NEW YORK-BASED CASTLEOAK SECURITIES L.P. set out to prove that it was ready to play in the big leagues after only a few months in business. As a newly minted company in 2006, the firm was named sole co-manager for a $300 million floating-rate bond issue by General Electric—one of only two companies on the tombstone. The lead manager was one of Wall Street’s most venerable firms. CastleOak executed their end of the deal impeccably but some within the investment community placed a bet that of the two firms engaged in the transaction, the startup would not prove to be sustainable for the long haul.
Those forecasters were dead wrong. CastleOak turned out to be one of the sector’s fastest-growing boutique investment banks, involved in some of the biggest, game-changing bond and equity offerings over the past decade. By the way, the other firm was none other than Lehman Brothers, the then-158-year-old investment colossus that was among the first casualties of the financial meltdown in 2008.
Despite the doubters, CastleOak has morphed into a top-flight institution with an undisputed track record of performance and success. At its helm is David R. Jones, a 30-year Wall Street vet who built his rep as a virtuoso investment banker and ubiquitous rainmaker. Launching the firm with experienced partners—Managing Director and General Counsel Nathaniel H. Christian and CFO and Director of Operations Philip Ippolito—he struct