🎙SMB15: From Store Manager to Owner: Jeff Carroll on Starting and Scaling Wine Dads

This is SMB15, a rapid-fire interview series featuring small business owners, investors and service providers. We dig into different industries, business models, and SMB topics. Hosted by Will Fry, founder of Mainshares.

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From a life-changing trip to Sonoma to scaling three retail locations in New Jersey, Jeff Carroll’s journey with Wine Dads shows how passion and persistence can reshape a career. He shares the leap from Trader Joe’s into entrepreneurship, the million-dollar challenge of opening his first store, and why he calls Wine Dads “a boutique shop cleverly disguised as a liquor store.”

In this episode, we dive into the realities of alcohol retail: licensing hurdles, financing constraints, and cash flow management. Jeff also shares lessons on hiring sommeliers, curating a product mix, and finding expansion opportunities near Trader Joe’s. His story offers a candid look at how to build a retail brand in one of the most regulated industries.

Some takeaways:

1. Passion can pivot careers. A trip to Sonoma in 2008 transformed Jeff from a casual drinker into a wine professional determined to open his own shop.

2. Location is leverage. Positioning Wine Dads near Trader Joe’s allowed Jeff to capture traffic and build awareness while maintaining his boutique identity.

3. Licensing is the biggest hurdle. In New Jersey, retail liquor licenses can cost seven figures, and navigating regulation is half the battle.

4. Cash flow is king. With alcohol invoices due in 30 days, retailers need disciplined inventory turnover. Wine Dads manages 10–12 turns per year.

5. Hire for expertise. Sommeliers and certified staff not only elevate the customer experience but also give credibility to the shop.

6. Approachability wins. By disguising a boutique selection inside a standard liquor-store look, Jeff made Wine Dads welcoming to everyday shoppers.

Where to find Jeff and Wine Dads:

• LinkedIn: https://www.linkedin.com/in/jeff-carroll-61252364/

• Website: https://winedadshoboken.com/

In this interview, we discuss:

• 00:00 - Falling in love with wine

• 02:00 - Early retail lessons

• 04:00 - Opening the first Wine Dads

• 07:30 - Financing & licensing hurdles

• 10:30 - Expansion strategy near Trader Joe’s

• 13:30 - Pocket licenses & growth plan

• 15:30 - Hiring sommeliers & staff

• 17:00 - Delegating store management

• 20:00 - Cash flow challenges in alcohol retail

• 22:30 - Building a curated selection

• 24:30 - Advice for aspiring shop owners

• 26:00 - What’s next for Wine Dads