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Episode #964: Ross Alcorn: How to Travel in Luxury for Free Using Your Business Expenses

by | Mar 9, 2026 | Podcasts

Ross Alcorn is the founder of Itinerary Boss and helps business owners optimize their everyday spending to earn points and miles that translate into luxury travel for free. He’s built a successful coaching business in a unique niche and shares his approach in this episode!

What You’ll Hear In This Episode:

  • How Ross’ love of travel started young, organizing group trips to Europe and snowboarding destinations for friends in his 20s, learning the logistics and credit card points game along the way.
  • How Ross learned the ins and outs of hotel loyalty programs and airline miles firsthand, which became the foundation of his expertise.
  • Ross breaks down the competition in his space: travel agents and concierge booking services, while he focuses on the higher-level strategy of optimizing business spend to maximize points, cash flow, and even tax deductions.
  • The strategy that Ross used to build his business quickly: leveraging his sales background, hiring a VA early, launching a podcast (called “Points, Cards and Travel”), and investing in coaching – which he credits as the biggest accelerator of his growth.
  • What his biggest mistake was, and how he fixed it …
  • Ross’ thoughts about AI vs coaching!

LINKS

The 5-Step Roadmap to Your Next Free 5-Star Luxury Vacation

http://itineraryboss.kit.com/the-5-step-roadmap-to-your-next-free-5-star-luxury-vacation-the-1-card-that-gets-you-there

Points, Cards and Travel Podcast

http://open.spotify.com/show/1mmMJ6z3JdEOUJKUjLh8bD?si=db17ffbb2c5246d6&nd=1&dlsi=29f4de1f73d54514

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