Health insurancethat fitshow you work.
Fit First Health Insurance is Sam Clayland's agency in Ocean City, Maryland. Sam is a licensed health insurance agent who helps self-employed people find coverage: 1099 contractors, skilled tradespeople, restaurant owners and staff, real estate professionals, and small business owners. It starts with a free 25-minute call, and there is no form to fill out first.
- Based in Ocean City, MD
- Phone or video
- Marketplace plans included in the comparison Sam to confirm: you can place these
Start with how you earn a living.
If you work as a 1099 contractor
Your income moves, and nobody is splitting the premium with you. Sam starts with what you actually netted, then compares a Marketplace plan with anything else you may qualify for.
Health insurance for 1099 contractorsIf you work as a tradesperson
Electricians, plumbers, roofers, and HVAC techs have questions a desk worker never asks, starting with what happens when you get hurt on the job.
Health insurance for people who work with their handsIf you work as a restaurant
Owners and staff have different doors. An owner with employees may use SHOP. A server with no job-based offer may qualify for Marketplace savings, tips included in the income estimate.
Health insurance for restaurant owners and staffIf you work as a real estate pro
Commissions land when deals close, and you may have no employer plan to join. Sam starts with a realistic income estimate for the year, then walks through what fits it.
Health insurance for real estate professionalsIf you work as a business owner
With no employees you are self-employed for coverage purposes. With even one, other doors open. Sam looks at your head count and entity type before anything else.
Health insurance for small business ownersWhy self-employed people have a harder time with health insurance
"Did they ask us what we do for a living? ... Nope."Sam Clayland, on big insurance company websites. Fit First blog, August 30, 2021.
Nobody hands a self-employed person a benefits packet. You pay the whole premium, your income moves, and the rules changed again this year. That is the job Sam took on.
- 58%How much Marketplace premium payments rose on average in 2026 after tax credits, from $113 to $178 a month across all consumers, according to KFF's May 2026 analysis. The enhanced tax credits expired at the end of 2025.
- Jan 15The last day of Open Enrollment for 2027 Marketplace coverage on HealthCare.gov and in Maryland. Coverage that starts January 1 has an earlier deadline: December 15 on HealthCare.gov, December 31 in Maryland.
- 3 monthsThe limit on a short-term plan in Maryland, with no renewal, according to the Maryland Insurance Administration. Cheaper can have a catch. You should hear about it before you buy.
Measured first. Cut second.
A good tailor does not start with the fabric. Sam evaluates your health, income, occupation, and family before he talks about a plan.
- Measure 1
How you earn
1099, W-2, seasonal, or commission. Net income drives Marketplace savings, and your occupation shapes which other plans are worth a look.
- Measure 2
Who needs covering
Just you, a spouse, kids, or a crew. A spouse's employer plan or a single employee can change which options you have.
- Measure 3
Your doctors and prescriptions
Before you fall for a monthly price, check that the people and medicines you depend on are actually covered.
- Measure 4
A bad year
Not just what you pay monthly, but what a hospital stay would cost you under each option. That is the number that matters when you are self-employed.
What happens in 25 minutes.
Sam to confirm: this outline of the call
Five kinds of coverage, in plain English.
These get lumped together online, and they are not the same thing. Here is the plain version.
| Type | What it is | Pre-existing conditions | Wrong choice if |
|---|---|---|---|
| Marketplace (ACA) plan | Comprehensive coverage with 10 essential health benefits, sold through HealthCare.gov or your state marketplace. Savings depend on income. Source | Covered. A plan cannot reject you or charge you more because of a condition you already had. Source | You earn too much for savings, the premium is out of reach, or your doctors are not in the network. |
| Underwritten private plan | A private plan sold outside the Marketplace. The insurer asks health questions and decides whether to offer coverage and on what terms. Source (pre-ACA definition) | Can be declined, excluded, or limited, depending on your answers and the plan. | You have an ongoing condition, are planning a pregnancy, or could not afford a large gap in coverage. |
| Short-term plan | Temporary coverage for a gap. In Maryland it ends after three months and cannot be renewed. Other states differ. Source | May not pay for anything related to a pre-existing condition. It can also ask health questions. | You need more than a short bridge, or you need prescriptions or maternity care. Maryland does not require either. |
| Fixed indemnity plan | Pays set dollar amounts per day or per service, rather than a share of the bill. It is not comprehensive coverage. Source | Varies by policy. Read the exclusions. | It would be your only coverage and a large hospital bill would hurt. |
| Health care sharing ministry | Members share medical costs. It is not insurance and cannot guarantee that a claim gets paid. Source | Often limited by the program's rules. | You want a guarantee of payment or the protections of state insurance law. |
What clients say about Sam Clayland
"When we reached out to Sam, we immediately felt a sense of relief that he would help us to find the ideal insurance plan that was designed specifically for us with our budget in mind."John C., Ellicott City, MD
"Sam and his staff were highly prompt and professional. We had a slight issue with our initial application and his team helped us through it quickly."Holly D., Bishopville, MD
"I was reluctant but I decided to give it a try just to see how much it would cost me monthly. Sam met with me and discussed a couple of different insurance options."Shane C., Lexington, KY
"We finally found a health insurance plan that is affordable and user friendly. Our agent Sam recommended a plan that included doctor visits which we ended up using almost immediately."Kristen J., Lynchburg, VA
Client words from Sam's site. Individual results vary. Sam to confirm: these clients agreed to be quoted
"Not everyone is an orange. Some of us are bananas."
Meet Sam Clayland
Sam runs Fit First Health Insurance from Ocean City, Maryland. The clients on his site come from Maryland, Kentucky, and Virginia, and one remembers his first call from Sam in 2019. Sam to confirm: license number and states
His promise on the old site is still the right one: "We will never recommend a health insurance plan unless it fits your lifestyle and your budget."
More about SamStraight answers.
What is Fit First Health Insurance?
Fit First Health Insurance is a health insurance agency in Ocean City, Maryland, run by licensed agent Sam Clayland. It helps self-employed people, 1099 contractors, tradespeople, restaurant owners and staff, real estate professionals, and small business owners find coverage. "Fit first" means the plan has to fit your work, family, and budget before anything else.
Do I have to be physically fit to work with Sam?
No. Fit First started with a focus on healthy, active people, and Sam now works with people in many situations. Some plans ask health questions, and your health can affect what you qualify for and what it costs. Others, such as Marketplace plans, cannot turn you down for a health condition. Sam goes through which is which.
How much does the 25-minute call cost?
Nothing. There is no charge to talk with Sam, and you do not need to fill out a form first. Health insurance agents are generally paid by the insurance company when a plan is placed.
Are all of these plans ACA plans?
No. Marketplace plans follow ACA rules. Other plans Sam may discuss can sit outside the ACA, may ask health questions, and may decline or limit coverage for pre-existing conditions. You should know which kind you are looking at before you sign anything, and Sam will tell you.
Can a health plan turn me down because of a health condition?
A Marketplace plan cannot. HealthCare.gov says no insurance plan can reject you, charge you more, or refuse to pay for essential health benefits for any condition you had before your coverage started. Plans outside the ACA rules can be different. The Maryland Insurance Administration warns that short-term plans may ask health questions and may deny or limit coverage based on the answers.
Twenty-five minutes. No forms first.
Pick a time. If you would rather talk now, call Sam at 410-422-4977.