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
Build Your Business Like You’ll Sell It!
Most business owners don’t think about selling until they’re ready to walk away—then suddenly it’s a mad dash to clean things up. It’s like realizing your house needs work the day before the open house. Jonathan Brown (aka JB), Founder of White Buffalo Advisors, says that mindset is all backward. In this episode, he shares why building your business as if it’s for sale—whether or not you ever plan to sell—is one of the smartest things you can do.
We talk about what really makes a business valuable (hint: it’s not just your revenue), and why thinking like a buyer changes everything. JB has worn just about every hat in the entrepreneurial world—founder, investor, paid board advisor—and he doesn’t sugarcoat the hard stuff. He shares lessons from his own journey and gives practical advice for founders at every stage, whether you’re scaling or thinking about selling.
We also get into the stuff that usually gets left out of business podcasts—like what it actually takes to stay present at home while leading well at work and why being present with your people might actually be your best long-term business move. JB also opens up about how growing up in rural Maine shaped his values, and how he’s learning to build legacy without burning out. He keeps it real, shares the wins and the missteps, and reminds us that legacy starts with how you show up today.
Key Timestamps:
[00:00:00] Introduction.
[00:06:54] Entrepreneurial journey and background.
[00:11:15] College expectations and experiences.
[00:12:43] Academic challenges and triumphs.
[00:16:46] Entrepreneurial mindset in corporate America.
[00:19:46] Corporate resistance to change.
[00:23:15] Family vs. career dilemmas.
[00:27:36] Selling a business and life.
[00:31:46] Business exit preparation challenges.
[00:37:12] Exit planning as good business.
[00:40:10] Business valuation and improvement.
[00:43:11] Profitability gaps in business.
[00:45:00] Important gaps to measure in business.
[00:50:45] Founder psychology and business value.
Memorable Quotes:
"I'm going to ask myself, would I buy this company? And if the answer to that is no, which it almost never is when you do the exercise, you got work to do. Because if you wouldn't buy it, why in the world would somebody else?" [00:39:54] – Jonathan Brown
"I believe that every business owner at any time should always know the exact value of their business to a third-party real-world scenario." [00:42:01] – Jonathan Brown
Connect with Jonathan Brown:
Website: https://whitebuffaloadvisors.com/
Instagram: https://www.instagram.com/realjbbrown/
Facebook: https://www.facebook.com/yourbuddyjb/
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: www.evolvedpodcasting.com