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
Joe Apfelbaum on Scaling SaaS, Using AI, & Making LinkedIn Work for You
Sometimes the difference between struggling and thriving in business comes down to strategy, and knowing which moves actually matter. Joe Apfelbaum, LinkedIn Expert, AI Nerd, and CEO of evyAI, and former Rabbi, shares how he built his business from living in a Brooklyn basement to running a thriving SaaS company. He shares what he learned from his mom’s entrepreneurial spirit, how he navigated the ups and downs of the pandemic, and why having a solid plan really changes everything.
Joe gets real about the challenges of building a SaaS business and how he turned early setbacks into lessons that shaped his growth. We talk about strategy, resilience, and what he wishes he could’ve told his mom to help her business thrive. There’s also a ton of practical advice sprinkled throughout, information you can actually use, such as how to make LinkedIn work for you without it feeling like a grind.
And yes, we dive into AI too, how it’s changing the game and how Joe’s helping people use it without feeling overwhelmed. He shares honest stories about wins, losses, and the weird little hacks that make a big difference. By the end, you’ll have a bunch of ideas you can try right away, whether it’s on LinkedIn, building a product, or just thinking differently about your next move.
Key Timestamps:
[00:00:00] Welcome to Inside the Speakeasy Podcast!
[00:02:03] Joe's journey from rabbi to entrepreneur.
[00:05:55] Self-education for financial success.
[00:06:16] Building a successful website business.
[00:11:36] Strategic business growth strategies.
[00:15:43] SaaS solutions and business pivots.
[00:20:24] Business owner to investor transition.
[00:23:21] AI training for business owners.
[00:27:10] Pricing strategy for business growth.
[00:28:33] Creating irresistible offers.
[00:32:01] Selling courses through polling.
[00:34:44] Booking meetings using Calendly.
[00:38:13] Building deep relationships in tech.
[00:40:52] High-caliber entrepreneur networking.
[00:44:06] Personal strengths and networking.
Memorable Quotes:
"If you want to get to the next level, you got to go from being a business owner to being an investor." [00:20:11] – Joe Apfelbaum
"The competitive advantage is not how fancy your degree is. It's not even how much money you have. It has to do with your relationships." [00:38:34] – Joe Apfelbaum
Connect with Joe Apfelbaum:
Website: http://www.evyai.com
Instagram: https://www.instagram.com/joeapfelbaum
Facebook: http://www.facebook.com/joeapfelbaum
Twitter/X: http://www.twitter.com/joeapfelbaum
LinkedIn: http://www.linkedin.com/joeapfelbaum
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