Honest question: do you think you could have chosen that companies were not "losing bargains" seven years ago? How many companies are there today that you think would grant you significant equity and also will reach liquidity in the next seven years? How would this change if you were an early twenty-something with few connections and little savings?
Off the top of my head I can only think of a handful of companies today, and even with those I'm not sure I would take a six-figure gamble with most of them. If I were a decade or two older things would be significantly different.
Obviously I didn't choose right - the first two startups I worked for both failed. And then I was like "Never again" - I was the voice on HN saying that early employees get screwed, c. 2008 - and that blanket prohibition made me miss out on being employee #2 at DropBox (along with 10 or so other startups that went nowhere).
More to the point, though - I don't think that the point of a career should be to minimize risk. Or rather, you certainly can choose to minimize apparent risk - but that usually means that whoever owns the least risky option (probably Google, today) will use that as a lever to get you to accept whatever terms they give you, which is its own form of risk. Ironically, very few of the senior software engineers I knew at Google actually had "Work at Google" as a career goal - most of them were ex-startup-founders, or Ph.D dropouts, or had toured in a punk rock band decided they want an office job, or washed out of law school and figured programming looked more interesting. You gain a lot of confidence by failing at something you thought was important to you, and that helps you focus on the next thing that's important to you.
I think that your goal, when you're a 20-something with few connections and little savings, should be to gain experience as quickly as possible. That's what lets you take prudent risks when you do have the means to do so. If you've never failed at something or gotten screwed over when you're 40, you're probably about to start, and your failures will be much more visible, painful, and harder to recover from than if you fail when you're 22.
> and that blanket prohibition made me miss out on being employee #2 at DropBox (along with 10 or so other startups that went nowhere).
That seems to have worked out ok, though, if you only had a 1/11ish chance of jumping on a startup being the right decision at that time, anyway. It doesn't dissuade me from the "options are most likely worthless, and akin to a lottery" viewpoint.
However...
> I think that your goal, when you're a 20-something with few connections and little savings, should be to gain experience as quickly as possible.
This is good advice, and I'm no longer in the 20-something bucket myself, but the trap I see friends among that group falling into these days is jumping from the "akin to a lottery" thing into a "I'm going to gather as many tickets as possible" job-hop-every-year strategy.
The downside is they aren't gaining much useful experience, and their "connections" are mainly just to an insular group of VC-funded founders and other inexperienced engineers. Being the most experienced engineer (with 2 years of experience before joining) at a company of 20 people with all the other engineers being straight out of school isn't particularly useful experience. You can make it work, but it's much harder - nobody to learn from, no mentor, etc. And if the projects you're working on are just basic social or game apps over and over, your experience isn't very deep.
So if that tight-knit pool dries up... what are you bringing to the table when you're looking for a job at somewhere a bit larger and more stable?
What about the alternative of building up wealth? It's the conservative view, but if you get to 30 or 40 with significant assets, you have a lot more flexibility to explore what you want without worrying about money. With the supply demand curve favoring devs for the time being, why not jump from job to job taking the compensation increase each time? I think my 2-3 year stints will catch up to me at some point, but if I have 1-2m in liquid assets, I think I'll have a much wider set of means than if I had optimized for experience. You'll still fail and learn, but you'll be sitting on cash instead of worthless options
>> If you've never failed at something or gotten screwed over when you're 40, you're probably about to start, and your failures will be much more visible, painful, and harder to recover from than if you fail when you're 22.
Really good advice. Which at 40 I will now ignore ;-)
Off the top of my head I can only think of a handful of companies today, and even with those I'm not sure I would take a six-figure gamble with most of them. If I were a decade or two older things would be significantly different.