I worked at Apple Computer from April 1987 until February 1990 (a story unto itself), and I left Apple after having a falling-out with a boss over some, shall we say, ethical lapses on his part (yet another story unto itself). Happily, I had a job offer waiting for me which had three big things going for it: (a) it was a startup; (b) it was financial technology; (c) I would have a cool title – Vice President of Technology. All at the age of 24!
Cooler still, it was located in San Francisco’s financial district in the city’s most iconic building, 
the Transamerica Pyramid. Since my working life has been spent in jeans, khakis, and polo shirts, I was excited at the prospect of being a honest-to-God grown-up, putting on a suit, getting on a train, and heading to the big city each morning.
And that, my friends, was the high point of my entire stint with this new company, TriStar Market Data. The prospects were exciting, the (inflated) title was impressive, the pay was (at the time) excellent, and I had finally left the big corporation of Apple for a startup. This was no garage, however. TriStar was a seven-person outfit that had been put together by Montgomery Securities, a regional investment bank, based on technology it had bought from a firm in Chicago. (For those deeply in-the-know, Avram Grey was the original creator of this aforementioned system).
The product that TriStar owned was a Macintosh-based trader’s platform called MarketMax. Take note of that critical phrase: Macintosh-based. In 1990, approximately nobody on Wall Street used the Macintosh. That computer was the domain of desktop publishers, graphic artists, and other weirdos. It isn’t something you had on your desk at JP Morgan. Anyone who traded used Sun. Period.
So the first place that MarketMax showed up, naturally, was on the trading desks of the folks on the Montgomery Securities trading floor. Now this was a place, for someone like me, that was exciting. Every day, from 6:30 a.m. to 1:00 p.m., hundreds of people would be shouting orders, throwing balls of paper at each other, and, to my eyes, just having a great time. I guess, even though I didn’t know it yet, what I really wanted to do was be a trader, but just being on the fringes like this was exhilarating.
Don’t let my title fool you, however. I originally thought the Vice President of Technology would be guiding the development and feature set of the trading platform. Nope. The trading platform was pretty much as good as it was going to get, and they just needed to get it onto desktops. So it didn’t take me long to figure out that my generous salary was being paid out for me to open up new Macintosh boxes, set them up, install the software, make sure the network functioned, and help people out with trivial computer problems.
On top of this, it became clear to me that getting up early in the morning, getting showered, dressed, driving to the train station, jumping on the train, and taking a bus to work lost its glamour pretty quickly. In fact, it was a drag. I was really just beginning to learn who I was as a working person, and although I know all too well that I hate commuting, meetings, annual reviews, having a boss, and all the other stuff that goes with it, I was naive about myself at the time. It was only slowly occurring to me that having a “real” job wasn’t really for me.
My boss was a good old boy from the south named Leon Williams, which appealed to me, being a Cajun boy myself. He was a good boss, and someone I respected, because he was one of those guys who was down in the trenches. Like me, he was a very hands-on guy, not some guy in a corner office who just wrote memos. He was all about getting the product out and making sure the customers were happy.
That didn’t make my own tasks any more appealing, though. It got to the point where I was spending a good chunk of my time preparing boxes for shipment. I distinctly remember walking to the office one morning reciting to myself “seventy-seven thousand six hundred dollars a year; seventy-seven thousand six hundred dollars a year………” (hey, c’mon, in 1990, at the age of 24, that was pretty good pay). Deep down, I hated my job, but I wouldn’t admit it to myself.
Things turn a turn for the worse when they hired a young fellow just about my age to join us from New York, where he had been based installing MarketMax systems on Wall Street. This guy had a lot in common with me – – – an up-from-the-bootstraps kind of person, young, ambitious, eager to please – – and we were thus destined to come to loggerheads.
He wasted no time bad-mouthing me to the others in our tiny organization, and it was clear he didn’t like me and didn’t want me there. In April of 1990, my boss Leon announced he was leaving to head up the IT department at Sun Microsystems (as he put it at the time to us, “a bird in the hand is worth two in the bush”), so he was leaving TriStar, since Wall Street wasn’t exactly falling all over itself to get Macintoshes and the MarketMax software. The TriStar seeds had been sprinkled on rocky soil, and – surprise, surprise – nothing was growing.
It didn’t take long at all for the other young fellow I mentioned to install himself into Leon’s big corner office and assume the role of CEO for the time being. A few days later, I was called up to the office of Seth Gersch, who was the managing partner at Montgomery. When I got the call, I thought Seth wanted to talk to me about some more interesting projects that I wanted to do for TriStar.
I was quickly disabused of this belief when I walked in and saw Seth and two of his cronies (including my nemesis) standing in there. Seth asked me to close the door and he said, “We don’t like having these conversations, but we’d like you to work somewhere else.” It was humiliating for me, and upsetting too, because I had just signed a contract to buy a house in Palo Alto. I was escorted to human resources, asked to sign some paperwork excusing them from any liability, and I got my last paycheck.
I rode the train home in the middle of the day. Unlike the morning and evening commute trains, which were quick, this one stopped at every single station along the way, taking nearly an hour to return to Sunnyvale. I ambled over to the pay phone, called my wife, and told her I had been fired. “Oh, my God” she said. She knew as well as I did that we had just bought a house, and with the 1991 recession in full force, finding a new job wouldn’t be easy.
In retrospect, everything worked out. It took me three months, but I did find another place to work (Technical Tools), which would go on to be the last “real’ job I’d ever have in my life. We proceeded with purchasing the house, which is our residence to this day (and a fine place it is, I might add). And this rotten experience put into motion the direction I needed to start Prophet.
The fate of the handful of folks at TriStar has varied – some tragic, some fabulously successful – but I remain bitter to this day at the triumvirate of people in that room on that day (and one of them in particular). It certainly helped shape my disposition toward the world of unemployment and how small companies should and should not be run.
TriStar, not surprisingly, was ultimately a failure, so me staying there wouldn’t have made any real difference for me anyway. I can’t say I’m glad I had the experience, but I am glad for the place where the experience ultimately guided me. It all worked out in the end.
