In this episode, we talk about two key setbacks that shifted Jeff Anzalone’s mindset towards building multiple streams of passive income, why he doesn’t invest in single-family rentals, the lessons learned from losing his first $50,000 he invested in a syndication, and the great question he uses to find other potential groups to invest with.

Dr. Jeff Anzalone is a full-time practicing periodontist in the great state of Louisiana, author, and founder of DebtFreeDr.com. He focuses on teaching doctors and other high-income professionals to create passive income from real estate so that they can STOP trading their time for money.

In This Episode We Cover:

• How school may give you the knowledge to practice your profession but not prepare you for actually practicing it
• How a skiing accident helped him realize how precarious his economic future was even with a high-paying, safe, secure job
• Why 90% of all millionaires have real estate in their investment portfolios
• Why high-income earners should focus on their core money-making ventures and leave the active real estate investing to others
• Why he doesn’t invest in single-family rentals
• The lessons learned from losing the first $50,000 he invested in an apartment syndication
• Why he doesn’t like investing in syndications through crowdfunding platforms
• What led him to choose apartment syndications over other asset classes
• How he would go about educating himself on apartment syndications if he were starting over
• And much more!

Books and Resources Mentioned:

• The Road to Family Freedom: roadtofamilyfreedom.com
• Website: Dr Debt Free
• Resource: Free Doctor’s Passive Income Guide
• Email: [email protected]

Follow Us:

• facebook.com/roadtofamilyfreedom/
• instagram.com/roadtofamilyfreedom/
• twitter.com/r2familyfreedom

Other Stuff:

• If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than 60 seconds, and it really makes a difference in...

In this episode, we talk to Powell Chee about his start in real estate and why quickly he shifted into multi-tenant assets, the three main roles of a real estate syndication team, a key difference between residential and commercial lending that challenges many investors making the switch, and how to build relationships with commercial real estate brokers that last.

Powell Chee is a Los Angeles-based real estate investor who does all his investing out of state. After buying his first investment property in 2015, a single-family home in Kansas City, he came to the realization that one door at a time was not going to get him to his goals. Since 2017, Powell has partnered on 7 multifamily properties totaling over 1000 units. As Covid-19 affected the US in 2020, Powell shifted gears from multifamily and expanded his investments into self-storage. He closed his first self-storage property in January of 2021 and is operating it remotely.

In This Episode We Cover:

• How he got started investing in single-family rentals but quickly shifted into multifamily investing
• How he scaled from those early self-funded apartment communities into larger assets with groups of passive investors
• Why he shifted from investing in multifamily into self-storage investments
• Some tips on forming real estate partnerships
• And much more!

Books and Resources Mentioned:

• The Road to Family Freedom: roadtofamilyfreedom.com
• Website: www.multifamilymasters.com
• Email: [email protected]
• Facebook: https://www.facebook.com/powellbiz
• Twitter: @PowellChee

Follow Us:

• facebook.com/roadtofamilyfreedom/
• instagram.com/roadtofamilyfreedom/
• twitter.com/r2familyfreedom

Other Stuff:

• If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than 60 seconds, and it really makes a difference in helping to convince hard-to-get guests.
• For show notes and past guests, please visit

Landon and Teria Harris started out rehabbing single-family homes. After a few successful projects, they realized it was not the direction they wanted. The amount of time, work, and capital was more than they wanted to manage. Their love of real estate led them to other investing opportunities. After hearing a podcast on vacant land sales, they immediately knew land investing was the right direction for them!

Their land business began in 2019 where they immediately set up structure, processes, and tools to build their land business. Within a few short months, their business soared! They were able to build a successful land business and replace Landon’s full-time job in the first year. 

In this episode, we talk to Landon and Teria about the challenges of rental property investing as well as house flipping, how that experience led them to invest in raw land, how they purchased 10 parcels for just $14,000 on their first deal, and the systems and processes they’ve set up to make their raw land business run as passively as possible.

In This Episode We Cover:

• How Landon and Teria Harris got into real estate investing
• How their experience with house flipping and single-family rentals led them to shift to raw land investing
• How much it cost them to buy their first raw land deal
• How much it costs to market for raw land
• And much more!

Books and Resources Mentioned:

• The Road to Family Freedom: roadtofamilyfreedom.com
• Website: CreeksideDevelopments.com
• Facebook: Creekside Developments
• Resource:: The Land Geek
• Resource: Loom
• Resource: AirTable
• Resource: Trello

Follow Us:

• facebook.com/roadtofamilyfreedom/
• instagram.com/roadtofamilyfreedom/
• twitter.com/r2familyfreedom

Other Stuff:

• If you enjoy the...

Matt Gouge, aka Matt the Mortgage Guy, got his start in lending back in 2013. As a self-proclaimed math nerd and a people person, he burned his proverbial ships, leaving a steady paycheck with the State of California, for the commission-based world of brokering residential mortgages. He has excelled in the field because he himself is a real estate investor and he can advise clients at a high level. As a real estate investor himself, he is able to help clients not only analyze the mortgage on their primary residence but on potential investment properties as well.

In this episode, we talk to Matt about his journey from state employee to a commission-based mortgage broker, the power of taking the leap into the unknown from an unfulfilling job, the tale of buying his first property before the Great Recession that is still a rental, and his misadventures investing long-distance.

What You'll Learn in This Episode

• How Matt Gouge left a secure state job with a pension for a commission only job as a mortgage broker
• How lack of job satisfaction should be an indicator that something needs to change
• How to analyze the risk when planning to make a big decision
• How Matt Gouge bought his first investment property
• When buying a property to live in, you should keep in mind how well it will work as a rental when you move out
• How has he expanded his investment property portfolio
• How he got burned investing long distance and the mistakes he made
• Why you should always have an extra property manager ready to take over your rental properties
• Why you should NOT diversify your single-family rental portfolio across multiple cities
• Why you SHOULD diversify your real estate investments into syndications like apartments, self-storage, and mobile home parks
• How much time does take to manage a rental property portfolio
• How owning four or more rental units lowers your risk
• Where to learn how to buy investment properties
• Why you should buy real estate when everyone is afraid of buying real estate
• How to avoid paralysis by analysis
• How losing money on a deal can be a better education than a paid mentorship

Books and Resources Mentioned

• The Road to Family Freedom: roadtofamilyfreedom.com
• Website: Matt the Mortgage Guy
• YouTube: Matt the Mortgage Guy
• Twitter: @MortgageMattCA
• Phone: (916) 529-7600

Follow Us:

• facebook.com/roadtofamilyfreedom/
• instagram.com/roadtofamilyfreedom/
• twitter.com/r2familyfreedom

Mindy Templeton is a Kansas City-based real estate investor who was, at one time, $165,000 in debt. A mindset shift a few years ago led her and her husband to aggressively pay down that debt and start buying single-family rentals in the Kansas City area.

She and her husband have full-time jobs and are parents to two young children. She started Investinginyourwealth.com about two years ago as a way to track her journey to paying off that $165k of debt, and now that they are debt-free, she is working on building wealth through diversification. She is a firm believer in having multiple strategies for investing, so real estate is not her only strategy, but definitely her primary focus. 

In this episode, we talk to Mindy about the mindset shift she went through that led them to adjust their spending habits, the creative way she acquired the funds for the downpayment on their first rental property, and why she doesn’t want to build a huge portfolio of rental properties.

What You'll Learn in This Episode

• How Mindy Templeton and her husband dug themselves out of $165,000 in student loan and consumer debt
• The two mindset shifts that allowed her to pay down debt
• The generational divide when it comes to finances and retirement
• How they leveraged a loan from their 401k and a relative's HELOC to purchase their first investment property
• The difficulties of competing with cash buyers in this market
• Why real estate is the perfect vehicle for frustrated entrepreneurs
• Why Mindy is focused on building a small portfolio instead of a huge one
• Why it's important to know what you want your life to look like as an investor
• Why she prefers to invest in her local market
• Why she prefers to have professional property management take care of her properties

Books and Resources Mentioned

• The Road to Family Freedom: roadtofamilyfreedom.com
• Instagram: @LikeMindedInvestors
• Website: Investing In Your Wealth
• Book: Your Money or Your Life by Vicki Robin

Follow Us:

• facebook.com/roadtofamilyfreedom/
• instagram.com/roadtofamilyfreedom/
• twitter.com/r2familyfreedom

Other Stuff:

• If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than 60...

Sara Witz and Anthony Gair are a soon-to-be husband and wife real estate investing team focused on wholesaling, flipping, and the BRRRR strategy. Two oil and gas employees from Houston, Texas who decided to take advantage of the extra time they had after their wedding was delayed by the Covid pandemic. They started investing less than 12 months ago and already have 13 deals under their belt. At the beginning of 2021, they set a goal for themselves of earning $100,000 in three months from real estate, and as of this recording, they are just $15,000 away from that goal. 

In this episode, we talk to Anthony and Sara about how they got into their first BRRRR property for less than $10,000, the multiple exit strategies that they use to make use of nearly every deal they come across, why they now have a rule against doing any rehabs after dark, and the key expense many people forget about when buying a property to wholesale, flip or BRRRR.

What You'll Learn in This Episode

• How Anthony Gair and Sara Witz got into real estate investing
• How working from home during the pandemic accelerated their investing journey
• How they bought their first rental property using almost none of their own money
• Why not do the rehab on the rental property themselves
• How they were able to do 13 deals in less than one year
• How they are finding their deals
• The challenges of finding deals during the pandemic
• How getting their July 2020 wedding canceled help their real estate investing journey
• The one thing they would throw money at to improve their real estate investing business
• How they are using door knocking to build rapport with sellers and find deals
• Why they no longer do renovations in the dark
• What's the most important thing to know when analyzing a potential BRRRR deal

Books and Resources Mentioned

• The Road to Family Freedom: roadtofamilyfreedom.com
• Instagram: @Gair.RealEstate
• Resource: Deal Machine

Follow Us:

• facebook.com/roadtofamilyfreedom/
• instagram.com/roadtofamilyfreedom/
• twitter.com/r2familyfreedom

Other Stuff:

• If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than 60 seconds, and it really makes a difference in helping to convince hard-to-get guests.
• For show notes and past guests, please visit roadtofamilyfreedom.com/episodes/
• Discover the tools and services we use,...

Shane Sigsbee – Short Term Rental Investor and CEO or Sigsbee Homes talks to Neil Henderson and Brittany Henderson, the hosts of The Road to Family Freedom podcast. Shane graduated from Notre Dame in 2007 with a degree in finance. He became a derivatives trader right out of school but lost his job in the financial crisis in 2009. He then left to pursue a career in gambling, starting the venture Imawhale Staking in 2010, which he still runs to this day. In 2017 he began investing in real estate in southern Alabama, focusing on the BRRRR method using short-term rentals. He’s currently sitting on 35 doors with a goal of reaching 100 doors.

In this episode, we talk to Shane and Rachael about beginning their journey to real estate investing in 2017, how they scaled their portfolio from 1 to 35 doors, why they have converted most of their properties to short-term rentals, and tips and tricks on rehabbing and furnishing a short-term rental.

What You'll Learn in This Episode

• How Shane Sigsbee went from unemployed finance guy to professional gambler during the Great Recession
• How he started a business being the financial backer for professional poker players
• How he bought his first long-term rental property in Southern Alabama
• Using the BRRRR strategy to scale from 1 to 35 doors
• How to negotiate good terms on a seller finance deal
• How they are finding short term rental deals
• How they discovered the extraordinary cash flow of short-term rentals over long-term rentals
• A short-term rental doesn't necessarily have to be in a vacation market
• How to manage a short-term rental long distance
• Tips on automating 80% of your Airbnb guest communication
• Tips on furnishing a short-term rental
• Tips on making your Airbnb guest experience stand out from the competition
• How much does it cost to furnish a short-term rental?
• What amenities and property characteristics give you the best ROI (Return on Investment) with short-term rentals?

Books and Resources Mentioned

• The Road to Family Freedom: roadtofamilyfreedom.com
• Website: I’m A Whale Staking Group
• Instagram: @shanesigsbee
• Twitter: @ssigsbee
• Facebook: Shane Sigsbee

Follow Us:

• facebook.com/roadtofamilyfreedom/
• instagram.com/roadtofamilyfreedom/

Moe Kruger – Senior Loan Officer at Live Oak Bank talks to Neil Henderson and Brittany Henderson, the hosts of The Road to Family Freedom podcast. Moe Kruger is a 30-year banking veteran that specializes in storage financing for small business owners. Over his 30 years in banking, Moe has been a branch manager, bank business development officer, residential mortgage specialist, private banking manager, commercial relationship manager before settling in and focusing on helping small business owners. He has a great love for entrepreneurs and has spent the past 16 years financing business acquisitions, real estate acquisitions, and construction lending utilizing the Small Business Administration programs. He has closed close to a billion dollars in loans over his banking career including $250 million in storage loans. Moe joined Live Oak Bank in 2015 as a senior loan officer for the self-storage vertical. At Live Oak Bank, he is focused on loans that include construction deals, acquisitions, conversions, and mobile storage deals. 

In this episode, we talk to Moe about how he got into self-storage lending, the keys to successfully getting an SBA loan for self-storage, the difference between SBA versus traditional commercial loans, and the common gotchas you should avoid.

What You'll Learn from This Episode

• How Moe Kruger became a senior loan officer at Live Oak Bank
• How Live Oak Bank became the leading SBA Lender by dollar volume in the United States, especially for self-storage
• How to ensure a smooth SBA loan process when applying for financing on a self-storage facility
• Tips for successfully applying for SBA lending on self-storage
• Why you should look at lenders as a partner in your self-storage business
• Key things that will cause your SBA loan application to be denied
• SBA loans - What's the difference between a 7a and 504?
• What are the differences between SBA loans and traditional commercial lending?
• Can you bring in investors on a deal with SBA lending?
• Instances when a storage deal has gone bad and how having an experienced self-storage partner can save you
• Key questions to ask any potential SBA lender before using them to fund a self-storage deal
• Tips and considerations for new self-storage investors on how to successfully get an SBA loan

Books and Resources Mentioned

• The Road to Family Freedom: roadtofamilyfreedom.com
• Website: LiveOakBank.com
• Email: [email protected]
• Phone: (910) 550-2907

Follow Us:

• facebook.com/roadtofamilyfreedom/
• instagram.com/roadtofamilyfreedom/
• twitter.com/r2familyfreedom

Neil Wahlgren – Chief Operations Officer at MAG Capital Partners, talks to Neil Henderson and Brittany Henderson, the hosts of The Road to Family Freedom podcast. MAG Capital Partners is a private equity firm that specializes in sale-leaseback and industrial real estate investments. Neil brings nearly two decades of leadership in operations and capital markets. Prior to MAG Capital, Neil led a Bay Area real estate investment firm, raising capital for over $200M in projects. He came to real estate investing following a career in military aviation as a C-130 pilot in both the Air Force and Navy, logging over 2500 flight hours with combat tours to both Iraq and Afghanistan. 

In this episode, we talk to Neil about the details of investing in single tenant net lease industrial properties, the keys to building trust with potential private equity investors, the unique benefits to investing in a net lease industrial, and the key lessons from his military background that helped him to be successful raising private equity.

Books and Resources Mentioned

• The Road to Family Freedom: roadtofamilyfreedom.com
• Website: MAG Capital Partners
• Email: [email protected]

Follow Us:

• facebook.com/roadtofamilyfreedom/
• instagram.com/roadtofamilyfreedom/
• twitter.com/r2familyfreedom

Other Stuff:

• If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than 60 seconds, and it really makes a difference in helping to convince hard-to-get guests.
• For show notes and past guests, please visit roadtofamilyfreedom.com/episodes/
• Discover the tools and services we use, visit roadtofamilyfreedom.com/resources/

Mark Podolsky – aka The Land Geek, talks to Neil Henderson and Brittany Henderson, the hosts of The Road to Family Freedom podcast. Armed with only $3,000, Mark bought his first few parcels of raw land in 2001. Today Mark is the author of Dirt Rich, the ultimate guide to helping you build a passive income, and owner of successful and investing company Frontier Properties.

Prior to his land investing success, Mark felt trapped in a high-stress, corporate job. Escaping the rat race changed Mark’s life in so many positive ways that he decided to teach, coach, and mentor others to help them achieve their financial goals.

In this episode, we talk to Mark about how he first got into raw land investing, the dead-simple way he seeks out raw land to buy, the extraordinary systems he sets up to automate 95% of his business, and the ways he designs his week to maximize productivity and happiness.

Books and Resources Mentioned

• The Road to Family Freedom: roadtofamilyfreedom.com
• Website: The Land Geek
• Website: Frontier Properties USA
• Resource: AirTable
• Resource: Follow Up Boss
• Resource: Landmodo
• Resource: What Three Words

Follow Us:

• facebook.com/roadtofamilyfreedom/
• instagram.com/roadtofamilyfreedom/
• twitter.com/r2familyfreedom

Other Stuff:

• If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than 60 seconds, and it really makes a difference in helping to convince hard-to-get guests.
• For show notes and past guests, please visit