Joining us on this episode of Living Off Rentals is an award-winning attorney, entrepreneur, and mom of three who owns seven businesses—including her own law firm.

Diana Khan, named one of the Top 40 Young Lawyers in the country, simplifies the legal side of real estate investing and shares how to structure your business to protect your assets and scale with confidence.

From LLCs to holding companies to personal trusts, she walks through what each one is and what every rental property owner needs to know to grow the right way.

Whether you’re buying your first rental or rapidly scaling your portfolio, this episode is packed with legal insight that could save you a lot of money (and headaches) down the line.

Enjoy the show!

Key Takeaways:

[00:00] Introducing Diana Khan and her background

[01:45] Her time management as a business owner, attorney, and mom of three children

[03:13] Operating her businesses independently

[07:04] Best entity set up for rental property owners

[14:35] Diana's simple explanation about LLC and personal trust

[17:48] Setting up a trust

[20:22] Biggest mistakes for rental property owners

[24:51] The process of failure to pay rent

[28:26] How do you get a rental license?

[37:40] What is an umbrella policy in real estate investing?

[43:59] Connect with Diana Khan

Guest Links:

Website: https://www.dklawmd.com/

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

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 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

Joining us in this episode of Living Off Rentals is someone with a 20-year background in the digital media space. Kamille Longstreet is a real estate investor, influencer, and co-founder of Stay Booked, a company that helps vacation rental owners master independent marketing to grow their bookings.

With over 20 years of experience in the media and digital marketing industry, Kamille was able to generate over $50K in direct bookings (on top of her Airbnb revenue) and grow her Instagram following to 10K+ in less than 9 months.

Listen as she shares the social media strategies to get direct bookings for your properties, how to work with social media influencers, and why social media marketing is a great tool for property hosts. Enjoy the show!

Key Takeaways:

[00:00] Introducing Kamille Longstreet and her background

[02:02] Getting into short-term rentals

[09:07] Barriers to moving to another country

[19:02] The eight playbooks of how to start getting more direct bookings

[25:52] How do you hire an influencer?

[28:03] Negotiating and making an agreement with influencers

[30:54] Branding is very important

[33:18] Content creation

[37:53] Creating the direct booking website

[49:32] About email marketing

[01:00:10] Connect with Kamille Longstreet

Guest Links:

Website: https://staybooked.net/

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