The Roadshow (aka The Worst Private Plane Trip Of All-Time)

To commemorate the paperback release of the New York Times bestseller, Straight to Hell: True Tales of Deviance, Debauchery, and Billion-Dollar Deals, here’s the chapter that started it all. Without a manuscript and having never written a book, this story was enough to get me a six-figure book deal.

Selling a new high-yield bond for a company usually involves conducting a full investor roadshow. It is an integral part of the deal marketing process and can be of pivotal importance in terms of lowering a company’s cost of borrowing. London-Paris-Frankfurt-Milan-Madrid is a typical European circuit, often traveling by private plane, always dining at the best restaurants and staying at the finest hotels. This might sound exciting and glamorous, but I can assure you, it’s anything but.

In a nutshell, a roadshow involves taking borrowers — the bond issuers — to meet and sell their story to potential investors, who range from hedge funds and asset managers to insurance companies and pension funds. The issuers and their bankers go through a scripted PowerPoint presentation; address any structural, disclosure, or financial issues in the offering prospectus; and finish with a Q&A.

Each day is a series of back-to-back meetings and group investor lunches, flanked by market update and strategy conference calls and punctuated with mad dashes to…