I’ve started a Substack! It’s called Dreams of Electric Sheep and it’ll be where I do the bulk of my writing from now on. I’ll leave the blog for more personal updates.

My first post was on the first venture capitalists – whalers who pioneered the current VC organizational structure and learned how to invest under massive uncertainty.

“Just like phenomenal startup founders, the best captains avoided the herd. The herd mentality became apparent with the > 50% of whaling voyages entering the North Pacfic in the 1850s. So many captains copied each other that when the Bering Strait was blocked due to icebergs in 1851, the whaling season ended in failure.

So why did young men decide to risk their lives as captains when the odds were entirely stacked against them? Herman Melville’s quote says it all: the thrill to rise above the rest and the “everlasting rich for things remote” characterized remarkable captains. Being a whaling captain is much like being a startup founder. The question of when one quits; when one listens to their team (who you have a responsibility to) versus your intuition; and most importantly, when one feels satisfied with their accomplishments.“

I also wrote about why tech M&A is a power law with Auren Hoffman. Link.