Thread by @DCoolican

1/ As founder I prioritized meeting investors who would jam with me on product. I thought they "got us." I wanted to work with them for 10+ years.

I was totally wrong.

Should have prioritized ones that asked the frustrating, hard, uncomfortable questions.

Here's why 👇

2/ When I'd meet someone who grokked Frank (our startup) I'd walk out super energized. I thought we'd found our sympatico partners! I imagined every board meeting, investor update and phone call being like that.

3/ When they'd ask about our next product feature I'd instinctively start my response with "that's a great question." Turns out those weren't great questions. Or for us at least they weren't.

4/ As a 1st time founder, I was completely naive. All the investors who just talked product eventually passed. They were intrigued by our idea but didn't take us seriously as an investment. I spent a lot of time that I didn't have trying to get them beyond product ideas.

5/ The fact that they didn't push us on the hard parts of the business (👋 go to market plan) was the tell I didn't see. They'd probably already decided to pass, I just didn't know it yet. Maybe it was subconscious and they didn't know it yet either.

6/ On the flip side, the ones who only focused on our GTM strategy were trying to convince themselves to invest. They only had an hour, why waste time jamming on product when they already understood it? They were in a check writing mindset not a brainstorming one.

7/ Those meetings were a lot less exciting. We didn't have all the answers. The ones we did have were kind of flimsy. Everyone pointed that out. But we were a start-up that needed capital to go figure these answers out. Everyone has to start somewhere. Didn't they get that?

8/ We'd usually walk out a little bit smarter but a lot more discouraged. It reminded us that we had a lot left to figure out. And it wasn't obvious that anyone was willing to take that risk with us.

9/ In retrospect I should have prioritized *every one* of those meetings. These were the investors that eventually supported us. They knew we hadn't de-risked everything, but they were willing to take a calculated risk. As one told me, that's why it's called 'venture' capital. 🤪

10/ So when you're deciding which investors to prioritize, give a little thought for the ones that don't "get you." The ones asking the demoralizing, frustrating, unanswerable questions. These might be just the people you need!