Founder Story: Ryan Rybolt of Payload

Working on a vegetable farm, somewhere along the border of Indiana and Ohio, the rules were simple: nobody left until all the work was done. “You’re not going to leave the field until the last row is hoed,” Ryan Rybolt Co-founder and CEO of Payload, remembers. “If someone needs help, you’re going to finish that because everyone wants to get out of the field at the end of the day, right? One of the valuable lessons that came early on was that, you know, you have to pick others up, [and] they'll pick you up in some cases.” 

It’s a lesson that appears to have served him well, throughout his corporate career and as an entrepreneur. “That's probably my transferable when you're building a software company that is moving money: everything continues to evolve and so complacency is not an option”

That muscle memory - finish the row, help the team, and keep moving - has become the operating system for a career that has zig-zagged from the local ‘dream job’ working at Procter & Gamble to banking and then bootstrapped fintech, all the way to ringing the bell for an IPO on Wall Street. And now there is Payload, an embedded payments platform quietly moving billions, rooted in Cincinnati with no plans of moving.

When the Fortune 50 feels too slow

As a teenager working on that farm, Rybolt picked strawberries, pulled sweet corn, and learned to drive a tractor at the age of fourteen. It wasn’t the bucolic, set-it-and-forget-it kind of agriculture. “It was a vegetable farm… it wasn’t like cattle and things that just eat while you sleep. It was stuff that needs [to be] picked and sold,” he says. That pace set expectations for the rest of his life: get the job done, then look for the next improvement. 

Rybolt studied engineering at the University of Cincinnati but realized during the school’s co-op program that perhaps he didn’t want to be an engineer after all. Consulting at Andersen (now Accenture) followed, then P & G to his parents’ delight. He points out that it has historically been a company that you don’t leave, such that he imagined his parents doing “chest bumps in the back of church”. It’s an evocative, deeply wholesome image to which many of us can probably relate: parents congratulating themselves on a job well done in raising their kids.

But the corporate tempo clashed with Rybolt’s internal clock. “I wasn’t really excited about maybe having my boss’s boss’s job in 25 years. I had more of an entrepreneurial mind… maybe part of that was growing up working on a farm… it’s not on someone else’s timeline.” A move to Fifth Third Bank in 2001 introduced him to the world of payments, and planted the seed for what would become the rest of his working life up until now. 

Servant leadership before the startup

While he was making those early career moves and discovering his entrepreneurial streak, he created something from scratch which says a lot about how he thinks about work and life. With friends at P&G, they started Give Back Cincinnati, a social volunteer organization that began with - in his words - Saturday “random acts of kindness," and has now grown to over 5,000 members. Being in his mid-20s at the time, at an early stage of his career still working things out “it taught me a couple valuable leadership skills, that if you treat people as if they want to be there and don’t have to be there … there’s a lot more commitment … not being above any task when you're in an organization was highly transferable to when we launched our first startup.”

For Rybolt, that balance was a key element when he eventually started hiring for his own business. “When I launched Infintech… I had business partners at the time that recognized that that would be a priority for us and for me and for our employees as well to continue to balance giving back and sharing our time, talent, and treasure with the community.”

In 2004 he was still working as a Product Manager at Fifth Third Bank when the turning point in his working life arrived: he found out that the bank was going to get out of small business credit card processing.

He saw an opportunity for his own business and talked to his wife, who encouraged him to give it a try. And so this engineer who ended up in finance started selling his payment service to mom and pop businesses by going door-to-door.

At the time, the industry’s reputation was grim. “Some days I felt like I had to come home and take a shower before I sat down… someone had always been taken advantage of.” This insight led to an unglamorous choice in the finance world, one which became a key to their success: they standardized pricing for everyone and then approached their local Chamber of Commerce with the offer. With transparent pricing, he says customers no longer felt ‘taken advantage of’. “They all know exactly how much we make … we can build this, give them month-to-month agreements.” It worked. First in Cincinnati, then with over 200 Chambers of Commerce nationwide receiving their offer as a member benefit. 

All while bootstrapped, since the very beginning. “We were self-funded… continued to build as we continued to grow our revenue.” But, oddly after all this time, the naming still makes him laugh. “We wanted to call it Fintech… the domain wasn’t available…a squatter owned it and fintech wasn't even a thing, right? And so I was like … man, you know, they want like a couple thousand dollars for this domain.” His business partner, Tom, baulked. He laughs at what that domain may be worth now, but they went a different route and called the business Innovative Financial Technologies, Infintech for short. The cost of that particular domain? $10 a year.

Rolling up to ring the bell

By 2015, Infintech merged into a Nashville-based roll-up to form i3 Verticals, aiming for the public market and after the new entity acquired other platforms, it IPO’d in 2018. It was the culmination of a succession of choices that wasn't just about founders, according to Rybolt. “We wanted to make sure that our employees had a home after and beyond us being involved.” But for him, it provided something else: “It afforded me the ability to bootstrap Payload.”

Although Payload is the first time that he has taken outside investment into his own business in the form of a ‘friends and family’ round, he is still candid with his advice for first-time fundraisers: 

"If you can avoid raising outside capital, then, by all means, do so...however if you need to raise capital, do it when you don't necessarily need the money.  If you're raising at a point of desperation, you're doing yourself and your employees a disservice. Being capital efficient, making sure that you’re the last one to eat at the table… we’re five, six years in and still… my co-founder Ian and I are at the bottom of the totem pole of being paid… [that’s] deliberate because you want everyone… building the technology… You want them to be successful in their own right.” 

But he’s not anti-venture; he’s just pro-agency. 

“It’s easier to… dilute yourself [and] raise a bunch of capital… but… it’s only a matter of time before decisions are outside of your control… the journey suddenly isn’t yours. Being capital efficient and building a business that’s profitable… with bleeding edge technology is more of a unicorn than what we would inherently call a unicorn, a billion-dollar value company”

Payload: embedded rails for real industries

Payload’s thesis is simple and maybe even a little subversive: “We are an embedded payment platform that can automate any inbound or outbound payment.” Credit cards could be seen as table stakes, but are costly, whereas bank rails are under-loved. “Everyone treats… pay by bank transactions as a second-class citizen… but it is essential in order to automate every single payment transaction.”

So instead of selling merchant-by-merchant, Payload integrates at the system-of-record layer. This includes practice management in legal, transaction software in real estate, and beyond. “Let’s embed a way for someone to make a payment by bank… real-time payment, or by card. And then it syncs directly back with software… we’ll share our revenue with that software company… they become our distribution channel.”

Timing in business often matters more than many would like to admit, and so it was with Payload. The pandemic jump-started their product–market fit. Real estate found them first in the form of earnest money deposits. These are good-faith deposits made by a home buyer to show the seller they are serious about purchasing a property. “We created… an electronic avenue to facilitate that payment. [It] happens six to seven million times a year in the US alone.” All of which led them to today, where - according to Rybolt - Payload is the largest money mover of residential real estate purchases in North America, covering over 4,000–5,000 brokerages and more than $6 billion in payments through approximately two and a half million transactions. This early focus was intentional though: “We all zeroed in on, let’s just own real estate. The next verticals will happen,” he says, pointing out that the legal industry is a prime candidate of the ‘next vertical’, where the dominant incumbent’s “technology is tired.” 

Under the hood, Payload is betting on ubiquity, not novelty in the form of clean ledgering data, instant reconciliation, and real-time rails. “What our banking system has fallen short of is making pay by bank really ubiquitous and seamless… what we built… is that very seamless transfer… tied with ledgering data.” Consequently they’ve been one of the first to launch with FedNow and with The Clearing House. All of which they believe can help them to deliver 24/7/365 instant bank funding as a default, not a future promise. 

Why stay in the Midwest?

In our Founder Stories we often ask interviewees why they stayed in the region. It’s a purposefully ‘antagonistic’ question, but one that comes from the belief that we’re probably not the first to ask. In Rybolt’s case, working in finance, the pull of New York must’ve been strong, we wonder. But he says he never chased a coastal address. “Cincinnati’s home… a big city with a small town feel… through a couple connections, you could have… coffee with the CEO of P&G or Kroger.” Building here, he argues in counter argument to our friendly ‘antagonism’, isn’t a handicap. “Building businesses is easier… easier to gain support and trust of your peers,” he says.

The trade-off is visibility, but he believes that’s also by virtue of his bootstrapping. When you don’t announce mega-rounds, you have to fight for public attention. “We’re not at the top of the fold for industry rags for raising money… [but] that will come over time in an organic method which I think is more authentic.” In the meantime, in his view, the region offers everything that actually compounds. “We have good schools… no traffic… low cost [of] living… a yard,” he deadpans.

The through-line

Taken together, Rybolt’s choices could read like a manifesto for founders who want both freedom and endurance, and it’s one we hear a lot in our stories from those who’ve made it work in the Midwest:

- Start with the field in front of you. Finish the row. Help the person next to you.

- Learn to lead where people want to show up. Then take those habits to work.

- Don’t confuse capital with progress. Build pricing people can trust; distribution that scales; margins that survive.

- Keep control of the mission long enough to make correct, difficult choices.

- Find a market by looking at the real systems people already use; make the money movement invisible and the reconciliation instant.

It’s worth mentioning here, at the conclusion of his story, that Rybolt briefly learned to fly a plane. It explains a lot about the way he thinks, and how that thinking has led him to success. He took P&G’s retraining allowance when he left the company to get his pilot’s license as it had always been a dream and he figured it was as good a time as ever. But even that hobby bent toward practicality; when it stopped fitting the life he was building, he hung it up.

Payload, by contrast, feels like a long runway. 

The team is remote; the focus is sharp; the rails are modern; growth is deliberate. And the philosophy hasn’t changed since the fields: work until it’s done, then make it better. In his own words, again: “Everything continues to evolve. Complacency is not an option.”