The most common questions from people interested in investing in rental properties typically sound like this:
“How do I know when I’m ready?”
On last week’s Not Your Average Investor Show, I sat down with Reggie Faunce, who recently purchased his first JWB rental property after years of learning, asking questions, and wondering how he would make the first deal happen.
And his answer to those questions started with a property he helped his mom buy years earlier.
Overcoming the First-Time Investor Freeze
Reggie had plenty of life experience behind him. He spent three years in construction, served four years in the Navy, and later spent 25 years with the California Highway Patrol. Back in 2015, he even stepped up to help his mom buy her very first home.
But even with all that life experience and years of studying real estate on his own, taking that very first step into his own investment deal required him to push right through a wall of uncertainty.
He hit the exact same roadblock so many people face when they are trying to get started:
“Where am I gonna get that extra money to go?”
Financial hesitation can stall anyone, no matter how much life experience they have under their belt. But once Reggie changed how he looked at the problem, his entire strategy shifted.
Turning Questions Into a Plan
To move past the hesitation and get his first deal done, Reggie focused on three simple things:
1. Trading Excuses for Education
- The Turnaround: Reggie joined a real estate investing coaching program in 2017 and began learning more about rental properties, equity, retirement accounts, and the various ways people enter real estate investing.
- The Realization: That education helped him see that starting at 62 did not mean he was too late. He did not need to wish he had started decades earlier. He needed to make the best decision with the time and resources he had now.
2. Finding the Right Strategy Fit
- The Choice: With his construction background, Reggie naturally considered fixing and flipping houses. It made sense in one way because he understood the work involved.
- The Twist: But he also realized that model would require him to find funding, build relationships with investors, and organize the business around each project. As someone who had historically been shy, that part felt like a bigger hurdle.
- The Fit: Buy-and-hold single-family rentals gave him a different path: own properties for the long term, work with an experienced team, and begin building the kind of portfolio he could eventually leave to his family.
3. Using Existing Value to Work: The 1031 Exchange
One of Reggie’s biggest questions had been where the money for his first investment would come from.
- The Move: Through his education and conversations with the JWB community, he learned how a 1031 exchange could help him move the proceeds from an earlier investment property into a new rental property while following the required process to defer taxes at the time of sale.
- The Result: In January 2026, that process helped Reggie purchase his first JWB rental property on Lyle Road!
Reggie’s First JWB Property Portfolio Snapshot (Lyle Road):
|
Purchase Price |
$305,000 |
|
Financing Type |
Conventional Loan |
|
Initial Cash Outlay |
$99,225 |
👉 How One Investor Used Education to Unlock His First Rental Property Deal
The conversation also covered why Reggie chose new construction for his first rental property. Both options can be strong choices, depending on individual budget and investment goals.
- Renovated homes generally offer a lower cost of entry but will have slightly higher maintenance and vacancy costs.
- New construction homes generally have a higher price point but will have lower maintenance and vacancy costs.
Either investment is a winner; however, both tend to deliver roughly the same rate of return over a full market cycle.
For his first investment, Reggie went with the new construction option. He was looking to invest a higher amount because he wanted to maximize his tax savings and he loved the peace of mind associated with new construction. It is a wonderful way to begin his investing journey with JWB.
One Deal into a Multi-Generational Legacy
Reggie’s first property was never meant to be the finish line. It was the beginning of a larger family plan.
He has already created a trust and is considering how the rental properties he buys today could eventually be passed down to his children and future generations. More than anything, he wants his kids to understand how to care for those assets and continue building on what he started.
Here is how Reggie is mapping out his path to a 10-property portfolio:
- Protecting the Family: He has already established a family trust so that these properties will pass seamlessly to his kids and grandkids down the road, keeping the wealth inside the family and protected from heavy estate taxes.
- Different Generations, Different Paces: While younger generations often view things through a different lens, preferring to see the wheels in motion before jumping in, Reggie’s 25-year-old son is already watching over his shoulder and being inspired by the construction side of the business.
- House Hacking: Reggie is now exploring what the next three to five years could look like. He talked about potentially moving to Florida, using his VA eligibility to purchase a home where he could live in one portion while renting another, adding another JWB rental property, and possibly purchasing a fourplex in the future.
- Tapping into Growth: As his properties have time to build equity, Reggie also wants to understand when it may make sense to use some of that equity toward future purchases. That will not be the right move for every investor at every moment, but it is one more example of how the first property can become part of a longer plan.
👉 How This Investor Is Using His VA Loan to House Hack Into More Rentals
Real estate is a living system that builds upon itself over time. When you view it as a long-term structure, you realize that confidence isn’t something you magically need to feel before you act; it’s something you construct along the way.
NOT YOUR AVERAGE INSIGHT: Confidence is Built
👉 Investor Mindset Shift Most People Skip Before Their First Rental Deal
Many prospective investors believe they need to feel completely confident before buying their first rental property.
Reggie’s story shows us that confidence can come in another way.
It can come from…
- showing up to a live community
- listening to the numbers
- asking questions
- watching your peers successfully execute the process ahead of you
Once you have the right education and a trusted team at your back, the fear of the unknown naturally transforms into a clear, actionable plan.