Podcast Recap: Jorge Vazquez on the Westside Investors Network – From Losing Everything to Building a Real Estate Empire

By Jorge Vazquez, CEO of Graystone Investment Group

I recently joined Trent Werner on the Westside Investors Network (WIN) podcast. This wasn’t just another interview—it was a deep conversation about what real estate investing really looks like when you’re not following the hype. We covered everything from my biggest failures to the strategies I use today to help investors build true, long-term wealth.

Below is a breakdown of the biggest takeaways from our conversation. These are the principles that helped me rebuild from the 2008 crash to owning over 40 properties, managing more than 300, and running five real estate companies today.

1. From Financial Advisor to Real Estate Investor

My journey started in wealth management. I helped clients invest in stocks, bonds, and mutual funds. But many of them wanted to do what I was doing—buy real estate. Eventually, I stopped selling Wall Street products and started guiding clients through building real estate portfolios. The shift was driven by results. I saw firsthand how real estate created wealth faster and more predictably than the stock market.

2. Know the Last Property to Buy Before You Buy the First One

One of the first questions I ask new investors is, “What’s the last property you want to own?” Without that clarity, it’s impossible to map out the first step. Most people don’t have a short- or long-term goal. They’ve heard about BRRRR or house hacking but haven’t tied those strategies to their personal financial picture.

Your goal determines your lane. If you’re young with little cash, house hacking makes sense. If you have capital, focus on equity through BRRRR deals. If you’re wealthy and want passive income, consider becoming a private lender. Strategy must match profile.

3. Short-Term Rentals vs. Long-Term Rentals

Short-term rentals are riskier than most people think. You’re putting up high-quality finishes and furniture, hoping for high nightly rates. But if the bookings dry up, you’re stuck with a high mortgage and no backup plan.

Long-term rentals, on the other hand, are stable and reliable. You set them up once, and they become income-producing assets. For younger investors, it may make sense to go heavier into short-term rentals, but if you’re nearing retirement, the safer play is long-term.

4. Real Estate Diversification Isn’t Just Location

Diversification can mean a lot of things. Most people think of it geographically, but you can diversify by strategy too. Mix short-term and long-term rentals. Own properties and also act as a private lender. Use your equity to create new streams of income. Just make sure every strategy fits your goals and experience level.

5. Why I Avoid Small Multifamily Properties

Unless you have centralized management across 50 to 100+ units, small multifamily properties don’t give you true economies of scale. A plumbing issue in one unit can affect three others. Tenants in small multifamily buildings also tend to stay for shorter periods and treat the space less like home.

I prefer single-family rentals. Tenants stay longer. They take pride in the property. You also benefit more from appreciation because these properties are sold based on comps, not just income.

6. Where I Invest: The High End of the Low End

I look for areas on the verge of gentrification. These are neighborhoods where new construction is popping up around older homes. I call it the “high end of the low end.” That’s where I find the most appreciation potential. I rehab these properties strategically—roof, paint, systems—and then I ride the equity wave while rents rise with inflation.

7. Are 1% Properties Still Possible in Florida?

The answer is yes, but barely. Florida is still absorbing more new residents than any other state. While many buyers are hesitating due to high rates and insurance costs, sellers are also getting nervous. That creates a window of opportunity.

If you know how to spot value-add deals, especially single-family homes in emerging neighborhoods, you can still find properties close to the 1% rule while also gaining equity.

8. The Real Story Behind Florida’s Insurance Costs

There’s a widespread misconception that Florida’s insurance rates are high because of hurricanes. That’s not the full story. The real culprit has been years of fraud—false sinkhole claims, inflated roof repair lawsuits, and frivolous litigation.

New legislation in 2022 finally curbed much of that fraud. Since then, we’ve seen premiums begin to stabilize. Personally, my portfolio of 40 properties saw premiums go up by 400%—but they’ve begun trending down.

Most landlords are also over-insured. Many are carrying replacement cost coverage well above what’s needed, and they don’t even realize they’re paying for add-ons like leaky sink coverage. Review your policies carefully. You can likely reduce premiums without increasing your risk.

9. Focus on Strategy, Not Speed

After losing everything in 2007, I made a promise to pace myself. I buy two or three properties a year. I look for forced equity opportunities. I don’t chase the next hot trend. I work with vendors I trust. I protect my downside.

Whether you’re buying your first property or your fiftieth, the key is to stay strategic. Know your why. Pick a lane. Diversify when it makes sense. And most of all—enjoy the process.

Special Thanks

A big thank you to Trent J. Werner and the team at the Westside Investors Network for the opportunity to be part of their Deal Deep-Dive segment. Your thoughtful questions and preparation made for a meaningful conversation—and it’s clear you’re truly committed to helping real estate professionals grow into real estate investors.

I appreciate the warm welcome, the well-structured interview guide, and the care your team took in making the experience seamless. Looking forward to staying connected and collaborating again in the future.

Listen to the full episode:

https://www.westsideinvestorsnetwork.com/podcast

Connect with me directly:

http://graystoneig.com/ceo

Keep it consistent, stay patient, stay true—if I did it, so can you.

Ready to connect and strategize? Contact me at graystoneig.com/ceo – Jorge Vazquez, CEO of Graystone Investment Group & its subsidiary companies and Coach at Property Profit Academy.

Property Profit Academy:
✔ Learn to buy properties with little to no money down.
✔ Build a $10M portfolio step by step.
✔ Master strategies like BRRRR and house hacking.

Meet our Team of Experts!

My team and I bring over 20 years of real estate experience, with deep roots in Florida’s investment scene. As a licensed MLO, I’ve helped close millions in loans and investor acquisitions. We’ve built strong relationships with wholesalers, probate attorneys, and sellers to source real deals—not just listings. My goal is simple: align your investments with your vision and deliver results that exceed expectations. Connect with Cody at https://graystoneig.com/cody

Hi, I’m Lisa-Kaye Price, Real Estate Lending Specialist at Graystone Investment Group. With 20 years of experience as both a licensed Realtor® and Mortgage Loan Originator, I specialize in helping investors secure smart financing for powerful real estate moves. Let’s connect and talk strategy! Connect with Lisa at https://graystoneig.com/lisa-kaye-price

Jay Michalec is the COO of Graystone Investment Group and a proud U.S. Army veteran. With 25 years in hospitality, Jay brings leadership, service, and operational excellence to real estate. He’s known for keeping things running smoothly and supporting both the team and clients every step of the way. 📅 Connect with Jay: https://graystoneig.com/jay