Episodes

  • [EXPERT] The Kid-Friendly Details Every Vacation Home Needs

    [EXPERT] The Kid-Friendly Details Every Vacation Home Needs
    May 26 2026
    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! Hello@BuyYourSecondHomeFirst.com 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
    Show More Show Less
    28 mins
  • [REAL STORIES] This NYC Teacher Stopped Waiting for “Someday” and Bought a Cottage in the Poconos

    [REAL STORIES] This NYC Teacher Stopped Waiting for “Someday” and Bought a Cottage in the Poconos
    May 19 2026
    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! Hello@BuyYourSecondHomeFirst.com 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
    Show More Show Less
    48 mins
  • [REAL STORIES] She Escaped Texas Summers by Buying a House in Maine

    [REAL STORIES] She Escaped Texas Summers by Buying a House in Maine
    May 12 2026
    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! Hello@BuyYourSecondHomeFirst.com 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
    Show More Show Less
    43 mins
  • When Your Vacation Home Becomes a TV Star

    When Your Vacation Home Becomes a TV Star
    May 5 2026
    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! Hello@BuyYourSecondHomeFirst.com 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
    Show More Show Less
    21 mins
  • [EXPERT] Can Buying a Vacation Home Make Your W2 Optional?

    [EXPERT] Can Buying a Vacation Home Make Your W2 Optional?
    Apr 28 2026
    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
    Show More Show Less
    53 mins
  • Which is the Bigger Risk: Failing or Not Trying?

    Which is the Bigger Risk: Failing or Not Trying?
    Apr 21 2026
    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
    Show More Show Less
    20 mins
  • You Don't Need to Be Rich: The Real Numbers Behind Our Vacation Homes

    You Don't Need to Be Rich: The Real Numbers Behind Our Vacation Homes
    Apr 14 2026
    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
    Show More Show Less
    24 mins
  • [EXPERT] How to Buy a Vacation Home with Family or Friends

    [EXPERT] How to Buy a Vacation Home with Family or Friends
    Apr 7 2026
    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
    Show More Show Less
    32 mins