Investor Jarrod Dicker on how “the emergence of NFTs has brought provable digital ownership to the internet. This evolution can’t be overstated.”

And Why He Abandoned a Career in Web Ads for Leading Crypto Investing at The Chernin Group

Even before my Jarrod Dicker starting tweeting in his “web2 vs web3” style, I gave him shit about his thought leadership which seemed to be 80% “that’s smart” and 20% “what did you just smoke because I have no idea what this means?” Sometimes I’d just DM him the latter with “20” written alongside. But outside of this social media sparring, is a foundational friendship where I hold him in high admiration, not just professionally but as a human. He’s an expressive, passionate, principled person who cares deeply about his family and his community. So I used this Five Questions to get a bit more on his own background and push on web3 developments now that he’s slinging million dollar investment checks as part of The Chernin Group. Thanks JD for always being a good sport!

Hunter Walk: So you recently moved over to the investing side leading Crypto at The Chernin Group, but before we dive into your annoying web3 tweeting habits, let’s go backwards a bit. You did a lot of work in online advertising but also seem to really care about people and user experience. Reconcile that for me!

Jarrod Dicker: I started my career as a music journalist and the plan was to do that forever. I love music but am pretty shitty at playing instruments (though I collect guitars!). So the closest thing to becoming a rock star for me was writing about them. I had a blog and did a bunch of freelance work while bartending at night in Jersey, and in 2010ish accidentally fell into the media world by applying for a job on Craigslist at a blog called the Huffington Post. I wanted a writer role but the only thing they had was a business role aimed at trying to think of creative ways for the Huffington Post to make money outside of traditional means. That’s where I realized that if you like to be creative, the business side is actually way more liberating than the editorial side because you effectively could experiment and do whatever you want as long as you made money. It was permissionless as long as you delivered.

At the time it wasn’t as obvious as it is now that the bar for monetizing media and publishing was insanely low. So I carved out an ethos that…