Podcast Episodes

[REAL STORIES] This NYC Teacher Stopped Waiting for “Someday” and Bought a Cottage in the Poconos

Episode 27

How many of us are currently putting something off for the hypothetical “someday?” This guest realized he didn’t want to wait around to enjoy his lif…

4 months, 2 weeks ago

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[REAL STORIES] She Escaped Texas Summers by Buying a House in Maine

Episode 28

What if attaining your “dream life” didn’t require quitting your job, becoming a millionaire, or even moving someplace else? Today’s guest, a native …

4 months, 3 weeks ago

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When Your Vacation Home Becomes a TV Star

Episode 27

On this episode of Second Home First, I’m taking you behind the scenes of something I never could have predicted: my very first vacation home, Trout …

5 months ago

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[EXPERT] Can Buying a Vacation Home Make Your W2 Optional?

Episode 26

When COVID hit, I made three budgets: what would happen if I lost my job, what would happen if my husband lost his job, and what would happen if we b…

5 months, 1 week ago

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Which is the Bigger Risk: Failing or Not Trying?

Episode 24

What if I told you that the difference between the people who build the life they want and the people who just think about it isn’t timing, money, or…

5 months, 2 weeks ago

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You Don't Need to Be Rich: The Real Numbers Behind Our Vacation Homes

Episode 24

What if I told you that you don’t need to be rich to buy a second home? And that actually, buying that very home could be the thing that MAKES you ri…

5 months, 3 weeks ago

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[EXPERT] How to Buy a Vacation Home with Family or Friends

Episode 23

What if the fastest way to afford your dream vacation home was to buy it with someone else? On this week’s expert episode, we’re unpacking exactly ho…

6 months ago

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[REAL STORIES] He Turned His Home Into a Rental That Paid Him While Abroad

Episode 20

What if your primary home didn’t tie you down but actually gave you the freedom to leave? Today’s guest didn’t buy his second home first, but when an…

6 months, 1 week ago

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[EXPERT] Top 1% Realtor on the Money Mistake Keeping you Stuck (and What to Do Instead)

Episode 21

Do you ever feel like you’re doing everything right but still not getting ahead? Today’s expert guest, a top 1% realtor, is breaking down how the bel…

6 months, 1 week ago

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[REAL STORIES] Should this NYC Actress Buy a House in the Catskills? We Did the Math.

Episode 20

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 inve…

6 months, 2 weeks ago

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