Carrie Kerpen bought her first company this year, and she skipped the ones with the best branding. She chose Upwell Strategies, a small operations consultancy, because its books were clean and its founder had already made herself replaceable.
Kerpen is an exit advisor for the Whisper Group, an advisory practice she built specifically for women-owned businesses. Most days she tells other founders to do exactly what she just did as a buyer: fix the plumbing before anyone else sees the house. But her own research suggests that advice does not land evenly. Women capture less than a penny of every dollar spent on business acquisitions in the United States, by Kerpen’s own accounting, which is what makes operational readiness more than a nice-to-have for the founders she serves.
The Four-Point Test Buyers Actually Run
Forbes contributor John Hall talked with Kerpen after learning about her Upwell purchase, and she gave him a checklist that has nothing to do with logos or growth charts. It is about whether a business can survive its own founder taking a vacation.
- Build yourself out of the equation. Kerpen tested this on herself. Before each of her maternity leaves, she cross-trained her team and rebuilt processes so nothing in the business depended on her being in the room.
- Resist the urge to build proprietary systems. Custom software sounds impressive, but Kerpen has watched founders build tools their teams end up babysitting instead of using.
- Train people to be smart operators. A well-run team becomes a selling point on its own, especially when key people are willing to stay after the deal closes.
- Get the books in order now. Messy financial and operational documentation signals to a buyer that the processes behind it are not repeatable either.
Justin Donald, an investor who hosts the podcast The Lifestyle Investor, has made a related point on his show: a good exit depends on a business that runs smoothly without its owner propping it up day to day.
The proprietary-systems warning has an echo well beyond small business. Microsoft chief executive Satya Nadella has warned that companies risk paying for AI with their own institutional knowledge, the same trap Kerpen describes when founders build tools nobody else can maintain.
Why Upwell Strategies Passed Her Own Test
There is an irony in what Kerpen bought. Upwell Strategies exists to sell operational discipline to other people. The firm’s own description says it partners with impact-driven small business owners to build systems, tools and processes for sustainable growth, the exact product Kerpen was screening for as a buyer.
Upwell’s founder, Caitlyn, built the consultancy around that same idea: that a business should not run on one person’s memory. When Kerpen acquired the company, she kept Caitlyn on with equity and a voice in decisions, rather than replacing her. Caitlyn agreed to stay in part because of that stake.
That detail matters more than it might look. Kerpen was not just buying software or a client list. She was buying people, and when a founder sells, the team goes with the business to a new owner too. A workforce that already runs without hand-holding becomes part of the asking price.
Marketplaces built for exactly this kind of transaction are multiplying. Platforms like the 30-day model behind Sell Wasabi’s online business marketplace are trying to compress the buying process into weeks instead of the months a traditional broker deal usually takes, which only raises the bar for how clean a business needs to look on day one.
Women Founders Capture Less Than a Penny per Dollar
Kerpen did not arrive at her checklist by accident. After she sold her digital agency, Likeable Media, to the technology firm 10Pearls in an eight-figure deal in 2021, she went looking for other women who had been through the same process. She could barely find any.
That search turned into research, and the research turned into what she now calls the Exit Gap. She began digging into exits of women-owned businesses and found that women capture .8% of total dollars allocated to company acquisitions, or less than a penny for every dollar that changes hands in a deal.
A separate 10-year study by the London accounting firm Buzzacott backs up the scale of the problem. Fewer than one percent of businesses that sold a majority stake were female-founded, and in the United States that figure was 1.37%, compared with 0.35% across Europe and the rest of the world. Male-founded businesses in technology, media and telecommunications sold for one and a half times more, on average, than comparable female-founded ones. In consumer businesses, the gap ran 18%.
| Metric | Figure | Source |
|---|---|---|
| Female-founded businesses among majority-stake sales, U.S. | 1.37% | Buzzacott 10-year study |
| Same metric, Europe and rest of world | 0.35% | Buzzacott 10-year study |
| Share of total M&A dollars captured by women founders | 0.8% | Kerpen’s Exit Gap research |
| Valuation gap in tech, media and telecom deals | Male-founded businesses valued 1.5x higher | Buzzacott 10-year study |
| Valuation gap in consumer sector deals | Male-owned businesses valued 18% higher | Buzzacott 10-year study |
Kerpen has talked about how uncomfortable this data makes people.
And while women certainly are capable, our journey is unquestionably more difficult.
Kerpen said that in a 2024 interview about her research, and it is the reasoning behind everything the Whisper Group does now. The firm’s own roster of advisors reads like proof of what happens when the checklist gets followed: one sold a wellness platform to the baby products marketplace Babylist, another scaled a SaaS company to $5 million in annual revenue before a $25 million cash sale to a European public company.
A Retirement Wave Meets an Unprepared Market
Kerpen’s advice would matter even without the gender data behind it, because the broader small-business market is walking into a supply problem of its own making.
- Nearly half of small business owners plan to retire within 10 years, according to Chase’s 2026 survey on small-business succession readiness, yet only a small share have a fully developed plan for who takes over.
- 74% of employer-business owners nearing retirement plan to sell or transfer ownership rather than shut down, per Gallup’s research on business owner succession plans.
- 62% of small-business owners say the succession process itself feels overwhelming, and 56% worry they will not get a fair price when the time comes.
Owners with a documented plan are not just better prepared. Gallup found they are also more profitable: employers with a long-term plan reported median profits of $90,000, against $60,000 for those without one. A business that runs on someone’s memory is worth less even before a buyer walks through the door.
What Happens When a Business Can’t Find a Buyer?
Not every listed business finds a buyer, and the gap between a prepared seller and an unprepared one is widening. Well-run companies are drawing real competition right now. The International Business Brokers Association and M&A Source reported that 83% of deals over $5 million drew at least three offers in the first quarter of 2026, with nearly one in five attracting ten or more bids.
That kind of demand is not evenly distributed. It flows toward businesses that already look like Upwell did when Kerpen found it: documented, cross-trained, and free of a founder-shaped hole in the middle of the org chart. Sellers without that groundwork tend to sit on the market longer, cut their asking price, or walk away from a deal altogether.
For the ones that never find a taker, the alternative is rarely a graceful wind-down. It often runs through the same kind of process that helps companies step back from the brink of liquidation, a far costlier outcome than the paperwork cleanup Kerpen is describing. Get the operational hygiene right early, and a founder controls which of those two paths their company takes.
Frequently Asked Questions
What Is an Exit Readiness Advisor?
An exit readiness advisor helps business owners prepare their operations, finances and leadership structure for a future sale. Kerpen holds the credential of certified exit planning advisor, or CEPA, a designation focused specifically on this kind of pre-sale preparation.
Why Do Women-Owned Businesses Sell for Less Than Men’s?
Researchers point to a mix of causes: women founders often prepare later, have thinner access to networks of previously exited female founders, and face a shortage of female-led private equity firms and acquisition capital compared with their male peers.
How Long Does It Take to Make a Company Sellable?
There is no fixed timeline, but the pressure is real. A U.S. Bank survey found 37% of small-business owners plan to sell within the next 12 months, even though 62% describe the succession process as overwhelming and 53% report a lack of readiness to start it.
What Does It Mean for a Business to Be Founder-Dependent?
It means daily operations, client relationships or key decisions run through one person instead of documented systems. Gallup data shows the difference shows up in the numbers too: employer-businesses with a long-term ownership plan posted median profits of $90,000, compared with $60,000 for those without one.
Are Buyers Still Confident in the Small-Business M&A Market?
Yes, broadly. Intermediaries surveyed for the IBBA and M&A Source’s Q4 2025 Market Pulse report said nearly three-quarters expect conditions to match or beat the 2021 peak, even as they get pickier about which businesses clear their bar.
