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

In this episode of Living Off Rentals, we’re joined by UK-based short-term rental investor Ollie Laing, who’s cracked the code on direct bookings.

While most hosts rely heavily on platforms like Airbnb and Booking.com, Ollie generates over 50% of his revenue from direct bookings through his own website. In this episode, he shares exactly how he does it.

He also talks about some of the key lessons he’s learned while building a successful vacation rental business, including how he manages properties remotely, his go-to tactics for driving direct bookings, and the strategies he uses to mitigate risk.

Enjoy the show!

Key Takeaways:

[01:59] How Ollie started in short-term rentals

[05:11] Owning your properties vs managing others

[11:37] Mitigating problems in short-term rentals

[15:06] Ollie on remote management of properties

[21:21] About SuiteOp

[26:19] Tactics for getting direct bookings

[32:21] Mitigating the risk for direct bookings

[35:55] His advice for people starting their rental business

[43:56] Connect with Ollie Laing

Guest Links:

Website: https://www.perfectbooking.co.uk/

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 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 areas you need to focus on to achieve financial freedom, and why good financial planning is an ongoing process. He also breaks down the four domains of financial planning and walks us through the “mathematical equation” of financial freedom.

Enjoy the show!

Key Takeaways:

[00:00] Introducing Donald Pearson and his background

[08:02] Helping clients become more diversified and well-rounded

[12:59] The four domains of financial planning

[17:56] Living into someone's living balance sheet

[24:17] Good financial planning and decision-making is an ongoing process

[31:09] Where do successful people put their money?

[44:54] Connect with Donald Pearson

Guest Links:

Email: donald.pearson@westpacwealth.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

In this episode of Living Off Rentals, we are joined by Mark Lumpkin, a real estate investor who fell in love with short-term rentals 10 years ago.

Mark has helped over 500 short-term rental investors optimize their properties—handling everything from renovations to design—and has guided many others in establishing their own successful rentals.

Listen as Mark shares his journey with short-term rentals and how this investment strategy has provided him the flexibility to pursue his passions. We also dive into his work with STR Cribs, exploring how thoughtful design choices can make rentals stand out.

Plus, we discuss why furniture, décor, and strategic renovations are essential for maximizing cash flow in the short-term rental market. Enjoy the show!

Key Takeaways:

[00:00] Introducing Mark Lumpkin and his background

[04:19] How he got into the real estate industry

[07:21] Choose a property for short-term rentals with your guest avatar

[11:37] Recommended budget for furnishings and design for your property

[14:41] What is data-driven design?

[18:16] The importance of leaning on expert experience from professional designers

[27:57] Doing quick preventive maintenance regularly

[31:14] The shift in trends for short-term rentals

[36:22] Connect with Mark Lumpkin

Guest Links

Website: https://strcribs.com/

Email: mlumpkin@strcribs.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 us in this episode is someone who has been making waves in the affordable housing space. He is a returning guest, previously appearing on Episode 92 of Living Off Rentals in 2021.

Atticus LeBlanc is the founder of PadSplit, the country’s largest co-living marketplace, which helps property owners increase cash flow while providing affordable housing for thousands of residents. Since launching in 2017, PadSplit has housed more than 42,000 people and has grown to over 17,000 shared housing units across multiple U.S. markets.

An entrepreneur since 2005, Atticus was an affordable housing developer and contractor before founding PadSplit.

Listen as he shares more about how PadSplit works and discusses how he converts living spaces into bedrooms to create massive cash flow. Enjoy the show!

Key Takeaways:

[00:00] Introducing Atticus LeBlanc and his background

[03:47] How PadSplit works?

[11:22] Type of property that best works for PadSplit members

[17:10] The fractionalization of real estate by time versus the fractionalization of real estate by space

[26:25] Managing the challenges of bureaucracy and zoning issues

[33:53] How to manage different personalities under one roof?

[49:05] Connect with Atticus LeBlanc

Guest Links:

Website: https://www.padsplit.com/hosts

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

Is college the best path to financial success, or is there another way?

In this episode, Steven Rich shares his bold decision to drop out of his mechanical engineering program and dive headfirst into real estate investing.

Now, he is the owner of 50 service accommodation rooms with bookings across several online travel agency (OTA) platforms like Airbnb and Booking.com.

Steven reveals the experiences, lessons, risks, and rewards of building a real estate business instead of following the traditional college route.

Tune in to hear his story, and enjoy the show!

Key Takeaways:

[00:00] Introducing Steven Rich and his background

[02:57] His decision to leave college

[07:28] The worst-case scenario of leaving your full-time job or college degree

[11:14] Risky move to own a 22-room hotel

[23:05] Time frame between purchasing the property and start taking bookings

[31:38] Optimizing on- and off-seasons in property bookings

[41:54] FAIL: First Attempt In Learning

[49:20] Outro

Guest Links:

Follow Steven on Instagram: https://www.instagram.com/steven_rich_property/

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