We’ve all seen the HGTV dream—buy a house, slap on some paint, and flip it for a fortune. But what if we told you that’s… not real life?
On this episode of The Real Estate Pessimist Podcast, we’re sitting down with Rachel Chwaszczewski (@intentionalpropertyadvisors), a 30+ year real estate veteran who’s been through it all—market crashes, foreclosure crises, fix-and-flips gone sideways, and the hard reality of building a real estate business from the ground up.
Rachel started her career in title work, getting a firsthand look at the mechanics of real estate deals. From there, she moved into fix-and-flips, new construction, and ultimately building her own successful companies.
She’s breaking down:
✅ The truth about investing through market crashes (including ‘08)
✅ The biggest mistakes new investors make (and how to avoid them)
✅ Why boring, sustainable investments are often the smartest moves
✅ The real cost of real estate success (hint: it’s not just money)
Rachel has built multiple businesses that actually last—not just flashy success stories that disappear in the next downturn.
If you think real estate is all about fast flips and easy wins, this episode will open your eyes.
📲 Connect with Rachel & Her Companies:
🌐 Intentional Property Advisors – Helping investors create smart, strategic real estate portfolios.
🌐 Practical Luxury Builders – High-end new construction, fix-and-flip, and workforce housing development.
Want to become a STR Expert with Erik’s help? https://eriks-academy.teachable.com/p/str-in-an-hour
Ready to go from podcast listener to Local Developer with Kristi’s guidance?
Whether you're just getting started or ready to go all in, we've got the tools to help you build what matters in your own backyard.
→ Programs & Resources: https://www.localrealestatedeveloper.com/
→ 90-Day Masterclass: https://www.localrealestatedeveloper.com/build-it-course
→ Apply for the Mentorship Program: https://www.localrealestatedeveloper.com/dev-mentorship
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