Second Home First

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! [email protected] (mailto:[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. 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

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

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

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

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