Founders make their biggest mistakes when they treat funding like a transaction instead of a relationship.
The check comes fast, the deal looks good, and suddenly you’re in a long-term partnership with someone who doesn’t share your values or your vision. I’ve seen what happens when this goes wrong. It’s not just tension in a board meeting — it’s the beginning of a slow drift, or worse, a total derailment.
Every strong founder-investor relationship I’ve seen is built on three things:
Character: Do they do what they say they’ll do? Are they transparent and grounded in integrity? Or do you sense hidden agendas?
Competency: Are they offering insight, experience, or network access that sharpens your thinking and helps you grow? Money is table stakes — great investors bring more.
Connection: Do they believe in your Forever Agreements? Do you walk away from meetings aligned and energized or stressed and second-guessing?
Read more in How to Choose the Right Investors.
When all three are present, you’ve got a shot at building something great together. But if even one is missing, no amount of capital is worth the trade-off. Desperation leads to bad deals, and bad deals are hard to undo.
So before you say yes, ask yourself: Is this someone I’d want beside me ten years from now, through both the good and the bad?