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Start free trial →Breaking Bread with Tom Papa · Food & Beverage · October 2026
Tom Papa asked whether employer health insurance can be fixed. Cuban says most employers self-insure and hire big administrators whose contracts are too long for anyone to read, and he is now urging them to have AI read the contracts.
that's before you have to pay out of pocket for your deductible and everything else. Right,
exactly. And then I'm like, here with my little company, I'm like, how can I get insurance for everybody? It's like, you know, two to four grand per person. Yep. From crazy. It's insane. It's crazy. Yeah. Can you fix that?
…employer get it from an employer who self-insures, which means the employer actually pays the cost. They hire somebody to go through all the processes, deal with the claims and all that. Well, those companies that they hire typically these big companies that I mentioned. And like I was going through the City of Dallas contract. I'm really turned into a healthcare nerd. It's really crazy. So like the City of Dallas contract just for pharmacy was 1,333 pages. There's no human on the planet that can go. And so what these big companies do is they do contractual terrorism where they know they can slide things through that you're never going to see. And it doesn't only happen with the city of Dallas who doesn't have enough resources to fight. I've talked to huge companies. I mean, hundreds of thousands of employees and they get it wrong. They get ripped off. And so two parts to answer your question, right? Number one is, can we fix it? Number two involves, the answer is yes. And number two involves AI. So what I'm doing, I'm going to these…
Right.
And so all I say for your prompt, put the contract in as a PDF, you know, and you can do it for your insurance, everything. Yeah. Where are they fucking me? Really? That's it.
That's it.