John A. Sheppard (SHEP) is the CEO and Founder of Cross Street. He is an entrepreneur and investor with 20 years of experience in investment banking, venture capital, and mergers and acquisitions in North America and Europe. During that period, he reviewed over 500 deals and was involved in 15 buyouts, mergers and/or acquisitions with transactions totaling more than $5 billion.

SHEP’s goal is to assist 10,000 small businesses owners sell their companies or acquire new ones.

Over the course of his professional career, SHEP worked directly with Fortune 500 companies such as HP (formerly Compaq), Symantec, Lehman Brothers Hyundai, HarbourVest Partners, SXSW, UPS, IBM, AT&T, Home Depot, Wal-Mart, Bosch, and Microsoft. During the last 12 years, John has focused exclusively on small, fast growing businesses and has built up a current portfolio that consists of 8 companies which have aggregate sales greater than $150 million and a portfolio internal rate of return (IRR) of 50%.

SHEP was the founder of CDS Cares – a volunteering effort that assisted local charities, including the San Antonio Food Bank, Texas Special Olympics, Elf Louise, and Habitat for Humanity – and Classroom Arts – a social enterprise focused on providing free art supplies to schools.  He is a former Board Member of the Greater San Antonio Chamber of Commerce, Member of the Economic Council and a mentor to the UTSA Center for Innovation and Technology Entrepreneurship. John was recognized by the San Antonio Business Journal as a 2010 recipient of the Forty-Under-Forty award and is a member of the 36th class of Leadership San Antonio.

SHEP is currently on the board of 5 startups and holds a Bachelor of Science Engineering degree from Princeton University and a Masters of Business Administration from Harvard Business School.