I started selling payment processing in high school. Not a side hustle. The real product. I learned interchange before I learned how to file a tax return. The first lesson was that almost nobody in the industry wanted me to understand it.
I was supposed to read from a script, beat my quota, and never explain a statement. I broke the pattern in the first week. Owners would ask me a question, and I would answer it. The numbers were on the page. I translated them. That alone was enough to win business that I had no business winning at my age.
By the time I co-founded LastPay with Max Umlas, I had spent enough years inside the industry to see the shape of the problem. I knew the payments side cold. Max brought the operational thinking, how to scale client acquisition, how to build backend systems that hold up, how to turn a service-first idea into a real company. Owners do not need a payment processor to do something exotic. They need it to charge less and sit inside the tools they already use. The market had not been giving them that, because the market got rich on the fact that owners were too busy to look.
The hardest lesson, in the early months, was about credibility. I learned that you cannot argue your way past someone who thinks you are too young. You have to show. I started bringing a side-by-side audit to every meeting. The math did the talking. I was happy to let it.
The second hardest lesson was about pace. I wanted to ship features the way a tech company does. The customers I talked to wanted reliability first and features second. They wanted their funding to land on time. They wanted reconciliation that did not break. They wanted a phone number that a person picked up. I rebuilt my priority list around what they were telling me.
The third lesson is the one I will keep for the rest of my career. Simplicity wins. Every time I added complexity to the product, the sales conversation got harder. Every time I cut something, the sales conversation got easier. The pitch we use today is short. The product is short. The statement is short. The savings are not.
I do not think my age is an interesting story. I think the fact that the industry made it so easy to enter is the interesting story. Owners had been waiting for someone to lead with the audit. The age of the person bringing the audit ended up being the least important variable in every deal.
I learned to listen for the moment in a sales call when the prospect stops talking. That pause used to scare me. Now I welcome it. The pause means the math has landed. The math is the part of the conversation I trust the most.
I also learned that this work is not glamorous. The day-to-day of running a payment company is statements, settlement reports, support tickets, and slow trust. There are no cinematic moments. There is only the discipline of being the vendor who picks up the phone, ships the integration, and lands the funding on time. Owners who built businesses on legacy processors have spent years learning that those things are negotiable. Our job is to make them not negotiable.
The most useful piece of feedback I got from my first dozen customers had nothing to do with our pricing. It was about my voicemail. They told me that legacy vendors did not return calls. The vendors that did return calls were salespeople, not the people who could help. The customers wanted a phone number that a real person picked up. We built the support team around that piece of feedback before we built half the features that were on the original roadmap.
I do not have a grand theory about fintech. I have a list of things customers told me they wanted, and I am still working through the list.
I will keep building. I will keep cutting. The first year of LastPay taught me that the best fintech product, in this segment, is the one that does the boring job better than anyone else. Boring done right is what owners are paying for.
For a closer look at the platform, watch Sending Invoices On QuickBooks With LastPay on the LastPay YouTube channel.
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