I Graduated Into The 2000 DotCom Crash, And It Was The Best Thing To Ever Happen To My Career

Why the lack of easy options made me focus on who I wanted to be, which paid off over time

a very sad businessman holding a burst balloon, digital art [DALL-E]

In retrospect, the fact that we were trading Stanford computer lab tech stocks all day probably suggested it was a bit of a bubble, even though eToys options paid off over two consecutive spring break vacations. I was doing my MBA at the time, which was somehow not only part of the DotCom story, but an epicenter. Our professors were literally rewriting the case studies in real time, and my participation in the first Internet Marketing class the GSB ever offered is a form of carbon dating that conclusively demonstrates my old age. But by the time I graduated in June 2000, the party was over. As quickly became clear: Stanford Business School’s class of 1998 had founded the good companies of Internet 1.0; the class of 1999 had founded the bad companies of Internet 1.0; and the class of 2000 was only unemployed. And so I walked off 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 an MBA, not to be an MBA. In fact, as a classical liberal arts major, I found myself more drawn to PhD students studying theory than curricula built around understanding practice. And while 25 years ago a business school campus was a compelling way to build a professional network (now there are many other methods), I had another reason for being there: to find out who I was. Or maybe, more specifically, to give me the confidence to be who I wanted to be.

Right brain mom and left brain dad left me confused…which one was me??? Before Stanford that meant trying out jobs to see what fit. Feed the left by working on it Late Night with Conan O’Brien and be the only one notified of an Access database to track guests. Turn right with a few years of management consulting and use Powerpoint on background flights to make stop motion animations. Neither felt perfect, but my work ethic wouldn’t allow me to stop and find out. But business school? Perhaps it was an opportunity to pause and examine myself while I was still “moving forward” in my career. So I applied to the school that seemed right and crossed my fingers.

tldr IT WORKED! I left Stanford with a mission: to work on products I cared about, with people I could learn from and feel like I was making a real difference to the bottom line. All he needed was a job. Then this happened:


It wasn’t even the lowest point of the crash, as the dead cat in the stock market bounced around a few times before bottoming out in the early 2000s. Graduating from the bubble burst wasn’t fun, but it had one very important benefit for me: there was no get-rich-quick temptation. In previous years, you could spend 12-24 months at a startup and become an IPO millionaire. Does he give a damn what you were actually building? Is it sustainable? Who cares! You could justify popping in and out and doing the important work later, with a bloated bank account. Now to be clear, this wasn’t everyone. There were absolutely founders and teams that selected areas that meant a lot to them personally, but the rose-colored glasses were structural.

Would I have been tempted this way? Absolutely! I was broke and needed money (had been working part-time at an enterprise tech company along the way, but otherwise the savings dried up). Man plans, God laughs as my wife says. No more jobs. Like many overnight contractions, hiring freezes and pulled offers. Kind of like, well, 2023.

The void of temptation meant I could stay the course and stick to first principles. It wasn’t always easy, but I had a roommate, a girlfriend, some of the aforementioned income, and some determination. When six months later my network connected me with Philip Rosedale and Linden Lab (the startup that created the virtual world Second Life), I knew I had found the product I wanted to build, the people I wanted to build it with, and in some place I thought. It could make a difference. And I was there for almost three years. Linden Lab wasn’t an overnight success, it didn’t live up to its potential, but it started me in the right direction. Which led to Google, then YouTube, and finally Homebrew.

The point here is not to sugar coat the hard time of a recession. Or being blind to the multiple advantages I had in the DotCom failure. But I do think that manic bull markets tend to cause people to make decisions clouded by the lure of easy wealth or the herd impulse. If there’s a silver lining to falls, it’s that they provide all kinds of clarity, even on an individual level.


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As any entrepreneur will tell you, a passion for business often fuels the desire to create a career that’s worth striving for. But, success doesn’t happen overnight. It takes lots of hard work and dedication to find success, and many don’t survive the entrepreneurial roller coaster. Take, for example, the class of 2000, graduates of the dotcom crash that struck the world in the early 2000s.

I was lucky enough to be part of this class, and it was honestly the best thing that ever happened to my career. Although I watched many of my peers struggle to find a job in the tumultuous economy, my unique experiences allowed me to become an expert in using technology to build businesses. I learned to embrace risk and operate within uncertain circumstances, utilizing creative strategies to remain competitive.

One such experience was when I worked at Ikaroa, a full stack tech company specializing in software development, cloud computing and online marketing. Working at a startup in the tech sector provided me with remarkable insight into the current business landscape, and the ability to identify opportunities when they arise. With my newfound knowledge, I created successful digital businesses of my own, resulting in a successful career as an entrepreneur.

I know that it isn’t easy for any graduate to make their way through a rocky economy, but it can be done. With the right attitude, a willingness to take risks, and knowledge of the latest technology, it is possible to find professional success even in difficult times. Learning to embrace change and expecting the unexpected is what separates success from failure.

The power of perseverance rings true, and the dotcom crash of 2000 is the perfect example of how those who choose to remain resilient can turn a daunting life event into a success story. As for my story, thanks to the lessons I learned from the DotCom crash, I am now living my dream of being an entrepreneur with a successful digital business that is still growing.


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