The Rebooting Show

Jeff Selingo spent eight years at the Chronicle of Higher Education, serving as editor in chief and editorial director, before setting off on his own path. Jeff and I have traded notes on the independent path over the years, and I wanted to have him on The Rebooting Show to discuss what we’ve both learned on the independent path. We discuss the transition from editorial to sales, why treating “lifestyle business” as a pejorative is strange, and fighting the pull to rebuild what you left behind.

Blockworks, founded as a crypto events company in 2018, has rode these ups and downs. It began in the face of a crypto pullback with the thesis that crypto would become a major asset class and as it grew, institutional investors would need a credible source of information, analysis and research beyond an anonymous Twitter account with a monkey avatar shooting lasers from its eyes.As crypto recovered and headed into a bull run that accelerated during the pandemic into what I’d consider a bubble, Blockworks expanded from events into podcasts and news. With $12 million in VC raised in possibly the hardest time to raise for a crypto media company, Blockworks is building out a research arm.Jason Yanowitz, CEO of Blockworks, discusses the evolution of the company and the benefits of staying focused and being a "mile deep" vs an inch deep.

Defector is a worker-owned media company that was born out of disillusionment with the tradeoffs the digital media ecosystem often requires (or at least incentivizes). Instead of chasing traffic, Defector relies on a subscription model for a small but sturdy business.

My former colleague Mike Shields of Next in Media joins me to discuss what to make of Advertising Week, which is mostly a PR vehicle but a useful gauge of the prevailing winds of the media and advertising worlds.

On a crossover episode of The Rebooting Show and People vs Algorithms, Alex Schleifer and I discuss the end of the zero-interest rate policy era and how it will lead to cascading changes in tech and media.

Video is viewed paradoxically by publishers. They see budgets shifting to sight, sound and motion. Video ads, formerly known as TV spots, were always valued by advertisers far more than a standard display ad, no matter what efforts were made to gussy them up. Yet for many publishers, the costs associated with video creation are certainly high but the revenue while potentially big is uncertain. Tom Pachys, CEO of online video platform Ex.co, joined to discuss the challenge“The publishers that we work with say that this is their biggest line item when looking at the advertising part of their P&L. That definitely works, but the cost of opening studios, recording videos, taking the risk,  And also having that expertise – that's where the challenge is.”Thanks to Ex.co for sponsoring The Rebooting. Check out its recent guide to selecting an online video platform.

Before the Lumascape, there was another go-to conference and pitch deck slide for anyone betting on what was then called web advertising. The slide, updated annually by the financial analyst Mary Meeker, showed twin bar charts of time spent and budget spent by medium. The message was clear: the internet would win, it was just a matter of timing. The time spent gap did close, although a disproportionate amount of gains went to tech platforms rather than web publishers. The chart was always wrong, argues media analyst Brian Wieser. Time is simply one variable in assessing the value of a media impression:“It speaks to an incorrect framework. You look at the historical data, you ask why this happened, and you try to make sure the model mirrors why decisions are made. The common narrative was always that it's time. That's what drives the money. If that were true, radio would be a much bigger business.”

1440's CEO, Tim Huelskamp, discusses the revenue model of their newsletter, the challenges of unbiased news, the importance of paid growth, and monetizing newsletters. They also explore the advantages and disadvantages of email as a publishing channel and analyze Substack as a business.

Founded a decade ago, Team Whistle is a survivor. It sprang to life as a wave of multichannel networks that filled the need of aggregating YouTube properties to make buying easier. The biggest problem of the MCN model is that it takes a difficult business model (advertising) and makes it even more difficult because you’re taking a cut of a cut, after YouTube gets its taste. Most MCNs fizzled.Whistle shifted its focus to building its own properties, producing franchises like “No Days Off,” a series following incredibly focused child athletes. It still reps other properties, like Dude Perfect. It complemented that with an agency business that relies on the distribution and cachet of the original programming.  Whistle is part publisher, part agency.

The digital advertising system is in the midst of a shift, from an over-reliance on collecting vast amounts of data to crunch to do one-to-one targeting – dog owners getting dog food ads, cat owners get cat food ads – to a new landscape that gives people more say on data collection and pushes advertisers and ad tech companies to operate differently. In this episode, I had a conversation with Joe Root, CEO of Permutive, an audience platform that's used to deliver privacy-safe digital advertising. Among the topic covered:The shift in publisher incentives to build trust vs build trafficWhy direct sold advertising is back in vogueWhether GDPR’s implementation gives real consumer choice or just the illusion of itThe surprisingly large carbon footprint of digital adsWhy the loss of ad targeting signals has become an advertiser problemThe demise of the long tail in favor of top-tier publishersWhy the so-called ad tech tax will come downincrease revenue from first-party data by 46%.