© John Hubbard / ETA Street montage

John Hubbard does not fit the mold of the typical search fund entrepreneur. He does not wear a Patagonia vest. He does not speak in the polished, guarded tones of a newly minted MBA trying to impress investors. During a recent interview, he openly nursed a craft beer alongside his espresso at 10:00 AM, a visual testament to the autonomy he spent a lifetime chasing.

Hubbard is a man who has spent the majority of his adult life in high-stakes environments. He served 13 years in the Army, ending his tenure as a Special Operations medic. He spent his twenties jumping out of airplanes and patching up teammates in war zones. When he left the military, he tried to transition to law enforcement in Texas, becoming a 34-year-old rookie in a precinct full of twenty-somethings.

But one night, after chasing a suspect over a fence and drawing his weapon, a cold realization hit him. He had survived over a decade of overseas combat. To die in a backyard in Texas for a municipal salary, leaving his newborn child fatherless, was a risk calculation that no longer made sense.

He hung up his gun belt and decided to find a battlefield where the only thing at stake was capital.

The Platoon Leader’s Thesis

Hubbard’s entry into business was driven by what he calls "irrational self-confidence," but is perhaps better described as the demystification of authority.

While pursuing an Executive MBA, he took a job running operations for a small home remodeling company. He wanted to see under the hood of a small business. Within thirty days, the intimidation factor vanished. He realized that payroll, supply chains, and hiring weren't dark arts; they were just logistics. They were platoon-level operations without the gunfire.

"I realized I could run this company tomorrow," Hubbard recalls. "It’s just managing people and resources."

He launched his search in August 2020 with constraints that would make a traditional investor weep. He had no personal capital to deploy. He refused to move from the Tampa Bay area. He refused to work with a partner.

He simply posted a candid message on Searchfunder: Here is who I am, here is where I’m looking, hit me up if you want to invest.

It was audacious, and it worked. In February 2021, Hubbard closed on Express Trailers, a manufacturer in Clearwater, Florida. The business was generating $5.5 million in revenue and roughly $740,000 in EBITDA. He bought it for $2.5 million, securing a deal that many would consider a steal by agreeing to a stock purchase structure that saved the sellers significant taxes.

Firing the Customer

The transition from "Searcher" to "Owner" is usually characterized by caution. The standard advice is to change nothing for the first year. Hubbard, however, applied a triage mindset to the P&L statement.

He analyzed the company's revenue streams and discovered a fatal flaw. The business was split 50/50 between custom commercial projects and wholesale units sold to dealerships. The dealer trailers—commoditized, standard units—were actually losing money on every sale. The company was subsidizing its volume with its custom work.

Hubbard didn't wait for permission or a strategic review. One month into his tenure, he grabbed his VP, hopped in a truck, and drove around Florida firing every single dealer in their network.

"I just took half of our production board and dry-erased it," Hubbard says. "I told them I wasn't going to lose money for the next eight months just to keep them happy."

It was a terrifying gamble that paid off with immediate, violent efficiency. Hubbard refocused the entire factory on the B2B commercial sector—custom trailers for landscaping giants like BrightView, mobile command centers for police departments, and specialized rigs for pipe repair companies.

He raised prices by 30 percent to match rising material costs. The commercial clients, who valued lead time and quality over penny-pinching, didn't blink. The business began producing fewer units but making significantly more money.

The Lazy Efficiency

Hubbard describes his management style with a self-deprecating claim of laziness, noting that his motivation to be an honor graduate in the Army was solely to avoid marching in the Georgia heat. But this "laziness" is actually a ruthless prioritization of leverage.

He has no interest in building a massive corporate infrastructure. He rejects the idea of chasing top-line revenue for ego. "I don't care about revenue," he says. "I care about the margins. If we can make $2 million in EBITDA on $6 million in revenue, that’s a better year than doing $12 million in revenue to make $750,000."

This philosophy has transformed the financial profile of the company. In less than three years, he has nearly tripled the company's EBITDA to $2 million while only marginally increasing revenue. He has paid off his investors. He owns 70 percent of a cash-flowing machine that requires less of his time every day.

He manages his workforce with the binary clarity of a military leader. He pays above-market wages and demands high standards. "Treat them like soldiers, and they’ll act like soldiers," he explains. He doesn't micromanage; he sets the objective and protects his team from outside interference.

The Farm in New Hampshire

Today, Hubbard sits in a unique position. He has crossed the Rubicon from an anxious buyer to a potential seller. He looks at the multiples in the manufacturing sector and calculates that his $0 down payment investment could be worth $10 million in a sale.

He isn't building a legacy to hand down to his grandchildren. He is building an asset to buy his freedom. He talks openly about the "Blue Years"—the stress of the transition, the nights worrying about payroll—but he also talks about the endgame.

For Hubbard, the goal isn't to be a CEO forever. It is to pay off the debt, maximize the equity, and eventually trade the industrial park in Florida for a farm in New Hampshire. He wants to work hard—he enjoys sweating in his own backyard—but he hates having a job.

"I’ve spent 39 years falling face-forward into pots of gold," Hubbard says. "I’m just going to keep doing that."

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