I respectfully disagree about what it takes to be approved as a health insurance COMPANY (as opposed to a broker). In fact I am quite happy that regulators require you to show that 1) you know what you are doing 2) you have a massive balance sheet to protect your customers if they need it. The point 2 is super important in the context of VC-backed companies. There is simply no way to build a massive insurance company that way, the return on equity is too low. Unlike airbnb you just don’t go out and raised $2B in debt because you are running out of money and you can’t pay claims. Regulators would step in way before, and they have done that multiple times.

Witness what is happening today: I have not heard from any health insurance company requesting a bailout (unlike most companies). State regulators are a pain in the neck, are conservative but - in your interest - they control how the insurance company uses their capital (you grow too fast = you must add more equity, a bit like working capital), and how you invest your money (they restrict the amount of equity you invest in). All in the interest of the consumers.

Think for a second: if the balance sheet of your health insurance company looked like the balance sheet of Softbank’s vision fund? Would you like to hear “we are sorry, we’ll have to stop your cancer treatment, we are out of money”.

Health insurance companies are regulated at both the State and Federal level. The goal is to make sure that they are fair and will pay the claims when you need that down the road. Like everything in financial services (your savings, your retirement fund, your health for you and your family) this is not the place for fly by night startups. While it is visually appealing to see a better UI, you hear startups "disrupting this dinosaur industry" but very few of them succeeded. And maybe it would be nice, but smart investors (after say series B or C) realize that the returns are not that great and the company requires a massive amount of equity, in fact locked in low risk investments/stable bonds.

Sure, you can target a very young workforce and ignore the sick, the old, the crippled, those overweight or whatever else there is. And you can make money within the startup ecosystem, when everybody works out, eats well, and is super healthy.

But it is simply illegal and my advice for you is to buy insurance from an old, stodgy company. Maybe a mutual company? I don't care if wework is out of money, I can always find space somewhere else. When you have cancer, or when you child is disabled, you don’t want to deal with insurance regulators who have seized the assets of your shiny new health insurance company startup.

There is no room for mistakes when it comes to your health and your savings.

Disclaimer: I have Kaiser, I never use them, but I am sure they will be there when needed.