Living Off Rentals

Joining us on this episode of Living Off Rentals is someone who found a profitable niche right next to college campuses.

Ryan Chaw is a real estate investor who specializes in student housing and renting by the room. He started buying properties on the side while working full time as a pharmacist, inspired by the rentals his grandfather used to build generational wealth for their family. Today he helps busy professionals buy their first cash-flowing student rental.

Listen as he shares the $30,000 lesson from his first property and how one duplex rented to 12 college baseball players brings in $7,360 a month. He also explains how he picks the right houses near campus and screens tenants so shared homes run smoothly.

Enjoy the show!

Key Takeaways:

[00:00] Introducing Ryan Chaw and his real estate journey

[02:42] Getting into real estate investing as a young pharmacist

[04:39] Ryan's first rental property and the lessons he learned

[05:39] Finding better tenants by targeting graduate students

[06:44] Losing over $30,000 on his first property

[09:55] How Ryan worked out a deal with his dad after the unexpected repairs

[10:40] The three things you need to get right with student housing

[11:47] B.I.G. method for finding the right property

[13:49] Structuring student leases

[15:54] The ideal bathroom-to-tenant ratio

[17:13] Converting existing space into additional bedrooms

[18:51] Managing neighbors and student housing complaints

[20:15] The three-strike policy for head tenants

[24:05] Ryan's cash flow targets and the 2% rule

[25:42] The PRIME method for finding high-quality tenants

[29:56] Ryan's real estate investing community works

[31:53] Outro

Guest Links:

Website: https://www.newbierealestateinvesting.com/

YouTube: https://www.youtube.com/@ryanchaw1

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

Want to start investing in short-term rentals? Book a call to see if my STR Blueprint program is a good fit for you: livingoffrentals.com/call

Joining us on this episode of Living Off Rentals is someone who went from missing his kids' childhood overseas as an active-duty Marine to building a real estate empire that lets him be home with his family every day.

Keith Gillispie is a Marine Corps veteran and the founder of REI Automated. He served eight years on active duty, deploying overseas 13 times, before leaving in 2020 to build his business full time. He is a serial entrepreneur who has invested in 34 states and raised over $10 million in private capital.

Listen as he shares the moments that made him walk away from a Marine career, how he built his business in one-hour lunch breaks while still serving, and how he scaled from a few local deals to operating in markets across the country.

Enjoy the show!

Key Takeaways:

[00:00] Introducing Keith Gillispie and his real estate background

[02:08] How Keith first became interested in real estate while serving in the Marines

[04:42] Coming home to children who didn't recognize him

[06:19] Real estate became Keith's vehicle out

[08:08] Why being a father became more important than being a good Marine

[09:36] The biggest lessons Keith took from the Marines

[14:20] Buying and flipping his first house in Stafford, Virginia

[18:36] Growing from three deals to nine deals while keeping the same marketing budget

[19:41] Finding the "Goldilocks zone" for real estate investing

[22:19] Building six software companies under REI Automated

[23:12] Focusing primarily on single-family properties

[26:58] Why finding a proactive property manager can be difficult

[28:16] The three pillars of deal execution

[28:26] Pillar one: education

[30:05] Pillar two: systems/software

[33:44] Pillar three: coaching

[37:51] How much of real estate investing can actually be automated

[40:45] Learn more about REI Automated

[41:27] Connect with Keith Gillispie

[42:03] Outro

Guest Links:

Website: https://www.reiautomated.io/

Instagram: https://www.instagram.com/keithg_rei/

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

Want to start investing in short-term rentals? Book a call to see if my STR Blueprint program is a good fit for you: livingoffrentals.com/call

Joining us on this episode of Living Off Rentals is Bryan Driscoll, owner of Motivated Leads, a company that helps real estate investors connect with motivated off-market sellers through various marketing strategies.

Bryan shares his own experience as a real estate investor, from buying his first $33,000 property to building a rental portfolio.

Listen as Bryan explains how to find motivated sellers, when to start paying for leads, why having multiple ways to help sellers matters, and how staying focused can simplify the real estate investing process. Enjoy the show!

Key Takeaways:

[00:00] Introducing Bryan Driscoll and his background

[02:37] Transition from freelancing on Upwork to starting Motivated Leads

[03:45] Learning marketing and building a general agency

[04:59] Buying his first $33,000 investment property

[06:49] How Motivated Leads influenced Bryan's real estate investing

[08:29] The idea behind "gold-driven depression"

[10:02] Planting seeds for his future self through real estate

[12:24] Why Bryan focuses on one zip code

[13:48] How to find your first off-market deal

[18:23] Using bandit signs to find highly targeted leads

[19:23] Using a CRM to track leads and follow up

[21:58] Two ways to market on Facebook

[23:01] The special housing category on Facebook explained

[25:35] Generating leads nationally and passing them to local investors

[27:22] Real estate leads are still a numbers game

[27:56] Dispositions and novations explained

[29:58] Understanding lead volume and the cost of leads

[32:30] Common mistakes new investors make with off-market marketing

[34:19] Building the process around yourself before building a team

[36:06] Balancing a multi-million dollar business, real estate, family, and hobbies

[38:53] The story behind the Goodness Game

[45:08] Realizing that small things can make a difference

[47:22] Using a scorecard to measure effort, impact, and how you feel afterward

[49:49] Outro

Guest Links:

Motivated Leads Website: motivatedleads.com

The Goodness Game: goodnessgame.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

Want to start investing in short-term rentals? Book a call to see if my STR Blueprint program is a good fit for you: livingoffrentals.com/call

Joining us on this episode of Living Off Rentals is Maria Laoang, our Airbnb Manager who's been overseeing the day-to-day operations for my short-term rental business, Dune Dwellings, for the past two years.

Maria is a virtual assistant (VA) from the Philippines who manages our team of 3 full-time customer service team members. Together, they run the day-to-day operations of our Airbnb business.

Listen as she shares how her background in customer service led her to Airbnb management, her responsibilities, and what it means to hire for ownership rather than tasks.

She also gets into what onboarding and training VAs look like in practice, how something as simple as a daily Slack recap can keep a whole team on the same page, and just how many moving pieces a short-term rental operation actually juggles, from guest services and cleaning to maintenance, vendors, systems, processes, and more.

If you're looking to scale up your Airbnb operations with a virtual team, this one's for you! Enjoy the show!

Key Takeaways:

[00:00] Introducing Maria Laoang and her role as virtual rental manager

[04:21] Maria's background in customer service and training

[07:30] Responsibilities as a virtual short-term rental manager

[08:18] Improving systems, SOPs and processes

[10:28] The difference between a team member and a manager

[13:28] How Maria found the job opportunity

[15:15] Why clearly defining the role matters when hiring

[19:17] The right time to hire a virtual team member

[21:19] Language and communication in the Philippines

[26:41] Building the onboarding and training process

[31:37] Using Slack as the day-to-day communication hub

[34:16] Advice for rental property owners thinking about hiring virtually

[35:25] Being ready to delegate and build systems

[37:54] Rewarding your team as owners

[39:52] Outro

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

Want to start investing in short-term rentals? Book a call to see if my STR Blueprint program is a good fit for you: livingoffrentals.com/call

Joining us in this episode of Living Off Rentals is Dustin Heiner, a real estate investor behind several podcasts, including Master Passive Income, and the man behind Income Builder - a new tool that lets investors manage all their real estate tools in one place.

Dustin started investing in long-term rentals in 2006 after a wake-up call at his government job. Since then, he has built systems around his portfolio and created Income Builder, a business system designed to help investors analyze properties, manage their portfolio, organize documents, and track their progress toward financial freedom.

Listen as he explains why investors need to think like business owners, how to keep everything in one place, and how AI can help investors make better decisions and build systems. Enjoy the show!

Key Takeaways:

[00:00] Introducing Dustin Heiner and his real estate background

[03:42] Starting with long-term rentals in 2006

[04:38] Don't be an investor, be an income builder and business owner

[05:29] Why Dustin focuses on systems and processes

[07:26] The story behind Income Builder

[09:46] Investors need a complete business system

[11:03] Replacing multiple tools with one system

[15:38] Investors should organize everything from the beginning

[17:26] Getting started with Income Builder for free

[20:33] Tracking your financial freedom goal

[23:28] Building an AI investor coach

[24:57] How AI could impact real estate investing

[28:18] Nothing can replace mentors and community for real estate investors

[31:07] Learning from other people's mistakes

[32:44] Appreciation is icing on the cake

[37:30] The importance of community and surrounding yourself with investors

[43:04] 50% off the first month of Income Builder

[44:57] Outro

Guest Links:

Website: https://incomebuilder.io/

Get 50% off the first month of Income Builder.

Visit https://livingoffrentals.com/incomebuilder and use the promo code KIRBY.

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

Want to start investing in short-term rentals? Book a call to see if my STR Blueprint program is a good fit for you: livingoffrentals.com/call

In this episode of Living Off Rentals, Mike and Caroline Neubauer of the Our Family Invests podcast join us to share how they built financial freedom through real estate investing and short-term rentals in Maui.

Starting with an ADU on their primary home, they eventually built a short-term rental business that allowed Mike to leave the fire department. Along the way, they learned some hard lessons about financing, renovations, cash flow, and building systems.

Listen as Mike and Caroline share how they got started, the challenges they faced with their first short-term rental, the impacts of COVID and the Maui fire, and how having a clear family goal helped them keep moving forward. Enjoy the show!

Key Takeaways:

[00:00] Introducing Mike and Caroline Neubauer

[03:18] Building financial freedom in a really expensive market

[07:52] Building an ADU on their primary residence

[13:58] From being a firefighter to discovering short-term rentals in Maui

[23:00] The different path to financial freedom

[24:20] The lessons learned from landlording short-term rentals

[26:01] Finding and purchasing their first short-term rental

[29:30] How COVID affected their real estate operations

[31:09] Pivoting their short-term rentals during COVID

[33:36] Investing remotely and funding new properties

[40:44] Deciding when to leave the fire department

[46:18] How their real estate goals have changed

[48:18] Moving toward more passive investments

[53:16] Choosing properties based on location and lifestyle

[55:51] Mike's experience with the Maui fires

[01:00:59] The impact of the Lahaina fire

[01:03:06] Mike and Caroline's advice for those starting in real estate investing

[01:04:20] Connect with Mike and Caroline Neubauer

[01:05:13] Outro

Guest Links:

Website: https://ourfamilyinvests.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

Want to start investing in short-term rentals? Book a call to see if my STR Blueprint program is a good fit for you: livingoffrentals.com/call

On this very special episode of the Living Off Rentals podcast, I am joined by my wife Taryn Atwell, who is also my business partner and the designer behind all our short-term rental properties.

In this episode, we talk about how we started with a short-term rental in our basement and gradually grew the business by leaning into their different strengths. I focus more on the numbers and property decisions, while Taryn handles design, guest experience, and communication.

We also talk about tips on how to get your spouse on board with real estate investing, dividing responsibilities, setting goals around the lifestyle you want, and handling the unexpected challenges of running short-term rentals.

Enjoy the show!

Key Takeaways:

[00:00] Introducing Kirby and Taryn Atwell and their background

[02:53] Taryn's background and how she got into designing their rentals

[04:20] Starting with a short-term rental in their basement

[06:44] The mistakes they made along the way

[08:13] What it's like being married to an entrepreneur

[10:46] How to get your spouse on board with real estate investing

[14:25] The pressure of being the entrepreneur in the relationship

[15:48] How couples can divide responsibilities and make decisions together

[17:09] How their goals have changed over the years

[21:24] Starting with your ideal day and working backward

[25:33] Handling difficult guests and unexpected problems

[27:20] Dealing with unexpected wins and losses

[28:28] Negative guest experiences stick with you

[32:24] Best way to maintain a strong marriage

[36:53] Staying aligned on priorities and long-term goals as a couple

[39:00] Getting kids involved in the family business

[43:19] The most rewarding parts of the real estate lifestyle

[45:33] The trade-offs of working and living together

[49:03] Using challenges to create repeat guests and long-term business

[53:37] Outro

Guest Links:

Dune Dwellings: https://www.dunedwellings.com

Kirby's Instagram: https://www.instagram.com/kirbyatwell/

Taryn's Instagram: https://www.instagram.com/tarynlee85/

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

Want to start investing in short-term rentals? Book a call to see if my STR Blueprint program is a good fit for you: livingoffrentals.com/call

Joining us on this episode of Living Off Rentals is someone who went from one duplex to 38 rental units in just two years — and retired from her full-time job before turning 30.

Rachel Richards is a real estate investor and author of Money Honey and Passive Income, Aggressive Retirement. She built her portfolio using a rent-by-the-room strategy that generated far more cash flow than traditional rentals, and by 2022 had grown her passive income to $20,000 a month.

Listen as she shares how she scaled from one duplex to 38 units, why she focused on cash flow instead of counting doors, and how a $10,000 monthly income goal gave her the freedom to walk away from her job.

She also opens up about turning her Denver home into a 4-unit house hack she now lives in for free, getting burned by contractors along the way, and the hard lesson from her divorce that changed how she thinks about protecting what you build — including why she now recommends a prenup.

Enjoy the show!

Key Takeaways:

[00:00] Introducing Rachel Richards and her background

[02:20] Why Rachel wanted to pursue financial freedom

[05:38] How Rachel scaled to 38 units in just a few years

[07:52] Reinvesting cash flow to keep growing

[09:01] How pad split type of properties increased her cash flow

[11:54] Challenges in tenants sharing common spaces

[14:16] Finding her first off-market deal

[17:26] How to stand out in the MLS competition

[18:24] Cash flow number vs number of doors

[21:21] Reaching the number and leaving her job

[25:16] Rachel's books and teaching others about financial freedom

[26:40] Lessons she learned from dealing with tenants, property managers and contractors

[28:14] Finding the right market

[31:27] Why you still need to manage the manager

[34:48] Rachel's $750,000 Denver house hack

[39:29] Working with women investing with a spouse

[42:24] Managing risk in marriage and real estate

[44:24] Protecting businesses and assets built during marriage

[45:55] Connect with Rachel Richards

[46:34] Outro

Guest Links:

Website: https://moneyhoneyrachel.com/

Instagram: https://www.instagram.com/moneyhoneyrachel/

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

Want to start investing in short-term rentals? Book a call to see if my STR Blueprint program is a good fit for you: livingoffrentals.com/call

Joining us on this episode of Living Off Rentals is a real estate investor and private-money expert who has taught hundreds of investors how to raise millions of dollars for their deals.

Amy Mahjoory started raising private money when she was a new investor flipping houses in Chicago. Listen as she breaks down how new investors can overcome the fear of raising private capital, build relationships with potential lenders, and create a simple process to get deals funded.

She also shares what to do when a deal doesn't go as planned and why communication with your lenders is so important. Enjoy the show!

Key Takeaways:

[00:00] Introducing Amy Mahjoory and her background

[03:06] Becoming one of the leading experts on raising private money

[05:11] What is private money?

[06:33] Using private money as gap funding

[07:24] Using private money on different types of real estate deals

[10:35] Amy's step-by-step process for raising private money

[11:35] Four-second power pitch

[13:04] The biggest mistake real estate investors make

[16:52] Getting into the actual details of the deal

[20:54] How long to ask for private money

[25:17] The basic documents you need when working with private lenders

[27:11] Stay in touch with potential lenders

[30:58] Screening the ideal type of private lender

[35:06] The minimum investment amount

[36:20] Examples of investors who successfully raised private capital

[44:20] Amy's RPM Masterclass

[46:17] Connect with Amy Mahjoory

[46:40] Outro

Guest Links:

Website: https://amymahjoory.com/

Instagram: https://www.instagram.com/amymahjoory/

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

Want to start investing in short-term rentals? Book a call to see if my STR Blueprint program is a good fit for you: livingoffrentals.com/call

In this episode of Living Off Rentals, we are joined by Bri West, founder of Somerled Designs and a real estate investor with 36 short-term rental properties of her own.

Bri started investing in short-term rentals in 2020 and used her background in marketing to approach design from a different angle. Instead of designing a property based on personal preferences, she focuses on the target guest, the market, and the return on investment (ROI).

Listen as Bri explains how she uses data to choose amenities, set design budgets, and create short-term rentals that stand out. Enjoy the show!

Key Takeaways:

[00:00] Introducing Bri West and her background

[02:47] How Bri got started in short-term rentals and Somerled

[05:24] Using strategy and marketing before design

[07:25] Using data to build an ROI-focused design strategy

[09:39] Provide experience to charge premium rates

[11:56] Bri's strategy for market selection

[14:37] How Somerled is different from a typical design firm

[17:57] The amenity strategy explained

[21:14] Creating unique amenities for the target guest

[25:40] Bri's short-term rental design budget rule of thumb

[29:19] When to start working with the client

[33:42] Changing amenities and increasing competition

[36:40] No-brainer amenities for short-term rentals

[42:11] Connect with Bri West

[43:07] Outro

Guest Links:

Website: https://www.somerleddesigns.com/

LinkedIn: https://www.linkedin.com/in/bri-west-2a7a93288/

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

Want to start investing in short-term rentals? Book a call to see if my STR Blueprint program is a good fit for you: livingoffrentals.com/call