Wholesale real estate has created some of the most inspiring success stories in investing. One standout example is Tyrell Hayden, who made an impressive $35,000 on his very first wholesale deal in Central Kentucky.
What makes his story unique is that he didn’t even plan on wholesaling the property at first. He had intended to buy it for himself, but a series of events turned it into a profitable wholesale transaction.
His journey started with one simple but powerful strategy: driving for dollars.
Finding His First Deal Through Driving for Dollars
Driving for dollars is the practice of driving through neighborhoods to spot distressed properties or properties that look neglected. These are often homes that may not be listed for sale but could belong to owners willing to sell.
That’s precisely how Hayden found his first deal. While driving through a Lexington neighborhood, he spotted a house that showed signs of neglect. Instead of ignoring it, he took action.
To his surprise, the owner was a real estate broker who had been considering listing the property. Instead of going through the listing process, the seller offered to sell directly if Hayden could meet his price. Hayden quickly got the property under contract.
The next turning point came when he had breakfast with a friend who was an experienced wholesaler. That friend already owned properties on the same street and immediately recognized the value of Hayden’s deal.
He pursued Hayden for three straight days, eager to buy the contract. Eventually, Hayden agreed, walking away with $35,000 in assignment profits.
Spotting Distressed Properties in a Competitive Market
Lexington is a tough market with limited inventory. Unlike some cities where boarded-up houses or abandoned properties are easy to find, Hayden has to look for more subtle signs of distress.
He pays attention to details like:
- Gutters falling off
- Overgrown grass
- Broken concrete on porches or sidewalks
- General neglect in curb appeal
These small indicators often point to owners who might be ready to sell. In a market surrounded by well-maintained horse farms, Hayden says these subtle clues are his best way to uncover off-market opportunities through driving for dollars.
How Hayden Calculates Offers That Work
One of Hayden’s strengths is his disciplined approach to evaluating deals. His offer formula is simple and designed to protect his investment.
He aims for:
Purchase Price + Rehab Costs ≤ 80% of After-Repair Value (ARV)
This keeps him in line with what most lenders will finance, since many offer loans up to 80% loan-to-value.
As the owner of a contracting business, Hayden can estimate rehab costs quickly and with strong accuracy. He says he’s usually within 5% of the actual cost after just a five-minute walkthrough. In his market, a full renovation—covering kitchens, bathrooms, flooring, and paint.
Even with his expertise, Hayden always builds in a margin of safety. He knows that renovations often come with unexpected challenges, and leaving room in the numbers keeps him protected.
From Solo Deals to Running a Team
Hayden’s business looks much different today than when he closed that first deal. What started as a one-man operation has grown into a structured team.
His current team makes about 200 calls every business day to generate leads. They focus on property types that often indicate motivated sellers, including:
- Vacant lots, especially inherited land
- Properties owned free and clear by people in their 60s and 70s
Hayden especially values conversations with older sellers. This makes them open to creative financing solutions that can benefit both sides.
Hayden calls himself “the starter and the closer.” His team does the groundwork by identifying leads and warming up conversations. He only steps in once a serious opportunity is on the table.
This allows him to maximize his time and focus on the deals that matter most.
Why Hayden is Selective About Appointments
Another lesson Hayden has mastered is the value of his time. Unlike many new investors who rush to every possible appointment, Hayden takes a different approach.
He averages just one appointment per week, but nearly every one of those leads to a deal. He sets clear criteria before agreeing to meet a seller:
- The seller’s price must already be close to his target number.
- The deal must make sense even if no further negotiation happens.
This strict screening process ensures that his time is never wasted. According to Hayden, “Nine out of 10 times we’ll end up making a deal if I’m actually going out there.”
Building Long-Term Wealth Beyond Wholesaling
While wholesaling gave him his start, Hayden’s bigger goal is building lasting wealth through rental properties. He has set a clear target: to net $30,000 per month from his rentals after expenses, which he calls his “$1,000 a day” goal.
So far, he’s about 55% of the way there and expects to hit the full target within the next five years.
Here are some of the strategies he uses to reach that goal:
- Targeting 15–18% cash-on-cash returns on rentals
- Completing his first seller financing deal on new construction with just 7% down, producing a 30–35% return
- “Cycling” his portfolio every 3–5 years by selling smaller properties and upgrading to larger ones (for example, trading duplexes for fourplexes, or fourplexes for small apartment buildings)
By sticking to strict investment criteria and scaling strategically, Hayden continues to grow wealth while keeping risk under control.
Key Takeaways for Investors Using Driving for Dollars
Tyrell Hayden’s story offers several important lessons for investors considering driving for dollars:
- Simple strategies still work. Finding distressed properties through driving for dollars remains one of the most reliable ways to secure profitable deals.
- Numbers matter more than excitement. Having a formula and sticking to it prevents bad purchases.
- Time is your most valuable asset. By screening leads and only taking serious appointments, you’ll close more deals with less wasted effort.
- Think long-term. Wholesaling can create fast cash, but rental properties and creative financing build lasting wealth.
Frequently Asked Questions
Q: What did Tyrell Hayden do with the $35,000 from his first wholesale deal?
He reinvested about 80% of the profit back into his portfolio, using it for property improvements like new roofs, gutters, and concrete repairs. These upgrades boosted property values and reduced future maintenance costs.
Q: How does Hayden decide which seller appointments are worth his time?
He only meets sellers who already provide a price close to his target. If that price still leaves room for a profitable deal without heavy negotiation, he takes the appointment.
Q: What types of properties does Hayden target today?
He focuses on vacant lots, long-term owned homes, and properties held free and clear by older owners. These often present the best chances for creative financing and motivated sales.
Q: How much does a full renovation typically cost in Hayden’s market?
He estimates $25–$30 per square foot for complete renovations, including kitchens, bathrooms, flooring, and paint.
