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 the airport. Roadshows can be arduous, grueling, and often stressful.

So far, this particular roadshow has been a breeze. Investors love the deal. The client is happy, and the bankers are all playing nice. Heading into the home stretch, the day starts off just like the others. My BlackBerry alarm clock goes off at 6:45 AM The auxiliary wake-up call comes at 6:50 AM, and the “waffle wake-up call” arrives at 7 AM sharp. A “waffle wake-up call” is more or less exactly what it sounds like. Upon first checking into a hotel, I prearrange breakfast room service with strict instructions for the butler (their term, not mine) to come in and make sure that I am awake and/or still alive. You can’t risk waiting to arrange this until right before you go to sleep in the likely event that you won’t have any recollection of getting back to the hotel at night.

A 6:45 AM wake-up isn’t particularly early by my standards, but it is after the typical night…