223. This Tool Rebooks Your Flights for You When the Price Drops and Puts Cash (AND POINTS) Back in Your Pocket: Inside Autopilot with CEO Sam Hollander

What if you never had to manually check whether the price of your flight or hotel dropped after booking? In this episode, we sit down with Sam Hollander, founder of Autopilot, to discuss how his platform is helping travelers save money by automatically monitoring reservations and identifying opportunities for refunds, travel credits, and lower prices. For anyone who loves points, miles, and maximizing travel value, this technology could be a game changer.Sam walks us through how Autopilot works, which airlines and hotel programs are currently supported, and what's coming next—including Southwest integration, international bookings, upgrade tracking, and more. We also discuss security, award travel support, and how automation can help busy travelers avoid leaving money on the table. Whether you're booking with cash, points, or a mix of both, this episode is packed with practical tips to help you get more value from every trip.Mentioned in this Episode:Try out Autopilot hereCardpointersEmail Sam at [email protected] Us On Online:Girl's Trip Interest Form (April 7-10, 2027)Summer Road Trip Submissions ARE BACK!Sign Up for the Y! Wonder Travel NewsletterWonderland on Points Youtube ChannelMary Ellen | JoFacebook GroupAffiliate Links:Rakuten- Mary Ellen (Get 5000 AMEX or Bilt POINTS)Rakuten- Joanna (Get 5000 AMEX or Bilt POINTS)Comfrt.com 15% OFFSeats.AeroCardpointersHalara (use code "Wonderland" for 10% off)Our Favorite Credit CardsOur Favorite Travel NecessitiesWe receive a small commission when you choose to use any of our links to purchase your products or apply for your cards! We SO appreciate when you choose to give back to the podcast in this way!