The Rebooting Show

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%.

This is a bonus episode of The Rebooting Show, featuring a conversation I had on the People vs Algorithms podcast. We discuss why the conventions of media are giving way to new formats that dispense with the artifice in favor of something approximating real conversations.

Rich Routman is a veteran of the sports media industry. He recalls how if an advertiser discussed a cost-per-action deal with a major sports media company as recently as five years ago, the media executives would "run out of the room." That all changed with the legalization of sports gambling in 33 states and the District of Columbia. A giant industry would need customers, and sports media was there to help. That's led the Sporting News, which Rich joined as CEO last year, to raise a $15 million Series A a mere 137 years after its founding. Rich and I discuss how TSN is generating 40% of its revenue from affiliate and revenue-sharing deals from sportsbooks and other subscription services.

Bustle was founded a decade ago in a far different media environment, as big digital media companies, flush with VC cash, scrambled to acquire the biggest audiences possible. The supposition that those with the biggest uniques would be handsomely rewarded didn't turn out to be a durable model. Now, Bustle is looking like a different entity, as its CRO says typical ad campaigns are now just 15% of the company's revenue Instead, it is focused on using its stable of brands for bigger efforts more akin to what ad agencies provide. In this formula, traffic is far less important than brand affinity, client relationships and the ability to execute.

Puck's Jon Kelly discusses the success of their direct-sold ad business, the challenges faced by legacy publishing models, raising $10 million in a tough funding climate, the shift from institutions to individuals in media, the enduring value of scarcity, and the benefits of starting small.

CJ Gustafson, CFO who uses memes and a conversational style, discusses the challenges of being a CFO, the drivers of a sustainable media business, the advantages of SaaS businesses, evaluating financial health, changing dynamics of the ad ecosystem, and building a community.

Literally Media -- home to Cracked, I Know Your Meme and Cheezburger -- isn't going to fight creators. Instead, it's partnering with them to do everything from launch channels on new platforms, get access to brand partnerships and be part of live events. Literally Media CEO Oren Katzeff explains the approach, along with Literally's emphasis on IP-based video franchises and more.

This week, I spoke to Parquor’s Andrew Rosen, a former Vicom exec turned media analyst, to unpack Hollywood’s weird summer of transition. The challenge for media companies is moving from a wholesale model to a retail model. Andrew sees a group of leaders without a clear understanding of how to make that leap.