Simon was a pioneer of the leveraged buyout (LBO) in the 1980s. Following government service, Simon was a Vice Chairman at Blyth Eastman Dillon for three years, He and his partner, then co-founded with Ray Chambers, a tax accountant, Wesray Capital Corporation (Simon contributing the "Wes" and Chambers contributing the "ray" based on his initials), an LBO firm that bought and sold, among others, the Gibson Greeting Card Company, Anchor Glass, and the Simmons Mattress Company, typically investing tiny fractions of their own money and including significant debt to complete the purchase from prior shareholders, and then selling the companies whole or piecemeal after making changes that "often included job cutbacks and other short-term cost-reduction measures.". In 1982, Wesray invested approximately $1 million in equity capital (with Simon contributing $330,000) and borrowed another $79 million to take private a Cincinnati-based greeting card company, Gibson Greetings, for $80 million. Eighteen months later, the company was taken public again, with a value of $290 million, and Simon's $330,000 investment was worth $66 million.