Second Home First

Second Home First

What if your 401(k) came with a fire pit and a lake view? Hosted by hospitality veteran and short-term rental expert, Katie Cline, Second Home First is a brand new podcast that explores an unconventional path to homeownership. For Katie, living in New York City made buying a home feel impossible, so she decided to flip the script and buy her ‘second home’ first. With renting now more affordable than owning in all 50 of the largest U.S. metros, buying any home–let alone a ‘second’ one–has never felt more out of reach. But Second Home First shows listeners how to make homeownership not only possible, but profitable by purchasing a vacation home that can double as a short-term rental—building wealth for tomorrow while providing a place to vacation for free today! What 401(k) can do that? As a 3x vacation home owner, Katie breaks down her proven strategy step by step, sharing actionable lessons each week so listeners can do it too. In addition to tactical solo episodes, the show will feature exclusive interviews with experts, real stories from people who’ve done it too, and Q&A coaching sessions with aspiring second home owners. Second Home First gives listeners the tools, insights, and inspiration to make their dream vacation home a reality.

  1. HACE 2 DÍAS

    [EXPERT] Can Buying a Vacation Home Make Your W2 Optional?

    When COVID hit, I made three budgets: what would happen if I lost my job, what would happen if my husband lost his job, and what would happen if we both did. It was the first time I really understood how fragile a single stream of income can be—and how important it is to build something beyond it. This week’s expert guests, Grace Gudenkauf and Amelia McGee, are the co-founders of Women Invest in Real Estate (WIIRE), a community, podcast and series of retreats. They teach women how to become W2 optional so others can avoid feeling the same way I did. Tune in to learn: -Why the traditional path we’ve been taught (think 9-to-5 job, 401k investments) isn’t the only way to approach life -How certain beliefs are quietly holding us back -How growing up in the Midwest shaped their mindset around money, work, and doing everything themselves -Some tips and tricks on how to start thinking and operating like the CEO of your own business Key links: –Second Home First Academy: https://www.BuyYourSecondHomeFirst.com/academy *Use code PODCAST for 40% off –Use code KATIE for $200 off WIIRE Summer Camp, taking place this September in the Poconos: https://www.wiire.com/summercamp —Check out the Women Invest in Real Estate podcast: https://wiire.com/thewiirepodcast –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 For a limited time, use code SHF60 for 60% off their yearly and bi-yearly plans (*until April 30, 2026). 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

    53 min
  2. 21 ABR

    Which is the Bigger Risk: Failing or Not Trying?

    What if I told you that the difference between the people who build the life they want and the people who just think about it isn’t timing, money, or even confidence. It’s their willingness to take a risk before they feel ready. On this episode, we’re talking about how to know when it’s time to take a risk and the 3 things I wish I knew before I took my first. Tune in to learn: -How to know if a risk is actually “smart”… not just scary -The simple framework I used to make my first property feel safe enough to say yes -Why waiting for certainty might be the biggest mistake you can make Key links: –Second Home First Academy: BuyYourSecondHomeFirst.com/academy *Use code PODCAST for 30% off –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 For a limited time, use code SHF60 for 60% off their yearly and bi-yearly plans (*until April 30, 2026). 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

    20 min
  3. 14 ABR

    You Don't Need to Be Rich: The Real Numbers Behind Our Vacation Homes

    What if I told you that you don’t need to be rich to buy a second home? And that actually, buying that very home could be the thing that MAKES you rich!? On this episode, I’m pulling back the curtain on the real numbers behind our second homes. What they cost. What we invested. What they make. And why this strategy has completely changed the way we think about wealth. Tune in to learn: -How much you need for a down payment on a second home (hint: it’s not 20%) -The full cost breakdown—from purchase to furnishing to getting your first guest in the door -Negotiation strategies to reduce upfront cash -How much my vacation homes actually earn -The exact mindset shift that took us from “must be nice” to owning 3 homes in under 3 years Key links: –Set-Up Cost Calculator: BuyYourSecondHomeFirst.com/set-up-cost-calc –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 For a limited time, use code SHF60 for 60% off their yearly and bi-yearly plans (*until April 30, 2026). 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

    24 min
  4. 7 ABR

    [EXPERT] How to Buy a Vacation Home with Family or Friends

    What if the fastest way to afford your dream vacation home was to buy it with someone else? On this week’s expert episode, we’re unpacking exactly how to buy your second home with family or friends, and how to structure the partnership to protect both your finances and your relationship. This Week’s Expert Guest: I’m joined by Natalie Palmer, the host of the No Vacancy podcast, a seasoned short-term rental operator, a co-host, and most importantly for today’s discussion, someone who’s fundraised thousands of dollars for vacation home projects. She’s seen every version of partnership: couples who bought together and thrived; friends who had a falling out after 20 years; people who’ve built a real estate portfolio with millions without ever investing a dollar of their own money. Tune in to learn: -How to buy a second home with someone else, whether that’s a sibling, a best friend, or another family you love traveling with. -How to split equity, responsibilities, and usage so no one feels resentful down the line -What to include in your agreement to protect both the investment and the relationship -The biggest mistakes Natalie has seen in long-term partnerships—and how to avoid them -How to plan for the “what ifs” before they happen 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 For a limited time, use code SHF60 for 60% off their yearly and bi-yearly plans (*until April 30, 2026). 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

    32 min
  5. 31 MAR

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

    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

    44 min
  6. 24 MAR

    [EXPERT] Top 1% Realtor on the Money Mistake Keeping you Stuck (and What to Do Instead)

    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

    48 min
  7. 17 MAR

    [REAL STORIES] Should this NYC Actress Buy a House in the Catskills? We Did the Math.

    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

    46 min
  8. 10 MAR

    [EXPERT] How Much Should Guests Pay to Rent Your Vacation Home?

    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

    31 min
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What if your 401(k) came with a fire pit and a lake view? Hosted by hospitality veteran and short-term rental expert, Katie Cline, Second Home First is a brand new podcast that explores an unconventional path to homeownership. For Katie, living in New York City made buying a home feel impossible, so she decided to flip the script and buy her ‘second home’ first. With renting now more affordable than owning in all 50 of the largest U.S. metros, buying any home–let alone a ‘second’ one–has never felt more out of reach. But Second Home First shows listeners how to make homeownership not only possible, but profitable by purchasing a vacation home that can double as a short-term rental—building wealth for tomorrow while providing a place to vacation for free today! What 401(k) can do that? As a 3x vacation home owner, Katie breaks down her proven strategy step by step, sharing actionable lessons each week so listeners can do it too. In addition to tactical solo episodes, the show will feature exclusive interviews with experts, real stories from people who’ve done it too, and Q&A coaching sessions with aspiring second home owners. Second Home First gives listeners the tools, insights, and inspiration to make their dream vacation home a reality.

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