Never Worked Harder, Never Been Happier

July 7, 2026
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oday's guest joins us on her birthday.

And boy it makes a great birthday when you love what you do, love where you are professionally.

Which is the case for Gina Rosen, who bought a small jewelry wholesaling business in July of 2023, starting her pivot away from a 25-year corporate career.

Now despite that long tenure in corporate, Gina was always aware of how precarious W-2 income is. Early in her career, she'd been laid off 3 times in 13 months.

So having experienced the W-2 rug pull so early and so often, she had had her eye on income diversification and had dabbled in side hustles.

Well the dabbling became much more serious when she got a call from a couple owners looking to sell their business to her.

And so begins today’s story.

Christmas Retail show with three generations of Seasons Jewelry shoppers
Christmas Retail show with three generations of Seasons Jewelry shoppers

Now despite Gina's entrepreneurial pivot, she is conservative. She didn't actually quit her day job for the first year of owning the business she bought, and only then because she felt forced to.

Also, she's plowing all profits from the business back in, and expects to do so for a number of years. She is intent on building the business foundation before taking earnings out.

Listen for the deal terms, which we unpack to the dollar. Gina didn't do the typical SBA acquisition; she bought the business in cash with the help of a HELOC. It's always valuable to learn about alternative deal structures.

Here she is, birthday girl and owner of Seasons Jewelry, Gina Rosen.

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Never Worked Harder, Never Been Happier

After 25 years in corporate, Gina Rosen bought a jewelry wholesaling business with $635k in sales — now on track to $1m.

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Introduction

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T

oday's guest joins us on her birthday.

And boy it makes a great birthday when you love what you do, love where you are professionally.

Which is the case for Gina Rosen, who bought a small jewelry wholesaling business in July of 2023, starting her pivot away from a 25-year corporate career.

Now despite that long tenure in corporate, Gina was always aware of how precarious W-2 income is. Early in her career, she'd been laid off 3 times in 13 months.

So having experienced the W-2 rug pull so early and so often, she had had her eye on income diversification and had dabbled in side hustles.

Well the dabbling became much more serious when she got a call from a couple owners looking to sell their business to her.

And so begins today’s story.

Christmas Retail show with three generations of Seasons Jewelry shoppers
Christmas Retail show with three generations of Seasons Jewelry shoppers

Now despite Gina's entrepreneurial pivot, she is conservative. She didn't actually quit her day job for the first year of owning the business she bought, and only then because she felt forced to.

Also, she's plowing all profits from the business back in, and expects to do so for a number of years. She is intent on building the business foundation before taking earnings out.

Listen for the deal terms, which we unpack to the dollar. Gina didn't do the typical SBA acquisition; she bought the business in cash with the help of a HELOC. It's always valuable to learn about alternative deal structures.

Here she is, birthday girl and owner of Seasons Jewelry, Gina Rosen.

About

Gina Rsen

Gina Rsen
Gina Rsen

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