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Second Home First: Daily Summaries Delivered
by Second Home First
What if your 401(k) came with a fire pit and a lake view? Hosted by hospitality veteran and short-term rental expert, Katie Cline, Second Home First explores an unconventional path to homeownership. For Katie, living in New York City made buying a home feel impossible, so she decided to flip the script and buy her ‘second home’ first. With renting now more affordable than owning in all 50 of the largest U.S. metros, buying any home–let alone a ‘second’ one–has never felt more out of reach. But Second Home First shows listeners how to make homeownership not only possible, but profitable by purchasing a vacation home that can double as a short-term rental—building wealth for tomorrow while providing a place to vacation for free today! What 401(k) can do that? As a 3x vacation home owner, Katie breaks down her proven strategy step by step, sharing actionable lessons each week so listeners can do it too. In addition to tactical solo episodes, the show features exclusive interviews with experts, real stories from people who’ve done it too, and Q&A coaching sessions with aspiring second home owners. Second Home First gives listeners the tools, insights, and inspiration to make their dream vacation home a reality.
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- 1 weeks ago45 min
[REAL STORIES] They Skipped the Starter Home and Bought the Lake House from their Wedding Vows
Wedding vows usually include promises of love and commitment, but for today’s guest, they also included the dream of owning a lake house someday—something both she and her husband thought would take them nearly two decades to achieve. But instead of waiting, they first bought an investment property across the country, and its success made their waterfront dream come true in less than a year. This Week’s Guest: Megan Carter and her husband turned a second home in Minnesota into The Gofer House, a popular short-term rental for University of Minnesota game weekends. That single investment helped them purchase their dream Wisconsin lake house in less than a year, something they thought would take them 10 to 15 years. Tune in to Learn: –How Megan used a short-term rental to buy her dream lake house in less than a year –Why Megan chooses to manage her properties herself, even though she lives across the country –How to navigate a gut renovation, managed from afar –Why tax strategies specific to owning short-term rentals can help accelerate goals and fund future property purchases –What spending intentionally means to Megan and her definition of financial success 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 (mailto: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. Somerled: https://form.jotform.com/252193985491065?howDid=Referral&typeA19=Second%20Home%20First Use the link provided to schedule your free consultation call. Listeners of SHF also get $1,000 off virtual design & $3,000 off design & project management services. 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
- 2 weeks ago38 min
[EXPERT] The Truth About Vacation Rental Management Companies
Owning a vacation home that pays for itself sounds like a dream—but what happens when managing that property starts to feel like a second job? Today’s expert guest is pulling back the curtain on management companies, sharing what you really get for your money, the red flags to look out for, and how to decide when it might be time to hand over the reins. This Week’s Expert Guest: Jason Muth is the co-founder of Prideaway Stays, a boutique vacation rental management company based in Provincetown, Massachusetts, and the host of the SmartStay podcast. Jason shares what it's really like to work with a property management company, including what services they provide, how much they charge, and how to decide whether hiring one makes financial sense. Tune in to Learn: –When to hire a property manager versus self-manage your vacation rental –What management companies charge and how their fees affect your profits.The key green flags and red flags to look out for when choosing a property manager –How to handle guest feedback and decide which complaints are worth addressing –How to calculate the opportunity cost of enjoying your vacation home versus renting it out 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 (mailto: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. Somerled: https://form.jotform.com/252193985491065?howDid=Referral&typeA19=Second%20Home%20First Use the link provided to schedule your free consultation call. Listeners of SHF also get $1,000 off virtual design & $3,000 off design & project management services. 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
- 3 weeks ago31 min
[REAL STORIES] He Kept Renting in Williamsburg and Impulse-Bought a Beach Crash Pad
When most people think of an impulse buy, they probably think of a new pair of shoes. But for today’s guest, it was a beach crash pad. After feeling like he missed his chance to buy in New York City due to climbing real estate prices post-Covid, this banker decided to keep renting in Williamsburg and buy his “second home” first on Long Island in Long Beach. This Week’s Guest: Michael “Phase” Phelan has built an insanely successful career in banking and had considered buying a primary home in Williamsburg, where he’s been renting for more than a decade. But then, he made what he calls an “impulsive” decision and decided to buy his second home first: a one-bedroom condo in Long Beach. He plans to use the home as a beach crash pad for now and, eventually, turn it into a long-term rental. Tune in to Learn: –Why Phase chose to buy a vacation home in Long Beach instead of a primary home in Brooklyn –How he found a beachside condo for a fraction of the price of buying in NYC –Why buying a second home first can take the emotion out of real estate decisions –The biggest lessons from navigating the home-buying process as a first-time buyer –How Phase plans to enjoy his beach getaway now and turn it into a long-term rental in the future 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 (mailto: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. Somerled: https://form.jotform.com/252193985491065?howDid=Referral&typeA19=Second%20Home%20First Use the link provided to schedule your free consultation call. Listeners of SHF also get $1,000 off virtual design & $3,000 off design & project management services. 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
- 4 weeks ago48 min
[ABROAD] This Chicago Lawyer Bought a Farmhouse… in Italy
Second Home First is going international! This episode kicks off our brand-new Second Home First Abroad series with a trip to Italy, where a Chicago lawyer is transforming an old farmhouse into two luxury suites, complete with a pool, a sauna in the former stables, and a wine tasting room in the old cantina. This Week’s Guest: Claire Stephens is a lawyer who lives in Chicago but decided to buy a property in Liguria, Italy. This isn’t just any property, but a farmhouse next door to a home that’s been in her family for generations. She talks about challenges of buying a property in a different country from where you live—not to mention, in a different language! And she reminds us that while this is a slow process, something she estimates will take about five years, the finished product isn’t the only part of the process she’s looking forward to. Tune in to Learn: —What it’s really like to buy a home in Italy as a foreigner —The importance of building relationships with the local community —How to find and build a trusted local team you can rely on —Claire’s renovation plans for the property and the timeline —Why building strong relationships can be your biggest advantage when investing overseas. 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 (mailto: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. Somerled: https://form.jotform.com/252193985491065?howDid=Referral&typeA19=Second%20Home%20First Use the link provided to schedule your free consultation call. Listeners of SHF also get $1,000 off virtual design & $3,000 off design & project management services. 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
- Sep 29, 202642 min
[EXPERT] Is the Starter Home Dead? A New York Times Real Estate Journalist Weighs In
The housing market is constantly making headlines, whether it’s rising home prices, high interest rates, or a shortage of homes for sale. But today, we’re hearing from someone who covers the topic for one of the most influential publications in the world: the New York Times. Real estate journalist, Heather Senison, who wrote the full-page feature on Second Home First, is here to share what she’s seeing from today’s homebuyers—and where homeownership could be headed next. This Week’s Expert Guest: Heather Senison is an award-winning real estate journalist who writes for The New York Times. She takes us behind the scenes—what made my pitch stand out to her, what surprised her the most once she started reporting, and what journalists actually consider when they choose what (or who) to feature… and what or who to cut. Tune in to Learn: –Is the starter home dead? –Why she doesn’t believe today’s housing market is a bubble –What she thinks could change the way we buy homes in the years ahead. –How journalists evaluate sources, build stories, and decide what makes it into a major publication 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 (mailto:Hello@BuyYourSecondHomeFirst.com) A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y For a limited time, click the link and enter code SHF-60 for 60% off their Professional and Ultimate plans. *Offer good September 21-30, 2026 Somerled: https://form.jotform.com/252193985491065?howDid=Referral&typeA19=Second%20Home%20First Use the link provided to schedule your free consultation call. Listeners of SHF also get $1,000 off virtual design & $3,000 off design & project management services. 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
- Sep 22, 202640 min
[EXPERT] The Good Ol’ Days Are Happening Right Now
After her husband was involved in a serious car accident while on his way to a work conference, today’s expert guest began to reevaluate everything. What followed was a leap of faith to create more time and freedom for her and her family, while also solving a problem for others that they had experienced firsthand. This Week’s Guest: Rose Tipka is the CEO and Founder of Your Family’s Place, a vacation rental company in Ohio’s Amish country focused on larger homes spread across 75 acres. Not only is Rose’s company impressive, but what makes her story even more interesting is that she had no background in real estate at all. In fact, before creating Your Family’s Place, Rose was a schoolteacher who then became a stay-at-home mom, homeschooling all SIX of her children. Tune in to Learn: –How to identify an underserved audience by solving a problem you’ve experienced yourself –Why you don’t need a real estate or hospitality background to become a successful host –How thoughtful, low-cost guest touches can create memorable experiences and stronger loyalty –How to balance financial numbers with personal intuition when evaluating vacation homes –How vacation rentals can help you build the time, freedom, and family life you actually want 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 (mailto:Hello@BuyYourSecondHomeFirst.com) A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y For a limited time, click the link and enter code SHF-60 for 60% off their Professional and Ultimate plans. *Offer good September 21-30, 2026 Somerled: https://form.jotform.com/252193985491065?howDid=Referral&typeA19=Second%20Home%20First Use the link provided to schedule your free consultation call. Listeners of SHF also get $1,000 off virtual design & $3,000 off design & project management services. 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.
- Sep 15, 202636 min
[REAL STORIES] They Bought a Lake House Instead of an NYC Apartment and Paid it Off in 15 Years
Nearly two decades ago, today’s guests were a young couple living in Jersey City, dreaming of buying a home in Manhattan. But instead of stretching their budget to buy in the city, they decided to buy a lake house in the Poconos. In just 15 years, they used income from short-term renters to pay it off entirely—and now, they’re using the equity they built to construct their dream vacation home just down the road. This Week’s Guests: David Bigler and Jillian O’Neill are a married couple who bought their second home first almost two decades ago. They were living in Jersey City at the time, dreaming of moving into Manhattan, when they decided to do something different and buy a lakehouse in the Poconos instead. Tune in to Learn: –The difference between good debt and and bad debt –Why Dave and Jill started out as "First Dibbers" but now consider themselves "Profit Maximizers" (Take the Quiz to find out what type of vacation home owner you would be: https://www.buyyoursecondhomefirst.com/freebies#quiz) –How they paid off their lake house in full in 15 years, using income earned from short-term renters –Why building genuine relationships with neighbors is essential 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 (mailto:Hello@BuyYourSecondHomeFirst.com) A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y For a limited time, click the link and enter code SHF-60 for 60% off their Professional and Ultimate plans. *Offer good September 21-30, 2026 Somerled: https://form.jotform.com/252193985491065?howDid=Referral&typeA19=Second%20Home%20First Use the link provided to schedule your free consultation call. Listeners of SHF also get $1,000 off virtual design & $3,000 off design & project management services. 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
- Sep 8, 202635 min
[EXPERT] Think You Can’t Afford a Vacation Home?
Do you dream of owning a vacation home but think you can’t afford it? What if I told you that you might need way less cash than you think? Today’s expert guest is breaking down the money myths and mortgage misconceptions that cause so many of us to rule ourselves out. She’s also sharing why talking to a lender just might reveal that you’re closer to owning your dream vacation home than you think. This Week’s Expert Guest: Jessica Khani is a mortgage lender, who’s also an investor and an entrepreneur. Find her at HomesWithJessicaKhani.com or @HomesWithJessicaKhani on social. Tune in to Learn: –The difference between getting a mortgage for your primary home versus a second home –How lenders determine how much you can actually afford –What credit score you need to have in order to get the most favorable terms –How much time you’re required to spend in the property each year and whether or not there’s a maximum number of days you can rent it out –Actionable, tactical advice for improving your credit score before you buy Jessica was also featured on this episode of SHF: [EXPERT] How to Buy a House Apple Podcasts- https://podcasts.apple.com/us/podcast/expert-how-to-buy-a-house/id1849178409?i=1000774809997 Spotify- https://open.spotify.com/episode/1y5Bgc57iQWFKddPHySfJB YouTube- https://www.youtube.com/watch?v=JZRuM7vJ8ok 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 (mailto:Hello@BuyYourSecondHomeFirst.com) A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y For a limited time, click the link and enter code SHF-60 for 60% off their Professional and Ultimate plans. *Expires September 8, 2026 Somerled: https://form.jotform.com/252193985491065?howDid=Referral&typeA19=Second%20Home%20First Use the link provided to schedule your free consultation call. Listeners of SHF also get $1,000 off virtual design & $3,000 off design & project management services. Turno: https://go.turno.com/second_home_first Use the link provided to get $25 off your first clean. Flytographer: https://www.Flytographer.com/SHF Use code SHF25 for $25 off your first shoot PriceLabs: https://hello.pricelabs.co/signup/?referral=secondhomefirst Use code SecondHomeFirst (all one word) for a 30-day free trial, plus $10 off your first invoice
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About Second Home First
What if your 401(k) came with a fire pit and a lake view? Hosted by hospitality veteran and short-term rental expert, Katie Cline, Second Home First explores an unconventional path to homeownership. For Katie, living in New York City made buying a home feel impossible, so she decided to flip the script and buy her ‘second home’ first. With renting now more affordable than owning in all 50 of the largest U.S. metros, buying any home–let alone a ‘second’ one–has never felt more out of reach. But Second Home First shows listeners how to make homeownership not only possible, but profitable by purchasing a vacation home that can double as a short-term rental—building wealth for tomorrow while providing a place to vacation for free today! What 401(k) can do that? As a 3x vacation home owner, Katie breaks down her proven strategy step by step, sharing actionable lessons each week so listeners can do it too. In addition to tactical solo episodes, the show features exclusive interviews with experts, real stories from people who’ve done it too, and Q&A coaching sessions with aspiring second home owners. Second Home First gives listeners the tools, insights, and inspiration to make their dream vacation home a reality.
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