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Bob Leary

Robert J. Leary is Managing Director of Vineyard Point Associates (VPA) a boutique investment firm specializing in startups and smaller on-going concerns. VPA is currently invested in over three dozen companies in a range of disciplines including healthcare, technology, entertainment and consumer products. 


Bob is currently operating as the Chairman and CMO of the Miami Bay Beverage Company (MBB) which he co-founded in 2103. MBB’s flagship product, trimino – Protein Infused Water is one of the hottest beverages in the U.S. Market.

Mr. Leary is a nationally recognized expert on healthcare reimbursement, data analysis and software development. Prior to VPA, Mr. Leary was Vice President of Ingenix (United Healthcare) and founder, Chief Executive Officer and Chairman of the Board of HSS Inc., a leading supplier of software for hospitals and managed care organizations, acquired by Ingenix in May 2005. Mr. Leary acquired HSS as a $1.5M turnaround opportunity and grew it to a highly profitable $25M+ enterprise prior to exit. While his training and education is in software and technology most of his time with HSS was spent on positioning the business and marketing its brand and products. While at HSS, Mr. Leary pioneered the use of a “Software-as- a-Service” (SaaS) business model creating a company with a 98% recurring revenue stream.

Mr. Leary is the author of numerous articles on topics related to computer techniques and strategies for building and analyzing healthcare databases as well as on topics such as software inter-connectivity and healthcare reimbursement. He has, on many occasions, lobbied CMS (Medicare) and Congress to shape contemporary healthcare legislation. Mr. Leary served in an advisory capacity to Yale University on research into patient classification systems, and to the Agency for Health Care Policy and Research on the development and implementation of a national healthcare database from state data sources.

Mr. Leary and his wife Renee (a nationally recognized expert in healthcare reimbursement) live in Guilford Connecticut and have four children. Katie, a two-time graduate from the Tisch School at NYU is working in the entertainment industry. Sean, recruited to play Division I lacrosse at West Point, is now a captain in the Army. Kevin and AJ, recruited to play division I lacrosse at Hofstra finished their undergraduate work

at Dickenson College and University of Vermont respectively. AJ went on the obtain a Masters of Science in Nutrition and Exercise Science from the University of Tampa.

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