How Autopilot Helps You Never Overpay for Travel Again w/ Co-Founder Sam Hollander (Ep. 125)

In this episode of Revolutionizing Your Journey, DeAndre sits down with Sam Hollander, co-founder of Autopilot, the travel tool designed to help travelers stop overpaying for flights and hotels. Sam shares how a frustrating personal travel experience led to building a platform that automatically tracks reservations and rebooks them when prices drop.They break down exactly how Autopilot works, from importing reservations through Gmail, manual entry, or email forwarding to automatically monitoring price changes behind the scenes. Sam explains how the platform works with major U.S. airlines and expanding hotel partners to help travelers save money without constantly refreshing flight prices.The conversation also dives into Autopilot’s pricing model, which only charges users when money is actually saved, making it a low risk tool for travelers. Sam also shares details on the Pro Plan, which includes award ticket tracking, upgrade alerts, and lower service fees for frequent travelers.DeAndre and Sam discuss how tools like Autopilot can completely change booking behavior by encouraging travelers to book early, secure good deals, and let automation handle future price drops. They also touch on future plans for international airline support and expanded hotel integrations.Timestamps:(00:00) Intro: Why most travelers overpay for flights(03:49) Meet Sam Hollander, co-founder of Autopilot(07:13) How Autopilot works(12:00) Autopilot pricing model explained(18:20) How does Autopilot re-booking work in backend(27:50) Autopilot in the Points & Miles space(34:07) Risks, booking protection, and avoiding errors(38:49) Real-world cases - biggest savings within the app(44:02) Final questions, future growth, and key takeawaysKey Highlights:Autopilot tracks price drops automatically: It monitors flights and hotels after booking and helps travelers save money without manual work.Booking early becomes easier: Travelers can lock in trips sooner without stressing about future price fluctuations.You only pay when you save: Autopilot takes a percentage of savings only after successfully lowering your price.Pro features add more value: Award ticket tracking and upgrade alerts make it especially useful for frequent travelers.Expansion is coming: International airlines and more hotel partnerships are likely part of Autopilot’s future growth.Resources:Get Autopilot: Never Overpay for a Flight or Hotel AgainCheck out our Podcast LibraryBecome a BoldlyGo Blog contributorStart here to learn how to unlock nearly free travelSign up for our newsletter!BoldlyGo Travel With Points & Miles Facebook GroupNeed Global Travel Insurance? We recommend World NomadsGet a travel insurance quote hereSome of Our Favorite Tools For Elevating Your Points & Miles Game:Note: Contains affiliate/sponsored linksCard Pointers (Saves the average user $750 per year)Zil Money (For Payroll on Credit Card)Travel FreelyPoint.meFlightConnections.comThrifty Traveler PremiumLTH Online Points & Miles In Depth Course: Use coupon code "BOLDYGO" for a 50% discount!Connect with DeAndre & Taryn: Instagram: BoldlyGo.worldTikTok: BoldlyGo.worldWebsite: BoldlyGo.worldYouTube: BoldlyGoWorldYouTube: BoldlyGo.TravelsConnect with Sam Hollander: X: SamHollander_Mentioned in this episode:Check out all of our other travel podcasts from around the worldThis podcast is part of the Voyascape Travel Network, that brings together the world's best travel podcasts. You can find all of our podcasts from around the world at Voyascape.com. If you are interested in advertising or sponsered content on any of our shows you can find out more at the link below.Voyascape Podcast NetworkCheck out the Smart Travel PodcastThis week's show is supported by the new Smart Travel Podcast. Travel smarter — and spend less — with help from NerdWallet. Check out Smart Travel at the Link below:Smart Travel Podcast