Allow Le Batard and Friends to Reintroduce Themselves

A week after Meadowlark Media announced a $50 million partnership with DraftKings, nearly two-dozen of the company's employees gathered around a rectangular table in a chilly Miami conference room to discuss the next steps forward. To hear about the grand vision in the most detail to date. To further hammer out what kind of song the venture will sing.

The mood was casual. CEO John Skipper, with actual and metaphorical sleeves rolled up, addressed his team, filling in some of the blanks all startups are tasked with filling. It was the first in-person meeting of the expanded roster, which has been growing slowly and steadily since the content shop formed in January. Gone were the annoyances and delays of the Zoom world that gave birth to the project and served as a conquerable creative petri dish for the flagship Le Batard podcast.

It was new, but it felt normal.

For the last year the show has played out against a backdrop of tension. First it was the misshapen toy raging against the corporate constraints of ESPN. Then it was a pirate ship sailing uncharted waters with fans and experts alike trying to figure out which port would offer safe financial harbor.

The vaunted DraftKings partnership, a three-year deal that could become the new media template as the market most rewards outlets with loyal and engaged fanbases, begins June 1. It will mark the official beginning of a new era and close the door on an entertaining and surprisingly lucrative stretch few could have predicted when producer Chris Cote was laid off.

Most of the meeting centered on sketching out plans for a marquee event to mark the occasion — Freedumb, a 24-hour marathon of programming featuring the familiar and not-yet-familiar faces of the growing creative community. Kicking off Friday, June 4 at noon from outside the Clevelander on South Beach, the YouTube Live stunt will present both a giant challenge and a giant opportunity for the Le Batard and Friends universe to reintroduce itself to the world.

Though the broad strokes have been painted, there remains significant work to do around the edges. The event, which will have some telethon DNA — perhaps including a call-in line — has an obvious business purpose. DraftKings contests are expected to be integrated into the programming. The daily fantasy presenting partner is banking on increasing signups. Meadowlark is hoping to showcase just how loyal and engaged its audience can be, and what that means for bottom lines both internal and external.

How will those 24 hours be filled? The first three hours will resemble a typical Monday, Tuesday or Thursday show offering. After that? Expect out-of-the-box ideas. Like animal doctor Ron MaGill bringing his zoo friends in-studio like a modern day Jack Hanna. Or Stugotz trying to stay awake for the entirety of the broadcast. Or 12-minute riffs on random Florida Marlins middle relievers from the 1990s. For fans, part of the charm is the unpredictability and willingness to veer into unusual lanes.

It's a great weapon to have in one's back pocket. Because stringing together a full day's worth of content together is no small task, even for a company with big dreams. Up to this point, it's been more expedient to list the things Meadowlark doesn't want to do than what it aspires to do. This public performance will be a bit of an empirical progress report reflecting both talent and interest.

In the five months since Meadowlark's first public notes, the company has steadily built its roster. Yesterday brought news that Kate Fagan and Tom Haberstroh were coming aboard full-time. Hank Azaria, Jessica Smetana, Jemele Hill, Adnan Virk, Michael Schur, Adam McKay, Lynn Novick and others had previously joined. Gary Hoenig, Bimal Kapadia, Laura Albero and Carl Scott have been added on the executive side.

The early days have been romanticized, as one would expect from a Skipper-Le Batard joint venture. The duo is fiercely passionate about storytelling and has embarked on a quest to provide the most nurturing environment for creatives. There's a planned nobility but putting it into practice is no less daunting.

This event marries ideas from both the low-brow and the high-minded buckets, which feels appropriate. On one hand, the proceedings promise to be absurd. On the other, they'll be the most complete look at the company's creative core. A public heat check reflecting the new work culture.

It is no small thing to go from 15 hours of entertainment in a week to 24 in a day. And though Meadowlark has a completely different business model than some of its competitors in the cable business (the future lies not only in podcasts but also a third-party provider to streaming outlets), matching what Fox Sports or the Worldwide Leaders do every day will be a barometer of success.

But the most meaningful metric will be engagement. Showcasing a rabid fanbase that can be leveraged for symbiotic business relationships. The DraftKings deal is the first of its kind but won't be the last — neither for the industry as a whole or the Le Batard crew. Their three-year quest to increase their own value to current or potential partners begins with a wink and a nod but is still a serious marking post. A chance to get a lay of the new landscape. For everyone to get familiar with the players, many of whom will be wearing new uniforms after a busy transfer period.