Second Home First – Details, episodes & analysis

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

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

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 attitudes that shape the regulations of tomorrow. Tune in to learn: -How to figure out who’s actually in charge -The easiest way to check short-term rental regulations -How to gauge community sentiment and spot red flags before you buy -What permits you might need—and what’s required to get approved Key links: –Download the Due Diligence Worksheet: https://www.buyyoursecondhomefirst.com/the-red-tape/due-diligence-worksheet  –Download the Due Diligence Checklist: https://www.buyyoursecondhomefirst.com/the-red-tape/due-diligence-checklist –US Census Bureau's Geocoder website (choose “Stateside Parsed Address Processing” under “Find Geographies”): https://geocoding.geo.census.gov/geocoder/geographies/address?form  –Is Renting Your Vacation Home Even Legal? on Substack: https://secondhomefirst.substack.com/p/is-renting-your-vacation-home-even  –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 *Extended until December 12, use code BF65SHFVIP for 65% (!) off their yearly and bi-yearly Professional and Ultimate 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 Keywords: short-term rental regulations, STR regulations, short term rental regulations, Airbnb regulations, rules, permits

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 real estate investor extraordinaire, is breaking down how she used her 401(k) to buy her first investment property. She demystifies the risks and rewards, explains the step-by-step process, and shows how borrowing against your retirement savings can help you take your second home leap. Tune in to learn: -How a 401(k) loan works and why it’s different from cashing out (no penalties, no taxes, interest goes back to you!) -The exact steps Olivia took to buy her first investment property with her retirement funds -How to evaluate if this strategy makes sense for your own second home goals -Tips for navigating lenders, providers, and maximizing your investment Key links: –Olivia’s 401(k) loan Substack post: https://substack.com/home/post/p-172426546  –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  –Contact Olivia: @TheOliviaTati and OliviaTati.com A Special Thank You To Our Sponsors: Lodgify: https://lodgify.com/?afmc=28y *From now until December 4, use code BF65SHFVIP for 65% (!) off their yearly and bi-yearly Professional and Ultimate 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

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 boards! Grab a pack of sticky notes and tune in to learn: -The key questions to ask yourself to uncover what you want -How browsing Airbnb, VRBO, and Booking.com can spark ideas -Why ranking your wishlist helps you make smarter, faster buying decisions -Ways to align your vision with co-buyers (family, friends, a significant other) Download the Vacation Home Vision template for free- https://www.buyyoursecondhomefirst.com/your-ideal-vacation-home/vacation-home-vision Sticky Note Exercise- https://www.buyyoursecondhomefirst.com/your-ideal-vacation-home/sticky-note-exercise  Visit the website: BuyYourSecondHomeFirst.com Subscribe to the free weekly newsletter: BuyYourSecondHomeFirst.com/#subscribe  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 *From now until December 4, 2025, use code BF65SHFVIP for 65% (!) off their yearly and bi-yearly Professional and Ultimate 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

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 Plan B (and maybe even a Plan C) is essential. Grab a pack of sticky notes, because this week it’s all about location, location, location. Grab a pack of sticky notes and tune in to learn: -Why this is the most important decision you’ll make (no pressure!) -How to get started when you have no idea WHERE you want to buy -The sticky-note exercise that will help you define your ideal destination -Why you need a Plan A, a Plan B… and maybe even a Plan C Key links: –Sticky Note Exercise- https://www.buyyoursecondhomefirst.com/your-ideal-vacation-home/sticky-note-exercise –Take the Vacation Home Owner Archetype 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 *From now until December 4, use code BF65SHFVIP for 65% (!) off their yearly and bi-yearly Professional and Ultimate 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

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 which type you’d be: BuyYourSecondHomeFirst.com/Quiz  Tune in to learn: -About the three vacation home owner archetypes: Profit Maximizer, Sweet Spotter, and First Dibber -Why your archetype affects everything, from where you buy to what you can afford -How your archetype can shift over the course of a mortgage (or even a single year) Key links: Visit the website: BuyYourSecondHomeFirst.com Subscribe to the free weekly newsletter: BuyYourSecondHomeFirst.com/#subscribe  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 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

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 changing investment strategy for her. You’ll learn: –Why buying your second home first just might be the smartest way to build wealth and joy –How owning a vacation home can build equity and generate income while giving you a place to vacation for free –Why the “must be nice” mentality might be getting in your way –The five questions to help you decide if this strategy is right for you Plus, Katie shares free resources to help you get started:  –The ‘Should You Buy Your Second Home First’ Quiz –The Second Home First Starter Kit, with the immediate next steps to take to get closer to owning your dream vacation home (sent upon completion of the quiz) Visit the website: BuyYourSecondHomeFirst.com Take the Quiz: BuyYourSecondHomeFirst.com/Quiz  Subscribe to the free weekly newsletter: BuyYourSecondHomeFirst.com/#subscribe  Bankrate article: Bankrate.com/real-estate/rent-vs-buy-affordability-study/  Renting vs. Buying Spreadsheet: BuyYoursSecondHomeFirst.com/your-ideal-vacation-home/rent-vs-buy  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 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

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, and real-life examples to help listeners take action. Episodes fall into three categories: Real Stories: Guests share their journeys, challenges, and lessons learned from buying a second home first. Expert Advice: Specialists—from mortgage lenders and real estate agents, to designers and property managers—offer unfiltered guidance to help listeners make smart decisions. Deep Dives: Katie walks through her exact process for finding, furnishing, and financing now 3 vacation homes, providing actionable steps to evaluate potential properties and maximize results. If you thought owning any home, let alone a second one, was out of reach, this is the show is for you. This is Second Home First. Visit the website: BuyYourSecondHomeFirst.com Subscribe to the free weekly newsletter: BuyYourSecondHomeFirst.com/#subscribe Follow on Instagram and TikTok: @BuyYourSecondHomeFirst Find us on Substack: SecondHomeFirst.Substack.com Say Hi! Hello@BuyYourSecondHomeFirst.com

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.