The Rebooting
The Rebooting Show
Jarrod Dicker's sane person's guide to crypto

Jarrod Dicker's sane person's guide to crypto

Plus: Censorship fights, personal brands and teardown pieces

Something about the podcast highlights format wasn’t working for me, so I’m switching up the Monday version to feature highlights from the podcast as well as some thoughts on other matters in sustainable publishing. After all, formats matter. Let me know what you think. This week’s topics:

  • Going down the rabbit hole with TCG’s Jarrod Dicker

  • Censorship fights

  • Individual brands in publishing

  • Well-paid journalists

  • Company teardown pieces

The pivot to pragmatism, web3 edition

Crypto is polarizing. Talk to a web3 trust believer – I define web3 as encompassing crypto currencies, blockchain, decentralized finance and non-fungible tokens and decentralized autonomous organizations – and you’ll hear we are on the cusp of a blockchain utopia that sounds a lot like a kibbutz designed by Ayn Rand. And if you don’t see that, well, you’re ngmi. The doubters of this “pathetic tech future,”  scramble to dismiss the latest crypto craze as a “bust.” Most critiques at their heart are a version of this throwaway line in an otherwise quite interesting Time  profile of Ethereum creator Vitalik Buterin:

“Ethereum has made a handful of white men unfathomably rich, pumped pollutants into the air, and emerged as a vehicle for tax evasion, money laundering, and mind-boggling scams.” 

Well, when you put it that way…

I’m too much of a realist for these extremes. I believe crypto is, in some ways, inevitable based on the sheer amount of capital – financial, people and cultural – going into it. Kevin Roose, who has taken a moderate approach to the Crypto Holy Wars, has a very good web3 primer for those with open minds. The trough of disillusionment is a critical part of any adoption cycle.

I’m most interested in web3 through the lens of publishing models. For that, Jarrod Dicker is my web3 shaman, since as a longtime publishing executive at places like The Huffington Post and The Washington Post, he’s got a foot in the Old World of Web 1 and Web 2.0 and now one firmly in the New World as a partner at investment firm TCG.

What I like about Jarrod is, despite his affinity for Phish and cryptic tweets, he’s a realist. He knows how early it is for this set of technologies having tangible impact.

Some key takeaways from my conversation with Jarrod:

  • NFTs matter. Look beyond the speculative frenzy over ape drawings. The importance of NFTs are when they’re tied to access and community. In media, imagine moving people from a passive audience to active participants to owners.

  • Web3 needs better marketing. Let’s face it, crypto boosters do themselves no favors by coming across as Crazy Eddie on bath salts. The challenge of moving beyond the true believers is going to be as much a marketing challenge as a tech hurdle.

  • The wallet is critical. Anyone crypto curious should set up a wallet using MetaMask, Rainbow or another option. You can already log into your account using your wallet; that will shift more power over data to people, and it should allow for new ways for publishers to understand their audience/communities. 

  • Ownership is foundational. Rethinking ownership of organizations, whether through DAOs or other uses of tokens, is why so  many are excited by the potential of web3. Too many benefits have been accrued by platforms or capital holders rather than people who are creating a disproportionate amount of the value being realized by others.

  • Moving from subscriptions to investing. Crypto’s seeming obsession with “financializing” every relationship can be off putting. But it’s easy to see a future path where people in a community treat publications like investment vehicles, if only to will them into existence. You can already see this shift happening with the growth of Patreon and even crowdfunding campaigns for independent Ukrainian media.

Check out the podcast on Apple or Spotify. Also, if you’re an Apple user, please leave a rating and review. Big thanks to Double Monks who gave the podcast five stars and called it both “informative and highly entertaining.” Thank you, Double Monks, I appreciate it.

Free speech wars and returning to the middle

This is a strange time to tend to take moderate views on many issues. We live in a time of extremes, as most societal issues get treated as the zero-sum game our politics have become. Casting a slightly dissenting view on these topics risks opprobrium and even exile. The Twitter fighting pits were kinetic this week over what struck me as a fairly banal editorial in The New York Times that warned of going overboard with speech codes. Publishing this just a decade ago would elicit not much reaction, but we are in a different place now. My bet is this can’t last, and we’ll see again coalesce around the middle ground that, to my mind, are a mark of mature people in mature societies.

More on the individual brands in media

Kinsey Grant of Thinking is Cool was kind enough to have me on her new YouTube show. We discussed the shift to individual brands in media and how, in my view, that’s not a bad thing. Like above, I think the power will ultimately reside in organizations or collectives that find a middle ground along the institutional-individual brand continuum. There’s no reason to build the same hierarchical structures that have come up short so often in the past. Why not build new structures more in tune with how people work in the knowledge economy as opposed to how work was coordinated in the industrial age?

Pay the journalist

Nobody goes into journalism to make a lot of money. In ad-driven media, compensation is often higher on the “business side.” That needs to change. New Gawker broke the bombshell that Business Insider editor-in-chief Nich Carlson made $600k and doubled that comp with his bonus. Good for Nich. He built a 650-person newsroom, the heart of a big business. Nobody would give a shit if he was chief revenue officer. Also, I knew Nich going back to when he was out on the sidewalk in front of a Facebook launch event in 2007 hustling quotes from those invited to attend because he wasn’t allowed in. Get the bag, Nich.

Reminder: Every company is dysfunctional

The problem with these company teardown stories, most recently exhibited by Business Insider’s deep dive into problems at Glossier, is you could write a version of this story of just about every company. For too long companies were given fawning coverage as a default. Now, it seems like the Inside the toxic culture at X format is simply a template. You talk to 20 ex-employees. Plenty have axes to grind; they put you in touch with others similarly disgruntled, rinse and repeat. There’s always both truth to these pieces and also a heavy amount of gambling-in-Casablanca anecdotes that are everyday realities of work life. Every company is dysfunctional in its own ways.

Odds and ends

Local news is poised for a comeback. I don’t recall such energy being put into building new models. There is no way McClatchey or a private equity firm is going to solve this hard problem. I’m excited to spend more time with those building from scratch in an upcoming series for The Rebooting Show. 

Old-line publishers  like The New York Times are finding ways to occupy a middle ground on the institutional-individual brand continuum. David Leonhardt is a great example of how news organizations like the Times can build from their strengths to create new franchises.  An under-appreciated part of his appeal is how little he seems driven by dogma, which has someone become a rarity in The Discourse. 

The struggles at Disney are inevitable as the creative industries and technology collide. Alex Sherman has an in-depth look at the power struggle between Bob Iger and his successor, Bob Chapek. The personality stuff is less interesting to me — where people sit at parties — than the challenges of truly putting tech at the heart of a media company.

If you never trust platforms as a publisher,  you’ll never be disappointed. Vimeo is the latest to find its business model needs in conflict with its purported support for creators.

Personal brand activation alert: I’m speaking at the PRCA International Summit on Thursday along with Substack’s Lulu Cheng Meservey about DTC media.

Brand collaboration alert: I’m lining up partners for Q2. Check out the sponsorship kit and get in touch to discuss ways we can work together.

Thanks for reading. Let me know what you think of this tweaked format by hitting reply or sending me a note at

The Rebooting
The Rebooting Show
The Rebooting Show gets into the weeds with those building and operating media businesses, giving an open view into how the smartest people in the media business are building sustainable media businesses.