How They Bought an Off-Market, 20-Year-Old Water Sports Brand Using Creative Financing

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Meet Katie and John.

Katie has spent her career as a non-owner operator, managing teams and running operations across multiple businesses. John spent nearly a decade as a firefighter, and before that, worked in sales.

Before they ever met, they had something more fundamental in common: parents who built something from scratch. John is a first-generation Mexican-American. His mother cleaned houses. His father ran a landscaping business. Katie's father built and ran his own medical practice.

"We both came from hard-working parents," John said. "When Katie and I met, we connected on that. We both knew we wanted to be business owners."

They started by chasing the startup dream, jotting down ideas, trying to find the right one. Then a friend introduced them to business acquisition. They joined another acquisition program, got close on a few deals, but nothing clicked. In January 2025, after attending one of our virtual masterclasses, they joined the Contrarian Academy.

What followed was a rollercoaster year that tested them in ways they hadn't anticipated, but led them to a $2 million acquisition of Rubber Dockie, a water mat and inflatable manufacturing and e-commerce brand based in South Dakota.

Here's how they got there.

When Katie and John first started searching for businesses, they were thinking small.

Over the course of their search, they signed around 100 NDAs, submitted multiple LOIs, and entered due diligence multiple times.

"But every time we got to talking to the seller, things just didn't seem intuitively right," Katie said.

So, in May 2025, Katie attended our annual Contrarian Camp for business buyers.

After numerous conversations with our deal advisors there, she returned to John with one key realization: "I think we’re playing too small."

Like many buyers, they approached their acquisition wanting to “go small” to reduce risk. That’s understandable, but “small” often turns out to be surprisingly risky.

Katie and John agreed to expand their thinking. They weren't looking for a smaller deal anymore; they were looking for the right one, at the right size, and with the right seller.

Shortly after Contrarian Camp, Katie learned her father had been admitted to the hospital. A month later, sadly, he passed away.

In the weeks that followed, Katie and John put their search on pause. They traveled, they grieved, they were with family.

At her father's celebration of life in South Dakota, John found himself talking with a family friend. In the middle of the conversation, John mentioned that he and Katie had been actively searching to acquire a business.

The friend paused.

"My best friend is actually looking to retire and sell his."

And just like that, the very same day, Katie and John met the seller at his warehouse. They spent about six hours together, toured the facility, and grabbed beers.

Turns out, Katie’s father had been the seller’s physician and delivered his children. Oh, and the seller’s wife had been Katie's kindergarten teacher.

"John and I knew instinctively," Katie said, "this could be it."

After that first six-hour meeting, Katie and John didn't walk away and wait. They came back. Then they came back again.

They asked if they could spend a full week on-site just to learn the business. The seller said yes. They went through the financials together, got access to the books, and started to understand the real scope of what they were looking at.

The relationship deepened steadily. In November, they made a decision that signaled just how serious they were: John left his firefighting career, they relocated from California, and started working inside the business before the deal had even closed. No signed papers, no guarantee.

"You have to put skin in the game," John said, echoing something Codie has said that stuck with them. "You have to make some difficult decisions."

That level of commitment changed things. The seller could see they weren't just kicking tires. Over weeks of working alongside each other, real trust formed.

“Eventually,” Katie said, “he told us, ‘I know this deal is going to work, we just have to figure out how.’”

See, when you go off-market, without a broker, the relationship becomes a larger part of the process. Time that would normally go toward one thing might go into building trust instead.

It’s not necessarily a shortcut, but it can produce a level of access and transparency that a typical deal rarely offers.

The business had seen strong revenue during COVID, which created a complicated financial picture. When Katie and John tried to get SBA financing, lenders pushed back on the history of the financials, and the creative structure they'd built with the seller didn't get approved.

So they got even more creative, and the final deal landed at a $2 million purchase price, split roughly in half.

"It de-risked things for us quite a bit," Katie said, "in terms of the debt service coverage."

Friday, February 27th, is a date John says he'll never forget.

That day, John went to the bank, signed the paperwork with the seller, and around 2 in the afternoon, shook hands as a business owner for the first time.

Right on cue, the bank president then turned to him and said, "Well, John, it’s time to get to work."

There happened to be a local expo that weekend, so John went home, showered, and drove to the expo to represent the business. The seller came with him.

That evening, John made his first sale as an owner, with the seller standing right beside him.

Over that weekend, they sold multiple units, fielded media inquiries, and even managed a new intern, all while still figuring out what it meant to be owners for the first time.

What’s Next? The near-term focus is building out wholesale relationships with marinas, watersports rental operators, and outdoor and boat retailers, while strengthening the e-commerce side of the business.

Weeks into ownership, Katie and John are the first to admit they don’t have it all figured out. But they’ve got a seller who’s invested in their success, a strong understanding of the business’s operations, a product people actually want, and two years of hard-won lessons behind them.

It’s going to be so cool to see where they take things from here.

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