Firstly, the major insurance companies don't want to talk to you, so you need to buy through a broker. The broker is suppose to help you pick the plan that's right for you, but realistically they will email you a few PDFs with 5-7 plans that are all extremely similar, full of jargon, and difficult to understand.
Find a better broker? Hah, good luck...
So after you become an expert on insurance jargon, and ask your broker lots of question, you're now ready to start paying. For small plans with fewer than 5 people, get ready to pay anywhere from $700-1k per month for the most basic high deductible plan.
Then after about a year, you'll get an email and phone call from your broker because your plan is no longer available. So you need to pick a new one, that has slightly different features and costs $20-100 additional per-year.
The American health insurance is a parasite.