#271 - How He Replaced His Tech Salary with Short Term Rentals - Stylianos Kalamaras
Release Date: 04/23/2025
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#271 - How He Replaced His Tech Salary with Short Term Rentals - Stylianos Kalamaras
Living Off Rentals
Joining me on this episode of Living Off Rentals is someone who’s been an athlete, Navy veteran, cyber engineer, and now, a short-term rental investor. Stylianos “Steve” Kalamaras is a fighter in every sense of the word. A former boxer turned real estate investor, he’s built an impressive short-term rental portfolio that brings in solid cash flow to rival his tech salary. He is also a member of my First Vacation Rental Investment Blueprint Program, and since joining, he’s closed on a handful of standout deals, including one where he converted a two-unit into a three-unit...
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#268 - Figuring out your true net worth and gaps in your wealth - Donald Pearson
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Joining us in this episode of Living Off Rentals is Donald Pearson, a Wealth Management Advisor at Westpac Wealth Partners who holds an impressive list of certifications. Donald is a CERTIFIED FINANCIAL PLANNER™ (CFP®) and a Retirement Income Certified Professional® (RICP®), and he helps individuals and business owners reach their financial goals as efficiently as possible. A graduate of the United States Naval Academy, Donald was commissioned as a Marine Corps officer and later served as a Financial Manager in the Marine Corps. Listen as he shares his full financial journey, the key...
info_outlineJoining me on this episode of Living Off Rentals is someone who’s been an athlete, Navy veteran, cyber engineer, and now, a short-term rental investor.
Stylianos “Steve” Kalamaras is a fighter in every sense of the word. A former boxer turned real estate investor, he’s built an impressive short-term rental portfolio that brings in solid cash flow to rival his tech salary.
He is also a member of my First Vacation Rental Investment Blueprint Program, and since joining, he’s closed on a handful of standout deals, including one where he converted a two-unit into a three-unit property that’s already generating over $3,000 in monthly cash flow.
In this episode, we dive into how each chapter of his life, from sports to military service to tech, has contributed to his success as an investor. We also talk about the lessons he learned through the deals he’s closed, working with contractors, and why a good house hack might just be the best financial decision you can make.
Enjoy the episode!
Key Takeaways:
[00:00] Introducing Stylianos Kalamaras and his background
[02:24] Before getting into real estate
[05:28] Skills as a professional athlete and military that played a part in his success as a real estate investor
[08:18] His first deal and first full rental
[15:42] Launching a new property
[17:31] What is the BRRRR strategy?
[21:07] The bare minimum in considering a deal
[25:23} The biggest risk in business is a knowledge gap
[31:21] Getting the kids involved
[32:02] "Get started as soon as you can."
[37:26] Connect with Stylianos Kalamaras
Guest Links:
Instagram: https://www.instagram.com/thegoldengreek
Show Links:
Living Off Rentals YouTube Channel – youtube.com/c/LivingOffRentals
Living Off Rentals YouTube Podcast Channel - youtube.com/c/LivingOffRentalsPodcast
Living Off Rentals Facebook Group – facebook.com/groups/livingoffrentals
Living Off Rentals Website – https://www.livingoffrentals.com/
Living Off Rentals Instagram – instagram.com/livingoffrentals
Living Off Rentals TikTok – tiktok.com/@livingoffrentals