There’s a moment when an investor and a founder sit on opposite sides of the table. In almost every other interaction — the introduction, the whiteboarding, the calls at midnight — you are on the same side. But there is one conversation where the structure demands opposition. It starts with a number you believe is right. A number the founder believes is low. And between them, months of loyalty and time that neither figure can account for.
I had worked with a founder for the better part of a year before a dollar changed hands. When something outside his control threatened to undo everything — not the company, but him — he called. I listened.
Most investor-founder relationships start with a deck, not a person. A deal comes across a desk, a pitch is had, diligence is done, and a check is written. It’s a relationship of function.
But no two deals are alike. There’s no playbook when a crisis begins to unravel someone, let alone prior experience to guide. So you lean into where you feel there is something worth offering: how are you feeling right now?
We talked about what was real and what wasn’t. What he could control and what he couldn’t. I didn’t have answers to most of it. By the time we sat down to discuss terms, the number on the table carried weight that numbers aren’t built to hold.
He wanted a valuation that reflected how far he’d come. I held a number that reflected how much risk remained. Both were true.
I walked into this conversation knowing I wanted to start and end the negotiation before we left. And regardless of the relationship, it should have been simple. I had a number. He had a number, and the mechanics of a term sheet care little for midnight calls and emotional conversations.
But every time he pushed back against a position, I noticed something I hadn’t expected. I wasn’t defending my position. I was explaining his.
When he raised concerns about recruiting — that a lower valuation would make it harder to attract talent — I walked through why early employees benefit from a lower entry price. When he worried about what a lower figure would signal, I described what it would mean for the investors who came next — and why they’d read it as discipline, not weakness. When he named the gap between where we started and where I wanted to land, I did the math out loud: basis points at pre-seed are meaningless against what his company would be worth in a decade.
Each point I made was true. Each one was oriented toward his outcome. And yet none of them were generous. That’s the part that sat with me afterward. I wasn’t giving him what he wanted. I was giving him what I believed was right — for both of us — and asking him to trust that the discomfort was shared.
There’s a question I borrowed from a negotiation book: what would make this a hell yes for you?
I’ve used it before. It had never cost me anything to ask. This time it did. Because the answer might have been a number I couldn’t give — and then I would have had to hold the silence, hold the lower figure, and hold the relationship all at once.
He gave me his answer. I gave him mine. We closed the gap not because either of us conceded, but because somewhere in the exchange, we stopped negotiating against each other and started negotiating against the problem.
Afterward, I kept returning to a question I couldn’t quite name. The deal closed. The terms were fair. He felt good. I felt good. So why did it sit with me?
It took weeks to see it. I had walked into that room carrying two loyalties — one to the person across from me, one to the people who trusted me with their money. I assumed, without examining it, that those loyalties were in tension. That honoring one meant compromising the other. That the negotiation was the place where I’d have to choose.
Most people carry this assumption. Loyalty to the founder means giving them what they want. Duty to your investors means extracting what you can. Generosity or discipline. The person or the portfolio. Pick a side.
But that’s not what happened in the room. I held the lower number and told him why — not as a tactic, but because he deserved to see both sides of what I was holding. And somewhere in that transparency, the opposition dissolved. Not because I found a middle ground. Because there wasn’t one to find.
A coach once told me that I wouldn’t become a partner by conforming to what partnership has always looked like. That the role would evolve to me as I evolved into it. It took being in that room to learn what he meant.
It was the only time we sat on the other side of the table from one another, and even then, it was only in practice, not in intention.