I’ve been a 2x founder, so I remember what I used to say I wanted and what I really wanted as a founder. Related to that, one of those things was around investor communications.
I used to say “if an investor isn’t interested, don’t humor me” and that’s what I really wanted too.
But it turns out not every founder is the same.
I recently was working on a compelling project and after a ton of work I realized the day before the partner meeting that there was a key, missing gap in the opportunity. And that it wouldn’t be something we would ultimately fund, because there was no way I was going to hide that gap from my partnership.
So I called one of the partners, shared my findings, he agreed with me on the findings, and we spoke about what to do. And then it came down to the “compassionate” thing versus the “objective” thing to do.
The “compassionate” thing would be to sit through the meeting the next day and then update the entrepreneurs later that day. The “objective” thing to do would be to tell the entrepreneur clearly and asap what we found and to call off the meeting, to save them time and hassle, as well as not play a game of charades.
We debated this for a long time, this partner and myself, and we ultimately called off the meeting the next day. This gave the entrepreneur about a day’s notice, as opposed to sitting through the meeting and pretending like we were going to fund it, and wasting everyone’s time.
I obviously wish I had found that gap 2 or 3 days earlier. But it was hidden and I spent +20 extra hours working on the project over the weekend, so I don’t think I could have found it earlier.
I’m still thinking through the compassionate thing versus the objective right thing to do. Because I don’t want to be like most every other venture capitalist. I might get burned in this case for doing the objective right thing and it pains me that a great person might be hurt. But in the long run, doing the right thing over and over again is the way to do things, even if there are short term setbacks.