Second Home First

For a lot of people (myself included), the “dream” isn’t just owning a vacation home that pays for itself—it’s owning a place that your family genuinely loves to visit. But that creates an interesting challenge: how do you furnish and design a home in a way that works beautifully for you and your family while also appealing to other traveling families as guests? That’s exactly what we’re, ahem, unpacking today. This Week’s Expert Guest: Sarah Huff is a baby gear & family travel expert, host of the Tiny Travelers podcast, and the Senior Manager of Customer and Community at BabyQuip. *Check out BabyQuip: https://www.babyquip.com?a=e1afd34 and get $20 off using code SUITESUCCESS20 Tune in to learn: –Why designing around the rhythms of a child’s day can completely transform the guest experience –What creates the most stress for families while traveling and how thoughtful hosts can eliminate friction before guests even arrive –The biggest mistakes hosts make when trying to cater to kids –How to create spaces that feel functional for families without feeling cluttered or chaotic –Why family-friendly design can lead to better reviews, repeat bookings, and more memorable stays Key links: –Second Home First Academy: https://www.BuyYourSecondHomeFirst.com/academy *Use code PODCAST for 40% off –Subscribe to the free weekly newsletter: BuyYourSecondHomeFirst.com/#subscribe –Visit the website: https://www.BuyYourSecondHomeFirst.com –Follow on Instagram and TikTok: @BuyYourSecondHomeFirst –Find us on Substack: https://www.SecondHomeFirst.Substack.com –Say Hi! [email protected] A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Click the link and enter code HOME20 for an additional 20% off 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

How many of us are currently putting something off for the hypothetical “someday?” This guest realized he didn’t want to wait around to enjoy his life. So instead of buying a primary home in New York City, he and his family bought a cottage in the Poconos—and in the process, completely changed the way they think about home, family life, and the pursuit of “more.” This Week’s Guest: Tyler Moore is a NYC school teacher, but you might know him as “Tidy Dad”. Through his bestselling book, Tidy Up Your Life; his podcast, Tidy Tidbits; his Instagram, @TidyDad; and his newsletter, Tyler is known for sharing thoughtful reflections on parenting, routines, organization and intentional living. Tune in to learn: –How a simple question from a yoga teacher changed his approach homeownership –Why they intentionally searched for the cheapest homes in the nicest neighborhoods –How they bought a cottage in the Poconos for less than $170,000 –The hidden costs Tyler considers before making any big decision –Why Tyler believes learning to say “no” is just as important as knowing when to say “yes” Key links: -Tyler’s Book: Tidy Up Your Life - https://amzn.to/49ds3FM -Tyler’s Podcast: Tidy Tidbits - https://podcasts.apple.com/us/podcast/tidy-tidbits/id1816271318 –Second Home First Academy: https://www.BuyYourSecondHomeFirst.com/academy *Use code PODCAST for 40% off –Subscribe to the free weekly newsletter: https://www.BuyYourSecondHomeFirst.com/#subscribe –Visit the website: https://www.BuyYourSecondHomeFirst.com –Follow on Instagram and TikTok: @BuyYourSecondHomeFirst –Find us on Substack: https://www.SecondHomeFirst.Substack.com –Say Hi! [email protected] A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Click the link and enter code HOME20 for an additional 20% off 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

What if attaining your “dream life” didn’t require quitting your job, becoming a millionaire, or even moving someplace else? Today’s guest, a native Texan, bought her second home first in coastal Maine after falling in love with east coast summers. Now, she’s building a life around flexibility, optionality and of course, seasonality. This Week’s Guest: Texas native Taylor Summer is a digital nomad who fell in love with east coast summers. After falling in love with New England’s slower pace, cooler weather and historic charm, Taylor and her husband bought a home in Midcoast Maine with the goal of creating a seasonal lifestyle: east coast summers, Texas winters. Today, Taylor balances personal use of the home with mid-term rental income. Tune in to learn: –Why Taylor has no regrets buying at nearly an 8% interest rate –How Taylor manages to offset most of her expenses, even while enjoying the property herself in the peak summer months –Why buying in a completely different part of the country comes with brand new considerations, from basements and sump pumps to the realities of winter in Maine –The difference between short-term and mid-term rentals –The mindset shift that helped her ignore outside opinions Key links: –Second Home First Academy: BuyYourSecondHomeFirst.com/academy *Use code PODCAST for 40% 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! [email protected] A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Click the link and enter code HOME20 for an additional 20% off 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

On this episode of Second Home First, I’m taking you behind the scenes of something I never could have predicted: my very first vacation home, Trout Landing, being featured on an Emmy Award-winning TV show! But this episode isn’t really about TV. It’s about what happens when you put yourself in the game. When we bought this home, I thought I was making one decision—buying a place to make family memories. Along the way, I also realized what a smart financial decision it was. But what I didn’t realize is it was also opening doors to opportunities I couldn’t even see yet. In this episode, I share: –How Trout Landing was discovered by a TV producer –The behind-the-scenes process of getting selected –What it actually takes to prepare a vacation rental for filming –The last-minute chaos (and perfectionism spiral) before the shoot –And the bigger lesson: why the ROI of a second home goes far beyond income Key links: –Second Home First Academy: BuyYourSecondHomeFirst.com/academy *Use code PODCAST for 40% 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! [email protected] A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Click the link and enter code HOME20 for an additional 20% off 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

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! [email protected] 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

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! [email protected] 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

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! [email protected] 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

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! [email protected] 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

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! [email protected] (mailto:[email protected])  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

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! [email protected] 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

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! [email protected] 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

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! [email protected] 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

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! [email protected] 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

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! [email protected] 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

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! [email protected] (mailto:[email protected])  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

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! [email protected] 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

Imagine realizing that the down payment you’ve been saving to buy a primary home in Brooklyn would be enough money to buy your second home entirely in cash. On today’s Real Stories episode, you’ll meet Liz, who traded city price tags for the Hudson Valley, and hear why that property didn’t stay her ‘second home’ for very long. This Week’s Guest: Liz was born and raised in Brooklyn, New York. When she and her husband began househunting in Greenpoint, she was shocked to learn that a barely 3 bedroom fixer upper would cost $3 million. So instead, Liz decided to buy her second home first, a gorgeous a-frame in the Hudson Valley’s Dover Plains, for less than a fifth of what a smaller place would’ve cost her in Brooklyn. Tune in to learn: -Why making gingerbread houses with her kids sealed the deal on her second home -How “test-driving” a property by staying there first can change everything -Why emotional connection matters just as much as the numbers -The surprising outcome of this purchase that no one saw coming 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! [email protected] (mailto:[email protected])  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 Turno: https://go.turno.com/second_home_first  Use the link provided to get $25 off your first clean. 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 Minoan: https://www.Minoan.com/SecondHome   Use the link provided to sign up and receive a free $25 in credit.

What if I told you that setting up your dream vacation home didn’t have to take months? In this episode of Second Home First, host Katie Cline breaks down exactly how she and her husband renovated and furnished an entire waterfront vacation home in just seven days — with a newborn and a toddler — while she was only two months postpartum. Katie shares the full behind-the-scenes of buying the home site-unseen (!), designing the entire house from her apartment five hours away, and using systems, outsourcing, and help from family to get the home renovated, furnished, photographed and welcoming its first paying guest within just 20 days. Tune in to learn: –Why Katie felt confident making offer on a home without touring it first –The system she used to furnish the entire house remotely –Why using movers, painters, and landscapers saved months of work –How to trade money for time without burning yourself out –The real numbers from the first 10 weeks live on Airbnb Key links: –The Corresponding Substack Post: https://secondhomefirst.substack.com/p/how-i-renovated-and-furnished-an  –Regulations Podcast Episode: –”Is Renting Your Vacation Home Even Legal?” Substack: https://secondhomefirst.substack.com/p/is-renting-your-vacation-home-even  –Due Diligence Checklist: https://www.buyyoursecondhomefirst.com/the-red-tape/due-diligence-checklist  –Due Diligence Worksheet: https://www.buyyoursecondhomefirst.com/the-red-tape/due-diligence-worksheet  –Register your interest for the Set Up Checklist: http://buyyoursecondhomefirst.com/like-a-pro/set-up-checklist  –Unboxing Timelapsed Video: https://www.instagram.com/p/DNEt_FPPWsp/  –Tree Hair Cut Timelapsed Video: https://www.instagram.com/p/DNGjugNs0qX/  –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! [email protected] (mailto:[email protected])  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

Are you a “real” adult if you don’t own your primary home? Today’s expert guest, a generational researcher, explains how that definition of true adulthood was shaped by our parents’ era—and why it’s no longer relevant for Millennials and Gen Z. This Week’s Expert: Dr. Meghan Grace is a generational expert, researcher, and author who’s spent her career studying how Millennials and Gen Z are reshaping the way we think about careers, money, and yes, real estate. She’s here to share insights on why younger generations are especially drawn to strategies like Second Home First—from growing up in the sharing economy to coming of age in a digital-first world. She also breaks down the latest research which just might prove that my Baby Boomer Dad’s skepticism wasn’t personal—but generational. Tune in to learn: -Why the “forever home” is a myth  -How generational mindset shifts impact our approach to life -How younger buyers are using short-term rentals to offset mortgages and build equity -Why renting in high-cost cities can be a strategic financial move, not a failure -How buying a second home first can unlock both lifestyle freedom and long-term wealth 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! [email protected] (mailto:[email protected])  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

Imagine discovering that the thing that would unlock more freedom and flexibility for your family wasn’t scaling your business… but owning a vacation home. Today’s guest learned that firsthand when, instead of buying a primary home, she jumped into investing—and watched just two properties earn more in a year than her husband’s lucrative salary as a dentist. This Week’s Guest: Kacia Ghetmiri is the host of the wildly popular EmpowerHer podcast, which boasts more than 14 million downloads (!). Based in Denver, she and her husband were saving to buy a primary home when they decided to buy their second home first… or more accurately, homes. They wanted to invest in real estate to give their family more optionality in the future and to find a way to stop trading time for money.  Tune in to learn: -Why surrounding yourself with people who are already doing what you want to do is the fastest way to prove it’s possible. -How creative financing can make owning a vacation home far more attainable than you think. -That YOU are your own target guest. -Why Kacia believes NOT investing in real estate is actually the riskiest move of all. 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! [email protected]  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

Are you dreaming of owning a vacation home that looks like it was pulled straight from the pages of Arch Digest? Today’s expert episode breaks down exactly how to design with intention, and shares our expert’s predictions of the top interior design trends for 2026. What type of vacation home owner would you be?  Take the quiz to find out: BuyYourSecondHomeFirst.com/Quiz This Week’s Expert: Alex McBride is the Senior Brand Partnerships Manager at Minoan, a free platform that helps vacation-home owners furnish smarter and save on the brands they already love. In her role, Alex works closely with more than 180 premium home and lifestyle brands, giving her a front-row seat to the world of interior design. With her finger on the pulse of what’s in and what’s out, Alex helps translate industry trends into practical design decisions for second home owners. Tune in to learn: -The top interior design trends of 2025 -Expert predictions for the top three interior design trends of 2026 -Why vacation homes should be designed differently than primary residences -Why intentionality matters more than ever in vacation home design -The simple trick every owner should use before committing to design decisions -How to earn passive income by making your home shoppable 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! [email protected]  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

What if, a year from now, you were ringing in the New Year from your dream vacation home? One that builds equity, appreciates and grows your wealth, all while someone else is paying your mortgage. Oh, and gives you a place to vacation for free!  Sign Up for the Live Masterclass to Help You Buy Your Second Home in 2026: https://secondhomefirst.kit.com/7a034eb70d On this episode of Second Home First, host Katie Cline walks you through exactly how to turn the idea of “someday” into a plan (and a purchase!) in 2026. Instead of vague resolutions, she shares five clear, doable steps that move you closer to owning a vacation home that fits your life and your finances. Katie also shares her own story of buying her second home first, providing listeners and viewers with the master plan she wishes she had when going through the process herself. Whether you’re just starting to dream or already dabbling on Zillow, this episode is your roadmap to make 2026 the year you buy your vacation home. Tune in to learn: -Why talking to a mortgage lender early is a power move -How to decide where to buy, and why your first choice may not be your final one -The biggest mistakes people make when it comes to understanding short-term rental regulations -How to find the right real estate agent -Why touring homes before you’re “ready” is one of the smartest steps you can take Download the free Starter Kit: https://www.buyyoursecondhomefirst.com/set-goals-that-work-for-you/starter-kit  Vacation Home Owner Archetype Quiz: https://www.buyyoursecondhomefirst.com/quiz  Where to Buy links: –WHERE Should You Buy a Vacation Home? A Step-By-Step Guide: https://podcasts.apple.com/us/podcast/where-should-you-buy-a-vacation-home-a-step-by-step-guide/id1849178409?i=1000737452794  –The Secret to Picking the Perfect Place For Your Vacation Home on Substack: https://secondhomefirst.substack.com/p/the-secret-to-picking-the-perfect  Regulations links: –Download the Due Diligence Worksheet: https://www.buyyoursecondhomefirst.com/the-red-tape/due-diligence-worksheet   –Download the Due Diligence Checklist: https://www.buyyoursecondhomefirst.com/the-red-tape/due-diligence-checklist –Is Renting Your Dream Vacation Home… Illegal? https://podcasts.apple.com/us/podcast/is-renting-your-dream-vacation-home-illegal/id1849178409?i=1000740372286  –Is Renting Your Vacation Home Even Legal? on Substack https://secondhomefirst.substack.com/p/is-renting-your-vacation-home-even  Other 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! [email protected]  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

What if the most valuable part of owning a vacation home isn’t the real estate itself… but the moments the house makes possible? Just in time for the holidays, today’s expert episode explores how to make the most of the time we share with the people we love, and how to capture those memories to last a lifetime. This Week’s Expert: Nicole Smith, Founder and CEO of Flytographer, reveals how a single bad selfie in Paris sparked a global travel-photography company and completely changed the way millions of travelers document their vacations. Nicole breaks down why meaningful memories matter, how to be more intentional with the photos you take, and the simple storytelling techniques that make family trips (and vacation homes!) feel richer, more connected, and truly unforgettable. Tune in to learn: -Why most travelers are documenting their vacations all wrong (and how to fix it) -How to capture emotion, rituals, and micro-moments that make any vacation home stand out -The storytelling principles every vacation-home owner should use when photographing their property -The biggest mistakes people make when taking photos on vacation -Why your vacation home becomes a powerful marker of time and how to preserve those memories for years to come 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! [email protected]  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

What would you do if the only way to afford a home in your city meant compromising on almost everything you wanted — and spending close to a million dollars to get it?  On this Real Stories episode, you’ll meet Leanne, who realized that buying in New York City meant giving up too much… and instead chose to buy her second home first on Hilton Head Island for half the price. In this conversation, Leanne shares why working with a local real estate agent became a game-changer, how hiring a management company turned into an essential part of her success, and the one simple question her realtor asked that completely shifted her buying strategy. Tune in to learn: -The question her Hilton Head realtor asked her that changed everything -Why buying a vacation home made more financial sense than buying in Manhattan -What she learned about closing costs, timelines and out-of-state ownership -Why hiring a local management company became a key to her success -How she balances personal use vs. maximizing revenue -Her advice for anyone scared to take the leap — especially doing it alone 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! [email protected]  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

If you’re dreaming of owning a vacation home that pays for itself, there’s one thing you simply can’t ignore: regulations. On today’s episode, we’re diving into this crucial (and often overlooked) step of the buying process. I’ll walk you through exactly how to find out if a property can be legally rented, what existing rules mean for your purchase, and how to track the trends and community attitudes that shape the regulations of tomorrow. Tune in to learn: -How to figure out who’s actually in charge -The easiest way to check short-term rental regulations -How to gauge community sentiment and spot red flags before you buy -What permits you might need—and what’s required to get approved Key links: –Download the Due Diligence Worksheet: https://www.buyyoursecondhomefirst.com/the-red-tape/due-diligence-worksheet  –Download the Due Diligence Checklist: https://www.buyyoursecondhomefirst.com/the-red-tape/due-diligence-checklist –US Census Bureau's Geocoder website (choose “Stateside Parsed Address Processing” under “Find Geographies”): https://geocoding.geo.census.gov/geocoder/geographies/address?form  –Is Renting Your Vacation Home Even Legal? on Substack: https://secondhomefirst.substack.com/p/is-renting-your-vacation-home-even  –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! [email protected]  A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y *Extended until December 12, use code BF65SHFVIP for 65% (!) off their yearly and bi-yearly Professional and Ultimate 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 Keywords: short-term rental regulations, STR regulations, short term rental regulations, Airbnb regulations, rules, permits

What if the money you’ve been saving for retirement could actually help you buy your dream vacation home now… without paying a single penalty? Today’s expert episode unlocks a little-known strategy that could completely shift your mindset around affordability—and show you that your down payment may already be within reach. This Week’s Expert: Olivia Tati, founder of Wanderlust Wealth Academy and real estate investor extraordinaire, is breaking down how she used her 401(k) to buy her first investment property. She demystifies the risks and rewards, explains the step-by-step process, and shows how borrowing against your retirement savings can help you take your second home leap. Tune in to learn: -How a 401(k) loan works and why it’s different from cashing out (no penalties, no taxes, interest goes back to you!) -The exact steps Olivia took to buy her first investment property with her retirement funds -How to evaluate if this strategy makes sense for your own second home goals -Tips for navigating lenders, providers, and maximizing your investment Key links: –Olivia’s 401(k) loan Substack post: https://substack.com/home/post/p-172426546  –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! [email protected]  –Contact Olivia: @TheOliviaTati and OliviaTati.com A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y *From now until December 4, use code BF65SHFVIP for 65% (!) off their yearly and bi-yearly Professional and Ultimate 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

Before you fall in love with a pool, a fireplace or a view, let’s get clear on what exactly you’re looking for in a vacation home. This week, I’m helping you define your vacation home vision—the details, big and small, that would give a home the real wow factor to you. And by the end of this episode, you’ll have a personalized checklist to scroll Zillow with confidence. Prepare the Pinterest boards! Grab a pack of sticky notes and tune in to learn: -The key questions to ask yourself to uncover what you want -How browsing Airbnb, VRBO, and Booking.com can spark ideas -Why ranking your wishlist helps you make smarter, faster buying decisions -Ways to align your vision with co-buyers (family, friends, a significant other) Download the Vacation Home Vision template for free- https://www.buyyoursecondhomefirst.com/your-ideal-vacation-home/vacation-home-vision Sticky Note Exercise- https://www.buyyoursecondhomefirst.com/your-ideal-vacation-home/sticky-note-exercise  Visit the website: BuyYourSecondHomeFirst.com Subscribe to the free weekly newsletter: BuyYourSecondHomeFirst.com/#subscribe  Follow on Instagram and TikTok: @BuyYourSecondHomeFirst Find us on Substack: SecondHomeFirst.Substack.com  Say Hi! [email protected]  A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y *From now until December 4, 2025, use code BF65SHFVIP for 65% (!) off their yearly and bi-yearly Professional and Ultimate 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

You know you want to own a vacation home, but you’re not sure WHERE it should be. The coast? The mountains? The countryside? Choosing the right spot is overwhelming—and getting it wrong can cost you time, money, and stress. On this episode, we’re tackling the biggest question in your second-home journey: Where should you actually buy? We’ll show you how to find your perfect spot—and why having a Plan B (and maybe even a Plan C) is essential. Grab a pack of sticky notes, because this week it’s all about location, location, location. Grab a pack of sticky notes and tune in to learn: -Why this is the most important decision you’ll make (no pressure!) -How to get started when you have no idea WHERE you want to buy -The sticky-note exercise that will help you define your ideal destination -Why you need a Plan A, a Plan B… and maybe even a Plan C Key links: –Sticky Note Exercise- https://www.buyyoursecondhomefirst.com/your-ideal-vacation-home/sticky-note-exercise –Take the Vacation Home Owner Archetype 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! [email protected]  A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y *From now until December 4, use code BF65SHFVIP for 65% (!) off their yearly and bi-yearly Professional and Ultimate 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

What type of vacation home owner would you be? And more importantly, why does that matter? Before you start scrolling Zillow or shopping for throw pillows, this is one question you have to answer. On today’s episode, we’re breaking down the three vacation home owner archetypes—and how knowing yours will influence every decision you make. Take the Vacation Home Owner Archetype Quiz to find out which type you’d be: BuyYourSecondHomeFirst.com/Quiz  Tune in to learn: -About the three vacation home owner archetypes: Profit Maximizer, Sweet Spotter, and First Dibber -Why your archetype affects everything, from where you buy to what you can afford -How your archetype can shift over the course of a mortgage (or even a single year) Key links: Visit the website: BuyYourSecondHomeFirst.com Subscribe to the free weekly newsletter: BuyYourSecondHomeFirst.com/#subscribe  Follow on Instagram and TikTok: @BuyYourSecondHomeFirst Find us on Substack: SecondHomeFirst.Substack.com  Say Hi! [email protected] 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 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

What if your best investment account isn’t your 401(k)… but a vacation home? On the very first episode of Second Home First, host Katie Cline explores why buying your ‘second home’ first could be the smartest way to build wealth and vacation for free. Katie shares her own journey from renting in New York City to buying a vacation home in upstate New York, and how that decision became a game changing investment strategy for her. You’ll learn: –Why buying your second home first just might be the smartest way to build wealth and joy –How owning a vacation home can build equity and generate income while giving you a place to vacation for free –Why the “must be nice” mentality might be getting in your way –The five questions to help you decide if this strategy is right for you Plus, Katie shares free resources to help you get started:  –The ‘Should You Buy Your Second Home First’ Quiz –The Second Home First Starter Kit, with the immediate next steps to take to get closer to owning your dream vacation home (sent upon completion of the quiz) Visit the website: BuyYourSecondHomeFirst.com Take the Quiz: BuyYourSecondHomeFirst.com/Quiz  Subscribe to the free weekly newsletter: BuyYourSecondHomeFirst.com/#subscribe  Bankrate article: Bankrate.com/real-estate/rent-vs-buy-affordability-study/  Renting vs. Buying Spreadsheet: BuyYoursSecondHomeFirst.com/your-ideal-vacation-home/rent-vs-buy  Follow on Instagram and TikTok: @BuyYourSecondHomeFirst Find us on Substack: SecondHomeFirst.Substack.com  Say Hi! [email protected]  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 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

What if your 401(k) came with a fire pit and a lake view? On Second Home First, host Katie Cline flips the script on traditional homeownership. After years of believing buying a home in New York City was impossible, Katie bought her “second home” first—a vacation property that not only became a personal retreat but also a profitable short-term rental. Each week, Katie shares strategies, insights, and real-life examples to help listeners take action. Episodes fall into three categories: Real Stories: Guests share their journeys, challenges, and lessons learned from buying a second home first. Expert Advice: Specialists—from mortgage lenders and real estate agents, to designers and property managers—offer unfiltered guidance to help listeners make smart decisions. Deep Dives: Katie walks through her exact process for finding, furnishing, and financing now 3 vacation homes, providing actionable steps to evaluate potential properties and maximize results. If you thought owning any home, let alone a second one, was out of reach, this is the show is for you. This is Second Home First. Visit the website: BuyYourSecondHomeFirst.com Subscribe to the free weekly newsletter: BuyYourSecondHomeFirst.com/#subscribe Follow on Instagram and TikTok: @BuyYourSecondHomeFirst Find us on Substack: SecondHomeFirst.Substack.com Say Hi! [email protected]