TL;DR: On business listings, 90 to 180 days on market is the sweet spot for buyers. The seller's enthusiasm has cooled. The broker has run out of buyers willing to pay asking. Price reductions become acceptable. The deal you want is not the brand new listing with the curated photos. It is the 6 month old listing that nobody else is calling on right now.
Every Tuesday I get the same question from somebody who saw a fresh listing on Friday. Should I move fast before someone else takes it.
The honest answer is almost always no.
Fresh listings are the worst priced listings on the market. They are priced at the broker's marketing number with full commission baked in. The seller is still emotionally anchored to that number. Any competing buyer who walks in this week is going to anchor to it too. You will either overpay or you will lose the deal to someone who does. Either way you do not get the price discipline the Bulletproof method demands. The deal you actually want has been sitting for a while, and most buyers will never look at it.
What Days on Market Actually Tells You
In real estate, more than half of February's listings nationally had been sitting on the market for 60 days or more without going under contract. The highest stale share since 2019. The pattern in small business listings is similar with a longer cycle. Most healthy listings either go under LOI within 90 days or sit for the duration of the listing agreement at six months to a year.
Each milestone tells you something specific. A listing under 30 days is a fresh inquiry environment. The seller is still receiving calls and the broker is still pitching at asking. A listing at 60 to 90 days is in the awkward middle, where the broker is starting to mention price flexibility but the seller has not fully accepted it yet. A listing at 90 to 180 days is where the math starts to work. The seller has had enough quiet weeks to absorb the new reality. The broker is hungry for a closing. The asking price becomes negotiable in ways it was not 90 days ago.
Past 180 days you are in a different conversation. Either the price is still wrong and the seller is unwilling to move, or there is something material about the business that buyers keep finding in diligence. Treat past-180 listings as a do the diligence twice category. Sometimes they are gold. Sometimes they are a problem that has not surfaced yet. The age of the listing is the question, not the answer.
Three Questions Before You Make an Offer
Three questions to ask the broker on any listing over 90 days old.
One. How many LOIs has the listing received, and what happened to them. If a listing has had three LOIs and all three fell apart in diligence, that is the most important piece of information on the listing. You need to know what they found. The broker is not obligated to tell you, but a good one will hint at the category. If the broker says nothing, that tells you something too.
Two. Has the asking price been reduced, and if so by how much and when. A listing that started at $1.2M and dropped to $950K over six months is telling you the seller has accepted reality. A listing that has held firm at $1.2M for nine months is telling you the seller has not. Those are different deals at the same nominal price. The deal where the seller has moved is the deal where the deal will close.
Last year I walked a buyer through a manufacturing listing that had been sitting for eight months at $1.6M. Two prior LOIs had walked. The broker hinted at customer concentration. We dug into that and found one customer at 38 percent of revenue. We restructured the offer at $1.2M with an earn-out tied to retention of that customer. The seller, who had refused $1.5M offers three times in earlier months, took the $1.2M structure within two weeks. The age of the listing made the deal possible.
Three. What is the seller's actual timeline. A seller in month seven of a year-long listing agreement has roughly five months to find a buyer before they are back to square one. That is leverage you do not have at month one. Most brokers will tell you the timeline if you ask directly. Some will lie. The ones who lie usually do it in a specific direction. They will tell you the seller is in no hurry, because they are trying to defend the asking price. Read between the lines and you see what is actually happening.
How to Price the Offer
Stale listings deserve different math. After 35 years of looking at these, the pattern I keep seeing is that every 90 days a listing has been on the market, the seller's anchor on asking price loosens by another 5 to 8 percent. A listing at 90 days might be negotiable to 92 percent of asking. A listing at 180 days might be negotiable to 85 percent. A listing at 270 days might be at 78 percent.
Those are not promises. They are starting points. Banks will not catch this for you. Neither will the broker. Run the deal through the Bulletproof calculator at DealScore Pro to find your actual ceiling on stress tested DSCR, then anchor your offer to that number. If the stale listing discount math gets you there, you have a deal. If it does not, the listing is still overpriced even at 78 percent of asking, and you walk away.
The buyers who win in this market are not the fastest. They are the ones who understand that patience is a pricing tool.
Here is the part that takes most buyers years to learn. Your watch list is your edge. Build a list of 20 businesses you would want to own at the right price, then track them. Check the listings every two weeks. The third or fourth time you check in on a listing that has been sitting for five months, you will find a different seller across the table. More flexible. More honest. More willing to structure a deal that works. That is when you write the offer.
Smart buyers do not chase. They wait for the math to come to them, and when it does, they have already done the work.
The free Masterclass below walks through the full Bulletproof framework, including how to price an offer on a stale listing without overpaying.
What This Means For You
If you are hunting deals right now, stop chasing fresh listings and build a 20 listing watch list of businesses you would want to own at the right price.
— Mike
Want to see how I stress-test every deal against cost shocks, revenue dips, and hidden liabilities before I'd put a dollar at risk? I walk through the entire Bulletproof method in a free 28-minute masterclass.
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