They could have saved a lot more by not doing so many stupid investments.

Think of all the stupid jobs that wouldn't have been created if they didn't make their stupid investments.

There'd be a total collapse in the stupidity market.

Pedantically, that statement isn't fair, an investment is only stupid or genius in hindsight, at the time it is just a choice.

They could have saved a lot more by making better choices about what to invest in. :-)

I'm not sure I agree. I think some of them were stupid at the time of the investment. The larger the wishful thinking component, the more likely it's a stupid investment.

I hear you. I did an experiment post dot com crash which was to add notes in my journal about investments that were announced. I added my own evaluation next to it as 'makes sense' or 'doesn't make sense.' That helped me contextualize my looking back at things.

I did this after I had turned down a high level engineering job at Netscape pre-IPO because, in my evaluation, every time they tried to charge money for their main product "Communicator" nobody would buy it, and I felt the market for their ecommerce server software was competing against a free alternative. That choice, leave Sun (an Internet powerhouse) or join a startup that couldn't sell its primary product, I considered the leave Sun choice 'stupid' at the time. It cost me about $7M in theory because that is what my options would have been worth (and yes they would have vested before the crash hit).

Since I spent an unhealthy amount of time self criticizing my "choice mistakes" I took it upon myself to figure out if I was being realistic or not. My experience, based on my journal notes, was that I was wrong about half the time. So my criticism was unwarranted. It also helped temper any unrealistic feelings about my own abilities based on successes that were, largely luck driven.

That's... sobering. But were you wrong about Netscape? Or were you right, but it took the market long enough to catch on that you left a lot of money on the table? I think the latter, but would defer to your opinion if you disagree.

I have since come to the conclusion that I was both right and wrong.

If you analyze the meta-branching of that decision you can see at least three branches.

1) The one I took which was to stay at Sun. In this universe my employee purchase options continued to grow, Sun's stock split again, and my net worth grew by more than my annual salary that year.

2) In this first alternate, I take the job at Netscape in May of 1995, and become a multi-millionaire (on paper) in August. Using historical data for Netscape, and knowing that when they went public they had a 1 year lockout on employee sales, if I were to have sold 1/4th of my option on the anniversary of the IPO in each of 1996, 1997, 1997, and 1998, my net worth would go up to roughly $9.8M net of income taxes assuming I didn't file an 83b election (not that I could of come up with the cash to vest all my shares anyway at that time but whatever)

3) I take the job at Netscape, I am holding multiple millions of dollars in stock which become AOL stock in 1998 and don't sell them, they become nearly worthless 5 years later.

The illustration is that there is a path and different choices along the path end in different endings.

As it turned out, after Netscape went public, realizing that I was not going to make a whole lot of money on Sun stock as an employee, I left and started a startup with some other ex-Sun employees.

My take away from all of this was that decisions are neither "right" nor "wrong", rather they are just inflections in the timeline. Sometimes the timeline has given you additional advantage, and sometimes it has taken it away, the trick for me was to not get greedy. When there was "enough" advantage, lock in the benefit and move on, when there was "enough" disadvantage, stop digging the hole and move on. But most importantly for my mental health, as long as the slope was generally on the upswing, then don't sweat the choices that didn't work out.

With all that being said, I'm also a big fan of learning from decisions and trying to put into my toolkit things that would have illuminated the upside and downside more clearly if I had done them at the time. Case in point, "Never join a startup where the two senior leaders are both in a relationship and their reporting relationship at home is different than the one they have at work." and "Never join a startup that has never had to defend its existence to a skeptical investor."

You can try to make better decisions, but it's hard to have better timing. While, a gut feeling or a statistic for the market's rationality curve might be possible, it certainly seems wiser to make better decisions.

In today's economy Netscape's value would be in its user base in the same way one would expect chrome to be valuable. In the data marketing world, nothing is really free.

Fair enough.