Working with Penelope Trunk — Tales from a Startup Soap Opera

Published by Ryan Paugh on November 15th, 2007 in Entrepreneurship, Site Related, Work/Life | 17 Comments

People ask me all the time, "What's it like working with Penelope Trunk."

I questioned whether or not I should answer that question in a blog post. But what the hell! I gave her some huge leeway with her post about Ryan Healy and me. So here's the other side of the reality-show startup saga that's consumed our lives.

P is a raw, business-driven machine. I'm pretty sure she's a robot. She literally doesn't sleep. I'm not even sure if she owns a bed.

You'd think she would eventually collapse, have a meltdown or something. Well, Healy and I have been here over a month and she's still going strong.

Eight-thirty in the morning – it's time to get to work. Healy and I meet P at Thieves, the infamous coffee shop that headquartered her blogging operation before we came along. And yes, people really do want to murder her there. I find it amusing. Still, it's not exactly prime locale for doing business.

P has already been there for hours, probably eaten about three bagels (it's all she eats) and she's already pissed off anyone looking for a few hours of peace and quiet. We get our morning cup of joe or tea, whatever the lack of sleep the night before calls for, and sit down.

The owners are replacing the art display in the shop and I'm a little irritated. I had been admiring the previous display for a week. It was sort of a dark fantasy world on canvas. And yes. It was predominantly sexual.

"You don't know what great art is," P says.

The walls are now covered with spectrums of neon.

"Now this is great art!" she says.

She explains to me how great art forces me to see the world in a new and interesting way. I watch my favorite piece get packed into the back of a van…

It only took a week before our workdays started to creep from the coffee shop locale to a new site – our apartment. Naturally, that didn't add any normalcy to our lives.

If you know P at all, you know about the time she spent as a professional volleyball player. It's the icing on the cake for any bio she's ever given.

What she doesn't explain in her bio, however, is that she still harnesses her athletic gifts on a daily basis. Only she's not playing volleyball, she's leaping around my apartment like a 5-year-old kid.

If you ever get P on the phone, ask her what the hell she's doing while you're on the line. Chances are its ballerina spins, shoeless skating across a wood floor or handstands in the hallway.

Occasionally P stops by our apartment for an evening meeting. Usually around the time I'm making dinner. She can't get over the fact that I'm a guy who cooks. She calls me gay. I tell her to shut her mouth or she's not getting any stir-fry.

Cooking to P is ordering Chipotle burritos for dinner guests or nuking Lean Cuisines so she doesn't waste away during her all-night work binge.

I tell her about Parent's Weekend at our college fraternity; a 2-day bash that's actually one of the best times all year. She can't get past the fact that we drink with the parents. She's flabbergasted. I wonder what shocks her more, the drinking or the fact that we actually want to hang out with our parents.

If it's the drinking, I totally get it. She can't handle a glass of chardonnay without getting all loopy. How can she even fathom the idea of college-level inebriation?

The parent thing is another story. At the risk of making generational speculations, I wonder if people in her age realm just don't get the bond between millennials and their family. Is rocking out with your kids considered helicopter parenting?

P's college years were far from what I would consider normal. She didn't go to parties and rarely had a sip of alcohol. Her idea of a good time was, as she puts it, "people watching." Which I totally get, but honestly, what's more fun than watching drunk people?

What I really admire about P is her consistent ability to bring out the best in people. The past few weeks have been especially tough for me. I really miss the east coast. So P and I took a walk and discussed my separation anxiety.

We sat in an old Willow tree that arched over the water's edge on Lake Mendota. It was a completely ridiculous location, but sort of standard for our working relationship.

She recognized right away that I felt trapped, that I needed something I could use an escape from the day-to-day startup hustle. So she recommended I do some volunteer work.

I loved the idea.

I almost couldn't believe how easily my angst was laid to rest. It's rare for someone so foreign to influence your life like this. And that's possibly the best part about our working relationship.