How 3 People Bought Their Way to Ownership

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.

And after numerous conversations with our deal advisors there, Katie 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.

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.

This business turned out to be the perfect fit, but if they had refused to expand their price ceiling, they would’ve missed out.

Don’t let the sticker price scare you, because there’s often more cushion than you might think.

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This is Rachel.

Rachel spent roughly 30 years in banking on the technology side, eventually leading tech support for her Minnesota region. Most of those years were great. Then, in February 2025, came the “good ol’ chopping block notice,” as she puts it.

Surprisingly, Rachel’s reaction wasn’t panic. It was a celebratory cocktail. After three decades of service, her severance package included 16 months of full pay and benefits.

Suddenly she had runway, and after attending one of our events, she decided to buy a business.

When Rachel started searching, she looked toward what a lot of first-time buyers do. Laundromats. Car washes. Storage. A pet shop. A coffee shop.

“We were just looking at all this lame, cliche, small business owner crap,” she told us, joking. “Nothing clicked!”

Even some of the deals that looked good on paper didn’t have one of her key criteria: geography.

Many of the businesses that crossed her desk were across the river from her, a 50-minute commute each way.

So she ruled them out.

Then a broker email landed with something she’d never heard of: a senior move management company (seven miles from her house). She signed the NDA, read the description, and walked upstairs to tell Tony she’d found her business.

Rachel loves organizing and has a soft spot for seniors. “The end of your life should be the best part of your life,” she said.

The financials put it in the lower end of what she and Tony were prepared to spend (their deal box could handle an SBA loan in the $1M to $1.5M range).

But the fit was the point.

When you start your own search, don’t rule out location as one of your criteria.

Take a drive through your local neighborhood or business park and check out the for-sale signs, the perfect business might be just a few minutes away.

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Erika spent her early career in cost management for a military contractor. Her husband Kevin was active duty Navy for years, before shifting to aviation maintenance. Their life followed the military rhythm: deployments, cross-country moves, a young family to raise, and a steady but constrictive paycheck.

Their business buying spark came from Erika’s dad. As Erika put it, “He loves to browse listings and dream.” One time, he showed her a local bar listed for $68,000. “Relatively speaking, I didn’t know businesses sold for that little,” Erika said. “We could buy that.” That specific listing didn’t go anywhere, but the idea took hold.

In May 2025, with Kevin’s active duty contract ending in December, they sold a rental property in Washington to free up acquisition capital and on March 17, 2026, they closed on a profitable scratch-and-dent appliance store that’s been operated out of the same Central Valley, California, building since 1968.

Here’s the interesting part, the seller wasn’t necessarily looking for the highest bidder.

He was looking for buyers who would take care of something he had spent his life building, and do it fast.

You have to remember, when you’re buying a mom-and-pop business, you aren’t just swiping a card on Amazon: you’re buying from a person.

And their feelings can matter just as much as the financials.

Early in their conversations, the seller was guarded with his financials. He was eager to sell, but wasn’t opening the books until he knew the buyers were serious.

“We absolutely want the building with the business,” Erika told him. “We just don’t know if we can afford it on the financials you’ve provided so far.”

He brought them back in and laid it out. Mid six-figures for the business. Full seller financing on the building at 4%, balloon payment in five years.

They dug deeper into the financials.

At least $1 million in annual sales, every recent year, on zero advertising, with paper invoices and no digital infrastructure.

The core of the model is scratch-and-dent appliances: cosmetically damaged returns from big-box stores, bought in manufacturer lots at steep discounts and resold at 40-50% margins.

Everything held up, and they moved on it.

Plenty of other people had approached the owner about buying his business, but Erika and her husband took the time to understand what he wanted to achieve by selling.

Don’t neglect the emotional aspect of acquiring something someone spent their lives building. It could be your edge.

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FROM THE COMMUNITY

Buying businesses is hard, so we love celebrating our members when they make progress. Here are some recent wins:

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