It was April. I can’t pin down the exact calendar date, but it was right around 2009 or 2010 when I decided it was finally time to bet 100% on myself.
At the time, I was managing a Dollar General. It was a long way from my earlier days of selling wholesale fish to restaurants, but it was a grueling grind all the same. I was clocking endless hours, trading my life for a steady paycheck. When the opportunity to step full-time into merchant services presented itself, I knew it was my moment. No more safety nets. It was time to put all the chips on my own work ethic.
I remember the mixture of absolute terror and excitement. Back then, friends and family looked at me like I had lost my mind. “Credit card processing? You’re going to give up a steady management gig to sell those little grey boxes?”
They didn’t see what I saw. They didn’t understand the beautiful, life-changing engine of residual income. Looking back over the years, I realize that April wasn’t just the start of a new career—it was the day my entire life truly began.
If you’ve been pounding the pavement in this industry for a minute, let’s take a little trip down memory lane.
The Era of the “Heavy Lifting”
To the newer agents running around with sleek iPads and selling integrated software solutions: we love you, but you have no idea how good you have it.
When I started back in ’09/’10, the grind hit different.
- The Statement Slashing: We didn’t have AI, ISO Amp to analyze merchant statements. We had a yellow highlighter, a pen, a basic calculator, and a dream. We sat at coffee shop tables manually calculating basis points and transaction fees, trying to prove we could save a dry cleaner $40 a month.
- The Hardware Haul: Remember the Verifone Omni 3750? Or the Nurit 8020 if a merchant wanted to go “cellular “? Those things were built like tanks. THe shadyiness was real. Leases were everywhere back then and it was usually easy to save them their lease payment to switch to me.
- The Dial-Up Drama: “Ma’am, please don’t pick up the landline phone, I’m trying to run a test transaction.” We spent half our deployment time waiting for that familiar, agonizing screech of a dial-up modem connecting to the network.
Building More Than Just a Portfolio
What I love most about looking back isn’t just how the technology evolved, but how we evolved.
Merchant services has always been a relationship business disguised as a numbers game.
In 2010, the economy was still licking its wounds from the 2008 crash. Small business owners were scared, protective, and skeptical of anyone walking through their door with a clipboard. Earning their trust didn’t happen over a Zoom call (There as no zoom calls, Skype, yes) It happened by showing up, looking them in the eye, listening to their struggles, and genuinely trying to help them keep more of their hard-earned money.
Some of those merchants I signed in my first year? They’re still on my book today. I’ve watched their kids grow up, watched them expand to second and third locations, and stood by them through every industry shift.
The Great Tech Shift
We’ve survived an incredible amount of disruption since I took that April leap. Think about what we’ve navigated together:
- The EMV Migration: Remember the “Chip Card” panic of 2015? We had to educate millions of business owners on liability shifts.
- The Rise of the Smart Terminal: Watching the industry shift from dummy terminals to beautiful Clover and Poynt systems that actually helped merchants run their businesses.
- The Pricing Revolution: Moving from complex, hidden-fee tiered pricing to Interchange Plus, and eventually into the Cash Discounting and Dual Pricing boom.
Every time the critics said our industry was going to get commoditized or wiped out by big tech, we adapted. We learned. We grew.
The Best Business in the World
If I could go back in time to that April morning and talk to my younger self—the one sitting in the car outside my first pitch, gripping the steering wheel, trying to build up the courage to walk in—I’d tell them this:
“Take a deep breath and open the door. Leaving the retail clock behind and betting on yourself is the best decision you will ever make.”
This industry is a grueling, humbling, and relentlessly challenging career. But for those who have the grit to stick it out, it is the most rewarding business on the planet.
To everyone else out there who has been in the trenches since the days of paper applications and physical carbon-copy imprinters: cheers to how far we’ve come. And to the newer reps: treat this industry with respect. It can truly change your life if you let it.
Happy Selling,
David
