Effortless
Skip the research rabbit hole. We compare the plans, handle the paperwork, and walk you through enrollment from start to finish.
Built for entrepreneurs earning $125K+
Health Insurance that Finally Fits the self-employed life
When you work for yourself, health insurance lands on your plate along with everything else. We take it off. Bay Insurance Group helps freelancers, founders, and small business owners find coverage that fits their income and their life, and we handle the hard parts for you.
Independent & unbiased
Licensed specialists
No cost to you
Client reviews
Rated 5.0 from 50 reviews on Google
Real, verified reviews from Bay Insurance Group clients.
★★★★★
"As a small business owner, I was struggling to find affordable health insurance with good coverage. Trey was extremely knowledgeable, patient, and helpful throughout the entire process. He answered all of my questions and helped me find a plan that met my family's needs. I highly recommend working with him!"
★★★★★
"Trey was very professional and worked at guiding me to the right solution that fits me, and was also very good at explaining things. I greatly appreciated his help on this important decision."
★★★★★
"Trey was EXTREMELY knowledgeable, very efficient, and easy to work with! Highly recommend him for any insurance needs."
Why Bay Insurance Group
An expert who actually gets your situation
You didn't start a business to become an insurance expert. That part is our job. We look at how you earn, what you need, and what you can write off, then bring you a plan that makes sense.
Fast
Most clients get a personalized plan recommendation within 10 minutes.
Expert
We work with self-employed clients every day, so we know the ACA rules and the tax angles that keep more money in your pocket.
Peace of mind
We don't disappear once you sign up. We're here at renewal, at tax time, and whenever your life changes.
15 minTo a clear plan-fit recommendation
30+Carriers compared on your behalf
$0Cost for our guidance & service
100%Focused on the self-employed
What we do
What we can help you with
Whether it's just you or you have a team to cover, here are the ways we help you get protected.
Individual & Family Health Plans
ACA and private plans matched to your budget, your doctors, and the prescriptions you already take.
- Keep your preferred doctors
- Subsidy & tax-credit review
Self-Employed Tax-Smart Strategies
Set up your coverage the smart way, so your premiums work with your taxes instead of against them.
- Premium deduction guidance
- HSA-eligible plan options
Supplemental & Small-Group Coverage
Dental, vision, life, and team plans to round out protection for you and any employees.
- Dental, vision & life add-ons
- Coverage for a growing team
Meet the team
The people behind Bay Insurance Group
Two entrepreneurs who've been in your shoes, now working for you.
1,000+ families helped
Trey Sayles
Insurance Advisor · Clearwater, FL
Over the last eight years, I've helped more than a thousand self-employed families, contractors, and business owners find insurance that actually fits their lives. I specialize in high-income earners, I'm licensed in over 40 states, and I know this business from every angle: health and life insurance, health savings accounts, and tax-free retirement strategies.
Before insurance, I took a different route. I grew up in Southern Indiana, and I spent years traveling the world working on superyachts. That work taught me how to take care of people at the highest level and pay attention to the details that matter, and it's the same standard I bring to every client today.
When we work together, you're not getting a call center or a script. You're getting me: someone who knows this industry inside and out and genuinely cares about getting it right for you and your family.
High-income specialist
Health & life
HSAs
Tax-free retirement
Licensed in 40+ states
Licensed insurance producer · National Producer Number (NPN) 17409756
Brady Halbasch
Partner, Bay Insurance Group
I've been an entrepreneur my whole life. It started with a paper route at age seven, where I learned sales, fulfillment, and customer service firsthand. In my early twenties, I founded a company in the automotive aftermarket industry and grew it to more than $50 million in sales over its 15-year run.
Building an eight-figure business from scratch teaches you things nothing else can. You find out what actually works, your mistakes come with real financial consequences, and you learn to stay resilient under pressure.
After stepping away from that company, I partnered with Bay Insurance Group. Our mission is simple: give self-employed individuals and families the kind of service they deserve.
Licensed insurance producer · National Producer Number (NPN) 22252493
Questions & answers
Common questions from the self-employed
Straight answers about how we help and what it costs.
Do you charge a fee to help me find insurance?
No. Our guidance is completely free. We're compensated by the insurance carriers, so there's no cost to you for our help comparing plans and enrolling.
I'm self-employed — how does health insurance work for me?
When you're self-employed, you buy your own coverage instead of getting it through an employer. We compare ACA marketplace and private plans, check whether you qualify for subsidies or tax credits, and match you with coverage that fits your income and your doctors.
What states are you licensed in?
We're licensed in over 40 states, so we can help self-employed clients across most of the country, not just Florida.
What types of insurance do you offer besides health?
Along with health insurance, we help with life insurance, health savings accounts (HSAs), tax-free retirement strategies, dental, vision, and small-group coverage.
How fast can I get covered?
Most clients get a personalized plan recommendation within 10 minutes.
Do you work with high-income earners?
Yes. We specialize in self-employed professionals and business owners, including high-income earners who don't fit a standard employer plan.
Get in touch
Have a question? Talk to Trey directly.
I'm Trey Sayles, and I'll be the one you actually talk to. Call, email, or send a note below, and I'll get back to you within one business day.
Phone(727) 263-3636
Schedule onlinePick a time on our calendar
HoursMonday–Sunday, 8:00 AM – 8:00 PM