With two-tenths of a second left, there is not enough time for philosophy. There is barely enough time for a whistle. In February 2016, Colby College trailed Hamilton by two when Ryan Jann rose for a three-pointer and drew a foul. He walked to the line needing two makes to keep the game alive. He made the first two, missed the third, and sent it to overtime. Colby won.
The neat temptation is to turn that possession into a parable about pressure. It is better as something less ornamental: a glimpse of a person working inside a system, aware of the clock, the options and the consequence attached to each small decision. Jann was a senior forward wearing No. 23. He started all 25 games that season, averaged 15.2 points and led the Mules with 101 made free throws. The arithmetic was public and unforgiving. A scoreboard does not accept a persuasive memo.
A decade later, Jann works with a noisier scoreboard. As chief business officer of Wave Sports & Entertainment, he oversees strategy, revenue and business operations around shows led by Kylie Kelce, Ilona Maher, Carmelo Anthony, Dude Perfect and other personalities. Views arrive by the million. Clips scatter across feeds. A joke can become a headline before the recording session has cooled. The job is to make that commotion legible, repeatable and worth paying for.
First, learn what the numbers are hiding
Jann's route to media went through the least showy door available. At Colby he studied Economics-Mathematics and earned a place on the National Association of Basketball Coaches Honors Court. After graduating in 2016, he worked as an investment-banking analyst at Chestnut Securities. In 2018 he moved to Hulu, first in content planning and analysis, then in original-content strategy. It was excellent preparation for a business in which instinct gets the applause but distribution often sends the invoice.
He joined Wave in March 2021 as vice president of content strategy and distribution. The company had already spent years building enormous audiences through social video, investing in Instagram and Musical.ly before TikTok acquired its present tense. Its foundational bet was generational as much as technological. People of Jann's cohort were consuming entertainment on phones, not waiting politely for linear television to catch up.
The bet needed a business model. Wave began pairing its digital reach with major athletes and personality-led shows. Production became more efficient. Monetization grew more deliberate. Jann describes the progress in "step functions": solve one consequential problem, do it well for a while, and go looking for the next. It is not the sort of language that causes champagne corks to tremble, which is probably why it is useful.
The model found its most conspicuous expression in New Heights, the show Wave launched with Jason and Travis Kelce in 2022. Jann was credited as vice president of content, strategy and monetization when the program appeared on the 2023 Hashtag Sports Awards shortlist. In 2024, Amazon's Wondery announced a distribution and ad-sales agreement for the show. The cameras kept rolling, the audience kept choosing its preferred door, and what began as two brothers talking football demonstrated that a talent-led program could behave like a modern media franchise.
A podcast with the camera left on
Jann's clearest heresy is also his simplest sentence: “We think about YouTube first, social channels second, and audio as a third place to consume our content.” The order overturns the old notion that a podcast is principally something heard. At Wave, video was the first thought for New Heights. The long episode lives on YouTube. Social clips do the traveling. Audio remains available, but it no longer gets to insist that the medium belongs to it.
That hierarchy reflects more than picture quality. YouTube gives a host a comment section and gives the audience a sense of participation. It also gives the producer organic discovery and a catalogue that can surface long after publication. When streamers began courting video podcasts, Jann saw the attraction but resisted treating reach as a simple number. A large subscription base is valuable. A direct relationship is valuable in a different currency.
“YouTube offers a direct connection to your fans.”Ryan Jann on what streaming platforms struggle to replace
The distinction explains his caution around exclusivity. Wave has discussed live events and tent-pole collaborations with streamers, including possibilities around ceremonies and major sports weekends. But moving a show behind one gate can surrender the audience behavior that made it matter: clips, comments, recommendations, replies and the pleasant digital chaos of fans making a program their own.
Jann is not protecting a quaint corner of the internet. He points out that the largest podcasts draw millions of viewers per episode, audiences larger than many television series. The phrase “video podcast” may be an awkward compromise, but the economics are learning to ignore the linguistic problem. These shows are talk television with cheaper furniture, faster feedback and hosts who arrive with communities rather than merely résumés.
The machinery must not become the personality
By 2026, Jann's title had widened to chief business officer and Wave's staff had grown beyond 100 people. He called the next challenge “building the machine of people”: deciding how everyone fits together and how the company continues to grow. The phrase sounds industrial. The product is anything but. A talent-led show works because it can feel loose, intimate and unprocessed even when a considerable operation is arranging production, sales, distribution and rights behind the curtain.
Wave's portfolio now includes Not Gonna Lie with Kylie Kelce, House of Maher with Ilona Maher, 7PM in Brooklyn with Carmelo Anthony and Almost Athletes with Dude Perfect. The company has also carried its model beyond sports into comedy, music and the wider creator economy. The expansion tests whether Wave's advantage is a genre specialty or a transferable method: find distinct talent, build for digital consumption, distribute without nostalgia, and create several ways for success to pay its rent.
Talent recruitment has changed with the record. Early conversations required Wave to pitch aggressively, explaining why its social footprint and video expertise mattered. Visible hits brought inbound interest. Jann says the company can now be more selective, looking for partners who share its ambition to build both audience and business. Success has not abolished the sales pitch. It has allowed Wave to choose the room.
“Once we figure out one big thing, we do it really well over a period of time, and then find the next big problem to solve.”Ryan Jann on growth by step change
There is a useful lack of romance in this. Media mythology adores the lightning strike: the unexpected clip, the suddenly famous host, the show that seems to arrive fully furnished in the culture. Jann keeps returning to the work after the hit. Can the production repeat? Can the revenue travel across platforms? Can more than 100 employees coordinate without turning spontaneity into beige paste? Fame may be accidental. Payroll rarely is.
A human advantage, stubbornly retained
The same emphasis shapes Jann's view of artificial intelligence. He does not deny its utility. He doubts its ability to replace the qualities that make personality-led programs worth watching. A computer personality, he has argued, cannot readily reproduce Funny Marco's humor or Kylie Kelce's realness. Improvisation is not simply another production input, and chemistry is an unruly line item.
That is a commercially practical defense of humanity. If production tools become cheaper and content supply becomes effectively infinite, distinct people become more valuable, not less. The operation must use technology without confusing efficiency for affection. Audiences can detect the difference, often with the merciless speed of a comments section.
The physical company is growing too. In June 2026, Wave signed a long-term lease for an 8,320-square-foot full floor near Penn Station in Manhattan. Jann highlighted the larger footprint, the convenience for people moving through the city and the flexibility to keep building in New York. It is a charmingly tangible development for a company devoted to media that slips through every available screen.
The basketball ending is available, but it should not be overworked. A court and a media company are different places. Still, both reward an eye for spacing and an acceptance that the apparent star is supported by movement most spectators never watch. Jann's career has placed him in that movement: from the box score to the spreadsheet, from content analysis to the operation behind the show. He is still reading the floor. The floor has simply become very crowded, and almost everyone on it is holding a phone.