Here are a few tips for others startup employees: 1. Take the least amount of stock possible - your startup is statistically unlikely to succeed. It'd be better to bump your salary up $10-20K than to get the stock. 2. Unless it's liquid - it's worthless. 3. Valuations pre-cashflow - are useless. Anybody can value anything at insane levels using just one dollar. I value HN at $1 billion by offering to buy only 1 share…
It's unfair to characterize all startups as nirvana, and it's likewise unfair to label them all as run by evil masterminds taking advantage of their employees. Sure, some startups are total shit, others are actually pretty enjoyable places to work. So let's not paint this as either black or white. You make some great points that a lot of "wide eyed" grads could use to hear more of. There are also a few things I take…
An investor's job is to catch the winners. An employee's job is to avoid the losers.
As an employee, your main interest is not in what the top end of the stock may be, you don't have a portfolio, you aren't doing "black swan investments" you are investing your life and your time. It makes sense for professional investors to go in even at ridiculous valuations because one win can carry 19 losses.
As an employee you do not have a 20 strong portfolio. If you start young you have maybe five or six swings at bat and then you'll have a mortgage, kids, family. The return as an employee simply doesn't justify high levels of risk, the main job is just to ensure you're a part of something that works.
So how can you do that? Ask the questions you know make sense. Are you working for company run by founders who can sensibly and calmly articulate why they will succeed. Do the people around them also believe this and do you trust their judgement? Does the company have a justifiable burn rate and is it on track to make sustainable money in a market that's not unreasonably small? Would you pay money for the product or do you feel your customers are being duped? If the answer to the above questions is yes then put value in your stock. If not then don't.