Second Home First

Second Home First
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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.

  1. 4D AGO

    [EXPERT] How Much Should Guests Pay to Rent Your Vacation Home?

    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: Richie Khandelwal is the Co-Founder of the dynamic pricing software PriceLabs, a tool that helps hosts stop guessing and start setting prices based on real demand. Richie shares the biggest pricing mistakes new hosts make and how to avoid them; how shifts in supply and demand change what your home can earn night by night; and how PriceLabs’ algorithm analyzes more than 20 million data points every single day to take both the uncertainty — and the emotion — out of our pricing decisions. Tune in to learn: -Why most new hosts price their vacation home incorrectly (and how to avoid the most common mistake) -What is dynamic pricing works (hint: airlines and hotels have used it for decades) -How supply and demand should change your home’s nightly price -Why pricing can feel emotional and how data removes the guesswork Want to own a vacation home that pays for itself? Learn more about the Second Home First Academy at BuyYourSecondHomeFirst.com/Academy Key links: –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! Hello@BuyYourSecondHomeFirst.com A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Use code SHF20 for an ADDITIONAL (!) 20% their yearly and bi-yearly plans Minoan: https://www.Minoan.com/SecondHome Use the link provided to sign up and receive a free $25 in credit. 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

    31 min

  2. MAR 3

    [REAL STORIES] Rent-Stabilized in the West Village. Vacation homeowner in Connecticut.

    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-upper in Connecticut— turning his love of architecture from something he writes about into something he actually owns. This Week’s Guest: Paul Jebara is a freelance journalist who writes about travel, architecture and design. Even though he has found the unicorn of Manhattan real estate—a rent-stabilized apartment in the coveted West Village—he considered giving it up to buy in Brookly. But as his search went on, his budget kept climbing, the neighborhoods he could afford kept getting further out, and the compromises within the space kept stacking up. Eventually, Paul decided to keep renting in the West Village and buy his second home first, a mid-century modern fixer upper in Litchfield County, Connecticut. Tune in to learn: -Why buying a fixer-upper became Paul’s strategic advantage to avoid bidding wars -How writing a thoughtful letter to the sellers helped Paul’s lower-priced offer win out -How Paul navigated financing as a longtime freelancer, including mortgage options available to self-employed buyers that many traditional lenders don’t even know about ***Paul is currently a “Sweet Spotter”. Take the quiz to determine what type of Vacation Home Owner you would be: BuyYourSecondHomeFirst.com/quiz Want to buy a vacation home that pays for itself? Learn more about the Second Home First Academy at BuyYourSecondHomeFirst.com/Academy Key links: –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! Hello@BuyYourSecondHomeFirst.com A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Use code SHF20 for an ADDITIONAL (!) 20% their yearly and bi-yearly plans Minoan: https://www.Minoan.com/SecondHome Use the link provided to sign up and receive a free $25 in credit. 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

    40 min

  3. FEB 24

    [EXPERT] The Side Hustle That Comes With Free Vacations

    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 the management and marketing of your vacation home. He breaks down how self-managing a vacation rental can be far easier than most people think, especially when you have the right systems in place. Tune in to learn: -What it actually takes to manage your home as a short-term rental. -How Lodgify helps hosts get more bookings with less effort -Ways to spend less time managing and more time enjoying your property -How advancements in AI are shifting software to become your personal assistant Want to own a vacation home that pays for itself? Learn more about the Second Home First Academy at https://www.BuyYourSecondHomeFirst.com/Academy Key links: –Lodgify: https://lodgify.com/?afmc=28y –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! Hello@BuyYourSecondHomeFirst.com A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Use code SHF20 for an ADDITIONAL (!) 20% their yearly and bi-yearly plans Minoan: https://www.Minoan.com/SecondHome Use the link provided to sign up and receive a free $25 in credit. 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

    29 min

  4. FEB 17

    [REAL STORIES] The Decision That Gave Her More Freedom Than a ‘Forever Home’ Ever Could

    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 inaugural class of the Second Home First Academy. Join the waitlist to receive priority access, plus a special launch discount available only to subscribers. https://www.buyyoursecondhomefirst.com/academy *** This Week’s Guest: Blythe Graham-Jones was living in Brooklyn when she started exploring what it would take to buy in her neighborhood. The numbers were staggering. Instead of locking herself into that version of homeownership, Blythe chose a different route. She purchased a home in the Hamptons and thanks to strong summer rental demand, literally received a check at closing—the rent payment from the summer tenants, that would cover her costs for the next year.  Tune in to learn: -Why Brooklyn’s price tags pushed her to question the “primary home first” narrative -The biggest misconceptions about buying in the Hamptons -How to get paid at closing -How buying her second home first unlocked a whole new career Key links: –What type of vacation home owner would you be? Take the Quiz- BuyYourSecondHomeFirst.com/Quiz  –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! Hello@BuyYourSecondHomeFirst.com (mailto:Hello@BuyYourSecondHomeFirst.com)  A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Use code SHF20 for an ADDITIONAL (!) 20% their yearly and bi-yearly plans Minoan: https://www.Minoan.com/SecondHome   Use the link provided to sign up and receive a free $25 in credit. 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

    27 min

  5. FEB 10

    [EXPERT] This Real Estate Agent Says the “Forever Home” is a Myth

    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 in the world of real estate agents. Jonathan breaks down how old school mindsets: like “renting is just throwing money away” or you “NEED” a forever home - are not only outdated, but harmful. He also shares insider guidance on how to evaluate prospective agents for your home search, what really matters in an agent-client relationship, and why he believes that 99% of real estate agents are the wrong agent for you. Tune in to learn: -Why buying a “forever home” may not be the smartest strategy -Why more wealthy people are choosing to rent -What to look for when picking a real estate agent -Red flags to look out for in the home buying process Key links: –What type of vacation home owner would you be? Take the Quiz- BuyYourSecondHomeFirst.com/Quiz –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! Hello@BuyYourSecondHomeFirst.com A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Use code SHF20 for an ADDITIONAL (!) 20% their yearly and bi-yearly plans Minoan: https://www.Minoan.com/SecondHome   Use the link provided to sign up and receive a free $25 in credit 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

    40 min

  6. FEB 3

    [REAL STORIES] Her Brooklyn Down Payment Bought a Second Home—In Cash

    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 she and her husband began househunting in Greenpoint, she was shocked to learn that a barely 3 bedroom fixer upper would cost $3 million. So instead, Liz decided to buy her second home first, a gorgeous a-frame in the Hudson Valley’s Dover Plains, for less than a fifth of what a smaller place would’ve cost her in Brooklyn. Tune in to learn: -Why making gingerbread houses with her kids sealed the deal on her second home -How “test-driving” a property by staying there first can change everything -Why emotional connection matters just as much as the numbers -The surprising outcome of this purchase that no one saw coming Key links: –What type of vacation home owner would you be? Take the Quiz- BuyYourSecondHomeFirst.com/Quiz  –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! Hello@BuyYourSecondHomeFirst.com (mailto:Hello@BuyYourSecondHomeFirst.com)  A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Use code SHF20 for an ADDITIONAL (!) 20% their yearly and bi-yearly plans Turno: https://go.turno.com/second_home_first  Use the link provided to get $25 off your first clean. 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 Minoan: https://www.Minoan.com/SecondHome   Use the link provided to sign up and receive a free $25 in credit.

    19 min

  7. JAN 27

    How I Renovated and Furnished an Entire Vacation Home in 7 Days, While 2 Months Postpartum

    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 site-unseen (!), designing the entire house from her apartment five hours away, and using systems, outsourcing, and help from family to get the home renovated, furnished, photographed and welcoming its first paying guest within just 20 days. Tune in to learn: –Why Katie felt confident making offer on a home without touring it first –The system she used to furnish the entire house remotely –Why using movers, painters, and landscapers saved months of work –How to trade money for time without burning yourself out –The real numbers from the first 10 weeks live on Airbnb Key links: –The Corresponding Substack Post: https://secondhomefirst.substack.com/p/how-i-renovated-and-furnished-an  –Regulations Podcast Episode: –”Is Renting Your Vacation Home Even Legal?” Substack: https://secondhomefirst.substack.com/p/is-renting-your-vacation-home-even  –Due Diligence Checklist: https://www.buyyoursecondhomefirst.com/the-red-tape/due-diligence-checklist  –Due Diligence Worksheet: https://www.buyyoursecondhomefirst.com/the-red-tape/due-diligence-worksheet  –Register your interest for the Set Up Checklist: http://buyyoursecondhomefirst.com/like-a-pro/set-up-checklist  –Unboxing Timelapsed Video: https://www.instagram.com/p/DNEt_FPPWsp/  –Tree Hair Cut Timelapsed Video: https://www.instagram.com/p/DNGjugNs0qX/  –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! Hello@BuyYourSecondHomeFirst.com (mailto:Hello@BuyYourSecondHomeFirst.com)  A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Use code SHF20 for an ADDITIONAL (!) 20% their yearly and bi-yearly plans Minoan: https://www.Minoan.com/SecondHome   Use the link provided to sign up and receive a free $25 in credit. 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

    39 min

  8. JAN 20

    [EXPERT] Are You a “Real” Adult if You Don’t Own a Home?

    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 reshaping the way we think about careers, money, and yes, real estate. She’s here to share insights on why younger generations are especially drawn to strategies like Second Home First—from growing up in the sharing economy to coming of age in a digital-first world. She also breaks down the latest research which just might prove that my Baby Boomer Dad’s skepticism wasn’t personal—but generational. Tune in to learn: -Why the “forever home” is a myth  -How generational mindset shifts impact our approach to life -How younger buyers are using short-term rentals to offset mortgages and build equity -Why renting in high-cost cities can be a strategic financial move, not a failure -How buying a second home first can unlock both lifestyle freedom and long-term wealth Key links: –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! Hello@BuyYourSecondHomeFirst.com (mailto:Hello@BuyYourSecondHomeFirst.com)  A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y Use code SHF20 for an ADDITIONAL (!) 20% their yearly and bi-yearly plans Minoan: https://www.Minoan.com/SecondHome   Use the link provided to sign up and receive a free $25 in credit. 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

    29 min
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Trailer

5
out of 5
22 Ratings

About

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.

Information

  • Creator
    Second Home First
  • Years Active
    2025 - 2026
  • Episodes
    20
  • Rating
    Clean
  • Copyright
    © 2025 Second Home First
  • Show Website
    Second Home First

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