Dear startup CEOs: stop chasing that customer who has been on the fence for six months. They're just not that into you.
It starts the same way every time. A buyer shows up and the founder gets super excited. We'll get another logo on the website! We'll have real revenue in the bank!
Then the buyer go dark for three months. They pop their head up to say "no, no, we're still excited" and then more months of silence.
That initial dopamine boost has turned into existential dread. Are they ever going to close? What can I say to get this deal over the finish line? I don't want to push too hard, but I also don't want to sit here in purgatory anymore because it makes me feel sad.
Sound familiar?
At the end of the day, the person with the most leverage is the person who isn't married to the outcome. The person willing to lose the deal.
But early stage founders don't operate that way. When you have four (or zero) existing customers, very deal matters. So they suck up the delays. They suck up the broken promises. They suck up the "let me get back to you next week" that turns into next month. All under the guise of "I can't lose this deal."
Meanwhile the prospect is doing exactly what you'd do in their shoes. You've told them, implicitly, that they have infinite time to act. There's no penalty for taking another day.
Dude, why the hell wouldn't they take another day to decide?
It's probably time to reach out to that prospect who's been stringing you along and say: "We're happy to take your money whenever you're ready to pay. But I need to be clear — after X date, the number goes up 20%. After the new year, it's 50%."
One of two things happens.
Sometimes the prospect finally tells you what they've been too embarrassed to say for months — they're not actually moving forward, things changed, sorry.
Fantastic! Now you have your focus back to spend on someone who'll actually buy.
But more often? A check shows up.
Nobody likes spending money. But people hate losing money even more.
You only get to play this card if you've genuinely made peace with losing the deal. The leverage isn't the email. The leverage is meaning it and moving on.
Good luck!