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Mark Cuban at Dreamforce: Thank me for your cheap Cialis, fellas

As Salesforce takes on AI, Cuban pivots to selling prescription drugs online.

Two men sit in armchairs on a stage with a waterfall backdrop. One, in a suit and blue sneakers, raises his hand while another, in casual attire, looks at him.
Marc Benioff, left, and Mark Cuban speak Thursday at the Dreamforce conference. | Source: Amanda Andrade-Rhoades/The Standard

Mark Cuban, fresh off the $4 billion sale last year of his beloved Dallas Mavericks basketball team to the controversial Adelson family, arrived in San Francisco eager to assume the role of entrepreneur again.

At an onstage Dreamforce appearance Thursday alongside Salesforce CEO Marc Benioff, the “Shark Tank” star recounted how he started his sales career at age 12, hawking unused garbage bags to neighbors in the Pittsburgh suburbs to raise money for basketball shoes.

Five decades later — with a lot more cash on his hands — Cuban is selling medication online. Mark Cuban Cost Plus Drug Company is attempting to disrupt the pharmaceutical industry by selling prescription drugs directly to consumers.

By skipping the middleman between a doctor’s notepad and the pharmacy, Cost Plus eliminates the markup on drugs, Cuban told conference attendees. “For men our age, that means we can get our Cialis,” he quipped.

Benioff uncomfortably glided past the joke and pivoted the conversation. Their relationship dates back to the late 1990s and the emerging dot-com industry: Benioff was trying to move customer service and sales software to the cloud, while Cuban created an innovative streaming service that was eventually purchased by Yahoo.

Benioff, meanwhile, proclaimed that Salesforce is now firmly in the AI business. Specifically, this year’s Dreamforce has been about selling the company’s new Agentforce platform, which allows users to design and deploy autonomous AI-powered agents to handle administrative tasks and front-line customer complaints.

“Did you guys have fun at Pink and Imagine Dragons last night?” Benioff asked the audience, referring to the conference’s Dreamfest concert. “But more importantly, did you all build your own agent yet?”

On the ground floor of the city’s biggest convention and trade show, Salesforce laid out rows of laptops where guests were encouraged to design AI-powered assistants.

People fill a tech conference hall, working on laptops at long tables under signs reading "Platform Park" and "Admin Meadow," and other designated areas.
Dozens of Dreamforce attendees sat down to build custom AI agents as part of Salesforce’s push of its new Agentforce platform. | Source: Amanda Andrade-Rhoades/The Standard

Benioff said he tried unsuccessfully to invest $10 million in Cuban’s drug venture after hearing about it while the pair were at dinner two years ago in Dallas.

Cuban demurred, saying he felt it was too early in the company’s lifecycle to take on outside investors. When pressed by Benioff to provide details, Cuban said Cost Plus Drugs is generating more than $100 million in annual revenue.

As Cuban attempted to outline the particulars of drug costs, the host butted in.

“You know, with a little outside help, you could scale,” Benioff said. “I hear building up your sales force is tough.”

“I know what you’re doing, and I’m not going for it,” Cuban responded. “You’re shutting down my sales pitch.”