Joining us on this episode of Living Off Rentals is someone who escaped the corporate grind and built a lifestyle by design through turnkey real estate.

Ali Boone is an engineer, rugby player, pilot, adventurer, and the founder of Hipster Investments. She’s also the author of three different real estate books, including Not Your How-To Guide to Real Estate Investing.

In this conversation, Ali shares how she transitioned from aerospace engineering to buying hands-off rental properties—and how that led to her helping others do the same. She breaks down the fundamentals of what turnkey investing really is, how to screen a good provider, and the mindset shifts new investors need to succeed.

Enjoy the show!

Key Takeaways:

[01:35] Introducing Ali Boone and her background

[02:30] Getting out of the corporate world

[03:16] Making a career out of turnkey rental properties

[12:04] What is a turnkey rental property?

[16:31] Ali's very first rental turnkey property

[29:18] How to screen a good turnkey provider?

[30:27] Where did the profits come from?

[40:14] Helping people who want to buy some turnkey property

[43:28] The fundamentals of turnkey real estate investing

[49:00] Ali's version of financial freedom

[54:05] Connect with Ali Boone

[55:25] Outro

Guest Links:

Website: https://www.hipsterinvestments.com/

Show Links:

Living Off Rentals YouTube Channel -https://www.youtube.com/c/LivingOffRentals

Living Off Rentals Facebook Group -www.facebook.com/groups/livingoffrentals

Living Off Rentals Website -www.livingoffrentals.com

Living Off Rentals Instagram -www.instagram.com/livingoffrentals

Living Off Rentals TikTok - www.tiktok.com/@livingoffrentals

Joining us in this episode of Living Off Rentals is Jonna Weber, a seasoned buy-and-hold investor with two decades of experience investing in single-family and small multifamily properties in Idaho.

Jonna runs the Boise Real Estate Investor Network, where she helps connect and support investors across the state. She is also the host of the Idaho Real Estate Investors Podcast.

Listen as she shares her journey from buying her first property in 2003 to building a thriving investor community. You’ll hear how she gradually grew her portfolio, why she chose to focus on one market, and how building relationships has been key to both her personal success and the success of those around her. Enjoy the show!

Key Takeaways:

[00:00] Introducing Jonna Weber and her background
[03:48] What got Jonna into real estate?
[07:50] Her very first rental bought in 2003
[09:51] Joining forums about real estate and getting help from other people
[13:58] Systems and screening in self-managing properties
[20:25] Jonna's exit plan for her assets
[22:13] Leaving a legacy in the market
[25:14] Connecting and building relationships with other investors
[32:08] Evaluate your best niche and strategy

Guest Links:

Website: https://jonnaweber.com/
Boise Real Estate Investor Network: https://www.boiserein.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’re joined by Henry Russell—a Navy veteran, entrepreneur, and multifamily real estate investor with over 15 years of experience.

Henry Russell attended the U.S. Naval Academy and went on to complete multiple combat tours in Iraq as a Naval officer. After leaving the Navy, he returned to Baltimore, where he founded a construction company, a property management company, and, in 2020, launched RFC Capital, a veteran-owned investment firm based in San Diego.

RFC Capital specializes in a unique and impactful strategy: converting underutilized carports and garages into affordable rental units. This creative approach not only delivers strong returns for investors but also helps address San Diego’s growing affordable housing crisis.

Listen to hear about Henry’s unique strategy and how to add tons of value to garage spaces by turning them into livable apartments.

Enjoy the show!

Key Takeaways:

[00:00] Introducing Henry Russell and his background

[03:17] His transition from the Navy to real estate investing

[05:04] Different ways to start in real estate investing

[13:45] Partnership to build a strong real estate resume

[16:34] Henry's strategy for success

[20:15] Converting garages to apartment units

[24:21] Defensive strategy to buy real estate

[30:01] Doubling the rental income by renovating existing units

[39:30] The Ideal type of investor Henry works with

[43:21] His advice for first-time investors

[46:55] Connect with Henry Russell

Guest Links:

Website: https://rfccap.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 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