepreneurs
Welcome to Inside the Speakeasy—the entrepreneur podcast that hands you the keys to rooms most never get access to.
Hosted by Eric Berman, this show is for founders, startup builders, marketers, and empire-minded creators who are done with surface-level noise and ready to unlock the hidden strategies, pivotal success stories, and raw truths behind elite business growth.
This is your key to the real game—the unfiltered conversations happening behind closed doors, at mastermind retreats, in late-night deal rooms, and during the “what the hell do I do now?” breakdowns that never make it to LinkedIn.
You’ll hear from the scrappiest, boldest, most unreasonably driven entrepreneurs in the U.S.—the ones who are scaling to 7–8 figures, failing forward, innovating under pressure, and rewriting the rules of success while no one’s watching.
No recycled advice. No fake “10X hacks.” Just what’s actually working right now—from people actually doing it.
Because let’s be honest:
You’re doing well.
You’re sharp.
But deep down… you know you’re still playing small.
So stop chasing comfort.
You’re not here for safe.
You’re here to evolve.
This is Inside the Speakeasy.
And once you’re in…
You don’t go back.
Inside the Speakeasy Podcast - Your Key to Hidden Strategies & Success Stories from Top Entrepreneurs
Building Masterminds That Matter with Glen Ledwell
Masterminds aren’t just about big business moves—they’re about finding your people, the ones who get it and push you to grow. That’s exactly what we’re talking about today with my partner and long-time friend, Glen Ledwell. He’s built a powerhouse mastermind (Flight Club) that’s about real connection, confidence, and community. Glen opens up about the early days, the awkwardness of charging his peers, and what finally clicked to turn it all into a thriving circle of high-level leaders.
We get into the behind-the-scenes stuff you don’t usually hear—what makes a mastermind actually work, how Glen balances fun with focus, and the unexpected things that make people want to come back year after year. This isn’t theory; it’s what’s worked for Glen and now he’s helping others do the same. He shares what he wishes he knew when he started and how learning to ask for help (and money!) changed everything.
There’s something powerful about being in a room where you’re challenged and supported at the same time. We talk about real relationships, the kind that lead to unexpected opportunities and next-level growth. It’s honest, it’s fun, and it’s packed with moments that’ll make you rethink how you build your own circle. If you’ve ever wondered what makes a mastermind actually worth it, you’re going to want to hear this.
Key Timestamps:
[00:00:00] Introduction.
[00:04:53] Massive success with a digital vision board product.
[00:07:22] Mastermind success and ROI.
[00:09:55] Overcoming pricing fears.
[00:12:31] Ultimate mastermind concept.
[00:15:11] Intimate masterminds – the ideal amount of people.
[00:17:54] Overcoming public speaking fears.
[00:22:59] Building community today.
[00:25:38] Quality control in networking.
[00:28:18] Cultivating strategic partnerships with masterminds.
Memorable Quotes:
"Generally, it always comes down to the people, the people. People are amazing. Connection's amazing." [00:27:05] – Glen Ledwell
"If you're not in a mastermind, get in one. Whether it's one of ours, that's great. If not, you've got to surround yourself with like-minded people, and you hear it all the time. Well, that's because it's true, right? There's nothing more powerful." [00:32:20] – Glen Ledwell
Connect with Glen Ledwell:
Website: https://flightclubmastermind.com/
Instagram: https://www.instagram.com/glenledwell/
Facebook: https://www.facebook.com/glen.ledwell
Twitter/X: https://twitter.com/GlenLedwell
Connect with Eric Berman:
Website: https://speakeasymastermind.com/
Instagram: https://www.instagram.com/speakeasymastermind/
Facebook: https://www.instagram.com/speakeasymastermind/
LinkedIn: https://www.linkedin.com/in/ericberman/
Produced by Evolved Podcasting: https:// www.evolvedpodcasting.com