Send us a text

Is fear keeping you from building wealth through real estate?

In this episode of The Wisconsin Investor Podcast, we sit down with Chris Charles—a real estate investor and title company professional with over 40 years of experience—for a raw, honest conversation about what it really takes to build a portfolio and create lasting financial freedom.

Chris shares his full journey:
 ➡️ From renovating "handyman specials" with his dad as a kid
 ➡️ To acquiring multiple rental properties and navigating the ups and downs of the market
 ➡️ Including getting served foreclosure papers during the 2008 housing crash—and how that moment became a turning point in both his life and his investing mindset.

“The next day, the air still breathed the same.”That realization changed everything. It’s one of the most powerful moments we’ve ever captured on the show.

🔑 What You’ll Learn:

• How to push through fear and analysis paralysis
• Why some investors freeze while others thrive
• The rent-to-own strategy Chris used to maximize cash flow and eliminate realtor fees
• Must-know title insurance tips (shared driveways, easements, and more)
• A balanced take on Dave Ramsey’s debt-free philosophy vs. strategic leverage
• How to invest wisely even when your spouse or partner is more risk-averse

Whether you're stuck on your first deal or trying to scale, this episode delivers the emotional clarity and tactical knowledge you need to take your next step.

🎧 Who This Is For:

• New investors afraid to pull the trigger
• Experienced investors reflecting on risk, debt, and long-term strategy
• Anyone interested in rent-to-own, off-market real estate, or building generational wealth

This isn’t just another real estate highlight reel. It’s real talk about fear, failure, and building a future anyway.