A while ago, I watched a founder walk away from a $5M term sheet.
A while ago, I watched a founder walk away from a $5M term sheet.
Not because the valuation was wrong. Not because of board control. But because the investor kept saying “trust me” instead of answering direct questions.
The founder asked about follow-on strategy. “Trust me, we’ll be there.”
Asked about portfolio support examples. “Trust me, we’re very hands-on.”
Asked why their last 3 investments failed. “Trust me, we’ve moved on from those.”
Trust isn’t given. It’s earned through transparency.
The best investor relationships I’ve seen start with brutal honesty:
– “Here’s where we can help, here’s where we can’t”
– “These are the 3 founders who hated working with us. Call them”
– “We’ve made these mistakes before, here’s what we learned”
That founder ended up raising from someone who opened their books, shared their failures, and connected them with portfolio founders, both happy and unhappy ones.
12 months later? They’re crushing it.
Because when someone shows you exactly who they are, you can decide if that’s who you want in the trenches with you for the next decade.
“Trust me” is what you say when you have nothing real to offer.
Real investors show, don’t tell.
