Nearly a month ago, Cooper Hefner — the 27-year-old son of Hugh Hefner who serves as chief of global partnerships at Playboy Enterprises — tweeted this cryptic message: "In the end what we regret most are the chances we never took. How important it is for all of us to keep this sentiment in front of mind."

It could've just been a boost of encouragement to his 134,000 followers or, perhaps, a telegraph that change was coming. On Friday, it looks like it was the latter. The Hollywood Reporter has learned that it was announced internally today at Playboy Enterprises that Hefner is exiting his top executive post at the company to strike out on his own by launching a media brand, the Hefner Media Corporation, complete with a digital content platform called HefPost that will feature everything from news to adult content.

Sources close to Cooper confirm that he is not cutting ties with Playboy Enterprises; he'll remain with the company as an adviser to the company's board and Playboy Enterprises CEO Ben Kohn. "Stepping away from my executive position at Playboy Enterprises was a difficult decision to come to, though it is the right decision to make," Hefner says. "The spirit and values of our Rabbit will remain with me always, as I with it, and I look forward to continuing to provide support in a board capacity as an advisor to the company’s CEO."

He has other adventures planned for this year, too. Cooper, who frequently posts about philanthropic causes, politics and meetings with high-profile individuals (like U.S. Senator Kamala Harris), revealed on Twitter March 7 that he has joined the United States Air Force Reserves. "Today I took an oath many others I respect and admire have taken. I am honored to serve my country in the United States Armed Services," he posted.

A Playboy rep confirmed the news on Friday, and delivered a statement from Kohn about Cooper's contributions the company. “I thank Cooper for the passion he has brought Playboy and for his continued support as he transitions from a full-time role to an advisor. We appreciate his service to our country with his imminent Air Force Reserves duty and wish him luck with all of his future endeavors," Kohn says. “I’ve been around Playboy since 2011 — first as an investor and, since 2016, as CEO — and I’ve never been more excited about the opportunities in front of us and both the team and strategy we have to help us attain them."

Clues about Cooper's exit and new ventures have been there for days. On his official Twitter bio, Cooper lists CEO of @HefPost on his credits scroll after his title with Playboy Enterprises. The HefPost Twitter account, which launched in March, has yet to post any tweets but its profile photo features a cup of coffee next to content on everything from news and sports to politics and featured interviews. Insiders note that the site, which will be geared toward millennials, will traffic in those beats but will also include lifestyle coverage and something that would likely make his father proud: adult content.

"Arouse. Inform. Live." is said to be an early slogan of HefPost, and one that teases its unique offering, mixing news with "sophisticated content" that aims to approach sex-related content and topics in an unapologetic way. A 2020 launch is expected.

Also likely: Some confusion or potential tongue ties with Verizon's HuffPost. But that's surely something Cooper considered when starting a new company, something he has experience with. Though he grew up at the Playboy Mansion and learned the business from his late father — he started working for Playboy while still in college and joined the board shortly thereafter — Cooper founded another media company, Hefner Operations & Productions, or HOP, at the beginning of 2016. That company specialized in video, content and events, and six months after it launched, Playboy Enterprises acquired HOP, bringing him back to the family fold in June 2016.

At that time, he took over as chief creative officer, overseeing all of the company's creative divisions including print, digital content and events. He also worked with advertising and licensing teams to look over the brand across all platforms and revenue streams. During an interview with THR in 2017, Cooper discussed his frustrations with various decisions that had been made with the brand, such as when the magazine made the move to the mainstream by excluding nudity from its pages and when a drama series was produced for network television (NBC) rather than a cable network on which more racy content could've been part of the show. "There was a lack of understanding of who we are," Cooper says in that story, which was published Aug. 24. His father passed away less than a month later, on Sept. 17, 2017.

Moving forward, Cooper sought to create a more streamlined vision of the brand as a whole, while also bringing in new readers and consumers in the digital age. "I think about the Playboy philosophy constantly, but I have my own point of view," he said. "It's what will have to carry me through." He carried on with the top creative post until January of this year, when he tweeted that he would take on a new, if not slightly more narrow role with Playboy Enterprises as chief of global partnerships. That job had him overseeing revenue and business development, and he tweeted his excitement about the new role on Jan. 8, posting, "I look forward to the year ahead." But who knew that it would be HefPost and the Air Force and not Playboy that would be on the horizon.