Losing Deals and Winning Anyway

I can still remember the knot in my stomach. I was new in the business, and I’d spent weeks working with a local restaurant I loved. I built a great relationship with the owner, showed him a clear $200 a month in savings, and laid out a plan to upgrade his old, clunky terminal.

He shook my hand and said, “Let’s do it. Get me the paperwork.”

I was ecstatic. I went back to my home office, drew up the agreement, and when I called to schedule a time to sign, he went cold. He told me another rep had come in and offered him a “free terminal” and a rate that was somehow even lower than mine. I knew it was a deceptive lease and a misleading tiered rate structure, but it was too late. I had lost.

I was furious, heartbroken, I remember thinking, “This isn’t fair. I did all the work. I was honest. I deserved that deal.”

If you’re reading this, I bet you know that feeling intimately. You’ve felt the sting of being ghosted, the frustration of being undercut by a shady competitor, the disappointment of a deal falling through for reasons that had nothing to do with you. You’ve probably said those same words to yourself: “This isn’t fair.”

You’re right. It isn’t. And one of the most important lesson I ever learned in this business was to accept that and move on.

For years, I let those “unfair” moments eat at me. I’d blame the merchant, my leads, or the dishonesty of my competitors. But all that complaining did was keep me stuck. It stole my power and my motivation.

The shift for me happened when I decided to stop asking, “Why did this happen to me?” and started asking, “What is this trying to teach me?”

I’ll give you a perfect example. Years ago, in my local market, we had a company that would always write a merchant high and lease a terminal to everyone—yes, a basic terminal! Was this fair to the merchants? Absolutely not, and it was infuriating to see. But for me, it was like finding gold. Because they wrote every account so high, I could walk in, run an analysis, and usually save the merchant what they were paying on the lease and still make good money on the account.

That unethical company, by being so unfair to its clients, made it incredibly easy for ethical reps like me to do right by the merchant and clearly demonstrate our value. The “unfairness” in the market created one of my biggest opportunities.

Every painful loss or frustrating situation became my personal sales coach once I started looking for the angle.

  • That big retail account that ghosted me? I realized I never confirmed the final buying process. It taught me to become a master of discovery.
  • Losing to the business owner’s deep loyalty to their bank taught me how to create a more compelling and urgent case for change.

I’m telling you this not to dismiss your frustration, but to free you from it. You can’t control the market, but you have absolute control over how you respond. You can let the unfairness of this industry or whatever’s out there to defeat you, or you can decide to let it forge you into a smarter, tougher, and more strategic salesperson.

The choice is yours, every single day.

Oh, and that restaurant I mentioned at the beginning? The one that ghosted me and went with the other guy? About a year or so later, after the hidden fees and terrible lease, the owner called me. He asked if I was still in the business. and wanted to work with me. I signed him up that week, and he’s been a loyal client of mine for several years now.

So, take that tough loss from last week. Let it sting for a minute. Then, pull the lesson from it and nail it to the wall. Let it be the fuel that helps you win the next one. You’re in a tough business, but I know you have what it takes. Now go prove it.

Happy Selling,

David

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Author: David Matney

Payment Technology Specialist at Payment Lynx

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