Second Home First

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...

Imagine discovering that the thing that would unlock more freedom and flexibility for your family wasn’t scaling your business… but owning a vacation home. Today’s guest learned that firsthand when, instead of buying a primary home, she jumped into investing—and watched just two properties earn more in a year than her husband’s lucrative salary as a dentist. This Week’s Guest: Kacia Ghetmiri is th...

Are you dreaming of owning a vacation home that looks like it was pulled straight from the pages of Arch Digest? Today’s expert episode breaks down exactly how to design with intention, and shares our expert’s predictions of the top interior design trends for 2026. What type of vacation home owner would you be?  Take the quiz to find out: BuyYourSecondHomeFirst.com/Quiz This Week’s Expert: Alex Mc...

What if, a year from now, you were ringing in the New Year from your dream vacation home? One that builds equity, appreciates and grows your wealth, all while someone else is paying your mortgage. Oh, and gives you a place to vacation for free!  Sign Up for the Live Masterclass to Help You Buy Your Second Home in 2026: https://secondhomefirst.kit.com/7a034eb70d On this episode of Second Home First...

What if the most valuable part of owning a vacation home isn’t the real estate itself… but the moments the house makes possible? Just in time for the holidays, today’s expert episode explores how to make the most of the time we share with the people we love, and how to capture those memories to last a lifetime. This Week’s Expert: Nicole Smith, Founder and CEO of Flytographer, reveals how a single...

What would you do if the only way to afford a home in your city meant compromising on almost everything you wanted — and spending close to a million dollars to get it?  On this Real Stories episode, you’ll meet Leanne, who realized that buying in New York City meant giving up too much… and instead chose to buy her second home first on Hilton Head Island for half the price. In this conversation, Le...

If you’re dreaming of owning a vacation home that pays for itself, there’s one thing you simply can’t ignore: regulations. On today’s episode, we’re diving into this crucial (and often overlooked) step of the buying process. I’ll walk you through exactly how to find out if a property can be legally rented, what existing rules mean for your purchase, and how to track the trends and community attitu...

What if the money you’ve been saving for retirement could actually help you buy your dream vacation home now… without paying a single penalty? Today’s expert episode unlocks a little-known strategy that could completely shift your mindset around affordability—and show you that your down payment may already be within reach. This Week’s Expert: Olivia Tati, founder of Wanderlust Wealth Academy and r...

Before you fall in love with a pool, a fireplace or a view, let’s get clear on what exactly you’re looking for in a vacation home. This week, I’m helping you define your vacation home vision—the details, big and small, that would give a home the real wow factor to you. And by the end of this episode, you’ll have a personalized checklist to scroll Zillow with confidence. Prepare the Pinterest board...

You know you want to own a vacation home, but you’re not sure WHERE it should be. The coast? The mountains? The countryside? Choosing the right spot is overwhelming—and getting it wrong can cost you time, money, and stress. On this episode, we’re tackling the biggest question in your second-home journey: Where should you actually buy? We’ll show you how to find your perfect spot—and why having a P...

What type of vacation home owner would you be? And more importantly, why does that matter? Before you start scrolling Zillow or shopping for throw pillows, this is one question you have to answer. On today’s episode, we’re breaking down the three vacation home owner archetypes—and how knowing yours will influence every decision you make. Take the Vacation Home Owner Archetype Quiz to find out whic...

What if your best investment account isn’t your 401(k)… but a vacation home? On the very first episode of Second Home First, host Katie Cline explores why buying your ‘second home’ first could be the smartest way to build wealth and vacation for free. Katie shares her own journey from renting in New York City to buying a vacation home in upstate New York, and how that decision became a game changi...

What if your 401(k) came with a fire pit and a lake view? On Second Home First, host Katie Cline flips the script on traditional homeownership. After years of believing buying a home in New York City was impossible, Katie bought her “second home” first—a vacation property that not only became a personal retreat but also a profitable short-term rental. Each week, Katie shares strategies, insights,...