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Our Background

Personal Profile

Mr. Bailey serves as the CEO and Chief Investment Officer of Oak Stone. He is a senior executive with 25+ years of experience in the public and private capital markets. Mr. Bailey has been involved in the Life Settlement Market since 2003 and the broader capital markets since the late 90's.  He has been an active participant in both the private and public securitization markets and has expertise across a broad range of financial products

Mr. Bailey has spoken about life settlements, fixed income, securitizations, and other assets classes at numerous national and international investment conferences over the past two decades and is a widely recognized expert and leader in the space.


Mr Bailey 
Work Experience


Prior to forming Oak Stone, Mr. Bailey was the Chief Investment Officer of GWG Holdings and the CEO and Chief Investment Officer of GWG Life. At GWG, Mr. Bailey directed the allocation of company capital to various investment opportunities and led the firm’s life settlement investment division.


Prior to GWG, Mr. Bailey was a Managing Director with Beal Bank where he led a number of investment teams. Most notably, Mr. Bailey founded the Longevity Group at Beal Bank which he grew into one of the largest sources of capital to the life settlement market between 2011 and 2018. In addition, Mr. Bailey led the bank’s Interest Rate Derivatives and Hedging teams as well as the Real Estate team which focused primarily on running off the banks legacy real estate assets acquired during the credit downturn from 2007 to 2011


Prior to joining Beal Bank, Mr. Bailey was a Senior Vice President with Wells Fargo Capital Finance (f/k/a Wells Fargo Foothill) where he was responsible for building out a structured finance investment vertical focused on providing below investment grade credit to commercial specialty finance companies

Prior to joining Foothill, Mr. Bailey held various senior leadership positions in the public and private capital markets where he provisioned risk based capital to a variety of asset classes ranging from the investment grade and high yield public debt markets, to the derivatives markets, to the equity and futures markets

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