Billionaire investor Mark Cuban shared how he automates his work with AI in a post on X at 10:43 a.m. KST on August 22, 2026. He said he hands recurring research tasks to Anthropic's Claude CoWork and OpenAI's ChatGPT Scheduled tasks and gets the results by email every hour or every week.
Cuban called this approach a "productivity hack," writing that "it's not always accurate, but it's a lot more accurate than the time I used to waste clicking Google search links one by one."
The prompts Cuban runs every hour
One of the instructions he shared reads like this.
"Check every hour for developments in the Mark Walter investigation and similar regulatory scrutiny of PE (private equity)-linked insurers such as Apollo/Athene, KKR/Global Atlantic, Brookfield, Blackstone, Carlyle/Fortitude Re, Ares, and Sixth Street, and email me if anything significant changes."
Another instruction was for a weekly email roundup of PBM (pharmacy benefit manager) developments. He asked it to collect changes in regulation, litigation, markets, manufacturers, wholesale, employers, transparency, rebates, and formularies, and to write the briefing while "separating confirmed facts from analysis." A third instruction was to find and list every PBM, ASO, and TPA contract signed since January 2024, and to email him each week when new contracts appear. He added that he has already run the same kind of research on the City of Denver. (Source: X, Mark Cuban, 2026-08-22)
Why Cost Plus is so focused on PBMs
In 2022, Cuban co-founded the low-cost prescription drug company Mark Cuban Cost Plus Drug Company with radiologist Alex Oshmyansky. It sells generic drugs at cost plus a 15% margin, and its business goal is to strip out middle layers of the distribution chain such as PBMs. (Source: Cost Plus Drugs, Wikipedia)
His handing PBM, ASO, and TPA contract searches and weekly briefings to AI is directly tied to that business. It means the recurring research he delegates to AI isn't just an experiment but a work tool he actually consults every week.
Why he keeps using it at roughly half accuracy
Cuban admitted this approach isn't always accurate. He keeps using it because he judges it still comes out ahead of the time he spent finding things by clicking links himself. In a reply, he explained that he gives each contract search to only one tool at a time, and that he uses Claude and ChatGPT side by side to watch how the two platforms keep developing.
Claude CoWork launched in beta in July 2026 and expanded to paid plans in August, and ChatGPT's scheduled tasks feature launched on June 17, 2026 (beta on web, iOS, Android, and macOS for Plus, Pro, and Team). Both support the same pattern of "check a certain condition on a schedule and notify only when something changes," so Cuban's approach can be followed with plain-language instructions and no special setup.