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 whichever way the wind was blowing on the business side of media (programmatic ads, etc.), I would argue, develop and build an opposite approach. That worked out for me over the past decade. We created the Native Advertising model at HuffPost, developed new ways to build media businesses in the social era at RebelMouse and created two SaaS businesses at The Washington Post. The story is often as important (if not more) than the product itself, and in the media business taking the approach to build better experiences for consumers and new profit streams that support the core value of the projects wasn’t necessarily revolutionary, but it was an opposite approach that the industry could get behind. I like to try and enforce a beginner’s mindset in everything I do.

HW: I also associate you with a love of music, especially songwriters, jam bands and live performance. Is this an escape for you from tech stuff, or do you see parallels between Software Jarrod and Phish Jarrod?

JD: Maybe so, maybe not. But seriously… Music is definitely the best representation of me. My identity is directly connected to it. I was fortunate growing up in a family that believed in the importance of having music around 24/7. My mom was a dance choreographer and owned three studios in central Jersey. In those days, you would get your music at record stores and I remember her making it a weekly thing for us to go to Jacks in Red Bank or Coconuts in Sayreville and just buy everything off the wall. Because she owned studios, CDs were a business expense so I had a full go on everything.

It’s wild to think about the 90s because you would hear a song on the radio and try to find it or would go to the record store and buy a CD for a single song and discover the rest of the band through the album. Anyway I’m ranting but it was a very fucking cool way to discover something new. Everything felt new and hard to find, and when you found something special it was always an incredible feeling.

The parallels of music head and tech head are that when you’re constantly in a chase for something new, you have a different chase on things that often others can’t feel or see. Unless you know the feeling of the chase, you don’t know what you’re hunting for. I think it’s important in tech to try to constantly think and find something new. To understand that many people feel or see different things, and the importance of being open to a bunch of different flavors and sounds. Maybe the word I’m looking for is openness. Or maybe it’s like being in a dark room and feeling for the light switch and that moment when the lights turn on and you see everything in front of you. Anyway, go see Phish live. You’ll understand.

HW: Were you a well-behaved kid or pain in the ass kid?

JD: What do you think? 😉 I would say I was a loud kid. And when you’re loud, you are often unfairly characterized by your teachers as a pain in the ass. School was interesting for me. I loved it, but more so because I love people. I wasn’t a great student, but I wasn’t a bad student. I liked the things I liked and spent most of my time there. I am not a loner and definitely, if you met me, not an introvert. I’m all about being on the move and want to constantly be surrounded by people. I’d say the things that used to get me in trouble back then (social, loud, on the move) are the things that make me successful today. So I’m happy I didn’t listen to those teachers.

HW: Ok, now we can do two questions on the web3 stuff. Knowing what you know now, was (where you were CEO several years ago) just too early or would you have approached the project differently?

JD: I think it’s definitely a little bit of both. We were definitely too early. It’s crazy because if you think of the pitch back then (“we want to put all digital content on chain”) it sounds like a billion dollar idea today. But back then it just wasn’t as clear to creators and consumers. The emphasis was really anchored in the notion of provenance; in an era of fake news, deep fakes and attributing quantifiable value to quality content, having a supply chain of information could provide a base layer to build products that solve for that. But the market and our approach wasn’t yet ready. We also aimed to do it on bitcoin which in hindsight would have eventually shifted to ethereum or another L1 quickly.

We also aimed to get big publishers on board. New York Media was incredible and took a bet on us, integrating the protocol into their CMS. But again, others weren’t yet ready. Looking back, I would have leaned heavier on attributing value and ownership to assets over having a supply chain of creative process. I also would have focused more on the long tail than the short tail. We had a highly active community of developers that were building the function of in their creative flow. There are projects today that have executed a part of that vision and have taken it a lot further that I’m insanely excited about. But in the end, got me technically very deep in the crypto space and much of the relationships, learnings and lessons are the reason I’m doing what I’m doing today.

HW: One criticism hurled at web3 devotees is that it’s a bunch of pronouncements about decentralized, liberated futures that are just disguising a greed to make money. How do you feel about those opinions, given that you’re specifically in the business now of making money off of web3?

JD: There are some parts of web3 that I believe are hard to argue. One of the biggest, and most important, is that the emergence of NFTs has brought provable digital ownership to the internet. This evolution can’t be overstated. We’ve spent decades building products on the internet with the presumption that most digital content and IP can’t be proven scarce, or valuable, or 1:1. Now we can. So not only are we seeing an emergence of new platforms and products driving this, but also seeing many existing companies starting to think about what that now means for their business and experiences on the internet.

It’s actually funny because in the 2010s social world, the challenge was the there were all of these users but no way to monetize them. Now we have all of this monetization, and are looking for users. Matt Huang has a great tweet here .

It’s so new, and we’re taking a different approach to getting to a new space. What the term web3 has shown us is we’re now seeing crypto or blockchain in every pocket of the web. Every industry. Every interest group. So it is going to take time and experimentation to see how that fits in to both existing paradigms and newfound ones.

A part of it being focused on the creator space makes sense. There are many creative businesses that don’t have a strong online economic foundation (digital art, photography, dance) and face little headwinds. If the opportunity is in web3, then we’re starting to see how this comes to life organically. I also think it’s not binary. Arguments are also “why do you need web3 for this?” and maybe the question to ask is “why are we using web3 for this?”. Having a new option to own and distribute IP is amazing for both creators and consumers on the web. If they choose to use it, and prove it’s opportunity, then we all win.

Thanks Jarrod! You can follow him on Twitter @jarroddicker.