1/ I am seeing more and more founder secondary in venture rounds (Secondary = founders selling some of their shares before some other shareholders are able). Series B-D. I see both as an investor and through entrepreneur circles.
2/ I like secondary for entrepreneurs. Moderation is key but in a lot of situations I think it helps accelerate the co. Lots of very smart investors disagree. Here are my thoughts.
3/ Magnitude: My basic rule of thumb from what I see is market is 4+ yrs and up to 10% of founder’s equity stake with some $ cap that makes sense given stage etc. (typically <$10m)
4/ The entrepreneurial journey is brutally hard. Giving some financial relief helps remove one piece of pressure. I don’t think that secondary in the magnitude mentioned impacts the drive/persistence of great entrepreneurs.
5/ That secondary means they will be able to just sleep knowing they can pay their kids’ tuition. Secondary will make most founders better at their jobs, thus accelerating the co.