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 that she had largely written off homeownership altogether. But when she received a large residual check from the Emmy-award winning show she does voiceover work for, she immediately knew she wanted to buy her second home first. In fact, she became the very first person to sign up for the inaugural class of the Second Home First Academy, which officially opened for registration today.

Join us at BuyYourSecondHomeFirst.com/Academy
Use code PODCAST for 40% off the Academy

Tune in to learn:
-How to evaluate a Zillow listing to see if it can pay for itself
-What tools and websites can help estimate a property’s income potential
-How to think about risk, budget, and financial comfort when buying your first investment property
-Where to look to check short-term rental regulations

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! [email protected]

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 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! [email protected]

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 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! [email protected]


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

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! [email protected]


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 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! [email protected] (mailto:[email protected]) 


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! [email protected]


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

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! [email protected] (mailto:[email protected]) 


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.

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! [email protected] (mailto:[email protected]) 


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

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! [email protected] (mailto:[email protected]) 


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

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 the host of the wildly popular EmpowerHer podcast, which boasts more than 14 million downloads (!). Based in Denver, she and her husband were saving to buy a primary home when they decided to buy their second home first… or more accurately, homes. They wanted to invest in real estate to give their family more optionality in the future and to find a way to stop trading time for money. 

Tune in to learn:
-Why surrounding yourself with people who are already doing what you want to do is the fastest way to prove it’s possible.
-How creative financing can make owning a vacation home far more attainable than you think.
-That YOU are your own target guest.
-Why Kacia believes NOT investing in real estate is actually the riskiest move of all.


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! [email protected] 


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