“Trust me” is what bad investors say when they have nothing real to offer.

The best investor I had in my founder years taught me something brutal: “Trust me” is what bad investors say when they have nothing real to offer.

Now as an investor, I tell every founder the same thing:

Reference check us harder than you’d check your CTO.

Because once we’re on your cap table, we’re there forever. No divorce. No ctrl+z. Just you and us for the next decade.

Here’s what founders never ask but should:

“Show me the last 3 founders who hated working with you.”
Not the success stories. The disasters. If an investor won’t share these, run.

“What happens when our startup is dying?”
Do they ghost? Do they try to force an acquihire? Do they actually help? Most founders find out too late.

“What’s the worst advice you’ve given a portfolio company?”
Good investors learn from their mistakes. Bad ones pretend they don’t make any.

I’ve been on both sides. As a founder, I had investors who picked up the phone at midnight during crisis. And I had others who start showing their toxic side, or just disappeared the moment growth slowed.

The difference wasn’t their check size. It was whether they’d been transparent from day one.

The investor who adds the most value? Often the one who was brutally honest about what they couldn’t do. Not the one with the fancy pitch about their “platform” or “industry network.”

Before you take anyone’s money:
– Call founders from their failed investments
– Ask specific questions about actual help provided
– Get examples of hard times, not just the wins

Your cap table is permanent.
Your due diligence shouldn’t be optional.

If you find out your investor is useless or, even worse, toxic, only after they have taken 20% of your company, that is a mistake you will live with until exit.

Choose wisely. You’re not just raising money.
You’re choosing who’s in the trenches with you when everything goes wrong.