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

Joining us in this episode of Living Off Rentals is someone who is helping make travel easier for people with disabilities while showing short-term rental owners how accessibility can also be a smart business decision.

Lorraine Woodward is the CEO and founder of Becoming RentABLE, a platform that helps travelers find accessible short-term rentals across the United States.

Listen as she shares practical ways property owners can make their rentals more accessible without major renovations, simple improvements that can make a big difference for guests, and why accessible rentals are in high demand and very profitable. Enjoy the show!

Key Takeaways:

[00:00] Introducing Lorraine Woodward and her background

[02:25] Starting a listing platform for accessible short-term rental properties

[08:20] What is considered wheelchair accessible in the short-term rental industry?

[09:10] Accessibility means more than just wheelchair access

[12:03] Simple updates that make a rental more accessible for guests

[16:38] The best accessibility improvements to make during a renovation

[23:29] Accessible short-term rentals are an underserved market

[26:27] The business benefits of investing in accessibility

[29:14] The growing demand for accessible vacation rentals

[31:55] Becoming RentAble as one source shop for accessible short-term rentals

[36:09] Ideal locations for accessible rentals

[47:31] Lorraine's recommendations for investors building an accessible rental today

[49:31] A powerful story about how an accessible rental gave a family precious time together

[51:22] Connect with Lorraine Woodward

[51:43] Outro

Guest Links:

Website: https://www.becomingrentable.com/

Email: [email protected]

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 a real estate investor who scaled from zero to six short-term rental properties (very soon to be 7) in just 13 months by using nearly every financing strategy available, from DSCR loans, to HELOCs, to a self-directed IRA.

Joanna N is the co-owner of One Life Getaways and a member of my STR Blueprint program.

Before real estate, she built a career as a chiropractor, then pivoted through sales, sales training, leadership development, and recruiting — a path she once saw as a string of failures, but now credits as the foundation for how she successfully runs her STR business today.

Listen as Joanna shares the financing strategies that helped her get started, buying the right property, building a team, and the practical advice she has for anyone looking to invest in short-term rentals. Enjoy the show!

Key Takeaways:

[00:00] Introducing Joanna N. and her background

[02:57] How she got started with short-term rentals

[04:55] The benefits of short-term rentals

[06:51] Picking the right market

[10:21] Assessing your best place to buy property

[11:44] Confidence of investing remotely

[14:31] Working with a listing agent

[15:53] The metrics Joanna use in selecting a property

[23:25] Managing multiple short-term rentals while continuing to grow

[26:39] Creating a team from scratch

[35:18] How to balance conflicting ideas in your team

[40:08] The different financing deals Joanna use

[45:58] Building confidence in your team and lenders

[54:21] Doing house tours on all her properties

[57:30] Connect with Joanna N.

[58:09] Outro

Guest Links:

Airbnb: https://www.airbnb.com/users/profile/1526349716038260752

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 someone who has built an incredible real estate portfolio while serving as a Green Beret in the U.S. Army.

Sterling Seizert is a real estate investor, entrepreneur, and the author of Buy Your Freedom. From balancing military service, deployments, and training, he built a $60 million self-storage portfolio and created a path to financial freedom through disciplined investing.

Listen as Sterling shares how he got started in real estate, why self-storage became his investment of choice, and the mindset that helped him build wealth while serving his country. Enjoy the show!

Key Takeaways:

[00:00] Introducing Sterling Seizert and his background

[02:21] Investing in self-storage while on active duty

[07:30] Mid- to short-term rental play

[10:48] Structure can make almost any deal work

[13:54] Finding time in real estate between deployments, training exercises

[17:32] How compounding works in real estate investing

[19:30] Business plan for the deal vs what actually plays out

[21:23] The four drivers of appreciation

[23:50] Partnership structure problem

[27:11] The five stages of income and how income works

[35:07] You can be in multiple stages of income

[39:43] How does the freedom matrix work

[48:35] The accumulation trap

[51:36] Using the value loop

[57:39] Understanding your market and market dynamics

[58:31] What would Sterling have done differently in the past

[01:02:28] Connect with Sterling Seizert and buy his book

[01:04:41] Outro

Guest Links:

Website: https://www.sterlingseizert.com/

Buy Your Freedom Book: https://www.amazon.com/dp/B0H2NSLJVZ

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 the CEO of Simple CFO and the author of "Profit First for Real Estate Investing."

David Richter returns to the show to explain why so many real estate investors struggle with cash flow, even as their businesses grow.

Listen as he explains how the Profit First system helps investors gain financial clarity, reduce stress, and build a business that supports the life they actually want. You'll also learn practical strategies for managing cash flow and making smarter financial decisions as your business grows.

Key Takeaways:

[00:00] Introducing David Richter and his background

[03:42] His background in real estate

[07:20] Understanding the Profit First system and how it works

[09:18] The actual Profit First setup

[11:22] The five core bank accounts every real estate business should have

[12:57] First account: Income account

[13:10] Profit Account, Owner's Comp Account, and Tax Account

[14:22] What is an OpEx Account?

[19:30] Weekly, monthly, and quarterly habits for managing cash flow

[26:28] The four stages of becoming a successful business owner

[34:17] What a fractional CFO does

[36:33] How a fractional CFO lays the financial foundation

[41:25] The habits that separate successful business owners from those who struggle

[46:48] Systems matter more than hustle for long-term success

[47:45] Profit First is not just a system but a tool for your business

[49:47] Connect with David Richter

[51:28] Outro

Guest Links:

Website: https://simplecfo.com/gift

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 someone with nearly 30 years of experience in the engineering and construction industry.

Sandy Lee is a former engineer and construction professional who retired early by building a portfolio of just four short-term rental properties. She discovered short-term rentals, developed what she calls the "Path of Progress" strategy, and created enough passive income to leave her full-time job.

Listen as Sandy shares how she transitioned out of her corporate career, the lessons she's learned as a short-term rental investor, and why keeping your investing strategy simple can lead to financial freedom. Enjoy the show!

Key Takeaways:

[00:00] Introducing Sandy Lee and her background

[02:40] Getting into short-term rental investment

[04:24] Buying her first short-term rental property

[06:41] What gave Sandy the confidence to purchase a big rental investment

[10:35] Looking beyond today's cash flow when buying properties

[12:20] Determining if a property is going to appreciate in cash flow

[18:29] Importance of hiring a revenue manager

[20:24] Hospitality is the most important part of the business

[21:55] How does she get high reviews

[24:26] Managing her properties in four different locations

[26:12] How technology helps simplify property management

[29:15] The milestone that gave Sandy the confidence to leave her full-time career

[31:14] What separates people who have more success from those who struggle

[32:41] The importance of building the right tech stack from day one

[33:46] Software tools Sandy recommends for managing short-term rentals

[35:49] Sandy shares details about her upcoming book, Building Joy

[36:56] Connect with Sandy Lee

[38:11] Outro

Guest Links:

Website: https://www.strjumpstart.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 in this episode of Living Off Rentals is Yiwei Cheng, a short-term rental investor and the founder of Pink Cash Cow Property Management.

Through plenty of trial and error, she built a portfolio and a successful property management company while proving that strong cash flow doesn't have to come from expensive vacation markets.

Listen as Yiwei talks about finding profitable deals in the Midwest, managing short-term rentals, avoiding common investing mistakes, and why she believes the best opportunities are still ahead.

Enjoy the show!

Key Takeaways:

[00:00] Introducing Yiwei Cheng and her background

[03:35] What more do people actually make money on real estate?

[06:04] The first property she purchased

[09:02] Her real estate experience during COVID

[12:23] Replacing her corporate income through short-term rentals in 2022

[16:38] Choosing profitable properties over popular vacation destinations

[23:50] What makes a perfect deal for Yiwei

[32:04] How Yiwei finances her rental properties

[35:24] DSCR loans explained

[38:40] Yiwei on managing her team

[46:10] Quality matters more than growing a large management company

[51:19] Building systems to manage rental properties efficiently

[55:20] Connect with Yiwei Cheng

[56:16] Outro

Guest Links:

Website: https://www.pinkcashcow.com/

Instagram: https://www.instagram.com/yiweicheng1/

YouTube: https://www.youtube.com/@YiweiCheng1

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, Kirby Atwell sits down with Melissa Nash, a real estate investor, wealth strategist, and host of the Passively Rich with Rentals podcast.

After losing a multimillion-dollar clothing business during the 2008 financial crisis, Melissa rebuilt her financial future through real estate investing. Today, she has built a seven-figure rental portfolio using what she calls the "Lazy Investor Method."

Listen as Melissa shares how she got started, why she believes long-term rentals remain one of the best wealth-building tools available, how she evaluates deals, and the strategies she teaches busy professionals who want passive income through real estate.

Enjoy the show!

Key Takeaways:

[00:00] Introducing Melissa Nash and her background

[03:14] Losing a multimillion-dollar business during the 2008 crash

[06:43] The confidence that made her move forward with real estate

[08:18] Purchasing her first out-of-state rental property in Birmingham, Alabama

[10:00] Defining the "Lazy Investor Method"

[13:47] Redefining the word "turnkey"

[15:29] Relationships are critical when investing out of state

[21:28] The key metric Melissa uses to evaluate every rental property

[25:05] Different ways investors can fund rental property purchases

[26:41] How DSCR loans make investing easier for busy professionals

[27:40] Building long-term wealth through a rental portfolio strategy

[30:14] LLCs, insurance, and protecting rental property assets

[32:52] Transitioning to short-term rentals

[37:23] Lessons learned from investing in short-term rentals

[39:50] Relationships still matter in the age of AI

[43:07] Connect with Melissa Nash

[45:03] Outro

Guest Links:

Website: https://www.passivelyrichwithrentals.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 for today's episode of Living Off Rentals is Anthony Lynn Miller, a young real estate investor with a unique background and an inspiring story.

Anthony shares what it was like growing up Amish without electricity, leaving school after eighth grade, and eventually stepping into the world of business and real estate investing.

Despite having no traditional real estate background, he built momentum through short-term rentals, private money, and smart investing strategies.

In this episode, Anthony talked about buying his first properties, managing short-term and midterm rentals, and building a path toward financial freedom through real estate.

Listen and enjoy the show!

Key Takeaways:

[00:00] Introducing Anthony Lynn Miller and his background

[02:51] Growing up Amish and life without electricity

[04:29] The transition from no electricity to using modern technologies

[07:32] How the Amish business mindset shaped his confidence

[08:52] Buying his first short-term rental property with his sister

[12:44] Why multifamily short-term rentals stood out to Anthony

[15:21] Using private money and DSCR loans to fund the deal

[18:54] What a Helping Fund is

[22:30] Lessons learned from his first larger investment

[24:40] Anthony's future investing plans

[26:57] Anthony's long-term goal of financial freedom through rentals

[30:51] Advice for people wanting to get started in real estate

[32:21] His experience inside the Blueprint program

[33:58] How to connect with Anthony Lynn Miller

[34:21] Outro

Guest Links:

Airbnb: https://www.airbnb.com/users/profile/1463687994996193041

Instagram: https://www.instagram.com/thevibrantcollections2025/

Show Links:

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

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