Hey There—Welcome to the Only Travel Insurance Site That Gets Gig Life

How This Little Corner of the Internet Came to Be

It all started when I missed a flight to Lisbon because my scooter-share app glitched—and my standard travel insurance wouldn’t cover a single euro. I was stuck, stressed, and totally blindsided. That moment cracked something open: most travel insurance is built for employees with W-2s, not freelancers juggling gigs across time zones. My own journey—from backpacking through Southeast Asia to working remotely as a graphic designer while hopping between Airbnbs—showed me how deeply underserved we gig workers are. So I dug in. First, I researched general travel coverage. Then, I zeroed in on policies that actually acknowledged our reality: no fixed office, no HR department, just hustle and heart. And that’s how Jesse Hiller was born—not as another generic advice hub, but as your go-to friend who’s been there, booked that, and got the (sometimes messy) receipts.

Here’s Why I Show Up Every Day

I’m here to help you navigate gig worker insurance with clarity, confidence, and zero jargon. No fluff, no fear-mongering—just real guidance from someone who lives the gig life too. Whether you’re driving for rideshare apps between border crossings or freelance-writing from a beachside café in Bali, you deserve protection that fits your work, not fights it. That’s the promise of Jesse Hiller.

What Matters Here

Real Talk: Like when I shared exactly how much I overpaid for a policy that didn’t cover my camera gear—and what I switched to instead.

You First: Your DM about “what if I’m insured in two countries at once?” sparked our whole guide on multi-jurisdictional gig coverage.

Quality Over Hype: I’ve tested 14+ travel insurance plans personally—only the ones that actually answered *my* gig-specific questions made the cut.

Curiosity Rules: I spent three weeks digging into fine print so you don’t have to—because “accidental injury” shouldn’t be a guessing game when you’re delivering food on a rented e-bike.

Let’s Chat?

Got a question about whether your side hustle is covered abroad? An idea for a guide? Or just want to swap travel war stories? I read every message, and I’d genuinely love to hear from you.