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

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 Points, Cards and Travel Podcast Book a no-obligation 1:1 strategy call with Marc for your coaching business: If you'd like more coaching clients without sending cold messages or spending money on ads, the Natural Born Coach Program is for you. Get the details here! Join The Coaching Jungle Facebook Group! Become a Coaching Jungle VIP member which includes special posting perks in the group to reach almost 30,000 potential clients! Grow your business with The Coaching Jungle Mastermind! If you have a product or service that helps coaches, and you'd like to get it in front of 100,000 of them:

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Episode #964: Ross Alcorn: How to Travel in Luxury for Free Using Your Business Expenses is an episode from Natural Born Coaches by Marc Mawhinney.

This episode is 22:55 long.

This episode was published on Mar 9, 2026.

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