Ep 12: How To Find Affordable Health Insurance For Entrepreneurs With Julie Sears
Health Insurance for Entrepreneurs: What You Need to Know (Lessons from Julie Sears)
By Sherry Sutton | Heart of the Hustle Show
Introduction: Health Insurance—The Hidden Fear of Entrepreneurship
One of the most common fears I hear from entrepreneurs (and let’s be honest, one I had myself) is this: "But what about health insurance?"
Walking away from corporate life comes with a lot of freedom—and a lot of terrifying paperwork. Health insurance tops that list. That’s why I sat down with Julie Sears from Integrity Health Insurance Advisors. Julie has built a thriving business helping small business owners navigate the health insurance maze without losing their sanity (or their shirts).
If you're about to make the leap—or if you've already jumped and are wondering what you've gotten yourself into—this one's for you.
Yes, You Can Get Health Insurance as a Small Business Owner
First, the good news: You are not doomed to a life of paying cash at urgent care and praying you don't get hit by a bus.
The not-so-good news? It’s different. And sometimes, it’s more expensive.
One of the big mindset shifts Julie shared is understanding that corporate insurance is heavily subsidized. Your employer was covering a big chunk of that premium—you just didn’t see the true cost. Now that you’re the boss? You see every penny.
Reality Check: Health insurance premiums are a business expense. They’re tax-deductible. That doesn’t make it free, but it does soften the blow.
Bottom line: You have options. They just require a little more strategy.
Marketplace vs. Private Insurance: Know the Rules Before You Play
When you're shopping for insurance on your own, you have two primary paths: the Marketplace (Healthcare.gov) and private insurance.
Each comes with its own set of rules—and traps.
Marketplace Coverage: Good News and Fine Print
Everyone qualifies. Pre-existing conditions? No problem.
Income-based subsidies might lower your costs.
Open enrollment windows are strict (and missing them is a real pain).
The Marketplace is a safety net. But it's not a silver bullet. Expect high deductibles and limited doctor networks.
How to Shop the Marketplace Like a Pro
Focus on the max out-of-pocket, not just the monthly premium.
Double-check your doctors and prescriptions. Networks are tricky.
Know your "worst-case scenario." If you get sick or injured, what’s the most you’d owe?
Private Insurance: Looks Good—Until It Doesn’t
Private plans might offer lower monthly premiums, but they often:
Exclude maternity and mental health coverage.
Require medical underwriting. Translation: They can decline you based on your health history.
If you’re perfectly healthy, private insurance could work. But Julie warns: one wrong diagnosis, and it’s game over.
Word to the Wise: Sometimes that cheaper plan leaves out exactly what you’ll need most.
Qualifying Life Events: When You Can Change Plans (and When You’re Stuck)
Outside of open enrollment, you need a "qualifying life event" to make changes. These include:
Having a baby (baby gets the special event, not you)
Getting married
Moving counties
Losing job-based coverage
Thinking you can sign up for insurance when you need gallbladder surgery? Nope. You’ll be negotiating cash rates instead.
Pro tip: If you lose coverage, you only have 60 days to get a new plan. After that? Options get a lot uglier.
Why Private Insurance Denies People (And What to Watch For)
Julie’s seen it all. Here's what could get you denied for private insurance:
Chronic illnesses like RA or diabetes
Mental health prescriptions (even common ones)
Use of weight-loss drugs like Ozempic (even if your doctor "coded" you for diabetes to save you money)
A DUI from a decade ago
Regular prescriptions for opioids or heavy painkillers
Insurance companies aren’t judging your life. They're judging your risk.
And let me tell you, they’re brutal about it.
Lesson: Don't assume your "little" health issues are invisible.
Concierge Medicine, Cash Pay Clinics, and the Myth of "I'll Just Pay Out of Pocket"
Concierge clinics and cash-pay primary care are awesome—for everyday stuff.
$100 monthly memberships for unlimited visits? Fantastic.
Same-day appointments? Love it.
But if you get hit by a car or need major surgery? That $100 membership isn't going to save you from a $100,000 hospital bill.
You still need catastrophic coverage.
Julie recommends layering coverage:
Concierge or direct primary care for everyday health
A high-deductible major medical plan for emergencies
An HSA account to build a cushion
It’s not sexy. It’s just smart.
Your Corporate Insurance Wasn't As Great As You Remember
If you’re mourning your old cushy corporate plan, here's a reality check:
Most employers subsidize your personal insurance more than family plans.
Every year, corporate plans cover less and cost more.
COBRA letters are your reminder of what you were really paying.
Corporate insurance isn’t disappearing—but it’s not what it used to be.
Marketplace Premiums Are Rising. Plan Accordingly.
Brace yourself: Marketplace premiums are climbing 15–20% each year.
And why? Because people are maxing out their plans. Julie joked (kind of) that Americans treat health insurance like a game: "Let's get every dime out of it this year!"
Spoiler: That’s not how insurance is supposed to work.
Healthcare isn't a punch card. It's protection for when life gets messy.
Why So Many Entrepreneurs Get Stuck (And How You Can Avoid It)
Mistakes Julie sees all the time:
Assuming you're too healthy to need insurance. (Until you’re not.)
Waiting until something bad happens. (By then, it’s too late.)
Assuming "I'll figure it out later." (Later gets expensive fast.)
If you're healthy today, get covered today. Lock it in while you can.
Because once you have a diagnosis or a major event? Your options shrink.
Building a Business Without Cold Calling (Thank God)
Julie’s business didn’t grow because she cold-called sad online leads. It grew because she showed up.
She networked. She built relationships. She stayed authentic (purple hair, sarcasm, and all).
Today? Her clients come from referrals—because people trust her to shoot straight.
Networking That Works (Without Feeling Slimy)
Lead with humanity. Not your business card.
Show up consistently. One mixer isn’t enough.
Add value without expecting something in return.
Follow up like a professional. (No weird "just circling back" emails.)
Networking isn’t about collecting business cards. It's about building your village. When you do that? Business flows naturally.
Final Thoughts: Protect Your Health and Your Business
Here’s the deal: Entrepreneurship is a leap of faith. You’re betting on yourself. But betting on yourself doesn’t mean betting against your health.
Health insurance isn’t a luxury. It's part of your business plan.
You owe it to yourself—and your family—to be protected.
And if you’re serious about building a sustainable, profitable business?
That’s exactly why I created the Heart of the Hustle Studio. It's where entrepreneurs come to:
Create consistent marketing content
Build real relationships (without the sleaze)
Get done-for-you marketing help that actually sounds like you
If you're tired of doing it all alone—or doing it badly—come join us.
Because your business deserves more than survival mode. It deserves a strategy that supports your dreams, your health, and your hustle.
Let's grow—smart and strong. Together.
