Ross Alcorn
Founder of Itinerary Boss who helps business owners and real estate investors convert everyday spending into large amounts of travel rewards, and a travel podcast host discussing points strategies for real estate and business owners.
Best podcasts with Ross Alcorn
Ranked by the Snipd community
13 snips
Dec 8, 2025 • 45min
He “Stacked” 5 Properties in 6 Years: Now He Lives and Travels for Free!
Ross Alcorn, a savvy real estate investor, turned his tax burdens into a thriving portfolio of five properties within six years. He discusses how strategic tax benefits can outweigh cash flow, particularly for high earners. Ross shares his journey from burnout in medical sales to discovering house hacking, which drastically cut his living expenses. He also reveals his travel-hacking side hustle using credit card points, allowing him to renovate rentals and explore the world for free. Tune in for invaluable tips and insights!
12 snips
Jan 13, 2026 • 29min
Maximize Credit Card Points for Real Estate with Ross from itineraryboss | Ep 271
Ross Alcorn, the founder of Itinerary Boss, shares his journey from travel sales to mastering credit card points for real estate investors. He reveals strategies for maximizing points on home expenses and using business cards for investments. Ross discusses how to maintain financial independence while growing a real estate portfolio, and the importance of building relationships with bankers for higher credit limits. With anecdotes and practical tips, he simplifies points earning, making the complex world of travel rewards accessible for everyday spending.
