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In a signal that Entercom plans to make podcasts a bigger part of digital audio platform Radio.com – and a vote of confidence for on-demand audio – the radio group is making its biggest investment in podcasting to date. Entercom will acquire Pineapple Street Media for $18 million and buy the 55% of Cadence 13 it didn’t already own.

 “We are poised to become one of the country’s three largest podcast enterprises in the United States,” CEO David Field said Wednesday on a conference call with analysts, while noting that podcast is the fastest-growing area of the audio market. “Together these two acquisitions will propel Entercom to a leading position in the podcast space with a stellar content lineup, strong monetization capabilities, and excellent distribution and discovery platforms across the company’s radio stations and Radio.com,” Field said.

Combined, Cadence 13 and Pineapple Street Media are said to have had 150 million downloads per month during the second quarter. And Radio.com already had more than 10,000 podcasts. Yet Entercom enters what’s increasing a crowded list of options for accessing podcasts. But Field told analysts he thinks the combination of all their assets will put it in the same league as NPR and iHeartMedia, which itself struck a $55 million deal to acquire Stuff Media last year and beef up the podcast offerings on iHeartRadio.

“We believe it’s a great fit and a logical adjacency,” Field said. “We think there’s a huge natural advantage to being an existing broadcaster — and we look at this as an area where we’ll be able to achieve some significant growth over time.”

The announcement that Entercom had signed an agreement to fully take over Cadence 13 was likely not much of a surprise to many podcasters. The broadcaster had previously bought a 45% stake in Cadence13, which was then known as DGital Media, in July 2017 for $9.7 million. Under the terms of that agreement, Entercom had an option to buy the remaining ownership interest in 2021. But with a sudden flurry of deal-making in the fast-growing podcasting industry, the two companies have decided to pull the trigger two years early. Terms of the latest agreement haven’t been disclosed but it reportedly pegs the value of Cadence 13 at roughly $50 million.

Cadence 13 co-founders will remain in place, including CEO Spencer Brown who will now report to Entercom Chief Digital Officer J.D. Crowley. Chris Corcoran, Chief Content Officer at Cadence13, will continue to lead content for the division, and John Murphy, Cadence 13’s President, will also be part of the leadership team.

“Consolidation with Entercom will greatly accelerate the next phase of our growth,” Brown, Corcoran and Murphy said in a joint statement. “Through its robust portfolio of broadcast radio stations and the Radio.com platform, Entercom offers Cadence access to a national audio platform that will accelerate revenue and development of our audience engagement efforts. This acquisition helps us extend the reach of our partners and build their audiences across the audio landscape.”

Cadence 13 plans to continue its work with outside podcasters such as Crooked Media and Pushkin Industries while also expanding its client roster, leveraging Entercom’s broadcast reach and Radio.com’s digital platform. 

Entercom’s deal to buy Brooklyn, NY-based Pineapple Street Media was the more unexpected component of the deal-making. The company had so far avoided venture capital dollars in order to embrace edgier content. Pineapple Street co-founders, Jenna Weiss-Berman and Max Linsky, will now join Entercom as co-heads of their division, also reporting into Crowley.

“This is an incredibly exciting day for us and our team of podcast producers,” said Linsky. “We started Pineapple three years ago with the simple goal of making great shows that found huge audiences, and joining forces with the amazing teams at Entercom and Cadence13 means we can do that at a scale we never imagined.” 

“This is an amazing time for podcasting,” added Weiss-Berman. “This moment is unprecedented – the energy, the growth, the talent coming to the medium. I am thrilled to be working with the incredible leadership teams at Entercom and Cadence13.”

In addition to its acquisitions, Entercom announced it will launch the Radio.com Sports Digital Network later this month. It will include a lineup of daily radio shows pulled from Entercom’s portfolio of sports talk stations as well as weekly podcasts on Radio.com.

For Entercom the series of digital moves is being billed as a “transformational” event for the company. “It is an exciting day for all lovers of audio—creators, listeners and advertisers,” said Crowley.