Which is the Bigger Risk: Failing or Not Trying?

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

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 [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 [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 [https://www.BuyYourSecondHomeFirst.com] –Follow on Instagram and TikTok: @BuyYourSecondHomeFirst –Find us on Substack: https://www.SecondHomeFirst.Substack.com [https://www.SecondHomeFirst.Substack.com] –Say Hi! Hello@BuyYourSecondHomeFirst.com A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y [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 [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 [https://go.turno.com/second_home_first] Use the link provided to get $25 off your first clean. Flytographer: https://www.Flytographer.com/SHF [https://www.Flytographer.com/SHF] Use code SHF25 for $25 off your first shoot PriceLabs: https://hello.pricelabs.co/signup/?referral=secondhomefirst [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

[REAL STORIES] This NYC Teacher Stopped Waiting for “Someday” and Bought a Cottage in the Poconos

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 [https://amzn.to/49ds3FM] -Tyler’s Podcast: Tidy Tidbits - https://podcasts.apple.com/us/podcast/tidy-tidbits/id1816271318 [https://podcasts.apple.com/us/podcast/tidy-tidbits/id1816271318] –Second Home First Academy: https://www.BuyYourSecondHomeFirst.com/academy [https://www.BuyYourSecondHomeFirst.com/academy] *Use code PODCAST for 40% off –Subscribe to the free weekly newsletter: https://www.BuyYourSecondHomeFirst.com/#subscribe [https://www.BuyYourSecondHomeFirst.com/#subscribe] –Visit the website: https://www.BuyYourSecondHomeFirst.com [https://www.BuyYourSecondHomeFirst.com] –Follow on Instagram and TikTok: @BuyYourSecondHomeFirst –Find us on Substack: https://www.SecondHomeFirst.Substack.com [https://www.SecondHomeFirst.Substack.com] –Say Hi! Hello@BuyYourSecondHomeFirst.com A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y [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 [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 [https://go.turno.com/second_home_first] Use the link provided to get $25 off your first clean. Flytographer: https://www.Flytographer.com/SHF [https://www.Flytographer.com/SHF] Use code SHF25 for $25 off your first shoot PriceLabs: https://hello.pricelabs.co/signup/?referral=secondhomefirst [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

[REAL STORIES] She Escaped Texas Summers by Buying a House in Maine

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 [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 [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 [https://go.turno.com/second_home_first] Use the link provided to get $25 off your first clean. Flytographer: https://www.Flytographer.com/SHF [https://www.Flytographer.com/SHF] Use code SHF25 for $25 off your first shoot PriceLabs: https://hello.pricelabs.co/signup/?referral=secondhomefirst [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 Your Vacation Home Becomes a TV Star

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 [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 [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 [https://go.turno.com/second_home_first] Use the link provided to get $25 off your first clean. Flytographer: https://www.Flytographer.com/SHF [https://www.Flytographer.com/SHF] Use code SHF25 for $25 off your first shoot PriceLabs: https://hello.pricelabs.co/signup/?referral=secondhomefirst [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

[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 [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 [https://www.wiire.com/summercamp] —Check out the Women Invest in Real Estate podcast: https://wiire.com/thewiirepodcast [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 [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 [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 [https://go.turno.com/second_home_first] Use the link provided to get $25 off your first clean. Flytographer: https://www.Flytographer.com/SHF [https://www.Flytographer.com/SHF] Use code SHF25 for $25 off your first shoot PriceLabs: https://hello.pricelabs.co/signup/?referral=secondhomefirst [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