I've made this point before, but since it's a bit relevant here, I'll make it again (sorry to repeat):
If you're primarily interested in making money, or if you love the startup but not the compensation, you should NOT work at that startup.
If you're a good developer, you can get a better deal by working at an established company and simply investing. This has been true for every startup offer I've ever seen. Ever.
I've considered lots of startup jobs because I believed strongly in the companies. Every single time, however, I was able to get a larger chunk of the company by keeping my current job and simply investing.
To give an example, my current job pays about $250k, and one year, I invested $100k of that into a startup, leaving me with ~$150k of salary. This $150k + startup equity was a better deal than the startup was offering in both salary and equity. Plus, equity bought as an investor is much less tax toxic than equity options received as an employee of a startup.
On the other hand, most people who work at startups aren't interested in money. If that's you, that's totally cool! I wish I could care less sometimes.
This is something else that needs to change: "equity bought as an investor is much less tax toxic than equity options received as an employee of a startup"
Even if your competing offer is ~$150k, it still makes sense to not work at the startup ALMOST every time (given that you are trying to maximize money--most are not). I've seen a few exceptions, but startup offers are usually that bad.
Also, based on my convsations with literally hundreds of startup engineers, I have seen three trends:
1. They care very little about how much they are getting paid due to being passionate about their work (awesome!)
2. If they do care about money, they are under the false belief that their startup options are worth more than than that startup's investors were willing to pay for them in the secondary market (i.e., the price of a nearby round)
3. They are almost always talented enough to get a high-paying job somewhere else
Although it's sometimes a bit of work to find these opportunities, there are enough people with good ideas who need money these days. Friend of a friend-type stuff.
Occasionally, after talking to a startup about a potential employment opportunity, I'll ask if I can simply invest. They are usually flattered that someone would be so excited, and they are usually quite happy to take your money.
A final option is to invest in one of these new index funds that track startup performance. E.g., the SharesPost 100.
I haven't ever tried that, but I'll certainly consider it if I ever feel strongly enough! For early-stage ventures especially, the quality of the people seems to matter a lot. Therefore, there's a high probability I'd know the founders (or at least some employees) before I put in any money, and therefore, cold emailing wouldn't be necessary.
If you're primarily interested in making money, or if you love the startup but not the compensation, you should NOT work at that startup.
If you're a good developer, you can get a better deal by working at an established company and simply investing. This has been true for every startup offer I've ever seen. Ever.
I've considered lots of startup jobs because I believed strongly in the companies. Every single time, however, I was able to get a larger chunk of the company by keeping my current job and simply investing.
To give an example, my current job pays about $250k, and one year, I invested $100k of that into a startup, leaving me with ~$150k of salary. This $150k + startup equity was a better deal than the startup was offering in both salary and equity. Plus, equity bought as an investor is much less tax toxic than equity options received as an employee of a startup.
On the other hand, most people who work at startups aren't interested in money. If that's you, that's totally cool! I wish I could care less sometimes.