Second Home First

When most people think of an impulse buy, they probably think of a new pair of shoes. But for today’s guest, it was a beach crash pad. After feeling like he missed his chance to buy in New York City due to climbing real estate prices post-Covid, this banker decided to keep renting in Williamsburg and buy his “second home” first on Long Island in Long Beach.

This Week’s Guest:
Michael “Phase” Phelan has built an insanely successful career in banking and had considered buying a primary home in Williamsburg, where he’s been renting for more than a decade. But then, he made what he calls an “impulsive” decision and decided to buy his second home first: a one-bedroom condo in Long Beach. He plans to use the home as a beach crash pad for now and, eventually, turn it into a long-term rental.

Tune in to Learn:
–Why Phase chose to buy a vacation home in Long Beach instead of a primary home in Brooklyn
–How he found a beachside condo for a fraction of the price of buying in NYC
–Why buying a second home first can take the emotion out of real estate decisions
–The biggest lessons from navigating the home-buying process as a first-time buyer
–How Phase plans to enjoy his beach getaway now and turn it into a long-term rental in the future

Key links:
–Second Home First Academy: BuyYourSecondHomeFirst.com/academy
*Use code PODCAST for 40% off
–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
Click the link and enter code HOME20 for an additional 20% off their yearly and bi-yearly plans.

Somerled: https://form.jotform.com/252193985491065?howDid=Referral&typeA19=Second%20Home%20First 
Use the link provided to schedule your free consultation call. Listeners of SHF also get $1,000 off virtual design & $3,000 off design & project management services.

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

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 sauna in the former stables, and a wine tasting room in the old cantina.

This Week’s Guest:
Claire Stephens is a lawyer who lives in Chicago but decided to buy a property in Liguria, Italy. This isn’t just any property, but a farmhouse next door to a home that’s been in her family for generations. She talks about challenges of buying a property in a different country from where you live—not to mention, in a different language! And she reminds us that while this is a slow process, something she estimates will take about five years, the finished product isn’t the only part of the process she’s looking forward to.

Tune in to Learn:
—What it’s really like to buy a home in Italy as a foreigner
—The importance of building relationships with the local community
—How to find and build a trusted local team you can rely on
—Claire’s renovation plans for the property and the timeline
—Why building strong relationships can be your biggest advantage when investing overseas.

Key links:
–Second Home First Academy: BuyYourSecondHomeFirst.com/academy
*Use code PODCAST for 40% off
–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
Click the link and enter code HOME20 for an additional 20% off their yearly and bi-yearly plans.

Somerled: https://form.jotform.com/252193985491065?howDid=Referral&typeA19=Second%20Home%20First 
Use the link provided to schedule your free consultation call. Listeners of SHF also get $1,000 off virtual design & $3,000 off design & project management services.

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

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 publications in the world: the New York Times. Real estate journalist, Heather Senison, who wrote the full-page feature on Second Home First, is here to share what she’s seeing from today’s homebuyers—and where homeownership could be headed next.

This Week’s Expert Guest:
Heather Senison is an award-winning real estate journalist who writes for The New York Times. She takes us behind the scenes—what made my pitch stand out to her, what surprised her the most once she started reporting, and what journalists actually consider when they choose what (or who) to feature… and what or who to cut. 

Tune in to Learn:
–Is the starter home dead?
–Why she doesn’t believe today’s housing market is a bubble
–What she thinks could change the way we buy homes in the years ahead.
–How journalists evaluate sources, build stories, and decide what makes it into a major publication

Key links:
–Second Home First Academy: BuyYourSecondHomeFirst.com/academy
*Use code PODCAST for 40% off
–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
For a limited time, click the link and enter code SHF-60 for 60% off their Professional and Ultimate plans. *Offer good September 21-30, 2026

Somerled: https://form.jotform.com/252193985491065?howDid=Referral&typeA19=Second%20Home%20First 
Use the link provided to schedule your free consultation call. Listeners of SHF also get $1,000 off virtual design & $3,000 off design & project management services.

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

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, while also solving a problem for others that they had experienced firsthand.

This Week’s Guest:
Rose Tipka is the CEO and Founder of Your Family’s Place, a vacation rental company in Ohio’s Amish country focused on larger homes spread across 75 acres. Not only is Rose’s company impressive, but what makes her story even more interesting is that she had no background in real estate at all. In fact, before creating Your Family’s Place, Rose was a schoolteacher who then became a stay-at-home mom, homeschooling all SIX of her children.

Tune in to Learn:
–How to identify an underserved audience by solving a problem you’ve experienced yourself
–Why you don’t need a real estate or hospitality background to become a successful host
–How thoughtful, low-cost guest touches can create memorable experiences and stronger loyalty
–How to balance financial numbers with personal intuition when evaluating vacation homes
–How vacation rentals can help you build the time, freedom, and family life you actually want

Key links:
–Second Home First Academy: BuyYourSecondHomeFirst.com/academy
*Use code PODCAST for 40% off
–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
For a limited time, click the link and enter code SHF-60 for 60% off their Professional and Ultimate plans. *Offer good September 21-30, 2026

Somerled: https://form.jotform.com/252193985491065?howDid=Referral&typeA19=Second%20Home%20First 
Use the link provided to schedule your free consultation call. Listeners of SHF also get $1,000 off virtual design & $3,000 off design & project management services.

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.

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 15 years, they used income from short-term renters to pay it off entirely—and now, they’re using the equity they built to construct their dream vacation home just down the road.

This Week’s Guests:
David Bigler and Jillian O’Neill are a married couple who bought their second home first almost two decades ago. They were living in Jersey City at the time, dreaming of moving into Manhattan, when they decided to do something different and buy a lakehouse in the Poconos instead. 

Tune in to Learn:
–The difference between good debt and and bad debt
–Why Dave and Jill started out as "First Dibbers" but now consider themselves "Profit Maximizers" (Take the Quiz to find out what type of vacation home owner you would be: https://www.buyyoursecondhomefirst.com/freebies#quiz)
–How they paid off their lake house in full in 15 years, using income earned from short-term renters
–Why building genuine relationships with neighbors is essential

Key links:
–Second Home First Academy: BuyYourSecondHomeFirst.com/academy
*Use code PODCAST for 40% off
–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
For a limited time, click the link and enter code SHF-60 for 60% off their Professional and Ultimate plans. *Offer good September 21-30, 2026

Somerled: https://form.jotform.com/252193985491065?howDid=Referral&typeA19=Second%20Home%20First 
Use the link provided to schedule your free consultation call. Listeners of SHF also get $1,000 off virtual design & $3,000 off design & project management services.

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

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 of us to rule ourselves out. She’s also sharing why talking to a lender just might reveal that you’re closer to owning your dream vacation home than you think.

This Week’s Expert Guest:
Jessica Khani is a mortgage lender, who’s also an investor and an entrepreneur. Find her at HomesWithJessicaKhani.com or @HomesWithJessicaKhani on social.

Tune in to Learn:
–The difference between getting a mortgage for your primary home versus a second home
–How lenders determine how much you can actually afford
–What credit score you need to have in order to get the most favorable terms
–How much time you’re required to spend in the property each year and whether or not there’s a maximum number of days you can rent it out
–Actionable, tactical advice for improving your credit score before you buy

Jessica was also featured on this episode of SHF: 
[EXPERT] How to Buy a House
Apple Podcasts- https://podcasts.apple.com/us/podcast/expert-how-to-buy-a-house/id1849178409?i=1000774809997 
Spotify- https://open.spotify.com/episode/1y5Bgc57iQWFKddPHySfJB 
YouTube- https://www.youtube.com/watch?v=JZRuM7vJ8ok

Key links:
–Second Home First Academy: BuyYourSecondHomeFirst.com/academy
*Use code PODCAST for 40% off
–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
For a limited time, click the link and enter code SHF-60 for 60% off their Professional and Ultimate plans. *Expires September 8, 2026

Somerled: https://form.jotform.com/252193985491065?howDid=Referral&typeA19=Second%20Home%20First 
Use the link provided to schedule your free consultation call. Listeners of SHF also get $1,000 off virtual design & $3,000 off design & project management services.

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 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 pay for itself!? I’m putting this real listing to test, and by the end of this episode, you’ll know exactly how I evaluate a vacation home before I even consider making an offer.

Tune in to learn:
–How to evaluate whether a vacation home can actually pay for itself before making an offer
–How to do your due diligence around regulations, local competition, HOA restrictions, and property condition
–How to analyze the numbers to determine how much this home would cost and equally, how much it could earn

Key links:
–Second Home First Academy: BuyYourSecondHomeFirst.com/academy
*Use code PODCAST for 40% off
–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
For a limited time, click the link and enter code SHF-60 for 60% off their Professional and Ultimate plans. *Expires September 8, 2026

Somerled: https://form.jotform.com/252193985491065?howDid=Referral&typeA19=Second%20Home%20First 
Use the link provided to schedule your free consultation call. Listeners of SHF also get $1,000 off virtual design & $3,000 off design & project management services.

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 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 content creators can help bring your property to life, including where to find them, how to work with them, and what you need to know to make a partnership successful.

This week’s expert guest:
Jamie Kraus is the founder and CEO of Postaway, the premier hospitality platform designed to bring creators and hosts together for collaboration and community. Bringing nearly a decade of hosting experience across her five properties alongside her background as a photographer and creator, Jamie leverages her unique perspective from both sides of the industry to help hosts choose the right partners, structure partnerships, and showcase their properties to drive guest interest. 

Tune in to learn:
-How to work with creators to commission photos and videos to market your property and attract more paying guests
-The inside scoop on what makes a great creator partnership
-The green and red flags to look out for when working with creators
-How to make sure a collaboration actually delivers value for your property

Key links:
–Postaway - https://www.postaway.com/
Use code KATIE50 for 50% off.

–Postaway Hospitality Summit - https://www.postaway.com/hospitality-summit 
September 27 - 29, 2026 in Breckenridge, CO
Use code KATIE15 for 15% off a ticket to attend.

–Second Home First Academy: BuyYourSecondHomeFirst.com/academy
*Use code PODCAST for 40% off
–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
Click the link and enter code: SHF-60
Discount: 60% off Professional and Ultimate plans (Yearly and Bi-Yearly)
Valid: August 25th – September 8th 

Somerled: https://form.jotform.com/252193985491065?howDid=Referral&typeA19=Second%20Home%20First 
Use the link provided to schedule your free consultation call. Listeners of SHF also get $1,000 off virtual design & $3,000 off design & project management services.

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 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 bought a beach cottage, site unseen, 300 miles north.

This week’s guest:
Seppe Tirabassi is a fashion stylist based in New York City who’s also the contributing fashion editor for GQ. Seppe lives in a rent-controlled apartment in the West Village, and after seeing how much it would cost to buy an apartment in Brooklyn, he decided to change course and buy his ‘second home’ first in his native state of Maine.

If the beginning of that story sounded a little familiar, that’s because Seppe’s partner, Paul Jebara, was also a guest of this podcast! Check out Paul’s episode:

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

Apple Podcasts - https://podcasts.apple.com/us/podcast/real-stories-rent-stabilized-in-the-west-village/id1849178409?i=1000752843325 
Spotify - https://open.spotify.com/episode/0fBz7sExkLgPeosCd6alLR 
YouTube - https://youtu.be/UHZ3HSFroKE

Key links:
–Second Home First Academy: BuyYourSecondHomeFirst.com/academy
*Use code PODCAST for 40% off
–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
Click the link and enter code HOME20 for an additional 20% off their yearly and bi-yearly plans.

Somerled: https://form.jotform.com/252193985491065?howDid=Referral&typeA19=Second%20Home%20First 
Use the link provided to schedule your free consultation call. Listeners of SHF also get $1,000 off virtual design & $3,000 off design & project management services.

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

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 practical tips for stocking a kitchen that both you and your paying guests will love.

This Week’s Expert Guest:
Caroline Chambers, New York Times bestselling author and Substack sensation, joins us to celebrate the release of her newest cookbook, What to Cook When You Don’t Feel Like Cooking: Make It Fast. Recently, Caro published a series on her Substack called “What to Cook at a Vacation House,” and the second I read it, I knew we had to have her on the show.

Tune in to learn:
-Why some of the most memorable moments on vacation happen around the dinner table
-How to feed a crowd when you're cooking in an unfamiliar kitchen
-The five spices every vacation home should stock
-What every kitchen in an Airbnb or a Vrbo should have—from pantry staples to pots, pans and utensils
-Her favorite crowd-pleasing recipes from her books that are perfect for feeding a house full of family and friends without getting stuck in the kitchen

Caroline’s Newest Book- What to Cook When You Don’t Feel Like Cooking: Make It Fast - https://amzn.to/4fmYnJK

Caroline’s What to Cook at a Vacation House series:
1- https://whattocook.substack.com/p/the-wtc-vacation-house-meal-plan 
2- https://whattocook.substack.com/p/what-to-cook-at-a-vacation-house 
3- https://whattocook.substack.com/p/what-to-cook-at-a-vacation-house-251 

Key links:
–Second Home First Academy: BuyYourSecondHomeFirst.com/academy
*Use code PODCAST for 40% off
–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
Click the link and enter code HOME20 for an additional 20% off their yearly and bi-yearly plans.

Somerled: https://form.jotform.com/252193985491065?howDid=Referral&typeA19=Second%20Home%20First 
Use the link provided to schedule your free consultation call. Listeners of SHF also get $1,000 off virtual design & $3,000 off design & project management services.

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