Is it standard to give healthcare benefits to the first employee at a 2-founder startup?

Rarely but it would help you get better candidates.

My boss found that it was cheaper to have his employees buy on the open market and then reimburse them. He has 4 employees and is in California. I am still on Cobra from my last job, so I am fine with this.

I don’t think there’s a standard that I’ve seen.

To me, it would depend on who you’re looking to hire. I’ve worked for equity in the past and was never worried about health care. Now that I have a child it’s a bigger concern, so that may shrink your hiring pool and those that will apply.

In your shoes, I’d let the salary/equity mix you are able to offer be my guide. If you’re asking someone to work for considerably below their market rate, then someone who’s considering that probably isn’t as stuck on healthcare. If you’re offering a decent salary and really want the best candidates then I’d do the research and figure out what your costs would be, then discuss it with the person you eventually want to hire as part of salary negotiations. In ads you could say you’re willing to work out a compensation package that works with the right person.

Probably not.

When I worked at a small company; it was the owners plus three employees; they did “offer” a plan that basically covered catastrophic. It simply saved me the hassle of having to find insurance on my own. They just really were directing me to an insurance agent who they had a relationship with. It was all up front, I don’t want it to sound like they were working some sort of deal at the employees expense.