
Episode #964: Ross Alcorn: How to Travel in Luxury for Free Using Your Business Expenses
From Natural Born Coaches by Marc Mawhinney
March 9, 2026 · 23 min · Episode 964
About this episode
Ross Alcorn shares how business owners can travel in luxury for free by optimizing their spending and earning points.
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…
People in this episode
Host: Marc Mawhinney
Guest: Ross Alcorn
Topics covered
- luxury travel
- business expenses
- points and miles
- coaching
- travel optimization
Keywords
- luxury travel
- business expenses
- points
- miles
- coaching
- travel optimization
- credit card points
Mentioned in this episode
Organizations: Itinerary Boss, Points, Cards and Travel
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