Jones is now at the helm of a prestige cable show, but his skill set was honed over years in local and satellite radio stations, often on the brink of cancellation. And he goes out of his way to talk about his career lows, and how they help him keep his work in perspective. “I am, you know, a fairly cocksure individual, but there is a humility that’s present,” Jones told Fortune. 

“Getting knocked down sometimes isn’t because there’s something wrong with you. I think that that’s an important thing that a lot of people need to hear,” Jones added. He said he’s learned to think of the stops in his career “in the context of what they were, not the context of how they ended.”

Jones shares a story from when he worked in local radio in North Carolina. After a successful season, he says he found out that his audience was up 200% and was preparing to ask for a raise. The next day, not only did the news break that the radio station was being sold, but also that his time slot had been given to someone else.

Years later, he scored the splashy star-vehicle ESPN show “High Noon,” a vehicle starring him and his friend Pablo Torre, only for it to be canceled after a two-year run because of low ratings. He told Fortune that he concluded ESPN was changing its programming choices, not that he need to change his approach. “I could have the greatest version of ‘High Noon’ that was possible [but] there’s not a place in [ESPN’s] line-up for that right now. That’s just not what they do, and that has zero to do with me.”

He likens the canceled shows in his past to a formative experience: flunking out of his graduate school’s economics Ph.D. program. “It’s not hard for me to talk about that, because I’m legitimately not ashamed of it,” he says. “What I learned from when I flunked out of graduate school really was: Even if the problem was that these shows were terrible, that’s not the worst thing in the world, either. What do I mean by that? I mean that if I did a bad show, then I did a bad show.”

Despite the cancellation of “High Noon,” Jones continued working with ESPN, and has been with the network in some capacity for the past 20 years (“It’s kind of crazy to look back at it,” he says). He had a long-running TV job on ESPN as the co-host of “Highly Questionable” and was a frequent guest on “Around The Horn,” created by “High Noon” producer Erik Rydholm. When his podcast started taking off in 2020, and Jones grew his audience by nearly 90%, it caught the attention of Warner Bros. Discovery. That led to a call from HBO in March 2021, and “Game Theory” premiered in March 2022 with a mix of analytical monologues, sketches, man-on-the-street segments, and interviews with guests from the sports world, such as ESPN’s Stephen A. Smith.

Jones said he really wanted the HBO opportunity and also wanted to continue his podcasting success with ESPN. “I thought that I was going to have to quit my job,” he says, but he’s glad he can still keep doing what he does in both networks. “This was never the plan. I just wound up here.” 

“Bomani’s perspective on sports comes from a great base of knowledge, unexpected insights, and a sharp sense of humor. He shows us a different side of the conversation, why it’s important and why we should care,” Nina Rosenstein, EVP of HBO Programming, told Deadline of the season two renewal of “Game Theory” in May 2022. The six-episode order for the first season was also expanded upon renewal.

It remains to be seen what will happen to “Game Theory,” which has struggled with ratings while winning critical acclaim. The show has managed a dose of virality on YouTube with Jones’ incisive takedown of the historical whiteness of Duke University’s basketball program in season one, or his confrontation with YouTuber-turned-boxer Jake Paul in season two. 

He says his HBO show is the closest he’s ever been to taking his vision and expressing it as clearly as possible, with the greatest resources ever made available to him. But all of his previous experiences have taught him that success will mean nothing if he has to compromise his voice.   

“You want to do your work in the place where it gets the most visibility so long as you can stay true to what it is that you’re doing,” he says. “Because once people can sniff that you not being true to yourself and what you’re doing, then they don’t care about anything else. It doesn’t matter. Your credibility is gone once they don’t believe that you’re being true to you.”