Selling Your Business? The Questions Founders Don’t Ask (But Should)
Most founders think selling their business will be a sprint to the finish line — list it, find a buyer, cash the check.
In reality, it’s more like a chess match. The best moves start months, sometimes years, before the deal.
And here’s the kicker: your ideal buyer might not be some stranger in a glass tower. They might already be in your inbox, your Slack, or your client list.
If you’re thinking about selling — whether soon or someday — these are the questions real founders should be asking (and the answers that’ll keep you from learning the hard way).
“Where do I even find a buyer?”
Here’s the truth: most small businesses don’t sell through billion-dollar M&A firms. They sell through relationships.
Your first stop? The people already in your orbit.
A long-time employee who runs things like an owner.
A client who depends on your product.
A vendor who knows how valuable your operation really is.
Even a family member with capital and business sense.
These are warm leads. They already trust you, understand the model, and might be motivated to carry it forward.
Action Step: Make a simple spreadsheet. Add:
Name and role
Relationship to the business
Level of interest (trust your gut)
Financial background or experience
Chances are, you’ll find more potential buyers in your contact list than you think.
“What if I don’t know anyone who could buy it?”
Then you widen the search. You don’t need to cold-call private equity firms, there are real platforms built for this exact moment.
Sites like Acquire.com, BizBuySell act as matchmaking hubs between founders and vetted buyers. They maintain confidentiality and handle much of the screening process.
If you’re in a specific industry, look for roll-up strategies — investors or operators buying multiple small businesses in one niche to consolidate market share.
And don’t sleep on search funds — small groups of professionals (usually ex-consultants or MBAs) looking to buy and run an existing business. They’re well-funded and serious.
Action Step: Search your industry on one of these platforms. See who’s buying, what’s selling, and at what price. That gives you real market data on how to price your business for a sale — not just a “feels right” guess.
“How do I know if a buyer is legit or just fishing?”
This is where most founders waste weeks, or worse, leak sensitive information.
A serious buyer can answer three questions without blinking:
Have you bought a business before?
Do you have proof of funds or financing?
Why this business, and why now?
If they can’t, they’re not serious.
Protect yourself early:
Use an NDA before sharing financials.
Start with anonymized or summarized data — revenue range, customer mix, margins, not the full P&L.
Only release detailed statements after a Letter of Intent (LOI) is signed and verified.
This is where having outsourced accounting or a fractional CFO helps. They know how to scrub, anonymize, and stage your numbers for due diligence — without oversharing.
Because curiosity isn’t commitment, and “interested” doesn’t mean “qualified.”
“Is it safe to sell to a competitor?”
It can be, if you handle it right.
Competitors can be strong buyers because they understand your market and may pay for strategic synergies. But they’re also the most dangerous window shoppers. They know exactly which questions will reveal your margins, pricing, and vendor relationships.
Here’s the rule:
Treat information like currency. Don’t spend it all in one meeting.
Share general metrics first (revenue range, headcount, customer type).
Get NDAs signed before sending financials.
Involve your CFO services team or legal counsel in every data exchange.
That way, if a competitor walks away, they don’t walk off with your playbook.
“What kind of buyer should I even be looking for?”
Not all buyers are built the same — and who you’re talking to changes everything.
Individual buyers want a turnkey business they can run hands-on.
Strategic buyers (competitors or suppliers) want to scale and cross-sell.
Private equity firms buy to grow and exit again — typically targeting $10M+ deals.
Search funds are hybrid operators backed by investors, looking for long-term ownership.
A fractional CFO can help tailor your financial presentation to the right audience.
Strategic buyers want margin analysis.
Private equity wants normalized EBITDA.
Individual buyers care about cash flow reliability and easy handoff.
The same business can look completely different — and more valuable — depending on how it’s framed.
“What’s my business actually worth?”
Let’s be honest: most founders overestimate this number.
Valuation isn’t about what you think it’s worth — it’s about what the next owner can make from it.
Buyers look for:
Clean financials: consistent, reconciled statements.
Normalized EBITDA: no one-time or personal expenses buried in the books.
Predictable cash flow: stable, recurring revenue.
Low dependency: your business should run without you.
This is where outsourced accounting pays off. Clean books build trust. Defensible numbers reduce discounting in negotiations.
If you can back up your story with data, buyers pay more. If you can’t, they’ll use the mess to chip away at your price.
“How do I get the business ready without turning into a full-time CFO?”
You don’t have to. But someone does.
This is the moment to bring in fractional help — a fractional CFO or outsourced accounting partner who can handle:
Audit prep and financial cleanup
Forecasting under different deal structures
Building a secure data room
Managing diligence requests without disrupting operations
They make sure you’re running your company while still making it sellable.
It’s not about window dressing — it’s about giving buyers confidence your numbers can hold up under forensic scrutiny.
“When should I start prepping for a sale?”
Now. Even if you’re not selling for years.
Deals fall apart because founders wait too long to clean up their numbers or formalize their systems. When that “perfect buyer” finally shows up, they can’t move fast enough.
Think of acquisition readiness as just another part of running a professional business — like keeping clean books or having a proper forecast.
Start early, get your financial house in order, and when opportunity knocks, you’ll already be standing at the door.
Final Word
The best exits aren’t lucky. They’re built.
You don’t rise to the occasion — you fall to the level of your preparation.
Selling your business isn’t about guessing what buyers want. It’s about building something they can trust.
And that starts with numbers that tell a clear, credible story.
Thinking about selling your business?
Book a Strategy Call with Ursa. We’ll help you tighten your books, prep your valuation, and build a clean, investor-ready story — whether you plan to sell in six months or six years.