Eastbound, to the old stomping ground. Back in 1998, as Harlequin (the first of my doomed startups) was in freefall, I’d started looking around for a safe landing. Shumeet and a few other friends were working at JPRC, a research lab in Pittsburgh funded by software sugardaddy Justsystem Japan. Sounded like nice work, but it was in Pittsburgh. And I’d married a fifth-generation Californian.

It must have been at ICML that Shumeet and Andrew cornered me over dinner. Shumeet must’ve been the one to start it: “Okay, I’d like to do an experiment. There are a couple of useful data points about peoples’ willingness to discuss Pittsburgh. Let’s say we were to offer you $10k per year to work in Pittsburgh – you’d say ‘Hell no!’ right? And if we offered you a million a year, you’d say ‘Hell yes!’, right? I’d like to find out where those answers flip. I’m going to start at $10k, and start counting up. Each time I say a number, you tell me what your answer would be. I’m not making salary promises here – I’d just like to figure out where ‘Hell no’ disappears, and where ‘Hell yes’ starts, okay?”

And off they went – $10k, $20k, $30k,… I was still at “Hell no” when they crossed my (soon to evaporate) Harlequin salary, but firmly in the “uhhh” region as they crossed the 150% mark without slowing down.

I was sweating when I stopped them – “Okay, okay, I can’t do this. I can’t do numbers like that without actually seeing the lab and visiting Pittsburgh” That, of course, was all they were after; the hook was set, and they reeled me into the interview.

No, you’ve never visited Pittsburgh, and that’s fine. Take that steelmill smokestack stereotype and hang on to it; it’s a comfortable image we all grew up with.

But I wasn’t ready for what I saw when I stepped out onto the street that morning. It just felt, well, right. This was the birthplace of public radio, the home of Mr. Rogers. And I wanted it to be my home, too. Walking Schenley park, along the old stone bridges of Panther Hollow, under ancient oak and maple, dodging the swarms of Hassidic kids decked out in broad black hats on Murray Ave, strolling under Pitt’s “Cathedral of Learning”, a gothic icon to make Batman homesick.

What got me was the complete lack of pretense – it was all just what it was. If California was the home of post-modern angst, Pittsburgh was the home of post-angst modern. Brad Yoder (a Pitt native) became my soundtrack:

“My old car, I never know what’ll go first
the body or motor, rusting through and wearing out.
But it slipped past inspection, and on further reflection
it gets me where I’m bound….”

You gots what you gots, and you find the beauty and joy within it.

It was an awkward conversation When I got back to home. “You really think we should move to P…P…Pitts… that place?!?” Devon wasn’t enthusiastic. Her entire family was all within 100 miles of where we lived in Menlo Park, and I was asking her to pack up for a midwest steel town.

Except that steel had been gone from Pittsburgh for 30 years by then. It wasn’t the place everyone remembered. I tried telling her about Schenley Park, Squirrel Hill, the trees, the rivers.

I wasn’t terribly convincing, but Andrew, the master of persuasion, was way ahead of me. “How about all of you come out to visit as a family. Stay with me and Donna, just to get a feel for the city. We’ll have dinner with friends, give you a sense of what life is like here…” And yup, she was just as hooked as I was. Three months later, the moving van pulled up and rolled our earthly belongings into what became known as Pittsburgh’s “ice storm of ’99.”

We’d bought the old “bus stop” house on the corner of Malvern and Plainfield, in the heart of Mr. Rogers’ real life neighborhood. We hadn’t been shuttling goods in through the door for very long when the neighbors started to show up. One shoveled our new driveway so the movers could get in more easily. One – several perhaps, it’s all a blur – brought cookies and cupcakes. The folks across the street offered to take Miranda for the afternoon so we could concentrate on getting our stuff in from the freezing rain.

And it was the start of something beautiful. We pretty quickly settled on the idea that this old house where we were going to raise our children. We were going to grow old here and watch the slowly changing seasons of our lives from the front porch. We’d pick cherries from our yard in the spring, dry apples the fall, sled down our street in the winter. We’s sip coffee and wave at passing neighbors on their way to the library; maybe their kids would come in for cookies and milk.

Reality intervened just over a year later, though, as the Japanese stock market crashed. Justsystem had their lunch money swiped by aggressive Microsoft marketing, and decided that the first step in their survival strategy involved jettisoning their American research lab. That meant us.

The conversation that night was a bit strained. I twisted the words around the inside of my head trying to figure out how I was going to convince my California bride to stick it out here in the midwest. While she was wondering silently how to convince me to stay.

Okay, we had a good laugh once we figured out that we both wanted to stay, but damn, that was awkward.

I found a job with some friends at another Pittsburgh startup, but that one lasted 16 months. Then another startup, which hung on for just over a year. Then a temporary stint at CMU. Then… finally, we decided it was time to throw in the towel. We’d burnt through our savings and it was time to get a “real job.” I had some solid offers in California, so we packed up our dreams, rented the house out and moved back west.

Anyhow, the point of the long story is that we’ve got a lot of emotion wrapped up in this old city. We’re going for a my friend Geoff’s wedding – I worked with Geoff at startup #3, but he had the good sense (and skill) to land a permanent research position at CMU.