From Driveway Delivery to a Dream Business: The Story Behind Crossroads Auto Leasing

B2B with Randy and Craig

What started as a simple search for a new car turned into a life-changing journey for married couple Daisy and Jeff, founders of Crossroads Auto Leasing. In this episode, we dive into how a convenient car delivery service sparked a business idea that would reshape their future. It all began when Jeff and Daisy were looking for a new car. When they discovered they could lease a vehicle and have it delivered straight to their doorstep, they were blown away. That single experience planted the seed — and by December of 2019, Crossroads was born as a side hustle. Then, when both were unexpectedly laid off in April 2020, they made a bold decision: go all in. Today, Crossroads Auto Leasing is a thriving, client-first business offering a smarter, smoother car-buying experience. Whether you want to buy, lease, or finance, Daisy and Jeff act as honest consultants — finding the right car to match your needs, budget, and lifestyle without the usual dealership stress. They’ll even bring the car to you and clean it, all while securing the best rebates, incentives, and pricing available. Daisy was able to apply the skills she acquired through previous jobs — including marketing, systems, and software — along with accounting courses she took, to help grow their business. She reminds us that working for others isn’t a setback — it’s a classroom, and the skills you gain can become your greatest asset as an entrepreneur. We also get real about what it’s like to run a business and a household as a married couple. Daisy and Jeff share the highs, the challenges, and the delicate dance of blending business with family life. If you’ve ever dreamed of turning a side hustle into a full-time business — or you just want to skip the car dealership drama — this episode is for you.

Thanks for tuning in to B2B with Randy & Craig, where we connect with local entrepreneurs to explore their journeys and inspire others to take the leap into entrepreneurship. We’re your host, Randy Goldbaum and Craig Rappaport.

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