Richard R. Waterfield is Chairman of the Board & CEO of Waterfield Enterprises, an American investment holding company with interests in technology, energy, financial services, defense, management consulting, real estate, hospitality, and agriculture. Waterfield has acquired operations dating back to 1887.

Mr. Waterfield serves as Chairman & CEO of Waterfield Enterprises (Est. 1999), and Waterfield Asset Management (Est. 1989). He also serves as a Managing Principal of The Waterfield Private Equity Fund(s) I (Est.1999), II (Est. 1999), and III (Est.2004), a Founding Partner at Waterfield Merchant Banking (Est. 1998), Chairman of Waterfield Utilities. Co-Chairman of Waterfield Energy (Est. 2009), Co-Chairman of Waterfield Technologies (Est. 1989), Co-Chairman of Waterfield Financial (Est. 1928), Chairman Emeritus & Former CEO of Waterfield Group (Est.1928), Former Chairman of YPO Orange County, Chairman of YPO | Northern Indiana, Chairman of Culver Military Academy Summer Schools & Camps, and a Director of Tevora, the largest data security consulting firm in Southern California. Mr. Waterfield also coaches a select group of high-potential CEOs. Their companies include: Ask The Circle, a global collaboration platform for ultra-high net-worth family offices, Desai Hotel Group, a hotel development and management organization, Federal International, an acquisitive waste recycling business focused on North America, CapView Partners, a single-tenant net lease 1031 Exchange Solution and real estate fund management organization, and Sante Realty, a real estate investment organization with properties in 12 states.

During his tenure at Waterfield, Mr. Waterfield has overseen over 70 acquisitions and divestitures, along the way founding Waterfield Asset Management, Waterfield Enterprises, Waterfield Merchant Banking, The Waterfield Funds, two of America’s first Internet banks (National InterBank & UFB Direct), and Waterfield Financial, which at one time owned and operated America’s largest independent affinity deposit origination network, a 90 million member network serving the NRA, Veterans of Foreign Wars, Firefighters, and the US Armed Forces, among others.

Prior to joining Waterfield Group, Mr. Waterfield was at Goldman, Sachs & Co. in New York, where he served under Goldman New York Institutional Equity (NYI) Partner Edward Spiegel. He later co-founded a hedge fund and private equity organization and reported, as Co-CEO, directly to the former Head of Goldman’s Global Bank Stock Group, as well as the former Chairman of Goldman Sachs International and the former Head of Goldman Sachs Financial Institutions Group.

From 1992-1994, prior to his employment with Goldman, Mr. Waterfield trained at Prudential Securities in New York under renowned bank stock analyst George M. Salem. Mr. Waterfield received his BA in Economics from Columbia University in 1994, and is a member of MENSA.

Mr. Waterfield trains under Martial Arts Hall of Fame Grand Master Steve Ross, and has a Black Belt in Karate.

Through Waterfield Foundation, Mr. Waterfield supports various charities and institutions of higher learning, among them Culver Military Academy, The NRA, Outward Bound, The Air Force Association, The Make A Wish Foundation, Columbia University, The Children’s Hospital of Orange County, The Robin Hood foundation, The International Association of Firefighters, The Heritage FoundationThe Cato Institute and The Navy Seal Foundation. Mr. Waterfield is also an avid supporter of the Republican Party.


Mr. Waterfield is currently, or was previously, a member of the following boards of directors:

  • Affinity Financial Corporation
  • Altura Communications Solutions
  • American Savings Bank
  • Blueworx, formerly IBM Websphere
  • Cappello, Waterfield & Co.
  • Columbia Economics Advisory Council
  • Culver Military Academy
  • Culver Summer Schools & Camps
  • DHC Communications
  • Desai Hotel Group
  • Dice Communications
  • Fife, Waterfield & Co.
  • First Mitchell Bancorp
  • Forty-Seven Ronin, Inc.
  • National InterBank
  • National InterBank (Now Capital One)
  • Roanoke Main
  • Speech Soft Solutions – India
  • Speech Soft Solutions – London
  • Tevora
  • The AARP Banking Center
  • The Canterbury Football Club (CFC), powered by Indy Eleven (C)
  • The Canterbury School
  • The NRA Banking Center
  • The Waterfield America Foundation
  • TheRateReport™
  • UFB Direct
  • Vox Artificial Intelligence
  • Vox Network Solutions
  • Waterfield Asset Management
  • Waterfield Bancorp
  • Waterfield Energy
  • Waterfield Enterprises
  • Waterfield Financial Services
  • Waterfield Group
  • Waterfield Luxury Properties
  • Waterfield Montminy & Co. (CREO)
  • Waterfield Private Equity Fund(s) I,II, & III
  • Waterfield Ranches & Farms
  • Waterfield Technologies
  • Young President’s Organization (YPO) | Northern Indiana Chapter
  • Young President’s Organization (YPO) | Orange County Chapter
  • Young President’s Organization (YPO) | Orange County Gold Chapter
  • Young President’s Organization (YPO) | Pacific Region


  • Republican Senatorial Inner Circle
  • President’s Club, Republican National Committee
  • California Business Council
  • Presidential Business Commission, National Republican Congressional Committee
  • Young Presidents Organization
  • The Republican Party
  • The Heritage Foundation
  • Culver Military Summer Academy – Former Co-Chair, Diversity Committee


  • Waterfield Foundation
  • The Navy Seal Foundation
  • The Pacific Council
  • Outward Bound
  • Howard University
  • Columbia University
  • The Canterbury School
  • Make A Wish Foundation
  • The Robin Hood Foundation


Mr. Waterfield is an active member of the Young President’s Organization (YPO), and has been involved with YPO since 1986. YPO, founded in 1950, has a membership of over 20,000 CEO members organized in 300 chapters in 125 countries. Mr. Waterfield served formerly as Chairman of YPO | Orange County, Area Chairman of YPO’s Pacific Region (Southern California), and currently serves as Chairman of YPO | Northern Indiana. Mr. Waterfield’s wife, Stefanie, served as Spousal Chairwoman for YPO’s Pacific Region, and currently serves as a Spousal Chairwoman for YPO | Northern Indiana.


Mr. Waterfield has been a guest speaker at The National Family Business Council, USC Marshall School of Business, Columbia Business School, Culver Military Academy, and Young President’s Organization (YPO). He has been quoted in the Wall Street Journal, CNBC, The Los Angeles Times, The San Francisco Examiner, The Orange County Register, and American Banker. Mr. Waterfield co-authored a published & Wall Street Journal referenced report in 1994 entitled “The Coming California Bank Crises” with George M. Salem, Head Bank Stock Analyst at Prudential Securities. He also authored a published report in 1994 entitled “The S&L Crises and It’s Impact on Market Volatility” while attending Columbia University.


Mr. Waterfield received a BA in Economics from Columbia University. He then joined Goldman Sachs & Co., where he met the Former Chairman of Goldman Sachs International, who mentored him for 15 years. He is a member of MENSA.

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