Check-In with Bryan

Black Friday Travel Hacks, Hilton Deals & The Sonder Fallout

Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.

0:00 | 33:09

Black Friday isn’t just about TVs and gadgets—this week we’re talking travel deals, Hilton’s huge sale, and what the Sonder–Marriott mess really means for guests.


In this Check-Out Friday episode of Check-In with Bryan, host Bryan Fish and producer Tyler Alexander catch up post-Thanksgiving and cover everything from Black Friday software buys to why airlines are in the business of service, not hospitality—a callback to a powerful analogy from recent guest Sarah Dandashy (@askaconcierge).


They also unpack highlights from this week’s long-form conversation with hospitality attorney and professor Stephen Barth (HospitalityLawyer.com), including:


  • The Sonder–Marriott case study and why it’s such a big deal for the industry
  • Who actually owns your hotel, who really has your money, and why that matters
  • Why travel insurance might be worth it—especially when you’re dropping $10K+ on a trip
  • How loyalty points, third-party ownership, and franchise structures can leave guests confused and frustrated


Then Bryan shifts gears into practical Black Friday and holiday travel tips, including:


  • Details on Hilton’s major Black Friday sale and how to maximize the promo window
  • Why you should avoid third-party booking sites like Expedia/Booking.com for “deals”
  • How to use airline vacation packages (like AA Vacations, Delta Vacations, etc.) to bundle flights + hotels for better value
  • How advanced pricing algorithms and AI-driven revenue systems changed the old “book on Tuesday” travel hacks


Along the way, Bryan and Tyler riff on:


  • Overhead bin drama, basic economy, and the eternal carry-on battle
  • Why some airline staff feel firmly “service only” while hotels lean into hospitality
  • Holiday chaos, family dinners, and the golden rule of returning the Tupperware


If you’re in hospitality, hotel ownership, or just a frequent traveler trying to protect your wallet and your sanity during peak travel season, this Check-Out Friday is for you.


🔔 Don’t forget to subscribe to Check-In with Bryan for more candid hospitality conversations every Tuesday, plus our lighter, fast-hit Check-Out Fridays with Bryan & Tyler.