Transforming Health Insurance with Ali Diab, CEO of Collective Health

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Ali Diab is the co-founder and CEO of Collective Health, a healthcare technology company that makes employer-sponsored health insurance more transparent and simple to navigate. Ali was motivated to start Collective Health after his own medical event. As he was busy recovering from a life saving operation, Ali was served numerous health care bills with no clear understanding of what was owed and for what. He had great health insurance too but even still, the bills were high and not clear or transparent. On a mission to understand the healthcare system, Ali founded Collective Health.

“You don’t need to know bond math to understand your mortgage, so why do I need to understand every acronym and every medical term to understand my health benefit plan? You shouldn’t, it should be plain English. I think that that’s intentional. That’s the way the industry keeps us out and keeps us from poking at the beehive.”

On this episode, Ian and Ali discuss the problems within the healthcare industry, how technology is making a difference, and what Collective Health is doing to move the industry closer to transparency and simplicity. 

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Quotes from Ali:

“My hope in all of this is that we transform the industry and how it treats its customers and behaves at large. Success for me would be if all large health insurance companies treated their customers like any great retail brand treats its customers.”

“Software will eventually enable all industry sectors to behave with the same kind of transparency and openness that the web does. And I think for me that’s one of the most exciting things about what we do. And while, yes, we are a technology company at heart, at the end of the day the greatest technology companies, the greatest companies period are customer-focused.” 

“The way that we consume health care is dramatically different than the way healthcare was consumed when the big health insurance industries came on the scene 50, 60, 70 years ago. Even 20 or 25 years ago, the principal way that you got healthcare was to go to the doctor’s office, or the emergency room or the hospital if you are really sick —  that was it. Now you can track your fertility cycle, you can have a behavioral health visit, a primary care visit, you can have medicines delivered and prescribed all using apps, all without ever having to leave your couch.”




Ben Horowitz 

Google Ventures


Maverick Capital



Episode 336