Meet Ryan Michalek
I'm Ryan Michalek, founder of Michalek Health Solutions — an independent health and life insurance brokerage based in Tampa, Florida and licensed across 31 states. I’m a licensed health insurance agent, not a lead form — the person who answers is the person who does the work. A Chicago native who came up bagging groceries and working jobs that never included a benefits packet, I built this practice helping the self-employed, families, and small business owners find under-65 coverage that actually fits — with no fee, and a phone I still answer year-round. Today I serve hundreds of clients, most of whom found me through a referral from someone I'd already helped.
Where I come from
I didn't come up in insurance boardrooms. I came up bagging groceries and working the kind of jobs that never included a benefits packet — the same spot a lot of my clients are in today. That's not a talking point; it's why I do this the way I do.
I'm not from here. I grew up in Darien, Illinois, earned dual degrees in business management and economics over in Naperville, and spent my first couple of years out of school in Chicago, working in employee health benefits at the Central States Health and Welfare Fund. Good job on paper. But I still remember the moment it hit me that I could see the whole road ahead — same desk, same grind, all the way to 65 — and it just wasn't the life I wanted.
So I did the thing that scares most people off: I left. I moved across the country to Tampa, got licensed in 2024, and started over on a blank canvas — building my practice one honest conversation at a time, with no cushion and nobody to fall back on but myself. It grew mostly by word of mouth: clients sending me their friends, their family, the person at the next booth over.
Funny how it comes full circle. I started my career inside the health-benefits world, walked away from the till-65 grind, and now I spend my days helping the people who took the same kind of leap — the self-employed, the ones betting on themselves, the early retirees bridging their own way to 65. I didn't learn their situation from a manual. I lived my own version of it.
Two years in, that’s still the part I like best — somebody trusting me enough to hand me their sister’s phone number. You don’t get that by being the cheapest.
Why being independent matters
Because I'm independent, I compare options across many carriers instead of pushing one company's product, and there's never a fee — the carriers pay me, not you. That independence is what keeps my advice honest. My job is to find coverage that fits how you earn and how you use care, not to move a particular plan. When two people walk in with the same budget and different lives, they usually shouldn't walk out with the same policy, and being independent is what lets me say so plainly.
I pick up the phone
What sets me apart is simple: I pick up the phone long after enrollment, year-round, when a lot of agents go quiet. Coverage questions don't keep business hours, and neither does life — a new baby, a move, a job change, a letter from a carrier you can't make sense of. When something changes, you get to call the person who set it up, not a call center and a hold queue. My belief is that people buying their own coverage deserve an advocate who actually answers.
You'll always start with me
However you find me, the first conversation is with me. I listen to what's actually going on, and most of the time what you need is exactly what I do — private coverage for people who buy their own.
Sometimes your situation calls for something else. When it does, you don't get sent anywhere. You get somebody added.
I work alongside a handful of people, each an expert in a specific corner of this business, and I trust every one of them with my clients and with my own family. Between us, there isn't a situation we can't put you in the right place for.
And it runs both ways. When one of them has somebody who needs private coverage — my corner — I'm the call they make. The trust here doesn't point one direction.
Reid has a real gift for helping the people the market makes it hard on — a rough health history, a past decline. He knows the private market deeply, he genuinely cares about getting folks covered, and he doesn't give up on a tough case; I've watched him find a path for people who'd already been told no. If getting approved is the part that worries you, he's exactly who you want in your corner.
Bjorn is a genuine pro at group and small-business coverage — it's all he does, and it shows. He reads what a company actually needs faster than anyone I know, and he's taken real care of clients of mine who outgrew an individual plan. Sharp, straight with people, and someone I trust without a second thought.
Will is who I want walking anyone onto Medicare. He's guided more of my clients through it than I can count — patiently, every time — and every one of them came away knowing exactly what they chose. That kind of clarity is rare with Medicare, and it's simply how Will works.
Vincent knows the marketplace inside and out and genuinely loves helping people there — it's his world, every single day. When someone's situation points to ACA coverage, he's the one I want on it, because he'll treat them right and make the whole thing feel simple. For a lot of families the marketplace is the right fit, and few people make it as easy as he does.
Tracy is who I trust with life insurance — she knows all four kinds inside and out, and she'll put you in what genuinely fits your family rather than what pays her most. She handles the ACA marketplace too, so there's a good deal she can take care of for you. What earns my trust, though, is simpler than any credential: she's reliable, she's the real deal, and she truly cares about every person she sits down with.
Here's exactly how it works.
First, you and I talk. One call, no forms, no queue. I ask about your situation and figure out where you actually belong.
Most of the time, that's with me, and we get to work.
If it's one of them, I'll tell you why — plainly, so it makes sense to you — and I connect the two of you myself. You never chase anybody down.
They'll already know your situation before that call happens, because I've told them. You don't start over and you don't explain yourself twice.
And you keep me either way. My number still works. Questions, second opinions, anything at all — you can always come back to me.
A few real questions people ask
Because handling something that's really someone else's specialty, just to keep it in my hands, would be about my ego — not your coverage. I do private coverage for people who buy their own, and I'm good at it. When your situation lives in a different corner of this business, putting you with the person who works there every day is me handling it. Doing right by you beats doing it all myself.
Because I've watched them work — for years, and with my own clients. I don't hand you off to a name on a list. Every one of them earned my trust the slow way, and I wouldn't put my own family with them if they hadn't.
Then we talk it through plainly. But I won't keep you in something that doesn't fit just to keep you as mine — that isn't taking care of you, and it isn't how I work. If one of them is genuinely the better hands for your situation, I'll tell you straight.
Nobody pays anybody here. We send people to each other because it's the right call, and because none of us wants a client sitting in a plan that doesn't fit. That's the whole arrangement.
Reid Demyan, Bjorn Dyberg, Will Rollinson, Vincent Saunders II, and Tracy Roccanello are independent licensed agents at their own agencies, not employees of Michalek Health Solutions.
Who I help
I work with people who buy their own coverage: the self-employed and 1099 contractors, families and individuals, and small business owners — generally under 65. If you're bridging the gap to Medicare in an early retirement, that's squarely in what I do too. Wherever you land, the goal is the same — honest guidance, plain English, and a plan that fits how you actually live. I'm licensed in 31 states, so the same help travels with you if you move or expand where you do business.
Credentials, and how to verify them
I'd rather you check than take my word for it. Here's who I am on paper, with links to verify at the bottom of this page:
- Licensed Health & Life Insurance Agent · NPN 21043091.
- Licensed in 31 states, so coverage help travels with you.
- Member of the National Association of Benefits and Insurance Professionals (NABIP).
- Principal of a BBB-accredited agency (A rating) and a Tampa Bay Chamber of Commerce member.
- Dual bachelor's degrees in Business Administration & Management and in Economics from North Central College (Naperville, IL) — the business and risk-analysis foundation behind the honest, numbers-based advice I give clients.
Guides I've written
I write the guides on this site myself, in the same plain English I'd use on a call — no jargon, no carrier hype, no pressure. Here are a few worth starting with:
- Self-employed & 1099 health insurance → — the core how-to for buying your own coverage.
- Private vs. ACA for the self-employed → — an honest comparison of who each fits.
- Health insurance for LLC & S-corp owners → — how business structure changes the tax treatment.
- COBRA alternatives → — your options when employer coverage ends.
- Early retiree health insurance → — bridging the gap to Medicare.
- Coverage cost estimator → — map your paths before we ever talk.
- Can I enroll right now? → — a quick check if a recent life change opened a window.
When I'm off the clock
Off the clock, I'm usually reading, in the gym or on a yoga mat, or out at a show — a concert (my taste runs to unapologetic dad rock) or a stand-up set (lifelong Seinfeld guy). If you're picking up a theme here, you're not wrong: dad rock, dad humor, full dad energy, and I've stopped fighting it. So when we talk, you're getting a real person on the other end — or honestly, something pretty close to your dad.
Let's talk
If any of this sounds like the kind of help you've been looking for, book a quick conversation or just call me. No pressure, no cost to talk — and you'll be talking to me, not a script.
What it's like to work with me
Is Ryan a pushy insurance salesman?
No, and that's rather the opposite of how I work. I don't work on pressure and I won't chase a sale that isn't right for you. I'll tell you honestly what fits and what doesn't, and if it's not the right time to buy, I'll say that too. You'll never get a hard sell from me, on the call or after.
What's it actually like to work with you?
It's a real conversation, not a pitch. You tell me what's going on, I listen, and I walk you through your options in plain English at your pace. No script, no rushing, no obligation. Most people leave knowing exactly what to do next, whether or not they enroll with me.
Will you tell me if I shouldn't buy from you?
Yes. If a plan doesn't fit, or the marketplace or another path is genuinely better for you, I'll point you there, even when it earns me nothing. Honest advice is the whole basis of how I work.
How did Ryan get into health insurance?
I started out in employee health benefits at the Central States Health and Welfare Fund in Chicago, then left the corporate grind for a fresh start in Tampa. I got licensed in 2024 and built Michalek Health Solutions from the ground up — helping the self-employed and others who buy their own coverage, the same leap I took myself.
Does Ryan charge a fee to help me?
No. As an independent broker, I'm paid by the insurance carriers, not by you — so my help costs you nothing. And because I'm independent, I'm not tied to any one company's products; I compare across many to find what actually fits you.
In their words
“In a sea of private insurance brokers vying for my time through myriad annoying methods, Ryan stood out in his honest, simple, and straightforward approach.”
— Matthew M.
“Very knowledgeable and very honest about options! I knew I wasn’t just talking to an insurance salesman … I was talking to someone who wanted to help folks out!”
— Katherine O.
“I really appreciated his wisdom and willingness to listen and spend time with me to make sure I was in the best coverage plan for my health insurance needs.”
— Joanna K.
“Although I did not ultimately get a policy through Ryan, he was very helpful in finding me the best solution. He took the time to provide several options and was very thorough. He is available anytime to answer questions or concerns. I would recommend Ryan for your health care plan options.”
— MP
Let's find coverage that fits your life.
Fifteen minutes to talk through your work, your family, and how you use care — then a clear, honest set of options.