Not only did everyone’s favorite late-night sweet spot disregard city ordinances, but it never paid its cookie-crazed staff.[/media-credit]

Full disclosure No. 1: I worked for Insomnia Cookies for a semester during my freshman year as a student marketing representative.

The other day on Bedford Street, I noticed something I never had before. There’s a parking lot that houses food-vendor carts that are a mainstay on Library Mall by day and various side streets by night. I slowed to look: Zen Sushi, Hibachi Hut, Teriyaki Samuri, JD’s – they were all there. That’s when a flash of purple through chain link caught my eye.

There, in all its behemoth, boxy, twin-ovened glory was that legend of the late night, mitigator of the munchies, street vendor of the sweet-toothed: The Insomnia Cookies truck, looking no worse for the wear. Is Insomnia planning a comeback? Why is their truck still here? Why did they leave town in the first place? I emailed Seth Berkowitz, CEO of Insomnia, looking for answers, and he called back to feed me turds and tell me they were cookies.

Full disclosure No. 2: I loved their product. Give me bite of that white-chocolate macadamia nut or a warm peanut butter chocolate cookie over pretty much any other dessert, and I’ll be completely content.

A primer for the uninitiated, the glucose intolerant and the underclassmen: Insomnia makes some amazing cookies. This isn’t a personal opinion – it’s verifiable Madison Truth. The spring 2009 Badger Herald Bar and Dining Guide proclaimed that Insomnia had the best cookies in Madison. In a 2008 round-up of State Street area food carts, The Herald spoke in near-religious terms about the delicious confections, calling them “more than a warm decadent treat right out of the oven […] an experience.”

Berkowitz was quick to agree: Madison and Insomnia were like chocolate and peanut butter. “I love Madison,” he said, “And Madison loved us. We plan on returning once we get everything sorted out.”

But then he handed me a bigger bite than I could chew. “The city’s actions are reprehensible, quite honestly. They’ve turned down every effort, every request we’ve made to bring our truck back.”

But wait – what about that local love? Why do the cookie kings no longer sit inside their motorized castle, ruling Thursday nights with an iron spatula? In short, Insomnia Cookies mismanaged themselves out of town. And Seth Berkowitz knows it, too.

Full disclosure No. 3: Insomnia never paid me a cent they owed for the hours I worked. After a year and a half I’ve now completely given up on ever seeing that $8.50 an hour. (The company has also failed to pay the Herald for a $1,500 insertion they made in fall 2008 – Ed.)

Berkowitz’s anger toward the city of Madison was astonishing, especially given his grasp on how Insomnia fell. Berkowitz stated the details of the case: Insomnia applied for and was granted a street vending license for April 2008-09, but five months into that term was notified that their truck didn’t fit city licensing specifications. Then, in the spring, Insomnia signed an agreement with Towers and began selling their baked goods from a small parking lot between the apartment building and City Bar, but was asked to cease operations.

Heatedly, Berkowitz summed it up, “The city of Madison decided to kick us off of State and boot us out of Madison!”

Unfortunately, his explanation was missing a key ingredient. Insomnia made error after comical error until the oven door of opportunity slammed shut on the Madison market.

Take my word for it: They were disorganized. As a marketing rep, I was asked to do everything from the inane (handing out T-shirts in front of college library) to the illegal (sneaking into dorms to drop flyers under doors) to the absurd (a 4/20 campaign that crashed the company’s servers). During that time, my co-workers and I (all UW students) never saw our supervisor face to face. When it came time for paychecks, none arrived.

And it’s plainly apparent that ineptitude extended to Insomnia’s dealings with the city. True, they were asked to leave five months into a year-long permit, but as Berkowitz surely knows, Insomnia didn’t actually do that, staying in Library Mall against city rules long past that notification.

His knowledge that the Insomnia truck was “illegal as per city ordinances” is a little confusing when combined with the fact that they attempted to continue operating from the lot near Towers after leaving Library Mall. In fact, according to a Nov. 2009 Herald story quoting Street Vending Coordinator Warren Hansen, Insomnia didn’t even hold a basic vending license during the time they ran their business from Towers, making both their truck and their delicious gooey cookies illegal.

So don’t count on seeing the big purple cookie-mobile back on the streets any time soon. When Berkowitz says, “We do plan on returning,” or “I will do what is necessary to stay on the Wisconsin campus,” as he did back in April 2009, you can almost taste bitterness and inevitable failure. As always, Insomnia’s intentions may be good, but their execution will be a little less than half-baked.