Running a Small Business: What You Owe, What You Do Not, and What You Are Missing

The three numbers

50 employees. Above it, an employer is generally required to offer coverage. Below it, it is a choice — and choosing not to is lawful and common.

20 employees. Two separate things attach here. Federal COBRA applies at 20 or more. And Medicare coordination flips: at 20 or more, your plan pays primary for an employee aged 65 and over; below 20, Medicare pays primary and your plan pays second.

2 employees. Where New York’s state continuation coverage begins for fully insured policies issued in the state, reaching the groups federal COBRA never covered and carrying the total to 36 months at the standard 102% of premium.

If you do offer a plan

Three things to be able to answer, because your employees will ask and the answers change their rights:

“Is it fully insured or self-funded?” Almost every genuinely small employer is fully insured, which is good news: it means New York’s protections apply — the state external appeal, the parity rules, the insulin rule, the surprise-billing framework. Say so plainly when asked. Why it matters.

“What is the exact date coverage starts for a new hire?” The waiting period may not exceed 90 calendar days, with an orientation period of up to one month permitted before it, and 1,200 cumulative hours where eligibility runs on hours. A rule pointing at “the first of the month after 90 days” is only lawful when that date lands inside the 90.

“What happens when someone leaves?” If the policy is fully insured and issued in New York, state continuation applies from 2 employees and runs to 36 months. Departing employees and their families have election rights, and the notices are part of running the plan.

If you do not offer a plan

Then the most useful thing you can do costs nothing and is not a benefit: tell people what exists.

Most people working in small businesses in this city do not know that:

• The Essential Plan costs $0 a month at or below 200% of the federal poverty level, with no deductible and no enrollment season. What it covers.
• Medicaid, the Essential Plan and Child Health Plus accept applications in any month — nobody has to wait for November.
• Child Health Plus reaches far above what parents expect, and regardless of the child’s immigration status.
• Being paid partly in cash is not a disqualification: New York accepts an attestation of income checked against data. How that works.
• Certified navigators and assistors help for free.

Printing that list and putting it where people are paid is a five-minute act with a larger effect on your staff’s actual access than most benefit packages a business that size could afford.

The Medicare question, for your staff and for you

At 20 or more employees, an employee turning 65 who keeps your plan can delay Part B without penalty, and an 8-month special enrollment period opens when they stop working.

Below 20 employees, the rule is the opposite. Medicare becomes the primary payer and your plan pays second — paying as though the employee had Part B whether or not they enrolled. An employee who “saves” the Part B premium is leaving the primary share of every claim unpaid.

This applies to owners as well as staff. It is the single most expensive misunderstanding in a small business at that age. The full Medicare timing.

What this page does not do

It does not advise on whether to offer coverage, how to price it, or which broker to use. Those are business decisions with tax consequences and they belong to an accountant and a licensed broker.

What is here is the set of rules that decide what your employees are entitled to — because those are the ones that get misstated, and getting them right costs nothing.