Midroll + Stitcher (acquired by Scripps)

Episode 16 is a self-aware "meta" episode about the podcast industry itself, covering EW Scripps' back-to-back acquisitions of Midroll and Stitcher. The hosts open with the running joke of thanking their single Zune listener and single Stitcher listener (David's wife, Jenny) — and the topic itself came from Jenny: searching "acquired podcast" on Google, she found the show nowhere near the top results, making this episode an unabashed SEO play.

In lieu of advertising, the hosts announce a "Community Showcase": at roughly the size where they could sell ads, they will instead feature a listener's project each episode — a free thank-you aimed at their Slack community, since so many listeners are entrepreneurs, product people, VCs, and operators. The inaugural shout-out goes to David Resnick (@the_rezonator), a former recording engineer helping with the show's audio quality and founder of BESTR, a curation platform.

EW Scripps, by tech standards a very old broadcast media company (and historically a newspaper publisher) operating cable networks and TV/radio stations nationwide, made two splashy podcast acquisitions within two years. The first target: Midroll, a bootstrapped startup. It began in 2010 as Earwolf, a comedy podcast network founded by Scott Aukerman and Jeff Ullrich around Scott's show — originally Comedy Death-Ray (roots in Hollywood's Upright Citizens Brigade standup scene), later renamed Comedy Bang! Bang!, which itself became an IFC television show — "the giant among midgets in the podcasting world."

For years Earwolf was purely a content network, selling ads directly for its own shows. In 2014, after advertisers kept asking to buy space on podcasts outside their network, they spun out Midroll Media — among the first (if not the first) ad networks for podcasts. The launch press release touted a "360-degree suite of production, distribution, and monetization services," 120+ shows, 15 million monthly downloads, and "the industry's first user-focused, self-service platform." The hosts marvel at the scale: in 2014 the entire self-service podcast ad platform had 120 shows, versus millions of advertisers on AdWords — "a grain of sand compared to every beach on earth." Midroll did sign genuinely large podcasts: WTF with Marc Maron (Barack Obama had recently appeared), Bill Simmons' shows, and The Ringer's podcasts.

About a year later, Scripps bought the company: a reported $50 million upfront plus a $10 million earnout — a strong return for a company that never raised outside capital. The dollar context: per The Wall Street Journal, advertisers were expected to spend only ~$35 million on podcasts that year, up ~2% from the prior year. A Midroll figure (30% take rate, a handful of podcasters grossing over $1M/year) implies Midroll's annual revenue was somewhere around $2 million. David's caveat: the biggest podcasts (NPR, This American Life) sit outside Midroll, though Ben argues the majority of independent-podcast ad spend does flow through it.