Uploaded July 2026 | Updated September 2026, 1 week ago
Before he built a $150M automotive empire, Brad Oleshansky was the lawyer for the company behind McDonald's toys — and the McDonald's Monopoly game. Then the scandal now known from HBO's "McMillions" hit: one insider was funneling the winning game pieces to criminals, and the fallout took down the entire billion-dollar business.
In this clip, Brad tells it from the inside — laying off 500 people, watching the company's reputation get destroyed in a single press conference, and turning into a "litigation machine" to hold the people who defamed them accountable. But he also explains why he looks back on it as the most valuable year of his career: a crash course in business, bankruptcy, tax, litigation, and insurance that shaped everything he's done since.
From the full episode of Cars and Culture with Jason Stein.
#CarsAndCulture #BradOleshansky #McMillions #McDonaldsMonopoly #Entrepreneur #BusinessStory #MotorEnclave #JasonStein
Before he built a $150M automotive empire, Brad Oleshansky was the lawyer for the company behind McDonald's toys — and the McDonald's Monopoly game. Then the scandal now known from HBO's "McMillions" hit: one insider was funneling the winning game pieces to criminals, and the fallout took down the entire billion-dollar business.
In this clip, Brad tells it from the inside — laying off 500 people, watching the company's reputation get destroyed in a single press conference, and turning into a "litigation machine" to hold the people who defamed them accountable. But he also explains why he looks back on it as the most valuable year of his career: a crash course in business, bankruptcy, tax, litigation, and insurance that shaped everything he's done since.
From the full episode of Cars and Culture with Jason Stein.
#CarsAndCulture #BradOleshansky #McMillions #McDonaldsMonopoly #Entrepreneur #BusinessStory #MotorEnclave #JasonStein
