‘I don’t think I deserve a profile in the YDN.’

Threesome with Max & Susannah
This is Jonathan Coulton '93, Drew's funny boss.
This is Jonathan Coulton '93, Drew's funny boss. // Creative Commons
By Max Saltarelli and Susannah Shattuck
Friday, January 18, 2013

For each installment of their new column, Max and Susannah will interview and profile a recent Yale alum, in order to show our readers what life after college is really all about.

“The bummer is Yalies trying banking.” Drew Westphal ’10 is adamant when it comes to consulting and investment banking as career tracks for recent graduates. “If the fact that you need something to do is the only reason you’re a consultant, then I don’t think you should be a consultant. I did that for a while, and I had to pay $10,000 to quit.”

After graduating with a bachelor’s degree in computer science, Westphal, like many of his classmates, moved to New York to begin a career in consulting. He was competent at his job, competent enough to earn a $10,000 bonus, which was contingent on his staying with the company for two more years. After nine months in the office, however, Westphal realized he would not make it another 15; working as a consultant had made him despondent. In his own words, “crying in a cubicle gets old after a while.”

It was at this point in his career, less than a year out of college, that he decided to throw caution to the wind and quit his prestigious, high-paying consulting job. Where he landed next, no one could have predicted.

“Life has a way of surprising you,” said Westphal in a phone interview. “Being a Whiff literally changed my life. For. The. Better.” Westphal described the sequence of events following his exit from consulting as weird and unexpected. By a stroke of fate, a sold-out Whiffenpoofs concert at Woolsey Hall drew audience members from around the country, including geek humor gods John Hodgman ’93 and Jonathan Coulton ’93, the latter an alumnus of both the Spizzwinks(?) and the Whiffenpoofs.

A year later, during the process of quitting his consulting job, Westphal contacted Coulton, known as an Internet presence and comedic musician. Of the drunken conversations that led Westphal to a job as Coulton’s fan mail answerer, Westphal simply says, “Once a Wink, always a Wink!” adding that if we could see him through the phone, we’d see him giving us a big, warm wink.

A few months into working with Coulton, Westphal helped the musician design his website and drove his tour van, eventually taking on the title of Coulton’s general manager — or “Scarface,” as he is known to Coulton’s numerous fans (if you want to know why, check out JoCopedia, the Jonathan Coulton Wiki). Westphal manages the official Scarface Twitter and occasionally turns up in Coulton’s music videos, including one in which he is run over by a zamboni.

Of course, when you spend your time around Internet-famous comedians, you experience your fair share of Web-fueled high jinks. Before a show on one of Coulton’s cross-country tours, Scarface tweeted that Coulton’s tour bus needed a cat and asked fans to bring stray cats to the show for adoption. Coulton tweeted right back that he didn’t want a cat for the bus but rather a pig. At the next show, one die-hard fan gave Coulton two beautiful, plastic, hand-painted German figurines — a cat and a pig — to that night’s show. Since then, Bus Cat and Bus Pig have been active tweeters (under the handles @RealBusCat and @RealBusPig), and the two have garnered a following that includes such esteemed fans as singer-songwriter Aimee Mann.

Westphal’s post-Yale journey has been a dynamic one, and he encourages graduating seniors to think about their immediate future not as a fixed time but one full of change and discovery.

“Everyone’s going to make you feel like shit because you don’t know exactly what you’re going do with your life,” he told us. “By the end of the second semester, there’s this atmosphere of who-are-you-going-to-be, as if you have to have an answer — and that’s bullshit.”

Westphal is quick to say that his current career — managing musicians — is not what he ever envisioned for himself, and he is not sure he wants to continue doing it forever.

“I’ve been doing stand-up in the city for the last couple of months,” Westphal said, “but I think you might have to be depressed to make jokes for a living, and I don’t think I’m depressed enough.” For now, Westphal is content to keep his stand-up on the side while he focuses on managing Coulton and the many adventures that come with his job.

We asked Westphal what parting words of wisdom he has for soon-to-be graduates. His advice? “Get good at Excel. And treat yourself to something sugary and scrumptious each day.”

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