As a serial entrepreneur and perpetual student, Reggie Middleton's unconventional experience has given him the ability to recognize value, or the lack thereof, well before much of the professional populace. His ability to identify opportunity and his "out-the-box" mind-set are due to years of entrepreneurial pursuits in insurance, financial valuation/modeling, technology, media, and real estate
attending Howard University in Washington, D.C. from which he obtained a BBA in
business management. Reggie returned to NY and joined the ranks of Prudential
Insurance, training in financial product sales. Feeling constrained in his
ability to pursue institutional clients, he moved to a small securities firm and
became a series 7 broker. Again feeling constrained in his ability to
creatively pursue his ideas, in his early twenties he struck out on his own and
created margined mutual fund timing programs for his own trading account. This
was the first in many unorthodox proprietary investment and risk management
strategies Mr. Middleton has created
In the early 1990s, Reggie, an entrepreneur in his early twenties, entered the insurance and risk management field by brokering insurance for entire municipalities and political subdivisions on an exclusive basis. He also conceptualized, marketed, jointly prepared and submitted LORIE (the Livery Organizations Reciprocal Insurer Entity - a reciprocal insurer owned by the insureds) - to the NYS insurance department for licensing.
Reggie then formed Municipal Risk Management - a venture with a major accounting/consulting firm to offer risk management, consulting and brokerage services to small and medium sized municipalities.
Mr. Miiddleton also pioneered derivative and structured product use in health insurance via his concept, "Financial Re", a tax advantaged, ERISA compliant, off shore financial reinsurer. It was designed to securitize FASB 106 retirement medical liability risk to be sold through the debt markets using Reggie's own ‘Max Notes' (option embedded notes linked to a proprietary medical loss index). He recruited the assistance of partners from the big five accounting and consulting firms for purposes of validating and marketing Financial Re's derivative debt securities. These securities (Max Notes) had near-zero correlation to conventional equity and debt markets and as such were designed to appeal to institutional investors looking to diversify risk.
In the midst of the DOT.com boom era, Reggie, a self-taught technology buff and student in financial valuation, recognized opportunities to incorporate his passions for technology and financial valuation and transitioned to the distributed technology and media industries Again, as an entrepreneur, Reggie created, marketed and sold web-based, decision support and financial modeling systems featuring file sharing, collaboration and team based productivity for M&A, LBO, private equity and corporate valuation deals. These high-end financial models, financial modeling techniques, corporate valuation techniques, and methodologies quantitatively captured the intangible assets from technology companies that represented a significant portion of their value such as human capital, brand value, viral marketing and network effects. Reggie's modeling experience includes information technology TCO/ROIC, LBO, M&A, private equity analysis and valuation, financial derivatives, partnership valuation, real estate analysis and valuation, derivative and structured product engineering, and corporate valuation via proprietary economic profit methodologies.
Mr. Middleton was one of the early entrepreneurial dot.commers to adopt the off shoring model, coding entire software platforms at below market cost through engineering relationships with off shore IT consulting shops & development sites in Bangalore, India. In addition, he expanded this platform to a full featured Application Service Provider platform, web-based office suite and web-based collaborative knowledge sharing platform - known as NuoMedia, which competed with Microsoft's Office suite as a desktop office productivity solution. NuoMedia was the first to market publicly available Web-based office productivity suite and first to be introduced to the public through the media (beating Microsoft and Sun Microsystems as seen in Reggie's interview on CNNfn's Digital Jam, Sept. 1, 1999).
Mr. Middleton began investing in residential real estate, sensing the boom portion of the boom bust cycle in the year 2000. He engaged in real estate investment/management, returning several multiples of the broad market averages, approaching four digit returns from 2000 to 2006.