Stop Overpaying for Flights: How to Get Refunds & Upgrades After You Book | with Sam Hollander of Autopilot #236
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 you in the travel space right now?
- In 2026, with airlines selling most premium seats, what actually works to get up front?
- Where can people find you and follow what you're building?
Main Topics Covered
- How the post-COVID end of change fees created the opening for Autopilot
- Lowest Fare Guarantee: automatic refunds when your booked fare drops $20+
- Automation as a money philosophy — low-cost, automated, diversified, simple
- Importing trips via Gmail sync, email forwarding, or confirmation code
- Free tier vs. 25% success fee vs. $9.99/mo Pro plan
- Upgrade-offer bidding and how to judge whether an upgrade is worth it
- Why 2026 airlines are pulling back on free elite upgrades
- Day-of-departure price drops and pricing anomalies (business cheaper than premium economy)
- Best days to book and fly, and why "book now" beats waiting
- Building Alaska/Atmos Rewards miles through Bilt
- Autopilot's new hotel repricing feature
Resources Mentioned
- Autopilot (withautopilot.com)
- MLA & SCRA fee waivers
- Google Flights (https://www.google.com/travel/flights)
- Seats.aero (https://seats.aero/)
- PointsYeah (https://www.pointsyeah.com/landing)
- ExpertFlyer (https://www.expertflyer.com/)
- CardPointers (https://cardpointers.com/)
- Travel Freely (https://travelfreely.com/)
- Max Rewards (https://maxrewards.com/)
- Flighty (https://flighty.com/)
- Bilt Rewards (https://www.bilt.com/)
- BofA Atmos Rewards Summit card
- Sam Hollander on X @samhollander_
- https://www.withautopilot.com/
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