Your Questions, Answered

Carriers generally want to see at least one full-time W-2 employee on the plan besides the owner — most set the floor at two enrolled members total. There is no upper limit: I work with teams from two people to fifty. If you are not sure your headcount qualifies, a five-minute call settles it.

This is actually my specialty. Solo entrepreneurs and 1099 earners usually cannot buy a traditional group plan, but you have strong alternatives: medically underwritten private plans (often the best value if you are in good health), ACA marketplace plans, and supplemental coverage like accident or fixed indemnity. As a bonus, self-employed individuals can typically deduct up to 100% of their premiums.

Yes — the legal structure is not the obstacle. What matters is having at least one eligible W-2 employee besides yourself on the plan. Multi-member LLCs and S-corps with staff qualify with most carriers. A single-member LLC with no employees does not, but that just moves you into the individual-plan lane, where I can usually find something comparable.

Usually not. Most carriers define an eligible employee as someone working 30+ hours a week. Some carriers bend on this, and choosing the right one matters if your workforce is mostly part-time — that is exactly the kind of carrier-by-carrier detail I sort out for you.

Plan on roughly $300–$700 per employee per month for employee-only coverage, depending on ages, plan type, and deductible. Employers typically pick up 50–75% of that, with employees paying the balance through payroll. Use the calculator below for a ballpark, then let me quote your actual numbers — it is free and same-day in most cases.

Not if you are under 50 full-time-equivalent employees — the ACA employer mandate only applies at 50 and above. But carriers will usually require you to contribute at least half of the employee-only premium to issue a group plan. Most owners I work with offer coverage anyway: it is tax-deductible, and it is the single most requested benefit when you are competing for good people.

Generally yes — employer contributions are treated as a deductible business expense. Businesses under 25 full-time-equivalent employees with modest average wages may also qualify for the Small Business Health Care Tax Credit, worth up to half of premiums paid. I am not a tax professional, so run your specifics past your CPA — but bring them the quote first so they have real numbers.

In most cases, yes — self-employed individuals can typically deduct up to 100% of health insurance premiums for themselves and their family, even without itemizing. It is one of the most overlooked write-offs I see. The estimator below shows what that could mean for you; confirm specifics with your tax professional.

An HMO gives you a lower premium in exchange for staying in-network and routing everything through a primary care doctor. A PPO costs more but lets you see any doctor, anywhere — no referrals, with some out-of-network coverage. Most of my self-employed and traveling clients choose PPO for the freedom; budget-focused teams often land on HMO. There is no wrong answer, only a wrong fit.

ACA marketplace plans accept everyone regardless of health history, and price accordingly. A medically underwritten private plan asks health questions up front — and if you are reasonably healthy, that often unlocks nationwide PPO networks and meaningfully lower premiums than the marketplace. It is not for everyone, which is exactly why you want someone who quotes both lanes and shows you the math.

No — those ride as separate, inexpensive add-on policies. I quote dental and vision alongside every health plan so you can bundle a complete package: preventative and major dental care, eye exams, frames allowances, and contact lens coverage.

Yes — group plans allow employees to enroll a spouse and dependent children (typically to age 26). You as the employer are not required to contribute toward dependents, though many owners do. Employees usually pay their dependent share pre-tax through payroll, which softens the cost.

Individuals: often within days — private plans can start as soon as the 1st of the next month, sometimes sooner. Small groups: budget 2–4 weeks from quote to active coverage, with the carrier processing being the long pole. I provide same-day quotes, so the clock starts immediately.

Their group coverage typically runs through the end of their departure month. After that, COBRA (for companies with 20+ employees) or state continuation rules let them keep the plan by paying the full premium, and losing job-based coverage also opens a special enrollment window for an individual plan. I help departing employees land somewhere — it costs you nothing and they remember it.

Zero. Brokers are paid by the carriers, and your premium is identical whether you buy through me or directly from the insurance company. The difference is that with me you get every major carrier compared side by side, plain-English explanations, and a human who answers the phone after you have enrolled.

Group and ACA plans generally lock you to the annual open enrollment window unless you have a qualifying life event — marriage, a baby, losing other coverage. But here is what most people do not know: many private medically underwritten plans can be applied for year-round. If you missed open enrollment, call me before you assume you are stuck.