A heuristic I’m playing with for assessing founders is how good they are at writing.
And while this approach to vetting a founder is a practical method (everyone writes) it’s obviously limited. But I think it is nevertheless sufficient for reaching an approximation of founder capacity in a swift and asynchronous way. I like to see examples of founder writing whether it is Tweets, blog posts, technical documentation or a Notion document.
It’s my belief that we’ve overweighted salesmanship, pitching & synchronic communication methods (remember reality distortion fields) which has led to prioritizing messianic style founders. A rousing keynote speech used to be the gold standard. But this may be less relevant as teams go fully remote and more work is done asynchronously. Your capacity to document and communicate meaning at scale is crucial as a founder.
The canonical example of a founder who telegraphed competence and meaning through writing was Joel Spolsky. The Joel on Software blog established him as ur technical writer and gave us documentation culture which blossomed in Stack Overflow.
A more recent example for me is Devin Finzer who I discovered through his technical writing. Long before OpenSea was a clear winner in the NFT space, Devin’s writing caught my attention as his crisp clear articulation on the basics non-fungible tokens was legible to everyone.
My guess is this heuristic of focusing on writing instead of showmanship will improve overall diversity of founders & companies in a portfolio as less bias creeps into asynchronous documentation whereas mirroring & social cues easily tilt pitching in favor of certain classes of people
I’m also keen on folks who like messaging culture. Being able to hop in and out of conversations is crucial to team building & scaling. Those that are happy to DM & chat to build rapport in distributed fashion more easily will succeed at building relationships in a remote first world.