On selling the thing you built.

Here’s a thing worth sitting with. The first time you do something with real stakes, the kind that matters for years afterward, you tend to walk in feeling reasonably prepared. You’ve read up. You’ve talked to a few people. You’re ready.

Then you sit down across from someone who has been at this exact table two hundred times, and something quiet happens. Your preparation, which felt so solid that morning, starts to come apart at the edges.

Selling a business for the first time is like that.

The buyer across from you has done this hundreds of times. You’ve done it once. They’ve watched the same mistakes happen so often they can predict the next one before it occurs. You’re figuring it all out in real time, while a clock you didn’t know was running ticks quietly along.

This is the asymmetry. It isn’t about intelligence. The seller is usually smarter than the buyer about the actual business. The asymmetry is about pattern recognition. The buyer has the patterns. You don’t.

What follows are eight patterns that show up in nearly every first-time sale of an Australian business under $20M. They aren’t technical. They’re behavioral. Almost all of them get decided in the first 10% of the transaction.

1. Calling your lawyer after the first conversation, not before.

The buyer’s first letter is flattering. It uses your business name three times. It quotes a number you weren’t expecting. Your instinct is to politely engage before involving advisors.

This instinct is wrong. Not morally wrong. Strategically wrong.

The first conversation sets the anchors. Anchors are hard to move once set. The buyer has done dozens of first conversations. You’ve done one. By the time you call your lawyer, the framing battle is over.

The first call with a lawyer is usually free. The cost of starting early is an hour. The cost of starting late can be several hundreds of thousands of dollars in lost leverage. This isn’t a particularly taxing calculation to do.

2. Treating the headline number as the deal.

The headline number is rarely what arrives in your bank account. Working capital adjustments, holdbacks, earnouts, indemnity caps, and financial definitions sit between the headline and the final receipt of the cash transfer.

A $14M offer can be worth less than a $13.5M offer if the structure underneath the $14M is hostile. This happens. Relatively often.

Price is one variable. The deal is a system. So sellers who optimise for the headline number are optimizing for one variable in the system. They commonly end up with less.

3. Working capital, discovered too late.

The working capital adjustment is a calculation that happens after completion. It directly affects how much of the purchase price you actually keep.

If you don’t think about it until signing, the buyer’s accountant has already chosen the methodology. The methodology favors the buyer. Not because the buyer’s accountant is dishonest. Because methodology choices are made by whoever shows up first.

Get your accountant and lawyer aligned on this at the start. Otherwise the calculation surprises you, when it’s too late to renegotiate.

4. Customer concentration, hidden rather than surfaced.

If one customer is more than 20% of your revenue, the buyer will find out. The only question is whether they find it in your disclosure or in their diligence.

A risk disclosed is discounted once. A risk discovered is used as ammunition forever.

This is a behavioral insight more than a technical one. Buyers reward sellers who tell them what’s wrong. Buyers punish sellers who hide it. The information surfaces either way.

5. Founder dependency, unaddressed.

Buyers are paying for cash flows that survive your departure. They’re not paying for you.

This is the hardest sentence in this article to write and probably the hardest to read. Founders built the business. Buyers are buying it because of what the founder built. But the EFT clears based on what runs without the founder.

If your business can’t operate for 60 days without you, the multiple compresses. The cure is operational, not financial. Document the systems. Hire the deputy. Reduce your indispensability before someone else measures it and prices it.

6. Tax structure, decided too late.

Share sale or asset sale. Small business CGT concession eligibility. Pre-sale dividend timing. These should be settled at the term sheet, in writing.

If they aren’t, they become bargaining chips later. Anything not pinned down in the term sheet becomes negotiable in the SPA. Anything negotiable in the SPA can tend to drift in the buyer’s direction.

Don’t take that risk.

7. Earnouts.

An earnout is the buyer’s way of saying: I’ll pay you the full price if the business does what you say it will do, in the years after you’ve left it, while I’m running it.

Earnouts aren’t inherently bad. But they’re often negotiated badly. Tired sellers, late in a process, agree to earnout terms that transfer the entire risk of the future onto a person who no longer controls the outcome.

Read the earnout carefully. Read it twice. Have someone else read it. Then talk to them about what it means.

8. Warranty caps that look standard but aren’t.

A “market” liability cap on a $15M deal can be significant. The cap is one number. The architecture around it (basket, deductible, survival period, knowledge qualifiers, materiality scrapes) determines what the cap actually means.

Two caps of the same headline size can carry very different exposures. This isn’t a place to defer to standard terms. Standard terms don’t exist. There are only the terms you negotiated.

• • •

The pattern beneath all of these:

Almost everything that goes wrong in a first-time sale was decided before the term sheet was signed.

The work that builds leverage is quiet. It gets done before there’s a deadline, before there’s a counterparty, before there’s a clock running. It’s unglamorous. Nobody is watching when you do it.

That’s the whole reason it works.

Owners who regret their exits tend to say a version of the same thing, which is that they didn’t get the right help early enough. The decisions that matter aren’t made on the night you sign the contract. They’re made in the quiet months before, when nothing dramatic is happening and there’s no obvious reason to be doing the work at all.

Which is the strange part. The most valuable thing you can do right now is the thing that feels, today, like it doesn’t really matter.