It's really promising to see that you value the time of the founders you fund so much that you are ready to talk to them in a way that suits them, not just you.
I like this.
I go to LP meetings from time to time and it’s fun to see the inversion.
But also, the way raise money for Earnest is very similar to Trailhead: https://twitter.com/tylertringas/status/1260972763285774337?...
Build a relationship and have a discussion over time is so much better for all parties vs "pitch me right now and I'll decide instantly"
You’re saying that a setting up a system where founders share confidential information (monthly!) with an investor who has zero timeline for providing any kind of feedback, let alone an investment decision, is a good thing?
Who benefits from that exactly?
However, their target market is bootstrappers, who are probably not actively fundraising.
For example, I'm not fundraising, but I have no problem replying to emails about how things are going. If Earnest finds the progress interesting, maybe we can talk about a partnership. If not, I probably didn't spend much time on it. (This is assuming the Trailhead updates are quick to answer, that remains to be seen.)
The model actually sounds somewhat similar to Pioneer, which also involves continuously providing data without a promised timeline.
Venture capital is a product, and almost no product can cover all use cases. Experiments like this enable VC's to cater to different types of founders.