Modern Meditations: Sam Lessin

I’m also proud of the companies I backed that might not have had the greatest financial return, but were culturally relevant. For example, I wrote the first and second check into Venmo – and then I got my dad to write the third check because no one would give them money. The financial return was fine, but it was a great cultural investment.

There is obviously leverage in AI, but it's almost certainly going to go to the big platforms. This is not a PC or internet-level disruption. This is an easy bolt on for the cloud providers, or for the companies who already have attention or data. There are going to be exceptions. Someone is going to build a $10 billion company out of AI. There wil... See more