I work for a PEO -- Professional Employer Organization -- and that's essentially what we do. Clients that come onboard with a co-employment contract for their employees. We pay their employees, our clients pay us and we become the employer (in most states though laws are always changing). This means we have 90k employees that help us negotiate some pretty good rates for Benefit plans. It's actually a pretty decent way for a smaller company to offer benefits to their employees that are competitive to larger companies.

We do try to take on companies of a minimum size (10+ employees) but sometimes end up taking on companies with 2 or 3 employees because the owner forecasts explosive growth -- which never happens. All that said, it's a freaking battle with the carriers every year to try to keep the increases at a lower rate. Also, we have "rate buckets" where we place clients according to risk and past medical history of its employees. It still tends to work out better than if they would attempt to get insurance on their own.

Haven't much looked into this (being as it now pertains to me, maybe I should!), but the Freelancers Union was making a bit of news last year[1].

Also, there are HR-outsourcing companies like TriNet that negotiate as a group for smaller/startup companies[2].

1. http://www.freelancersunion.org/

2. http://www.trinet.com/about_us/default.htm

I'm kinda wondering if YCombinator or one of the other incubators could do something like that. For me, a major reason why I'm not doing a startup now is that I'm not sure I could get health insurance. My last startup was done in Massachusetts when I was 25, so it was no problem to get an individual high-deductible policy. I'm not sure I could do the same thing in California, now that I'm pushing 30.

I've spent some time thinking about different startup ideas / permutations to address exactly this solution. In my research, I've found attempts at both methods you describe above, in various forms and various states, with widely varying degrees of success, but most have ended in failure. The "successes" tend to offer some limited choice in plans, but the rates certainly aren't great and the deductibles are still pretty high -- mostly it's a fallback safety net for serious emergencies.

I think a startup that can help tackle this issue would create tremendous value in the payor / consumer market, but the field is extraordinarly complicated and requires a very rare multi-disciplinary background in individual state law (CA's system alone is very different from, say, MA's bc CA is HMO-based and MA has a public option), behavioral economics, gov't regulation, insurance underwriting methods, insurance administrative practices. Oh, and if it's a tech startup, the team would obviously need web dev / product skills as well.

The problem is, developing a basic mastery of all these subjects takes a lot of time -- reading, thinking, and experiencing to understand the pain points deeply. That tends to cut against the stereotypical startup team of two young twenty-somethings hacking away and living on ramen, who have never studied the insurance industry or directly experienced the pain of searching for or relying heavily on health insurance (bc young 20 somethings tend not to have major health problems). I think that's a key reason why startups haven't done much innovation in the insurance payer market.

My latest line of thinking is about whether there are hacks around the problem that can incrementally chip away at and disintermediate insurance payers as the sole gateway to affordable healthcare.

Sounds like an umbrella company (http://en.wikipedia.org/wiki/Umbrella_company). Almost all contracting in the UK is through umbrella companies or a single member LLC's rather than directly between the employee and employer.

Just employ the employees in your 1-N person startup through TriNet and be done with it.

> As a group you have more leverage purchasing pretty much any service

although this is true, the leverage gained through group is different for other services, where a bulk order is much cheaper. Assuming everyone's making rational decisions, the only people that would want insurance would be the high risk ones. Insurance companies would loss money regardless of the rates they charge because the only rational people that would pay it would be the ones that think they would likely benefit from it, since they have additional information (eating habit, risk level, etc ) over the insurance company. By putting a lot of people (high risk and low risk) in a group, the insurance company can balance out the group and make a small gain on top of the expected payout.