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Road to Family Freedom

Neil and Brittany Henderson

How much Money does it take to get started in a specific real estate investing niche? How much Knowledge does it take? How much Time does it take once you're up and running? And how Location dependent is it? Tune in each week to follow our journey and learn as we interview successful investors and entrepreneurs who have achieved or are well on their way to achieving financial and location independence, with a special focus the Time, Money, Knowledge and Location dependence of their chosen investment niche.

  • 21 minutes 41 seconds
    Why Invest in Self-Storage? And Why Now?

    In the second part of our conversation with Clint Harris, we talk about how and why we are investing in self-storage. Clint is a successful active investor in short-term rentals, but he is transitioning into investing in self-storage. We talk about why he has made that shift, as well as the strengths of our partners at Nomad Capital. 

    In This Episode We Cover:

    • The Importance of Diversification into Passive Investing Assets
    • The Similarities of the Technologic Shifts that are Happening in Self-Storage and Short-Term Rentals
    • Who is Consuming Self-Storage Right Now?
    • The Opportunities that the Decline in Big-Box Retail Presents for Self-Storage
    • And much more!

    Schedule a Call with Us to Talk About Self-Storage


    Books and Resources Mentioned:


    Follow Us:


    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/

    28 January 2022, 11:00 am
  • 58 minutes 50 seconds
    How to Scale Your Short-Term Rental Business with Clint Harris

    Clint Harris – a short-term rental investor and owner of Salt and Soul Property Management talks to Neil Henderson, the host of The Road to Family Freedom podcast. When we last spoke to Clint Harris in February of 2020, he owned 14 short-term rental units. In this episode, we talk to Clint about how he has scaled his portfolio to over 60 units under management. Clint has been a real estate investor for over a decade with his wife, starting with long-term single-family home investing but has since transitioned into short-term rentals, including their own house on the beach.

    In This Episode We Cover:

    • The Top 3 Challenges a Short-Term Rental Investors Faces when Trying to Scale
    • The importance of working ON your business, not IN your business
    • Should you hire experienced short-term rental cleaners or regular cleaners and train them?
    • Where are the best places to invest in short-term rentals today?
    • And much more!

    Books and Resources Mentioned:


    Schedule a Call with Us to Talk About Self-Storage


    Follow Us:


    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/

    25 January 2022, 11:00 am
  • 1 hour 6 minutes
    How to Find Commercial Industrial Deals Like a Wholesaler with Darren Smith

    After serving almost six years in the Army, Darren Smith has spent the last eighteen years as a professional real estate investor. He has flipped, rented, and wholesaled hundreds of residential properties, and in recent years has purchased several million dollars of industrial properties as long-term holds. Darren’s greatest achievement has been to surround himself with an incredible team of industry and military veterans who are every bit as passionate about helping people as he is. His biggest supporters are his wife Lauren and his son Henry.

    In This Episode We Cover:

    • What is the best way to market for commercial real estate properties to purchase?
    • The incredible story of how he earned a $500,000 wholesale fee on one property
    • Why your marketing focus should be narrow and deep, not wide and shallow
    • Why you should analyze every deal that you come across at the beginning of your real estate journey
    • And much more!

    Books and Resources Mentioned:


    Follow Us:


    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/

    17 January 2022, 11:00 am
  • 36 minutes 59 seconds
    Building Your Network Using Clubhouse with Luke Wong

    Luke Wong, the founder of 9 Mile Capital, has been around real estate most of his life as his family has always been in real estate. From owning commercial and residential properties to land development. Luke grew up in Miami and graduated from Florida State University. He moved to Houston in 2001 and worked in land acquisitions acquiring land for residential subdivisions. From 2011 to 2020, he renovated houses and owned a wholesaling operation. In the last few years, he has also been actively investing in Commercial Real Estate, such as Retail Centers and Apartment Complexes. Currently, he is focusing on operating, growing, and acquiring more self-storage facilities. He owns/co-owns about 1200 storage units.

    In This Episode We Cover:

    • What is Clubhouse?
    • Luke Wong’s real estate background
    • His transition to commercial real estate
    • How he got started in self-storage investing passively
    • And much more!

    Books and Resources Mentioned:


    Follow Us:


    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/

    30 November 2021, 11:00 am
  • 1 hour 4 minutes
    Ditching the Grind of House Flipping for Self-Storage Success with Rob DuBroc

    Rob Dubroc is a 35-year-old real estate investor from Kansas City who went all-in on self-storage after testing the waters with house flipping, working as a realtor, and single-family rentals. After grinding those various side hustles he found his way into commercial real estate and self-storage.

    In this episode, we talk to Rob about how he bought his first facility for cash and then promptly quit his W-2 job, the challenges of transitioning a poorly check and cash facility into auto payments, the best investment he’s made to help his storage business run more smoothly, and the unique way he encourages stubborn sellers into giving him access to their financials. 

    In This Episode We Cover:

    • How he bought his first self-storage facility for cash and then promptly quit his W-2 job
    • How to transition a poorly run check and cash storage facility into a well-run auto payment facility
    • The best investment to help run your self-storage facility more smoothly
    • How to encourage stubborn self-storage owners to give them access to their financials
    • And much more!

    Books and Resources Mentioned:


    Follow Us:


    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/

    22 November 2021, 11:00 am
  • 54 minutes 45 seconds
    How to Analyze a Market for Self-Storage with Katherine D’Agostino

    Katherine D’Agostino is the founder and sensei of Self-Storage Ninjas. After selling a previous business, Katherine jumped into the storage business building three facilities from the ground up in three years. She also runs a feasibility-analysis firm focused on delivering unbiased reports to self-storage investors that result in facilities with high occupancy and the highest possible returns. 

    In this episode, we talk to Katherine about how she got into the self-storage business, how to pick a self-storage market to invest in, her unique plan to scale by building facilities from the ground up, and why she thinks boat and RV storage is a good business.

    In This Episode We Cover:

    • How Katherine D’Agostino got into the self-storage business
    • How to pick a self-storage market to invest in
    • Her unique plan to scale by building facilities from the ground up
    • Why boat and RV storage is a good business
    • And much more!

    Books and Resources Mentioned:


    Follow Us:


    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/

    15 November 2021, 11:00 am
  • 43 minutes 56 seconds
    Commercial Lending Tips for Self-Storage with Mandy Monson

    In this episode we talk to Mandy Monson about her background in finance, how she found herself in the self-storage business, what a self-storage borrower should do to ensure a successful loan application, the 5 C’s of credit, and the big one you should pay attention as a self-storage owner.

    Mandy Monson is the VP of Finance for Resort Lifestyle Communities, which manages a portfolio of senior independent living communities, but she’s also co-founder of Stor365 with previous guest Victor Diaz and today she’s here to talk to us about commercial lending on self-storage. Mandy is a finance professional and real estate developer that also works with other women to help them crush their limiting beliefs and fear of failure so that they determine their own destiny in the realm of career and money. She has spent a career in finance with everything from managed money portfolios, to commercial loan underwriting during the Great Recession, to today where she consults with potential borrowers on how to structure loans for the acquisition of self-storage and senior housing.

    In This Episode We Cover:

    • How to ensure a successful loan application on a self-storage deal
    • Some things that will surely sink a self-storage loan application
    • Common mistakes self-storage investors make in their underwriting
    • Examples of when a self-storage deal has gone bad
    • And much more!

    Books and Resources Mentioned:


    Follow Us:


    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/

    9 November 2021, 11:00 am
  • 16 minutes 32 seconds
    We are MOVING!

    In this episode, Neil & Brittany discuss their upcoming move to North Carolina to pursue self-storage full time and live in a house hack across the street from the beach.

    In This Episode We Cover:

    • We bought a house across the street from the beach with the intention of doing a house hack “someday maybe” - We will go into more detail on the house in a later episode.
    • What led us to decide to make the move now?
    • First, we call this podcast The Road to Family Freedom. Our goal is financial and location independence. We aren’t there yet. But we have achieved a level of independence with our investments that allow us to take this leap, which is a risk, to try an experiment in working for ourselves...while living at the beach.
    • Several things conspired to lead us to this decision:
    • The death of my father in March of 2020. A best friend worked alongside him for 18 years. I realized that so much of my joy of going to work every day came from the experience of getting to be with my dad on a daily basis. Making up for lost time from when he was in the Air Force. I found I missed being able to walk down the hall and tell him something cool I’d just read, or how much fun it was to whine to him about the challenges of being a father, or just getting to go to lunch with him nearly every day. Suddenly going to work every day became a sad reminder of what was no longer there.
    • COVID. Like many people, the pandemic has made us do a lot of soul searching about what’s important in life. As we prepared for my father’s long-delayed memorial, I was putting together a slideshow of his life. I kept coming back to these pictures of us from a time when we lived near the ocean. My mom and dad both describe those days in Florida as some of the happiest times of their life. Their kids were young, the work was easy, they were surrounded by other families, many of whom became lifelong friends, we lived near the water. I've always had a dream of living near the water, and I'd like to do it while our son is still young.
    • We love house hacking, and we have a lot of experience house hacking with a short-term rental. Right as COVID hit in March of 2020, the short-term rental regulations in Las Vegas finally caught up with us after 6 years. We got shut down. That, combined with concerns over what COVID was going to do to the Las Vegas housing market, caused us to sell our house that we had owned since 2013. We ended up with a healthy chunk of cash from the equity we had accrued. So, we bought a house across the street from the beach with the intention of house hacking it eventually way down the road. Obviously, things changed.
    • My work, since 2003, has been indirectly in support of the war effort in Iraq, Afghanistan, and the Global War on Terror. When the war in Afghanistan came to an end, it felt like the end of a chapter for me. 
    • So we sat down, did the math, and discovered we could financially take this risk. We aren't financially free. We don't have the income to sit on the beach all day drinking Pina Coladas. I prefer margaritas or Moscow Mules. But we've got savings and income streams to give us some time to work towards our next chapter. 

    Follow Us:


    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/

    12 October 2021, 2:00 pm
  • 1 hour 2 minutes
    Lessons for New Storage Owners from an Experienced Manager with Victor Diaz

    In this episode, we talk to Victor Diaz about how he got his start in self-storage, the mistakes he sees many new self-storage owners making, how to stand out from the crowd when marketing to potential sellers, and the changes he’s seen in the storage industry since he got into it.

    Victor Diaz is the co-founder of Stor365.com, a new consulting firm that specializes in helping self-storage owners operate their small storage portfolios the way a large REIT would. Victor’s entire adult life has been spent in the self-storage business where he was general manager and then an area field manager for U-Haul. He now oversees 8 facilities and over 670,000 square feet of storage for a private firm in Ohio.

    In This Episode We Cover:

    • Ways a self-storage owner can incentivize their on-site manager to achieve better performance
    • Emerging trends in the self-storage industry
    • The biggest mistakes new self-storage investors make
    • Why you should not rely solely on the self-storage supply index when evaluating a self-storage facility for purchase
    • And much more!

    Books and Resources Mentioned:


    Follow Us:


    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/

    31 May 2021, 11:00 am
  • 39 minutes 37 seconds
    Passive Real Estate Investing Strategies with Alka Kumar

    In this episode, we talk to Alka Kumar about how concerns over burnout as a doctor led her to pursue additional streams of passive income, how she scaled after buying that first single-family rental, how she purchased a small mobile home park using her self-directed retirement account, and why she is focused on investing passively in real estate syndications.

    Alka Kumar of YourWealthMD.com came to the United States from India with $40 in her pocket. Fast forward to today and she has been making a comfortable living working as a physician for the last 30 plus years. A few years ago, she realized that she was overworked and heading towards burnout. This forced her to look for passive and semi-passive sources of income which led her to real estate. She has now switched to working part-time as a physician and spends her free time focusing on expanding her real estate portfolio. That currently includes a local rental portfolio, a small mobile home park, and numerous passive real estate syndications.

    In This Episode We Cover:

    • Why high-income earners such as doctors, lawyers, corporate executives would want to pursue passive real estate investing
    • Why she chose to purchase a rental property in a coastal community with cash
    • How she went about scaling her real estate portfolio after that first single-family rental
    • Why she transitioned out of buying single-family rentals
    • And much more!

    Books and Resources Mentioned:


    Follow Us:


    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/

    23 May 2021, 2:00 pm
  • 53 minutes 29 seconds
    40,000 Square Foot Self-Storage Deal as First Facility with Christian Mercado

    In this episode, we talk to Christian Mercado about how he purchased his first piece of real estate using a VA loan, how a light bulb went off after he started renting one of his rooms out, how he purchased his first self-storage for zero money down, and the key to negotiating with self-storage owners.

    Christian Mercado is a full-time real estate investor and Army Captain. He got his start in real estate in 2017 with the purchase of his first house utilizing a VA loan. 6 months later, he rented a room out and discovered the power of house hacking. After a year, he purchased another home to live in using his VA loan and rented out the first, and he was off to the races. Since that time he has flipped at least 8 houses, opened up several short-term rentals, and purchased a self-storage facility.

    In This Episode We Cover:

    • How he bought his first property using a VA loan
    • The red flags that led him to walk away from his first self-storage deal
    • How he found his first self-storage deal
    • How he negotiated with the seller to purchase for zero down with seller financing
    • And much more!

    Books and Resources Mentioned:


    Follow Us:


    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/

    17 May 2021, 11:00 am
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