With over 10 years at Berkadia (A Berkshire Hathaway and Jefferies’ owned company), he achieved the role of Managing Director after 4 years. During his 10+ years at Berkadia Jackson was the lead originator on over $2.5 billion of debt and equity placements including transactions on debt/paper instrument trades, ground leases, and master leases. Jackson Cloak’s nearly 20 years of experience is qualified by originating and closing complex transactions utilizing the Berkadia Balance sheet, GSEs, Life Companies, Partner/Participating Banks, Non-Partner Banks, Conduits, and Debt Funds separates him from the crowd. Jackson has built his career on being responsive, transparent, and honest while delivering superior results. ​

The knowledge to have the correct capital structure for assets, (groups managing billions of dollars and putting 10-year fixed or only bridge debt on everything). Leaving tens of millions of dollars through prepayment penalties or inefficient capital requiring buyers to do “Loan Assumptions” or other costly mechanisms. Minimizing or eliminating these inefficiencies is generally not achieved in the market today. The ability to look at a deal and know the correct capital structure comes with 20 Years of closing transactions across the country. Both the ability to source transactions and recognize opportunities is a valued asset provided.​​​