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 Real Estate Market since 1997, the Life Settlement Market since 2003 and the broader capital markets since the mid-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
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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
2018-2023
Prior to forming Oak Stone, Mr. Bailey was the Chief Investment Officer of a publicly traded private equity firm and the CEO and Chief Investment Officer of that firm's primary operating subsidiary. There, Mr. Bailey directed the allocation of company capital to various investment opportunities and led the firm’s life settlement investment division.
2009-2018
Prior to that, 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
Pre-2009
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
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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