Eat, Shop, and Play: Vindigo

On my husband’s thirtieth birthday, we had dinner at Gennaro’s on the Upper West Side. He didn’t want a party or a meal with friends. He didn’t want the milestone mentioned. He was too old to be a prodigy, and that cut him deeply. I tried not to laugh; his misery was real.

His old company, which branded itself on hiring ‘superstars’, gave him a great gift. They didn’t pick him out as one of their chosen ones. He was smart, well-respected, competent, but they didn’t spot him as a star in their warped firmament of quantitative analysts and trading hotshots. After four years there, he wasn’t happy, and as was my way then I nagged him about this on his birthday.
“Of course you’re not happy. You’re in a rut, just like when you were doing your thesis. You need to start doing your résumé and looking for something that suits you better.”
Some birthday. Poor bastard.

Three weeks later, Jason started to talk openly about starting a business. He and his coworker David tossed around ideas on their Central Park runs. Jason was fixed on the possibilities of mobile devices, especially Palm Pilots. David had some other ideas, but after ten days or so emailed Jason to say that he’d seen the light. Palm Pilots were the way to go.

They began to come to our tiny apartment after work. Ceremoniously, I dragged out the unused artist’s easel I’d given Jason for another birthday. We balanced a whiteboard on it, and started to throw around ideas for Palm Pilot software. We talked earnestly about scheduling whole families for soccer moms, about handhelds you could roll up like a scroll, about controlling your fridge from your Palm. I loved this stage. Bob Geldof said that most Irish ideas get talked to death in pubs, and I was happy with pie in the sky. Jason and David wanted real pie, though. They emailed in a frenzy. They spent weekends pacing together and refining their ideas. They decided to build a search engine for the real world, starting with the only world that counted: Manhattan.

Jason wanted to quit his job immediately. I panicked, though I didn’t say. What was the rush? What about those trading bonuses? What about security, our visas, all that stuff? He was set on it. He had a real sense of urgency, of a door that was closing. This was 1999 and he was right, though I didn’t know it then.

Jason quit three years ago in April. The first task was to name this baby company, something that the books told us should take no more than a couple of days. Everyone sent suggestions. David lobbied for Streetmonkey. I pushed Afria, my middle name, wanting a label credit like every band girlfriend. We had Zambuck. JakPak. Blue-somethingorother. Jason came up with Vindigo, which I hated, and we fought about it.
“Ugh. Like vindictive, or Vindaloo. That’s really stupid!”

It’s hard to squabble with Jason. He wanted a name that was unique, easy to pronounce, that didn’t have to be spelled out over the phone. He narrowed down a list of five. David’s sister-in-law volunteered to stand on a street corner with a clipboard and get votes from 100 passers-by. I accused Jason, somewhat hysterically, of seeding the rest of the list with deliberately crappy names. But the people spoke, and Vindigo won. I like it now.

They had quiet discussions over who would be CEO and who would be president. Co-founders, David said. CEO, Jason said. They debated how to break down the work and decided that David would do all the coding while Jason would do the business research. In the middle of May, David quit his job too. I took a picture of them that night, standing proudly in front of the makeshift whiteboard that displayed a faked equation and the date. They have their arms around each other’s shoulders, and they look incredibly young and hopeful.

That whole summer, they worked every single day in our apartment. It was on the second floor of a building in the canyons of midtown and got no natural light. David sat at a little girl’s white dressing table that he had found somewhere. He couldn’t get his legs under it and wrote the entire first version of Vindigo sitting sideways on. Coming home from work, I’d find them exactly where I left them, blinking hard from looking at their monitors all day. While I cooked dinner for them, they would tell me about their progress, and then head back into the living room to work on into the night. We had no air conditioner, and no screens on the windows. I bought fly-swatters when I discovered that they had become obsessed with killing flies with our table napkins.
“So, how was your day?”
“Great! I got nine flies, and Dave got 11.”
In July we broke down and got an air conditioner, too.

David ate Snackwell cookies and rice cakes, and cranked through code. Jason paced, gestured, and fretted that he wasn’t progressing through the business plan as fast as David was getting through the hard slog of making an application that worked. In those heady days, all the so-called smart money said to just throw together a back-of-the-napkin business plan and some Flash mockups, and the money would follow immediately. Jason and David disagreed. They knew that Vindigo was the kind of product that would get polite nods if described, but once it was in someone’s hands, they wouldn’t be able to imagine it not existing.

There was a lot of 1999 nonsense that they ignored. They took no salary for months and sat in a cramped apartment rather than fancy venture-funded digs. Their first employee’s first job was to find a payroll system for himself, then to find office space.

In August, Vindigo’s little band moved to a grotty loft in Chelsea on the same block as the late, lamented Billy’s Topless, which by then had gone through a Giuliani-forced rebranding as Billy Stopless. I cried by myself the day they moved out of the apartment. It was the end of the beginning and I knew I would lose touch as they became a real company.

My officemate Tricia listened to my excited gabblings every day. I showed her every shaky version-in-progress, and painted wild pictures of success that Jason would never have let me get away with if he’d heard. I couldn’t join Vindigo myself—I needed to hold the work permit for both of us and I had to pay the rent until he drew salary—but Tricia got excited. She started to work for them in their new loft, in the evenings after her real job. They were lucky to get her.

I moved to another startup. I didn’t hear the daily stories any more, or the daily fly body-count. They had moved to bigger and better vermin and their trash bags squirmed with mice. The little office, originally designed as a one-bedroom apartment with a French travel agency at the back, slowly filled up. The engineers they hired were modest, literate, and brilliant, especially by New York standards. When the French travel agents lay on their couches smoking dope and giggling, the Vindigo engineers put headphones on. Tricia joined full-time, and complained about being the only one who bought toilet paper. There were ten men and Tricia, plus the French travel agents, and only one toilet with a saloon door that didn’t reach the ceiling.
“I never wanted to drink anything in case I’d have to pee,” she said, “I got really dehydrated that winter.”

We spent the night before new year 1999 fixing bugs and proofreading the web site. We ordered ice-cream from Kozmo, which they delivered with free t-shirts, cookies, fridge magnets, and gift vouchers, but without spoons. The ice-cream-fueled alpha version of Vindigo launched New Year’s Eve 1999 to one hundred handpicked users. I cried again.

The next few months were extraordinary. Vindigo’s underground cachet grew in a city obsessed with going out. Jason did deals with the New York Times, and then with Zagat. Thirteen former colleagues invested in the first financing round. These were the can’t-fail boom years, but it still makes me proud that people who had worked with them believed with their checkbooks. An Irish college friend who had started a business in London looked on with envy as the requests to invest poured in. People sent unsolicited ten thousand dollar checks to the new office. The press coverage for the product launch was fawning. The Times Metro section ran a bemused piece on watching Jason get mobbed at a venture conference, where investors begged him to take their cards even though he’d already raised all the funding he needed:
“Mr Devitt thanked them politely and turned to the next supplicant.”

When Glenn, the company dealmaker, went to conferences, he didn’t even put his own name on the Hello my name is… labels.
“They don’t care who I am,” he shrugged, “but when they see Vindigo on there, they go nuts. I feel like a fucking rockstar.” Once, at an industry event, Glenn turned to a woman who had ignored me for twenty minutes and introduced me as Jason’s wife.
“Oh my god, oh my god, I’m sorry! He’s a fucking genius! Are you guys hiring?” she said.

Back at the office, no one acted like a rockstar. The Globe’s spokesmodel cofounders were photographed dancing on nightclub tables, but Jason and David didn’t use their own product much. I threw tantrums when I realized Jason hadn’t taken a single weekend day off that whole first year, to little avail. When Vindigo threw rare parties, they were paid for by drinks company sponsors who wanted to be closer to these Palm-toting Manhattanites.

It was hard watching the company fill up slowly with staff who saw me as the CEO’s wife.
“I got the visas! I paid the rent!” I wanted to yell at the cool eyebrow-raises. “I worked in software before he did. I’m not some ditzy corporate wife bitch!”
The more successful Vindigo became, the more out of place I felt. I wasn’t part of this. I was both hugely proud and resentful. Though I worked just five blocks away, I stayed away more and more as Jason and Dave became completely absorbed. Jason didn’t need me to provide a work permit or pay the rent any more. I wanted them to ask me to join. They didn’t.

I finally joined that September. Vindigo had just moved to a new office in the very unglamorous Penn Station area. The previous occupants were 150 Puerto Rican jewelry cleaners crowded into a too-small space—I wonder what happened to them. The weather was still hot, and the street smell was a thick cloud of male piss. The office space was low-cost in a city still high on its own fumes, and the architects were glad to work cheaply for Vindigo. Everyone worked cheaply for Vindigo. The combination of glamour and sturdiness appealed to people who longed to deliver quality, and we felt lucky to be part of this adventure.

We hired a marketing staff, and grew to 50 people. Our billboards wrapped around our own seedy New York block, and Howard Stern gave us cut-price placement on his show. I remembered, three years earlier, getting excited by the first dot-com bus ad, but by now they were getting to be a grim joke.

2001 was a very different year. Jason and David, as usual, cottoned on sooner than most. In February, we quietly worked on a list of staff to lay off, well before the money ran out. It was clear that the next round of funding wouldn’t be made up of checks mailed to the office by desperate investors on spec, and also that there would be no more need for big print ad campaigns. On the morning of the layoffs I led the remaining staff to Chelsea Piers for glum beers while managers talked to those laid off. Everyone stayed together, downcast though we were. We went back to the office at three o’clock, and stared at the empty desks.

Companies started to close all around us, but Vindigo survived because of those early layoffs. We were cheerful about not becoming rich. Suddenly, in New York, it seemed enough to have a job. Jason struggled to raise more money, and managed it through sheer persistence. We laid off more staff to cut costs right down; this time, everyone who was left walked to Chelsea Piers together automatically. We sat outside in the sunshine with our pitchers of bad American beer and talked about our ex-colleagues. It would be tough to find a job. Everyone seemed a little lost.

David left shortly after we raised more money. Jason was gutted, but he understood. We held our breath and waited for his engineering team to quit, but nobody did. They were loyal to the new CTO, they liked the team and they got to work on stuff that their friends actually used. And there was nothing else out there. With 22 people left, we turned out more products than before. Dutifully, we rolled out a new software version every three weeks all through the summer and the winter that followed.

By now, Vindigo has gone from being Mac-cool to beige-box-workmanlike, and the user interface lacks the spare elegance it had before. We’ve bloated what we had rather than rolling out new products. Our Extreme Programming methods sometimes make me feel like a hamster on a very small treadmill. But none of that matters. Users like the product enough to buy it in droves. Nobody left. At Vindigo, smart people are gentle with each other, and I don’t even know how that’s possible in New York. Vindigo is going to survive.

And now that Jason and I have separated I am trawling through hundreds of résumés looking for my replacement and I feel more sad about that than I can say.