Why Lack of Easy Options Made Me Focus On Who I Wanted To Be, Which Paid Off Over Time

In retrospect the fact we were all day trading tech stocks from Stanford’s computer labs probably suggested it was a bit of a bubble, although eToys options did pay for two consecutive Spring Break vacations. I was getting my MBA at the time which in some ways wasn’t just part of the DotCom storyline but an epicenter. Our professors were literally rewriting the case studies in real time and my participation in the very first Internet Marketing class the GSB ever offered is a form of carbon dating that conclusively proves my old age. But by my graduation in June of 2000, the party had ended. As became clear quickly: the Stanford Business School Class of 1998 had founded the good Internet 1.0 companies; the Class of 1999 had founded the bad Internet 1.0 companies; and the Class of 2000 was just plain unemployed. And so I left the campus with student debt and limited prospects. But it turned out to be exactly what I needed.

My decision to attend business school wasn’t really about getting the credential. I was there to get a MBA, not be an MBA. In fact, as a classic liberal arts major, I found myself more attracted to the PhD students studying theory than the curriculums built around understanding practice. And while 25 years ago a business school campus was a compelling way to build a professional network (there are many other methods now), I had other reasons for being there: to figure out who I was. Or maybe, more specifically, to give myself confidence to be who I wanted to be.

Right brain mother and left brain father left me confused… which one was I??? Pre-Stanford that meant trying out jobs to seeing what fit. Feed the left by working on Late Night with Conan O’Brien and be the only one geeking out about an Access database to track guests. Pivot to the right with a few years of management consulting and use Powerpoint on cross country flights to make stop motion animations. Neither felt perfect but my work ethic wouldn’t allow me to just stop and figure it out. But business school? Maybe that was a chance to pause and examine myself while still ‘moving forward’ in my career. So I applied to the one school that felt like a good fit and crossed my fingers.

tldr IT WORKED! Came out of Stanford with a mission: to work on products which mattered to me, with people I could learn from, and to feel like I was making a real difference to the outcome. All I needed was a job. Then this happened:

It wasn’t even the lowest moment of the crash as the stock market dead cat bounced a few times before heading lower for the early 2000s. Graduating into the bubble burst was no fun but had one very important benefit for me: there was no temptation to take a ‘get rich quick’ job. Over the previous years you could spend 12–24 month at a startup and become an IPO millionaire. Give a shit about what you were actually building? Is it sustainable? Who cares! You could justify getting in and then out and doing the important work later, with a swollen bank account. Now to be clear, this wasn’t everyone. There were absolutely founders and teams who selected areas that meant a lot to them personally, but the rose colored glasses were structural.

Would I have been tempted by this path? Absolutely! I was broke and needed money (had been working part-time at an enterprise tech startup along the way but otherwise savings were depleted). Man plans, God laughs as my wife says. No more jobs. Like overnight lots and lots of contraction, hiring freezes, and pulled offers. Sort of like, well, 2023.

The void of temptations meant I could stay the course and stick to first principles. It wasn’t always easy but I had a roommate, a girlfriend, a little bit of the income mentioned above, and some resolve. When six months later my networking connected me with Philip Rosedale and Linden Lab (the startup building virtual world Second Life), I knew I’d found the product I wanted to build, the people I wanted to build it with, and somewhere I though I could make a difference. And that’s where I spent almost three years. Linden Lab wasn’t an overnight success, not did it fulfill its potential, but it started me in the right direction. Which led to Google, then YouTube, and finally Homebrew.

The point here isn’t to sugarcoat the difficult time of a downturn. Or to be blind to the multiple advantages I had going into the DotCom failure. But I do believe that manic bull markets tend to cause people to make decisions which are clouded by lure of easy wealth, or herd momentum. If there’s a silver lining to downturns it’s they provide all sort of clarity, even at the individual level.

GET ALL MY POSTS FREE TO YOUR INBOX BY SIGNING UP HERE