If you're a small business owner putting thousands of dollars on a credit card each month, this episode might save you tens of thousands in free travel... and completely change how you think about business spending.
Today I’m joined by Ross Alcorn, founder of Itinerary Boss and host of the World Travel Made Easy podcast. Ross helps entrepreneurs turn everyday expenses into first-class travel by using the right credit card strategies, automation, and systems. If you're still using a debit card or a rewards card that sounded good in a commercial, this is the conversation you need to hear.
Ross didn’t start in travel. He spent years in medical device sales, living out of hotel rooms and running himself into the ground. After realizing he was planning trips for friends better than most travel agents and wasting money on the wrong cards, he decided to build a business that gave others the freedom he was chasing himself.
Now, 18 months in, he’s helping business owners unlock the hidden value in their monthly spend, build systems to avoid burnout, and create more freedom without sacrificing growth.
The hidden cost of the wrong credit cardRoss explains why many business owners are missing out on thousands in free travel by using cards that don’t align with their biggest expenses. You’ll learn how a simple card change can lead to 3-4x the point value on the same spend.
Beginner-friendly credit card strategyForget confusing point systems and endless card comparisons. Ross simplifies what really matters: how much you spend, where you spend it, and which card gives you the best ROI. He also shares his top picks.
Delegation and automation that actually saves timeRoss shares how he built out systems using ClickUp, AI agents, and virtual assistants to grow faster without burning out. From podcast production to social media workflows, he explains how he decides what to keep and what to hand off.
How to build a business that supports your lifeBurnout taught Ross the importance of designing a business around your lifestyle, not the other way around. He explains how he audits his time monthly, sets up systems to stay lean, and keeps the long-term vision in focus.
Using AI to scale smarterFrom Zoom AI Companion to custom workflows in ClickUp, Ross shares the exact tools he’s using today, plus how he avoids the trap of experimenting with too many apps and not enough strategy.
Why podcasting accelerated his business growthLaunching a podcast helped Ross grow his network, land affiliate deals, and establish himself in the points-and-miles space. He shares why it’s one of the smartest moves he made early on—and how it continues to open doors.
What’s next: community and clarity for business travelersRoss is building a private community for business owners who want expert answers without digging through endless Facebook threads. He talks about how he’s shaping this space based on client feedback and what it will offer.
Business owners with $5K or more in monthly spend
Founders who want to travel more and work less
Entrepreneurs feeling stuck in the weeds or close to burnout
Anyone who’s never optimized their points strategy
Listeners curious about AI tools, ClickUp, Zapier, or automating daily tasks
🌐 ItineraryBoss.com: Free cheat sheet on points and miles
🎙️ World Travel Made Easy Podcast: Weekly episodes on travel strategy
📧 Sign up for his newsletter on the site
💼 LinkedIn: linkedin.com/in/rossalcornru
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