Second Home First

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 s...

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 vacat...

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...

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....

What if I told you that there’s a ski chalet in Vermont that looks like it was plucked straight out of a storybook currently for sale for less than $150,000!? That price sounds almost too good to be true, but the real question is - can it pay for itself!? I’m putting this real listing to test, and by the end of this episode, you’ll know exactly how I evaluate a vacation home before I even consider...

If you want your vacation home to pay for itself, you need to get people excited to actually book it. And one of the best ways to do that is with scroll-stopping photos and videos. Today's expert guest is breaking down how working with content creators can help bring your property to life, including where to find them, how to work with them, and what you need to know to make a partnership successf...

What do you get when you cross a New York City-based fashion stylist with a vintage beach cottage in Maine? A fully booked rental calendar, that’s what. Today’s guest decided to keep his rent-controlled apartment in the West Village and bought a beach cottage, site unseen, 300 miles north. This week’s guest: Seppe Tirabassi is a fashion stylist based in New York City who’s also the contributing fa...

Vacation homes are where some of life's best memories are made, and the kitchen is often the center of that. On this episode, Caroline Chambers shares her favorite recipes for feeding a house full of family and friends, along with some practical tips for stocking a kitchen that both you and your paying guests will love. This Week’s Expert Guest: Caroline Chambers, New York Times bestselling author...

Most vacation homeowners think great design is about picking pretty furniture. But today’s expert guest says it’s actually all about psychology. And when it’s done right, the result isn’t just a beautiful vacation home you love. It’s a place that stands out from the competition, attracts more bookings, and earns you more money. This week’s expert guest: Jordan McDonough is the Co-Founder of Somerl...

Nearly half of American households own a dog, yet less than a quarter of vacation rentals allow them to stay. We're unpacking if allowing pets in your vacation home is a smart business move or a very expensive mistake. Tune in to learn: -Why this is one of the most hotly debated topics in short-term rentals -How an email from a listener inspired this episode -Why allowing pets could increase your...

When her husband received military orders to move their family to South Korea, today’s guest made a decision that completely changed the way she viewed homeownership. What followed were some of the most unimaginable hardships someone could endure—but today, Alisha and her family are back in the States, choosing to rent their primary home as they build their dream vacation home on the Mississippi c...

Breaking news—Second Home First has been featured in the holy grail, the New York Times! I’m taking you behind the scenes on everything, from the cold pitch I sent to get the journalist’s attention to being photographed last week at my first vacation home, Trout Landing. But this episode isn’t really about the New York Times. It’s about how one unconventional decision can change the trajectory of...

How long would you wait to afford a home where you live? Five years? Ten? After more than 2 decades renting in Los Angeles, today's guest decided she was done waiting and chose to buy a cabin in the North Georgia mountains instead. This Week’s Guest: Dawn Asher is the founder of The Olive Jar, an experiential marketing studio that helps short-term rental hosts create unforgettable guest experience...

Buying a house is one of the biggest financial decisions most of us will ever make. So why does it feel like no one has ever taught us how to actually do it? There's no class in school that explains mortgages, offers, inspections, appraisals, or closing costs. Most of us are just piecing it together from Google searches, conversations with ChatGPT, and advice from our parents that's probably 30 ye...

After years of hustling, climbing, achieving, and building, many of us are looking around at our lives and thinking: is this really it? Our guest today felt exactly that, and she shares how buying her second home first in Lake Tahoe became the catalyst not just for financial change, but for reevaluating her life, career, and her definition of success. This Week’s Guest: Janel Gallucci is a short t...

What happens when a forgotten property becomes the beginning of something much bigger? In this deeply personal episode, host Katie Cline shares the story behind the abandoned Irish farmhouse her mother inherited—a home her grandmother grew up in that has sat empty for more than twenty years. What began as a trip to reconnect with her family's roots quickly turned into something she never expected....

Want to own a vacation home that pays for itself but don’t want to become a landlord? Today’s expert episode introduces us to the world of co-hosts — property managers who let you avoid those dreaded middle of the night phone calls while still enjoying the income. This Week’s Expert Guest: Natalie Palmer is the host of the No Vacancy podcast and co-founder of Level Up Your Listing Summit. She’s be...

If I told you someone was $1.7 million dollars in debt, you’d probably think: that sounds really bad. But today’s guest is all about leverage — using debt strategically to generate income, build equity, and create optionality. That debt is attached to properties worth roughly $4 million dollars, which make about $50,000 a month and have allowed her and her husband to leave their W2 jobs to stay ho...

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, un...

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...

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...

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 me...

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 R...

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 r...

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 y...