Know your walk-away point
Every negotiation you will ever have as a founder is decided before you sit down. Not by how persuasive you are in the room, but by how clearly you know what happens if the deal falls through. Negotiators call this your best alternative. I call it your walk-away point, because that is what it is for: the moment you can calmly stand up and leave.
Start by writing your alternatives down. If this investor passes, who else is in the pipeline, and how far along are they? If this senior hire says no, how long can the team run without the role? If the enterprise customer walks, what does the next quarter look like? Founders who skip this step negotiate against their own anxiety, and anxiety always accepts the first offer.
Then turn each alternative into a number. A walk-away point you can't put a figure on isn't one. It might be a minimum valuation, a maximum salary or a contract size below which the deal costs you more in support than it brings in. Write it down before the meeting and don't move it during the meeting. You can always revisit it afterwards, with a clear head.
Anchors and first offers
The first number on the table pulls every number after it towards itself. That is anchoring, and it works even on people who know about it. Your job is to decide, deliberately, whether you want to set the anchor or let the other side go first.
Go first when you know the market well and the other side doesn't. A specific number, like 4.2 million rather than about four, signals that you've done the work and is harder to argue down. Let them go first when you genuinely don't know what the deal is worth to them. Their opening offer is information you can't get any other way.
Whatever happens, never respond to an anchor you dislike by negotiating from it. Name it, set it aside and put your own number on the table with the reasoning behind it.
Reading the other side
Good negotiators spend more time listening than talking. Every question the other side asks tells you what they are worried about, and every concession they make easily tells you what they don't value.
Keep a simple list during the conversation: what they asked about twice, what they pushed back on, and what they gave up without a fight. After the meeting, those three columns are your map for the next round.