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From One Lot in Philly to a B2B Holding Company

The Story

Yossi’s career arc is three businesses inside one industry, each one bigger and more leveraged than the last.

Stage 1: His dad’s used-car lot. “My journey started at 14 on my dad’s used car lot in Philly, washing cars, closing deals, and seeing firsthand how much this industry needed better information and transparency.” (Source 1). He describes the original lot as “a side lot with 10 to 20 cars, just to make ends meet. Very small operation.” (Source 3). They scaled it to “$28 million a year, bootstrapped, fully profitable.” (Source 3) with a 25-27 person team.

Stage 2: Gettacar (2018-2023). “In 2018, I founded Gettacar, an online auto retailer backed by $50M+ from investors including 3L Capital, Luxor Capital, Headline, and Torch, scaling to $80M in annual sales.” (Source 1). Wound down 2023.

Stage 3: Car Dealership Guy / CDG. Started anonymously on Twitter December 2021 while Gettacar was being wound down. By the time of his bio update: “CDG reaches 55,000+ dealers and industry operators, generating over 20M monthly impressions. 98.5% of the top 150 dealer groups engage with CDG.” (Source 1, 2). The Growth in Reverse analysis (earlier snapshot) cites “over 80 million impressions a month across their channels” (Source 4).

The structure today is a holding company, not a personal brand. “CDG brings together media, software (Circles & Pulse), recruiting, content, and live experiences to help dealers learn, grow, and make better decisions. At the center is Car Dealership Guy, the industry’s leading independent media platform.” (Source 1, 2).

His own description of why each stage led to the next: “It has been just a constant exploration of what am I curious about, which has led me to working on very different types of businesses… It was never my intention to do these last two businesses.” (Source 3).

External recognition: “EY Entrepreneur of the Year and one of Goldman Sachs’ Top 100 Most Intriguing Entrepreneurs.” (Source 1).

Lesson for Creators

A media brand built on top of operational experience is harder to copy than one built on commentary. Yossi’s CDG works because each stage of his career produced credibility the next stage spent: the family lot taught him how dealers think, Gettacar taught him how investors and operators at scale think, and CDG sells access to both. The compounding doesn’t happen across unrelated industries. It happens when you stay inside a vertical long enough that every previous role becomes proprietary research for the next one.

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