Travel Insurance

I’ve had more conversations about travel medical insurance than I ever expected to have as an ecommerce guy. Running a dropshipping business from wherever I happen to be that month means health coverage isn’t optional, and it means dealing with the reality that most travel insurance is either too thin to matter or so confusing […]

I’ve spent enough years running my ecommerce business out of airports, coworking spaces, and short-term rentals to know that travel insurance is not something you want to figure out after something has already gone wrong. A single overseas ER visit can run $15,000 to $30,000 before you’ve even booked an evacuation flight, and if your […]

Here is a question I get from clients almost every time they start scaling a high-ticket dropshipping business while living overseas: “what happens if I get sick or hurt in a country where I don’t have health insurance.” It’s not a hypothetical. I have run my business from a dozen countries over the years, and […]

I’ve had more than one client ask me what happens if they blow out a knee while free diving in the Philippines or need to be evacuated off a trekking route in Peru, with no real plan for how they’d pay for it. If you’re running a high-ticket dropshipping business from a laptop and moving […]

I have had a flight rebooked twice in one week, a bag show up four days late in a country where nobody spoke English at the baggage counter, and a business trip to check on a supplier’s warehouse get cut short by a stomach bug that landed me in a clinic I had never heard […]

I get asked about travel insurance more than almost anything else that isn’t directly about dropshipping. Makes sense. Half the people building high-ticket dropshipping stores with me are also trying to run their business from a beach in Bali or a coworking space in Lisbon, and the other half are flying to trade shows or […]

I have had a trip get derailed by a stomach bug in Southeast Asia, a delayed flight that cost me a non-refundable hotel night in Lisbon, and one very expensive lesson about what “emergency medical” actually covers when you are running a business from a laptop in a country where you do not speak the […]

I’ve had a trip to Colombia get cancelled two days out because of a family medical emergency, and I’ve had a laptop bag go missing on a layover in Panama City with my entire business running out of it. Both times, the only thing standing between “annoying story” and “financial disaster” was a travel insurance […]

Last year one of my coaching clients tore his ACL doing muay thai in Chiang Mai while running his six figure dropshipping store off a laptop in a hostel common room. His US health plan covered exactly nothing overseas. The medevac quote to get him stabilized and flown somewhere with a real orthopedic surgeon came […]