Ownership

On dealmaking

Dealmaking isn't something you learn in books. Or courses. Or newsletters about someone else's acquisition.

You can't read your way to knowing when to walk away. You can't consume enough content to develop an instinct for when a seller is nervous versus when they're hiding something. You can't study your way into the room.

You have to do it.

You learn dealmaking by doing deals. Due diligence by doing due diligence. Negotiation by negotiating – badly at first, then less badly, then occasionally well enough that you stop thinking about it consciously.

We know this is true in other things. You wouldn't hand someone a stack of books on swimming and expect them not to drown. Or tell a musician to read about timing and call it practice.

And yet the internet is full of people selling frameworks for acquisition. Step-by-step guides to buying your first business. Checklists for due diligence. As if the thing that was missing was a better checklist.

The checklist isn't the problem. The problem is you haven't sat across from someone who is selling something they built, trying to read whether the number they just quoted is real or hopeful. That's not in any guide.

Some things can be taught. Valuation multiples. Deal structure. The difference between an asset sale and a share sale. This is knowledge – transferable, learnable, useful.

But the part that matters? Reading the room. Knowing when to push and when to let something breathe. Recognising the moment a deal is alive versus the moment it's already dead and no one has said so yet. That's not knowledge. That's pattern recognition built from hard-earned experience.

Dealmaking is muscle memory. It's built by being in deals – the ones that close, the ones that fall apart, the ones where you got what you wanted and realised too late it wasn't what you needed.

The only way to get better at it is to do more of it.

So go do a deal.

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