1. When Seller Pushes Back on Price • “How am I supposed to make that work if the house needs this much repair?” • “What makes that number feel right to you?” • “How did you come up with that figure?” 2. When Seller Hesitates or Goes Quiet • “What’s the biggest challenge with moving forward at this price?” • “What would have to happen for you to feel comfortable with this?” • “How far off am I?” 3. When You Sense They’re About to Walk • “What would I need to do to make sure this works for you?” • “What’s the real concern here?” • “If this number doesn’t work, what’s the next best step for you?” 4. When You Want to Test Their Bottom Line • “How flexible can you be if we take care of everything for you?” • “What’s the least you’d feel comfortable walking away with?” • “If someone else came in and offered the same service, what would they need to pay you for you to say yes today?” 5. When You Need to Reframe the Conversation • “How important is speed and certainty versus squeezing out every last dollar?” • “What happens if this doesn’t get sold in the next 30 days?” • “How would it feel if this were completely taken off your plate today?” Reminder: These questions aren’t about getting an immediate answer. They’re about creating a pause, making the seller do the work, and often revealing flexibility they wouldn’t have shown if you kept pushing numbers.

When I started wholesaling, I thought my first check was gonna be $30K. Truth? It wasn’t. It barely covered a couple bills. But that little win proved the business works—and that was all I needed. Don’t chase the big flashy deal right out the gate. Chase the process. The money will follow.

I’m 35, married with 2 kids and a dog. I’m an avid golfer and sports fan. I left the insurance world in 2019 to go full time in real estate. Once I flipped my first house in 2019, I got hooked and flipped 3 more that year. Since then I’ve done over 200+ deals (flips, wholesales, wholetails, and brrr’s), got my real estate license, co-launched the Joe Homebuyer Kentucky franchise, co-launched the Dumpster Today Louisville franchise, and built a team of rockstars to take our real estate operation to the next level. I love helping other investors go from hobbyists to true business owners!

In real estate, one of the biggest mistakes you can make is only having one exit strategy. Every deal should have multiple ways to win—whether it’s flipping, wholesaling, wholetailing, or holding as a rental. Markets shift. Contractors fall through. Buyers back out. But when you have more than one exit, you’re never stuck—you’re in control. The pros always play chess, not checkers. 🏡♟️ What’s your favorite strategy?