Ross Alcorn

Real estate investor and entrepreneur who built a five-property portfolio in six years, leverages tax benefits and house-hacking strategies, and operates a travel/points business to offset travel costs.

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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!

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