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October 14, 2025 45 mins

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

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