My First Wholesale Deal – Lessons in Trust and Persistence

[Jeremy Beland]

In March of 2017, I closed my first real estate wholesale deal. It wasn’t a huge payday—$5,000—but what I gained from the experience was far more valuable than the check.

It started when I got a lead from an older woman who owned a house in New Hampshire but lived in Maine. She needed to sell quickly to afford cancer treatment in Chicago that her insurance wouldn’t cover. 

The house needed a lot of work, and I was brand new to wholesaling. I had some training but no real experience, especially when it came to negotiating. So, I took a chance and was completely upfront with her: I was new to this and would be assigning the deal to a cash buyer.

Despite my inexperience, we built trust. She knew I was trying to help her, and that honesty became the foundation of our deal. After locking up the contract, I ran into my first problem: I didn’t have enough cash buyers. My coach had told me to have 150, but I had around 30. Still, I scheduled an inspection and invited the buyers I had. The seller drove two hours to unlock the house for me, and no one showed up. I was embarrassed, but I didn’t give up.

I called the buyers, and they all said the same thing: the property was overpriced. I went back to the seller and explained the situation. She agreed to lower the price, and we scheduled another inspection. This time, a few buyers came, but still no offers. The house needed more work than they were willing to take on. I felt discouraged, but the seller stuck with me because of the rapport we’d built.

After a final price reduction and a third inspection, things changed. About 20 buyers showed up, and one investor made an offer on the spot. We closed the deal, and I walked away with a $5,000 assignment fee.

The real value of this deal wasn’t the money—it was the confidence it gave me. I learned that persistence, transparency, and trust can get deals done, even when things don’t go as planned. The seller got her money, went to Chicago for her treatment, and even thanked me once she got there. That meant more to me than anything.

For anyone just starting out, remember: your first deal isn’t about making a fortune. It’s about learning, building relationships, and proving to yourself that you can make it. Be honest, take action, and trust the process. You’ll get there.