A new path

Standing in the suburban Cincinnati home of Procter & Gamble’s CFO, Derek Christian reflected on 13 years of corporate ladder-climbing. This particular gathering was to honor his achievements, and his career trajectory promised even greater heights. But as he stood watching well-heeled spouses paint Christmas ornaments imported from Germany, Christian felt a profound disconnect. 

“It was supposed to be, ‘This could be your life. Look at how wonderful this is!’ And I just kind of left saying, ‘Oh, I don’t want that. If that’s what success looks like, ugh. Nope. I’m out.’”

A few months earlier, Christian had engineered a software deal that generated $35 million in profit for P&G. His reward: a $5,000 bonus. 

“Why am I doing this for other people?” That question hit Christian nearly 20 years ago. Soon after, he purchased a local home-cleaning company in Cincinnati. Today, he and his wife live in Fort Collins, Colorado, and run All Star Cleaning Services, one of the largest home-cleaning companies in America, along with a coaching program for 100 cleaning business owners. 

The corporate-to-business-buyer path reflects a broader shift in American small businesses. An estimated 10 million small businesses are expected to change hands over the next decade as Baby Boomers retire, in what industry analysts call the “Silver Tsunami.” This generational shift has already begun: Baby Boomer participation among buyers fell from 33% in 2020 to just 17% in 2024, while younger generations increasingly dominate company purchasing activity. 

This trend coincides with other economic phenomena. Between 1979 and 2025, workers’ wages grew just 32% while productivity increased 86%, meaning that productivity has grown 2.7 times as fast as compensation. Additionally, job loss has led to much starker outcomes. In the 1970s, 90% of laid-off white-collar workers found similar jobs, but by the 1990s, only 25% did. Even at the executive level, the landscape has shifted dramatically: the general rule now suggests 1 month of job search for every $10,000 earned — meaning some senior leaders face more than a year of unemployment.

Entrepreneurship has become increasingly attractive to mid-career professionals seeking greater control over their financial futures. However, the entrepreneurship rate — the ratio of new firms to total firms — has nearly halved since the 1970s. Meanwhile, only 30% of family businesses survive the transition to the second generation, and only 12% make it to the third generation, according to SCORE.

While some employees head for the exits and on to found their own companies, Christian and a growing cohort of mid-career executives report that acquiring pre-existing small businesses offers opportunities corporate and startup life often does not: immediate cash flow, established infrastructure, and the autonomy to implement management expertise they’d developed over years in large organizations.

Christian’s Christmas epiphany represents just one path away from corporate life. For Adam M., who now runs a purified water delivery business called H2RO and operates arcade claw machines across North Dakota, the breaking point came during a 10-month stint at an environmental consulting job.

“I would show up about five minutes before I had to be in there, just stare at the building and imagine it on fire,” he said. That role had him living in hotels four days a week, away from his young children. “A week away from a two year old, you come back, and it’s a different person.”

Christine Traylor experienced a different but equally decisive shift. After 15 years in international development, she found herself disconnected from work that once felt meaningful. “I wanted something more tangible. I wanted to see the direct impact of my work,” she said. She’d long harbored a dream of running a bed and breakfast, though it felt like a distant fantasy. As her frustration with international development deepened, she found herself sizing up properties around Washington, D.C., fantasizing about a different reality.

On a particularly frustrating day at work, she took a walk and spotted the Swann House bed and breakfast in Dupont Circle, and the idea of owning a place like that — perhaps that place, even — began to crystallize into something more concrete. “I thought: let’s just go down this rabbit hole and see where it leads me,” she said.

For Jacob Voswinkel, it was something different still. Rather than needing a lifestyle change or feeling disconnected from his work, it was financial instability that drove Voswinkel from trading mortgage-backed securities to business ownership. While trading, he’d acquired rental properties and a storage facility in West Texas, but his habit of overleveraging — putting every dollar into every deal — left him perpetually cash-poor. 

“I had a deal going on in real estate and low six figures tied up in it with maybe $2,000 in my checking account,” Voswinkel said. “That was really just not fun.”

After a failed attempt to start a recruiting company and repeated near-bankruptcies, Voswinkel realized he needed businesses with steadier cash flow. That led him to Floors Galore, a North Carolina flooring company. 

All four executives emphasized the same advantage when acquiring a business over starting from scratch: immediate cash flow from day one. According to the U.S. Bureau of Labor Statistics, 20.4% of new businesses fail in their first year. (Of note, the “Information” sector — our closest proxy in this study to tech and tech-adjacent startups — has the second sharpest decline in survival rate just ahead of mining and related industries, with 25.1% of these businesses failing during year one.) These owner-operators instead skipped past that prove-it stage.

Acquiring established businesses means you’re not only inheriting proof that the business model works, but you’re also inheriting customer relationships and supplier networks. As a buyer, you can verify cash flow, examine tax records, and meet existing customers — all before writing a check.

“You can literally see it,” Adam said of evaluating his vending machine routes. “It’s money changing hands.”

When Traylor bought Swann House, she experienced this advantage firsthand. Starting from zero would have meant up to two years to get necessary zoning approvals, plus years to build name recognition. “Having that revenue stream day one is incredibly helpful,” she said. 

As you’re crunching the numbers, you can also be super systematic about how you approach the risk. For example, when Voswinkel set out to acquire a business, he first raised $850,000 through MainShares, a platform for buying and selling businesses. Then, he targeted businesses with more than one million dollars in earnings before interest, taxes, depreciation, and amortization (EBITDA). “If you’re buying something with a smaller net profit, you have less room for error,” he said.

In addition to the financial components, each executive discovered what Voswinkel called “geographic arbitrage” — finding overlooked opportunities in smaller markets where competition remains thin, and valuations are reasonable.

“It’s hard to find deals in the Dallases, Houstons — large primary cities of the world. But in somewhere like Odessa, a good deal can go overlooked,” Voswinkel said of his storage facility investment in West Texas. The same logic applied to Floors Galore in Jacksonville, N.C. — an hour north of Wilmington and two hours from Raleigh. 

But these owner-operators also found that success required real industry knowledge and operational expertise — far from the low-effort wealth-building strategies frequently promoted by TikTok and YouTube influencers selling courses on buying laundromats, car washes, or vending routes. The key was buying a business that already had critical operations figured out, then applying professional management skills to scale it.

“What is the definition of clean?” Christian said. “What is the scope of work? How do you do it in an efficient way where it’s good enough, but does not take 12 hours, because nobody wants to pay for 12 hours?” Because the previous owner had already solved operational challenges, Christian’s role was to professionalize the management side of the business — something he knew how to do well. 

Half of the equation around why acquiring a business works well is the proven model and the ability to hit the ground running. The other half is what each individual can bring to the table to cement that success.

In Christian’s case, his P&G management training gave him an edge that previous owners lacked. At P&G, he’d conducted regular “work and development plans” with employees — sitting down to discuss career goals and what they wanted long-term. When he brought this practice to his cleaning company, the response surprised him.

“I found that with these hourly employees, nobody had ever done that,” he said. One employee told him she didn’t want to be working for him in three years. “I said, great, I wouldn’t want you to be working for a cleaning company for the rest of your life. Where do you want to go?”

To someone without management training, having that conversation might seem counterproductive — why invest in someone who’s planning to leave? But Christian understood what many small business owners don’t: that helping employees work toward their goals, even when those goals involve eventually leaving, builds loyalty and commitment while they’re there. It creates a stronger working culture and directly addresses the turnover problem that plagues service businesses.

Research backs this up. A study of 35,000 manufacturing plants found that management practices account for more than 20% of total variation in productivity, while companies that focus on performance management are 4.2 times more likely to outperform their peers and realize 30% higher revenue growth.

So Christian’s advantage came from people management. For Voswinkel, his trading background taught him to avoid businesses where he'd be “really out of depth,” but flooring felt manageable. His real estate and renovation work had given him construction services familiarity, and flooring itself was conceptually straightforward. “In the end, it’s flooring, right?” he said. “There are only three different types of things that we could do: Carpet, plank, or tile.” Unlike in manufacturing, where he’d need deep technical expertise, he could grasp the fundamentals of flooring, even while relying heavily on the existing team for execution.

Ultimately, each owner-operator’s success came down to clear-eyed self-assessment — understanding not just what the business needed, but what they themselves could actually deliver. The businesses provided the foundation, but knowing where their own skills could add the most value, and where they needed to lean on others, makes the difference between acquiring a business and actually growing one.

Despite their success, each business owner faced unexpected challenges that corporate life hadn’t prepared them for. Voswinkel learned that even thorough financial planning couldn’t account for all variables. He originally projected returning all investor capital within five quarters, but now expects it to take seven or eight with the time it takes to grow organically with new hires and new locations. 

“If we had been able to scale to $10 million or $11 million [in revenue] immediately, it would have been probably five quarters,” he said. “But it’s just taking a minute to get there.”

The financial pressure can feel more palpable, too. Traylor and her husband put down more than one million dollars in savings and took out five million dollars in loans for their D.C. property. “We looked at many scenarios and ran through risks,” she said. “We were aligned about being willing to take on some risk for what felt like living a shared vision.”

Adam found that he had become indispensable to his operations, making extended time away nearly impossible despite his flexible schedule. “I am quite literally the most qualified person on the planet to work on my machines.”

Christian thought he knew how to fire people until his first termination as a business owner. In corporate, he’d been responsible for identifying employees whose performance led to their termination — but human resources did the dirty work.

“I would have told you that I fired people at Procter and been very confident in that answer, but it was only the first time that I was sitting down and face-to-face firing somebody that I realized I never had,” he said.

Wall Street Journal analysis of IRS statistics shows that business ownership, not high-paying jobs or tech startups, has become the dominant path to substantial wealth in America. Among the top 1% of earners, 34.9% of income now comes from business ownership, up from 30.3% in 2014. The businesses creating this wealth are often unsexy but profitable — auto dealerships, dental practices, beverage distributors, and boutique hotels with valuable real estate like the one Traylor purchased in Washington.

Christian’s results were the most dramatic. Within three years, he’d quadrupled his cleaning company’s revenue from $250,000 to $1 million and more than doubled his P&G salary. “I [originally] took about a 30% pay cut,” he said. “I think within a year I was back to my original pay, two years I was beating my original pay, and three years I doubled it.”

For Adam, who’d spent four days a week in hotels during his consulting career, the real payoff has been the flexibility. “I’ve been able to be a better dad and better husband,” he said. But, at the same time, he says that he’s always on call because he is so hands-on with the machines. “I never have a true day off.” Still, for Adam, being home but on-call beats being gone four days a week — even if neither offers complete freedom.

The autonomy appeals across industries. “I feel like I have 100% more control over my future,” Traylor said, contrasting her bed and breakfast with the abstract metrics of international development work.

As the Silver Tsunami continues, this corporate-to-owner pipeline may prove essential for preserving the small businesses that form the backbone of local economies nationwide — and an intriguing possibility beyond corporate life.