Stop Overpaying for Flights: How to Get Refunds & Upgrades After You Book | with Sam Hollander of Autopilot #236
About this episode
Spencer Reese interviews Sam Hollander about saving money on flights after booking, including refunds and upgrades.
The person next to you probably paid less for their seat than you did — and you'll never know it. Spencer talks with Sam Hollander, founder of Autopilot ( withautopilot.com ), about the overlooked art of saving money after you've already booked. Since U.S. airlines killed change fees, you can claw back cash every time your fare drops and snag last-minute premium-cabin upgrades for a fraction of the sticker price. Sam breaks down how to automate all of it, which tools every points-and-miles traveler should be using, and why free elite upgrades are quietly disappearing in 2026. Questions Asked What is Autopilot, and how does it save travelers money after booking? Are you canceling and rebooking the ticket, or filing a claim for the fare difference? What happens if the price drops multiple times? Does this work on codeshare flights? What do you need to share with Autopilot to get started? Does it work if you book with points or miles? How does the pricing and success-fee model work? How do the upgrade-offer alerts work, and do you recommend a bid amount? Do you need a credit card on file for the free tier? What travel tools are you using besides Autopilot? What's most exciting to…
More episodes of The Military Money Manual Podcast
- Military Credit Cards in 2026: How to Get Premium Cards With No Annual Fees #238
- "What If You Had to Start Over?" Brand New Military Officer and Enlisted Advice #237
- How to Use Your VA Disability, GI Bill & Healthcare Benefits While Living Overseas | Conversation with Fiscal Foxhole #235
- How to Travel for Free (Without Going Into Debt) | Fiscal Clinician #234
- Deployment Money & Survival Guide for Military Spouses | Wives of the Armed Forces #233
- PCS Season Payoff: How Military Families Turn Moving Expenses Into Free Vacations #232
Explore listener stats, chart rankings, contacts and more on the The Military Money Manual Podcast podcast page.