Episodes

  • [REAL STORIES] He Turned His Home Into a Rental That Paid Him While Abroad

    [REAL STORIES] He Turned His Home Into a Rental That Paid Him While Abroad
    Mar 31 2026
    What if your primary home didn’t tie you down but actually gave you the freedom to leave? Today’s guest didn’t buy his second home first, but when an unexpected job opportunity took him to Buenos Aires, he turned his primary home into a short-term rental, covering his mortgage and more. This Week’s Guest: Taylor Smith’s story is a little bit of a departure from what we usually talk about. He didn’t buy his second home first. Instead, he bought a primary home in Denver, with the intention of eventually turning it into a short-term rental. When an unexpected work opportunity in Buenos Aires arose, he was able to hop on a flight knowing his mortgage would be covered by his rental income. Taylor also works at Turno, a marketplace that connects short-term rental owners with cleaners and service providers, so he’s bringing an insider perspective on one of the most overlooked—but most important—parts of running a successful rental. Tune in to learn: -How growing up with parents in real estate shaped his path early on -The systems he put in place to manage his short-term rental from abroad -The conversation that changed how he thought about buying a home and why it’s simpler than we think Are you looking for more income, options and freedom in your life? Do you like the idea of owning a vacation home that pays for itself? If so, I hope you’ll join us in the inaugural class of the Second Home First Academy. We’re kicking off on April 8th, and in just five weeks I’ll teach you the exact four-step framework I used to find, finance, and furnish my three vacation homes so you can do it too. There are only a few spots remaining, so be sure to visit BuyYourSecondHomeFirst.com/Academy to sign up today. Key links: –Subscribe to the free weekly newsletter: BuyYourSecondHomeFirst.com/#subscribe –Visit the website: BuyYourSecondHomeFirst.com –Follow on Instagram and TikTok: @BuyYourSecondHomeFirst –Find us on Substack: SecondHomeFirst.Substack.com –Say Hi! Hello@BuyYourSecondHomeFirst.com (mailto:Hello@BuyYourSecondHomeFirst.com) A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Use code SHF20 for an ADDITIONAL (!) 20% their yearly and bi-yearly plans Minoan: https://www.Minoan.com/SecondHome Use the link provided to sign up and receive a free $25 in credit. Turno: https://go.turno.com/second_home_first Use the link provided to get $25 off your first clean. Flytographer: https://www.Flytographer.com/SHF Use code SHF25 for $25 off your first shoot PriceLabs: https://hello.pricelabs.co/signup/?referral=secondhomefirst Use code SecondHomeFirst (all one word) for a 30-day free trial, plus $10 off your first invoice
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    44 mins
  • [EXPERT] Top 1% Realtor on the Money Mistake Keeping you Stuck (and What to Do Instead)

    [EXPERT] Top 1% Realtor on the Money Mistake Keeping you Stuck (and What to Do Instead)
    Mar 24 2026
    Do you ever feel like you’re doing everything right but still not getting ahead? Today’s expert guest, a top 1% realtor, is breaking down how the beliefs around homeownership we learned growing up are still driving our decisions today. And how rethinking them can unlock more freedom than we ever thought possible. This Week’s Expert Guest: Lindsay Fricks is a top realtor in Arizona, not to mention a coach and mentor for fellow high achieving real estate agents. Lindsay and I discuss how the messages we learn in childhood are still influencing our purchasing decisions today; why an ideal second home is one that you can ‘lock and leave’; and, most importantly, that you don’t need to own where you live OR live where you own. Tune in to learn: -Why the traditional path to homeownership might be keeping you stuck -The biggest misconceptions people have about buying a second home -What “lock and leave” really means—and why it matters -How to start thinking like an investor (even if you don’t see yourself as one) Are you looking for more income, options and freedom in your life? Do you like the idea of owning a vacation home that pays for itself? If so, I hope you’ll join us in the inaugural class of the Second Home First Academy. We’re kicking off on April 8th, and in just five weeks I’ll teach you the exact four-step framework I used to find, finance, and furnish my three vacation homes so you can do it too. There are only a few spots remaining, so be sure to visit BuyYourSecondHomeFirst.com/ Academy to sign up today. Key links: –Subscribe to the free weekly newsletter: BuyYourSecondHomeFirst.com/#subscribe –Visit the website: BuyYourSecondHomeFirst.com –Follow on Instagram and TikTok: @BuyYourSecondHomeFirst –Find us on Substack: SecondHomeFirst.Substack.com –Say Hi! Hello@BuyYourSecondHomeFirst.com A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Use code SHF20 for an ADDITIONAL (!) 20% their yearly and bi-yearly plans Minoan: https://www.Minoan.com/SecondHome Use the link provided to sign up and receive a free $25 in credit. Turno: https://go.turno.com/second_home_first Use the link provided to get $25 off your first clean. Flytographer: https://www.Flytographer.com/SHF Use code SHF25 for $25 off your first shoot PriceLabs: https://hello.pricelabs.co/signup/?referral=secondhomefirst Use code SecondHomeFirst (all one word) for a 30-day free trial, plus $10 off your first invoice
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    48 mins
  • [REAL STORIES] Should this NYC Actress Buy a House in the Catskills? We Did the Math.

    [REAL STORIES] Should this NYC Actress Buy a House in the Catskills? We Did the Math.
    Mar 17 2026
    On this episode, we’re doing something we’ve never done before: we’re vetting a real Zillow listing to see if it could make a good vacation home investment. Join us as we walk through the exact process I use to evaluate a property’s income potential, risks, and overall potential to pay for itself. This Week’s Guest: Ruth Pferdehirt is an actress living in New York City. As an artist, Ruth shares that she had largely written off homeownership altogether. But when she received a large residual check from the Emmy-award winning show she does voiceover work for, she immediately knew she wanted to buy her second home first. In fact, she became the very first person to sign up for the inaugural class of the Second Home First Academy, which officially opened for registration today. Join us at BuyYourSecondHomeFirst.com/Academy Use code PODCAST for 40% off the Academy Tune in to learn: -How to evaluate a Zillow listing to see if it can pay for itself -What tools and websites can help estimate a property’s income potential -How to think about risk, budget, and financial comfort when buying your first investment property -Where to look to check short-term rental regulations Key links: –Subscribe to the free weekly newsletter: BuyYourSecondHomeFirst.com/#subscribe –Visit the website: BuyYourSecondHomeFirst.com –Follow on Instagram and TikTok: @BuyYourSecondHomeFirst –Find us on Substack: SecondHomeFirst.Substack.com –Say Hi! Hello@BuyYourSecondHomeFirst.com A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Use code SHF20 for an ADDITIONAL (!) 20% their yearly and bi-yearly plans Minoan: https://www.Minoan.com/SecondHome Use the link provided to sign up and receive a free $25 in credit Turno: https://go.turno.com/second_home_first Use the link provided to get $25 off your first clean Flytographer: https://www.Flytographer.com/SHF Use code SHF25 for $25 off your first shoot PriceLabs: https://hello.pricelabs.co/signup/?referral=secondhomefirst Use code SecondHomeFirst (all one word) for a 30-day free trial, plus $10 off your first invoice
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    46 mins
  • [EXPERT] How Much Should Guests Pay to Rent Your Vacation Home?

    [EXPERT] How Much Should Guests Pay to Rent Your Vacation Home?
    Mar 10 2026
    If you like the idea of owning a vacation home that pays for itself, it’s crucial to get your pricing right. Charge too much and no one books — charge too little and you’re leaving money on the table. This week’s expert episode breaks down the biggest myths, mistakes, and misconceptions about pricing so that your second home can help you build both memories and wealth. This Week’s Expert Guest: Richie Khandelwal is the Co-Founder of the dynamic pricing software PriceLabs, a tool that helps hosts stop guessing and start setting prices based on real demand. Richie shares the biggest pricing mistakes new hosts make and how to avoid them; how shifts in supply and demand change what your home can earn night by night; and how PriceLabs’ algorithm analyzes more than 20 million data points every single day to take both the uncertainty — and the emotion — out of our pricing decisions. Tune in to learn: -Why most new hosts price their vacation home incorrectly (and how to avoid the most common mistake) -What is dynamic pricing works (hint: airlines and hotels have used it for decades) -How supply and demand should change your home’s nightly price -Why pricing can feel emotional and how data removes the guesswork Want to own a vacation home that pays for itself? Learn more about the Second Home First Academy at BuyYourSecondHomeFirst.com/Academy Key links: –Subscribe to the free weekly newsletter: BuyYourSecondHomeFirst.com/#subscribe –Visit the website: BuyYourSecondHomeFirst.com –Follow on Instagram and TikTok: @BuyYourSecondHomeFirst –Find us on Substack: SecondHomeFirst.Substack.com –Say Hi! Hello@BuyYourSecondHomeFirst.com A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Use code SHF20 for an ADDITIONAL (!) 20% their yearly and bi-yearly plans Minoan: https://www.Minoan.com/SecondHome Use the link provided to sign up and receive a free $25 in credit. Turno: https://go.turno.com/second_home_first Use the link provided to get $25 off your first clean. Flytographer: https://www.Flytographer.com/SHF Use code SHF25 for $25 off your first shoot PriceLabs: https://hello.pricelabs.co/signup/?referral=secondhomefirst Use code SecondHomeFirst (all one word) for a 30-day free trial, plus $10 off your first invoice
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    31 mins
  • [REAL STORIES] Rent-Stabilized in the West Village. Vacation homeowner in Connecticut.

    [REAL STORIES] Rent-Stabilized in the West Village. Vacation homeowner in Connecticut.
    Mar 3 2026
    If you’re a self-employed freelancer and think getting a mortgage, especially on a second home, just isn’t possible, this week’s episode is for you. Our guest, a New York City–based travel journalist, didn’t want to give up his rent-stabilized apartment in the West Village. So instead of stretching to buy in Brooklyn, he leveraged little-known lending options to purchase a mid-century modern fixer-upper in Connecticut— turning his love of architecture from something he writes about into something he actually owns. This Week’s Guest: Paul Jebara is a freelance journalist who writes about travel, architecture and design. Even though he has found the unicorn of Manhattan real estate—a rent-stabilized apartment in the coveted West Village—he considered giving it up to buy in Brookly. But as his search went on, his budget kept climbing, the neighborhoods he could afford kept getting further out, and the compromises within the space kept stacking up. Eventually, Paul decided to keep renting in the West Village and buy his second home first, a mid-century modern fixer upper in Litchfield County, Connecticut. Tune in to learn: -Why buying a fixer-upper became Paul’s strategic advantage to avoid bidding wars -How writing a thoughtful letter to the sellers helped Paul’s lower-priced offer win out -How Paul navigated financing as a longtime freelancer, including mortgage options available to self-employed buyers that many traditional lenders don’t even know about ***Paul is currently a “Sweet Spotter”. Take the quiz to determine what type of Vacation Home Owner you would be: BuyYourSecondHomeFirst.com/quiz Want to buy a vacation home that pays for itself? Learn more about the Second Home First Academy at BuyYourSecondHomeFirst.com/Academy Key links: –Subscribe to the free weekly newsletter: BuyYourSecondHomeFirst.com/#subscribe –Visit the website: BuyYourSecondHomeFirst.com –Follow on Instagram and TikTok: @BuyYourSecondHomeFirst –Find us on Substack: SecondHomeFirst.Substack.com –Say Hi! Hello@BuyYourSecondHomeFirst.com A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Use code SHF20 for an ADDITIONAL (!) 20% their yearly and bi-yearly plans Minoan: https://www.Minoan.com/SecondHome Use the link provided to sign up and receive a free $25 in credit. Turno: https://go.turno.com/second_home_first Use the link provided to get $25 off your first clean. Flytographer: https://www.Flytographer.com/SHF Use code SHF25 for $25 off your first shoot PriceLabs: https://hello.pricelabs.co/signup/?referral=secondhomefirst Use code SecondHomeFirst (all one word) for a 30-day free trial, plus $10 off your first invoice
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    40 mins
  • [EXPERT] The Side Hustle That Comes With Free Vacations

    [EXPERT] The Side Hustle That Comes With Free Vacations
    Feb 24 2026
    Owning a vacation home that pays for itself doesn’t have to mean handing over control—or handing over your profits. This week’s episode reveals how technology has made self-managing your vacation home as a short-term rental easier than ever, allowing you to earn more while doing less. This Week’s Expert Guest: Shaun Shirazian is the CEO of Lodgify, a short-term rental software designed to simplify the management and marketing of your vacation home. He breaks down how self-managing a vacation rental can be far easier than most people think, especially when you have the right systems in place. Tune in to learn: -What it actually takes to manage your home as a short-term rental. -How Lodgify helps hosts get more bookings with less effort -Ways to spend less time managing and more time enjoying your property -How advancements in AI are shifting software to become your personal assistant Want to own a vacation home that pays for itself? Learn more about the Second Home First Academy at https://www.BuyYourSecondHomeFirst.com/Academy Key links: –Lodgify: https://lodgify.com/?afmc=28y –Subscribe to the free weekly newsletter: BuyYourSecondHomeFirst.com/#subscribe –Visit the website: BuyYourSecondHomeFirst.com –Follow on Instagram and TikTok: @BuyYourSecondHomeFirst –Find us on Substack: SecondHomeFirst.Substack.com –Say Hi! Hello@BuyYourSecondHomeFirst.com A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Use code SHF20 for an ADDITIONAL (!) 20% their yearly and bi-yearly plans Minoan: https://www.Minoan.com/SecondHome Use the link provided to sign up and receive a free $25 in credit. Turno: https://go.turno.com/second_home_first Use the link provided to get $25 off your first clean. Flytographer: https://www.Flytographer.com/SHF Use code SHF25 for $25 off your first shoot PriceLabs: https://hello.pricelabs.co/signup/?referral=secondhomefirst Use code SecondHomeFirst (all one word) for a 30-day free trial, plus $10 off your first invoice
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    29 mins
  • [REAL STORIES] The Decision That Gave Her More Freedom Than a ‘Forever Home’ Ever Could

    [REAL STORIES] The Decision That Gave Her More Freedom Than a ‘Forever Home’ Ever Could
    Feb 17 2026
    What if buying your second home first was the key to more freedom, flexibility, and options than you ever thought possible? That’s what happened for this week’s guest, whose decision to skip buying a primary home in Brooklyn set off a chain reaction that changed her career and her life for the better. ***Interested in learning to buy a vacation home that pays for itself? I’m launching the inaugural class of the Second Home First Academy. Join the waitlist to receive priority access, plus a special launch discount available only to subscribers. https://www.buyyoursecondhomefirst.com/academy *** This Week’s Guest: Blythe Graham-Jones was living in Brooklyn when she started exploring what it would take to buy in her neighborhood. The numbers were staggering. Instead of locking herself into that version of homeownership, Blythe chose a different route. She purchased a home in the Hamptons and thanks to strong summer rental demand, literally received a check at closing—the rent payment from the summer tenants, that would cover her costs for the next year. Tune in to learn: -Why Brooklyn’s price tags pushed her to question the “primary home first” narrative -The biggest misconceptions about buying in the Hamptons -How to get paid at closing -How buying her second home first unlocked a whole new career Key links: –What type of vacation home owner would you be? Take the Quiz- BuyYourSecondHomeFirst.com/Quiz –Subscribe to the free weekly newsletter: BuyYourSecondHomeFirst.com/#subscribe –Visit the website: BuyYourSecondHomeFirst.com –Follow on Instagram and TikTok: @BuyYourSecondHomeFirst –Find us on Substack: SecondHomeFirst.Substack.com –Say Hi! Hello@BuyYourSecondHomeFirst.com (mailto:Hello@BuyYourSecondHomeFirst.com) A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Use code SHF20 for an ADDITIONAL (!) 20% their yearly and bi-yearly plans Minoan: https://www.Minoan.com/SecondHome Use the link provided to sign up and receive a free $25 in credit. Turno: https://go.turno.com/second_home_first Use the link provided to get $25 off your first clean. Flytographer: https://www.Flytographer.com/SHF Use code SHF25 for $25 off your first shoot PriceLabs: https://hello.pricelabs.co/signup/?referral=secondhomefirst Use code SecondHomeFirst (all one word) for a 30-day free trial, plus $10 off your first invoice
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    27 mins
  • [EXPERT] This Real Estate Agent Says the “Forever Home” is a Myth

    [EXPERT] This Real Estate Agent Says the “Forever Home” is a Myth
    Feb 10 2026
    What if 99% of real estate agents are the WRONG agent for you? This week, our expert guest is exposing why that is—and what to look for in order to avoid a six-figure mistake. This Week’s Expert Guest: Jonathan Greene is a real estate agent, investor and the host of the podcast Zen and the Art of Real Estate Investing. He’s here to pull back the curtain and give us the good, the bad, and the ugly in the world of real estate agents. Jonathan breaks down how old school mindsets: like “renting is just throwing money away” or you “NEED” a forever home - are not only outdated, but harmful. He also shares insider guidance on how to evaluate prospective agents for your home search, what really matters in an agent-client relationship, and why he believes that 99% of real estate agents are the wrong agent for you. Tune in to learn: -Why buying a “forever home” may not be the smartest strategy -Why more wealthy people are choosing to rent -What to look for when picking a real estate agent -Red flags to look out for in the home buying process Key links: –What type of vacation home owner would you be? Take the Quiz- BuyYourSecondHomeFirst.com/Quiz –Subscribe to the free weekly newsletter: BuyYourSecondHomeFirst.com/#subscribe –Visit the website: BuyYourSecondHomeFirst.com –Follow on Instagram and TikTok: @BuyYourSecondHomeFirst –Find us on Substack: SecondHomeFirst.Substack.com –Say Hi! Hello@BuyYourSecondHomeFirst.com A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Use code SHF20 for an ADDITIONAL (!) 20% their yearly and bi-yearly plans Minoan: https://www.Minoan.com/SecondHome Use the link provided to sign up and receive a free $25 in credit Turno: https://go.turno.com/second_home_first Use the link provided to get $25 off your first clean Flytographer: https://www.Flytographer.com/SHF Use code SHF25 for $25 off your first shoot PriceLabs: https://hello.pricelabs.co/signup/?referral=secondhomefirst Use code SecondHomeFirst (all one word) for a 30-day free trial, plus $10 off your first invoice
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    40 mins