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Second Home First

by Second Home First

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Latest episodes

[ABROAD] This Chicago Lawyer Bought a Farmhouse… in Italy

October 6, 2026 · 49 min

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…
[EXPERT] Is the Starter Home Dead? A New York Times Real Estate Journalist Weighs In

September 29, 2026 · 43 min

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…
[EXPERT] The Good Ol’ Days Are Happening Right Now

September 22, 2026 · 40 min

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…
[REAL STORIES] They Bought a Lake House Instead of an NYC Apartment and Paid it Off in 15 Years

September 15, 2026 · 37 min

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…
[EXPERT] Think You Can’t Afford a Vacation Home?

September 8, 2026 · 35 min

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…

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Can This Vacation Home Pay For Itself? (Spoiler Alert: YES!)

September 1, 2026 · 24 min

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…
[EXPERT] The Secret to Getting Instagram-Worthy Photos and Videos of Your Vacation Home

August 25, 2026 · 37 min

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…
[REAL STORIES] This NYC Fashion Stylist Bought a Beach House in Maine Sight Unseen

August 18, 2026 · 39 min

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…
[EXPERT] What to Cook at a Vacation House with Bestselling Author Caroline Chambers

August 11, 2026 · 38 min

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…
[EXPERT] Vacation Home Design Secrets that Make You More Money

August 4, 2026 · 38 min

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…
Should You Allow Pets in Your Vacation Home?

July 28, 2026 · 21 min

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…
[REAL STORIES] From Military Orders in South Korea to Building a Vacation Home in Mississippi

July 21, 2026 · 38 min

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…

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About the show

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 is a brand new podcast that 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 will feature 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.