If you spend an evening on r/SellMyBusiness or r/Entrepreneur, you'll notice the same complaints in rotation. Every M&A advisor has turned them into a five-point checklist. The checklist isn't wrong. We just don't think it's the interesting part.
The interesting part is that the posts sound almost identical, even when the businesses are completely different.
The same voice, different industries
A construction company that fell apart in the final weeks of a sale reads the same as a software founder who spent nine months at his asking price before dropping it. A retiring bakery owner reads the same as an agency founder on his fourth attempt in thirty years. The industries are different. The dollar amounts are different. The voice is not. It's the voice of someone realising, out loud, that the thing they built is worth less than they thought it was — and looking for a tactical reason that makes that fact go away.
Here's one comment we keep coming back to:
Are you selling a business or a job? If your take-home after expenses is about the same as what you'd pay someone to do what you do, why would a buyer go into debt to get the same salary they could earn working for someone else, with none of the risk?
— r/SellMyBusiness
That's the whole thesis in one paragraph. It's not tactical advice. It's a buyer looking at the business the way buyers actually look at businesses. And the founders who eventually sell well are the ones who arrive at that view on their own, early, and adjust their expectations. The founders who post on Reddit are the ones who haven't gotten there yet.
The five problems, and what they really are
Let's take the list one at a time.
Overpricing
This is the most-cited problem on every sell-side forum, and it's rarely a spreadsheet error. It's a founder pricing the business against the years they put in, instead of what a buyer would pay tomorrow. One reply on r/SellMyBusiness, to a founder who'd been trying to sell for nine months, put it bluntly:
It seems you feel that the business OWES you. You want the buyer to pay you based on what they feel, not on what's actually in front of them.
— r/SellMyBusiness
The math isn't broken. The reference point is.
Messy books
This one gets treated as a bookkeeping failure. It's not. It's what happens when a founder never expected an outsider to read their financials. As one commenter on r/smallbusiness put it:
Sellers who hide cash transactions, have messy books, or skimp on their taxes will have a hard time selling.
— r/smallbusiness
The moment you decide to sell, your books stop being an internal tool and start being a document written for a skeptic. That's a different document, and most founders haven't written it.
Owner dependency
If the business stops working the day the founder walks out, buyers see a job, not a company. The r/SellMyBusiness quote earlier — “are you selling a business or a job?” — is the sharpest version of this. r/IndiaBusinessBroking says it more plainly:
If the business can't run without you, buyers see higher risk and lower value.
— r/IndiaBusinessBroking
You can't fix this in a month. But you can start fixing it a year out.
Bad timing
Most forced sales aren't forced by the market. They're forced by the founder's own life — burnout, a divorce, a partner leaving, a health event. And buyers can tell in the first meeting. One thread on r/smallbusiness about why 80% of businesses never sell said it directly:
The timing is wrong. Sellers are selling because the business is in trouble.
— r/smallbusiness
What looks like a timing problem is usually a preparation problem that ran out of runway.
Deals dying in due diligence
These almost never get killed by what the buyer discovered. They get killed by how the founder reacted to it — the defensiveness, the renegotiating, the numbers that suddenly appear or disappear. A post on r/Entrepreneur described a deal that collapsed at the eleventh hour, with the seller still puzzled:
Due diligence didn't reveal major red flags, no major issues.
— r/Entrepreneur
And yet the deal died. The finding is the trigger. The response is the cause.
Every one of these is real. And every one of them is the same underlying problem in a different costume: the founder hadn't yet accepted, before they started talking to buyers, the number the market was going to give them.
What a good advisor actually does
If you accept that, then the job of a sell-side advisor in the twelve-to-twenty-four months before a sale isn't what the brochure says.
It isn't to fix the five problems. Any competent broker can hand you that checklist.
The real job is to help you hear the number early enough to still do something about it. Early enough to build revenue that doesn't rely on your relationships. Early enough to reduce a customer that's become too big a share of the business. Early enough to clean up the books so a stranger can read them. Early enough that when the sale happens, it's a decision you made — not a decision the market made for you.
Founders who come to the process with that work done tend to close in ninety days at the price they wanted. Founders who come to the process still hoping the market is wrong spend eighteen months trying to prove it, and then post about it.
Why the good sales aren't on Reddit
There's one more thing worth noticing about those threads. The founders who exited well don't post there.
There's no story to tell. The preparation worked, the process was quiet, the buyer showed up, diligence was uneventful, the wire arrived. What would you write? “Everything went to plan” is not a thread anyone upvotes.
Which means if you're reading Reddit looking for a template of what to do, you're reading a filtered sample. You're reading only from the people something went wrong for. That's still useful — it tells you honestly what the failure modes look like. But it doesn't tell you what the successes did differently, because the successes aren't in the thread.
What they did differently, in almost every deal we've worked on, is start earlier than they wanted to, and price the business the way a buyer would — not the way a founder wishes they could. It isn't a clever tactic. It's a habit. And it's the reason the five problems, when they show up on Reddit, are almost always downstream of the same missing conversation a year earlier.
If you saw yourself in any of the voices in this piece — the nine months at the asking price, the fourth attempt, the buyer who “didn't understand the value” — that recognition is the useful signal. It's not a reason to wait longer. It's a reason to start the conversation now, while there's still time to move the number. Book a private consultation and we'll give you an honest read.
A note on the sources
The observations in this piece draw on public discussions across r/SellMyBusiness, r/smallbusiness, r/Entrepreneur, r/buyingabusiness, r/businessbroker, and r/IndiaBusinessBroking. Quotes are lightly edited for length.