LA woman spent $50K building a company that sold for $22M only to buy it back. What aspiring entrepreneurs should know

In the world of startups, the goal for many founders is not to grow their business into a mature operation, but to scale quickly and make a big exit.

Famous examples include Facebook’s multi-billion dollar acquisitions of Instagram and WhatsApp, as well as Microsoft’s acquisition of Github, which made the founders of those startups instant billionaires.

Even selling a relatively small business can make you an instant millionaire. That’s what happened to Jaclyn Johnson, the Los Angeles–based founder of the women’s business platform Create & Cultivate, who sold her company for $22 million in 2021 (1).

After selling Create & Cultivate, Johnson walked away from her role as CEO exhausted but financially secure. Yet, just two years later, she did something few entrepreneurs even consider: she bought back her own company.

How she got there is an interesting story that says a lot about our current obsession with overnight wealth, the motivations behind entrepreneurship and how to find meaning in life.

Before taking a chance on a multimillion-dollar exit, Johnson’s story began with a far less comfortable gamble. In her early thirties, she had a marketing business and $50,000 in savings. Create & Cultivate was her side hustle, but when it started to grow faster than her marketing agency, she decided to make the leap.

On her mother’s advice, she decided to put every dollar into growing that side hustle into a full-time job. By 2020, Create & Cultivate had grown into a national movement, hosting sold-out events featuring celebrities and business leaders.

One year later, Johnson sold a majority stake to a private equity firm. For many founders, that is the natural end of the story, and the next chapter would likely be becoming a venture capitalist.

But success brought its own complications. After the sale, Johnson realized the private equity firm that bought her business was itself trying to offload it. “I was blindsided,” she wrote in an article for Business Insider. “As the founder, the business was so important to me. It was a community that I built and had a kinship with.”

Two years after the sale, she made the rare decision to buy back the company at a lower valuation, stepping back into the driver’s seat. Her second act, she told the Los Angeles Business Journal (2), is about rebuilding the company “into a $1 billion brand.”

Johnson’s comeback story is both inspiring and atypical. While her experience demonstrates the rewards of bold risk-taking, it also highlights how exceptional such outcomes are.

According to the Commerce Institute’s 2025 data, roughly 20% of small businesses fail in their first year, and nearly 70% fail by their tenth (3).

The disconnect between entrepreneurial storytelling and statistical reality creates a kind of survivorship bias. For every founder who sells for millions, thousands more quietly shutter their ventures, often with debt and damaged credit following in their wake.

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Johnson’s success was built not only on drive and creativity, but also on favorable timing and market positioning, which are advantages that can’t easily be replicated by someone quitting their job to “follow their dream.”

The takeaway is not that risk is bad, but that the narrative of entrepreneurial bootstrapping oversimplifies the risks involved. For every story like Johnson’s, there are many others that end without fanfare or a safety net.

Entrepreneurship has long been romanticized in America, especially in the digital age. But the real financial cost of starting a sustainable business remains steep.

A Monefy analysis found that even modest ventures often require $50,000 to $150,000 in startup capital, especially for those that rely on inventory or physical operations (4). Online ventures are cheaper to start but scaling them to profitability still demands marketing, technology and labor investments that can quickly deplete savings.

According to Homebase, the biggest surprise for first-time founders isn’t the cost of launching, it’s the cash required to sustain operations through the first year (5). For many Americans, “risking it all” means draining personal savings, cashing out retirement accounts or taking on high-interest debt.

Unlike venture-backed founders, who operate with investor capital, most small business owners rely on their own funds. That can make the downside of the financial and emotional risk particularly severe.

Kyla Scanlon, a writer on economics who coined the phrase “vibecession,” described the current money mindset succinctly in a recent newsletter on Substack (6): “When the labor market tightens and upward mobility stalls, and when wealth is concentrated at the top and increasingly inaccessible, gambling feels like a rational response.”

If Johnson’s journey has a universal lesson, it’s about calculated risk, not reckless gambling. The most successful founders protect themselves before they leap.

According to Failory, 34% of the more than 80 failed startups the company interviewed didn’t succeed because there was no real market demand for their product (7). That makes testing the concept, identifying paying customers and securing critical early revenue crucial for success.

Financial experts recommend that would-be entrepreneurs maintain six to 12 months’ worth of business and personal expenses before leaving a full-time job. This “runway” gives founders the flexibility to navigate the inevitable early slow growth periods without jeopardizing personal solvency.

Prospective entrepreneurs should also be wary of debt. Though it is possible to get bank loans for reasonable rates through the Small Business Administration, those loans are often secured by the entrepreneur’s personal assets, and if the loan can’t be repaid, those assets belong to the bank.

Building downside protection through diversified income, flexible business models or part-time consulting can turn a risky leap into a strategic transition, and it can be the difference between burning the boats and building a bridge.

Johnson’s story encapsulates both the thrill and the burden of entrepreneurial success. Her $50,000 gamble paid off, but it also revealed that wealth does not always equal fulfillment.

By buying back her company, she reframed her journey not as a single high-stakes bet, but as an evolving pursuit of purpose, autonomy and creative control.

For today’s aspiring founders, that message may be the most valuable takeaway of all. Entrepreneurship remains one of the few viable paths to wealth creation in an economy defined by wage stagnation and corporate consolidation, but the stories worth emulating are those that pair ambition with prudence.

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Business Insider (1); LA Business Journal (2); Commerce Institute (3); Monefy (4); Homebase (5); Substack (6); Failory (7).

This article provides information only and should not be construed as advice. It is provided without warranty of any kind.