Second Home First

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...

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-te...

What if your primary home didn’t tie you down but actually gave you the freedom to leave? Today’s guest didn’t buy his second home first, but when an unexpected job opportunity took him to Buenos Aires, he turned his primary home into a short-term rental, covering his mortgage and more. This Week’s Guest: Taylor Smith’s story is a little bit of a departure from what we usually talk about. He didn’...

Do you ever feel like you’re doing everything right but still not getting ahead? Today’s expert guest, a top 1% realtor, is breaking down how the beliefs around homeownership we learned growing up are still driving our decisions today. And how rethinking them can unlock more freedom than we ever thought possible. This Week’s Expert Guest: Lindsay Fricks is a top realtor in Arizona, not to mention...

On this episode, we’re doing something we’ve never done before: we’re vetting a real Zillow listing to see if it could make a good vacation home investment. Join us as we walk through the exact process I use to evaluate a property’s income potential, risks, and overall potential to pay for itself. This Week’s Guest: Ruth Pferdehirt is an actress living in New York City. As an artist, Ruth shares t...

If you like the idea of owning a vacation home that pays for itself, it’s crucial to get your pricing right. Charge too much and no one books — charge too little and you’re leaving money on the table. This week’s expert episode breaks down the biggest myths, mistakes, and misconceptions about pricing so that your second home can help you build both memories and wealth. This Week’s Expert Guest: Ri...

If you’re a self-employed freelancer and think getting a mortgage, especially on a second home, just isn’t possible, this week’s episode is for you. Our guest, a New York City–based travel journalist, didn’t want to give up his rent-stabilized apartment in the West Village. So instead of stretching to buy in Brooklyn, he leveraged little-known lending options to purchase a mid-century modern fixer...

Owning a vacation home that pays for itself doesn’t have to mean handing over control—or handing over your profits. This week’s episode reveals how technology has made self-managing your vacation home as a short-term rental easier than ever, allowing you to earn more while doing less. This Week’s Expert Guest: Shaun Shirazian is the CEO of Lodgify, a short-term rental software designed to simplify...

What if buying your second home first was the key to more freedom, flexibility, and options than you ever thought possible? That’s what happened for this week’s guest, whose decision to skip buying a primary home in Brooklyn set off a chain reaction that changed her career and her life for the better. ***Interested in learning to buy a vacation home that pays for itself? I’m launching the inaugura...

What if 99% of real estate agents are the WRONG agent for you? This week, our expert guest is exposing why that is—and what to look for in order to avoid a six-figure mistake. This Week’s Expert Guest: Jonathan Greene is a real estate agent, investor and the host of the podcast Zen and the Art of Real Estate Investing. He’s here to pull back the curtain and give us the good, the bad, and the ugly...

Imagine realizing that the down payment you’ve been saving to buy a primary home in Brooklyn would be enough money to buy your second home entirely in cash. On today’s Real Stories episode, you’ll meet Liz, who traded city price tags for the Hudson Valley, and hear why that property didn’t stay her ‘second home’ for very long. This Week’s Guest: Liz was born and raised in Brooklyn, New York. When...

What if I told you that setting up your dream vacation home didn’t have to take months? In this episode of Second Home First, host Katie Cline breaks down exactly how she and her husband renovated and furnished an entire waterfront vacation home in just seven days — with a newborn and a toddler — while she was only two months postpartum. Katie shares the full behind-the-scenes of buying the home s...

Are you a “real” adult if you don’t own your primary home? Today’s expert guest, a generational researcher, explains how that definition of true adulthood was shaped by our parents’ era—and why it’s no longer relevant for Millennials and Gen Z. This Week’s Expert: Dr. Meghan Grace is a generational expert, researcher, and author who’s spent her career studying how Millennials and Gen Z are reshapi...