500 | 500 Episode Celebration! What We’ve Learned Investing Together Artwork

Not Your Average Investor Show

Rental Income Property investing doesn't need to be as difficult as you think it is. Why do we say this? Studies have shown that most Americans believe real estate is the best tool to accumulate wealth, yet only a minority of them use that tool... simply because it seems too complicated. The Not Your Average Investor show will show you how JWB has made it easy for people like you to invest in rental income properties by showing you the fundamentals that make rental income investments succesfull- cash flow, market dynamics, and (most importantly) people.We're glad you've decided you are NOT average!

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Not Your Average Investor Show

500 | 500 Episode Celebration! What We’ve Learned Investing Together

May 18, 2026 • Gregg Cohen / Pablo Gonzalez • Season 2 • Episode 500

0:00 | 1:21:58

We’ve officially hit 500 episodes of the Not Your Average Investor Show.

What started as a conversation about real estate investing turned into something more. A place where investors could find clarity, ask better questions, and stay grounded through every market cycle.

Along the way, there were challenges. Moments of uncertainty. Big decisions in real time. And conversations that helped shape how investors think and act.

In this special 500th episode, show host Pablo Gonzalez and JWB Co-Founder Gregg Cohen take a look back at the journey. Not just the highlights, but the moments that defined the experience of investing through it all.

Here’s what we’re diving into:

- What it felt like to invest through uncertainty and changing markets
- The real-time decisions and conversations that shaped outcomes
- How this community became a place for long-term thinking
- The lessons that still guide investors today

When you take a step back, you start to see how each moment connects.

This episode is about the journey we’ve all been on together and what it means moving forward.

Listen NOW!

Chapters:

00:00 500th Episode Kickoff
01:40 Intro Montage Madness
04:18 GC Nicknames and Roll Call
06:54 Humble Origins at Coop303
09:20 The Social Proof Bet
10:38 COVID Changes Everything
15:32 Leading Through Uncertainty
20:55 Celebrity Guest Highlights
26:04 Network Power and Takeaways
29:02 Jacksonville Future Teasers
31:14 Community Guest Investors
36:55 Investor Story Nuggets
38:25 Overcoming Investor Obstacles
39:51 Tacit Knowledge Exchange
41:45 Fan Appreciation With Greg
43:38 Going IRL With Meetups
47:17 Summit Origins And Vision
53:38 Downtown Jax Q&A
58:27 GC Market Update Receipts
01:06:36 How Market Updates Evolved
01:10:44 Final Takeaways And Thanks

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