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    You are at:Home»Entertainment»Sean Combs Spent His Time in Jail Teaching a Business Class
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    Sean Combs Spent His Time in Jail Teaching a Business Class

    Earth & BeyondBy Earth & BeyondSeptember 26, 2025005 Mins Read
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    Sean Combs Spent His Time in Jail Teaching a Business Class
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    Sean “Diddy” Combs spent a chunk of his time in jail over the past year instructing his fellow inmates in the ways of business management, entrepreneurship, and, apparently, how to be more like Sean “Diddy” Combs. 

    A description and curriculum for the course, dubbed “Free Game With Diddy,” was submitted to the court this week, along with testimonials from Combs’ students and a positive evaluation of the class from the jail’s Unit Counselor. All of this was sent to Judge Arun Subramanian as Combs’ lawyers work to secure their client the most lenient sentence possible following his conviction on two felony prostitution charges this summer.

    As they assured the judge in their letter of Combs’ course: “Notably, the evaluation acknowledges Mr. Combs as a tutor, gives him the highest possible ratings and concludes with ‘excellent class, keep up the great work.’ Furthermore, as stated in our sentencing memorandum, this course has had a substantial impact on fellow inmates.” 

    “Free Game With Diddy” is described as a “six-week educational program designed to equip participants with essential skills in business management, entrepreneurship, and personal development.” And Combs chose to impart this knowledge by, essentially, talking about himself. 

    “The course offers exclusive insights into the journey of Sean ‘Diddy’ Combs, tracing his rise from humble beginnings to becoming a globally recognized icon and influential business mogul,” the description reads. “Through firsthand accounts and real-world experiences drawn from Mr. Combs’ corporate endeavors and entrepreneurial ventures, the program provides a unique perspective on navigating and succeeding in the business world.” 

    Meanwhile, the class outline is a bullet point list of corporate-speak and cliché. “Successful People Do What Unsuccessful People Won’t Do,” states one header, beneath which are listed three follow-up criteria (two of which, go figure, have to do with managing one’s ego): “Never be embarrassed — No ego”; “Out Work the Competition”; “Ego — the conscious self/extreme.” 

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    Other classes had names such as “Just Do It,” in which Combs talked about short-term goals and making plans (“How much?” “How long?”); and “Time Waits for No Man,” where the importance of deadlines were discussed. Another bullet point — “You can make money but you can’t make time” — finds Combs ostensibly expounding on the parable.

    The most dense class topic was, “The Marathon 26.2,” with sub-topics including: “Nothing happens overnight,” “Trust the process,” “What does success look like,” “Heavy is the head,” “The price of success,” and “Success — Responsibility.” Combs even taught a bonus class called “Can’t Stop Won’t Stop,” with the sub-topics aptly listed simply as: “Don’t stop” and “Never give up.”  

    Now, none of this is to suggest that Combs, who was genuinely one of the most successful music producers and businessmen of the past 30 years, doesn’t have a wealth of knowledge on the subject at hand. But when one of the key class assignments is, “Write an essay which incorporates lessons learned from Sean ‘Diddy’ Combs’ journey, personal insights gained throughout the program and methods of achieving long term goals” — that might raise questions we’re not exactly convinced Combs’ courses on the ego will sufficiently address. 

    The course does not appear to mention any of Combs’ non-business history or lessons, or lack thereof, learned. Following CNN’s airing of Combs’ beating of ex-girlfriend Cassie in a Los Angeles hotel room, Combs claimed to have hit “rock bottom” in a video he posted to social media. “Had to go into therapy, go into rehab, had to ask God for his mercy and grace.” However, as a Rolling Stone investigation in January revealed, Combs’ allegedly remained sexually abusive, volatile, and wildly manipulative long after the 2016 hotel assault. 

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    Something about “Free Game With Diddy” — with its towering, charismatic central figure imparting wisdom at once specific and vague — feels like self-help guru crossed with career coach mixed with just a dash of multi-level marketing. Nevertheless, Combs’ charges had nothing but rave reviews for their tutor. 

    “Because of this class I have a purpose, something to look forward to every day,” one inmate wrote, while another stated, “He has showed us that it is the little adjustments to our everyday lives that add up to a big change.” Others highlighted the way Combs stressed the importance realistic goals, creating a successful plan, and putting one’s “pride aside.”

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    “Even behind bars and with limited resources [I] have witness this man do magical things,” one inmate and student wrote. “In a place of segregation [I] have seen Mr. Combs bring unity to all races and ethnics groups no matter the background.”

    The “Free Game With Diddy” course is far from the only item Combs’ lawyers have submitted to Judge Subramanian as he weighs Combs’ sentencing (scheduled for next week, Oct. 3). But considering Combs took it upon himself to spend his time behind bars coming up with and teaching a whole course, it seems plausible that it could have some kind of influence in the decision making process. Then it’s just a matter of parsing the complexities of whether it’s a net good to have Combs — who lest we forget is also an admitted domestic abuser — teaching others to be more like him. 

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