Working at a startup is overrated, both financially and emotionally

Agreed.

One of the key issue is that most people do not know or understand how the equity piece works, leaving the door opened for abuse.

It doesn't have to be complicated. Two things to check if one is granted equity or options: - What is the rough value of the stock when granted? 409A is the tool for that although it is usually quite conservative, which is good for the recipient. - Do I have the same class of stock as management/founders: ensures no funny business around dilution.

I can't be sure, but I think it was "Slack" by Demarco.

why not both? get the money and do something you enjoy?

I only ever worked at startups, always one of the first employees. Different projects, from consumer stuff to enterprise computer vision tech. Most of those companies failed. One was a moderate success (~100M valuation), and when a liquidity event came I made a decent chunk of money.

I love small companies, I love the chaos, I love having that bond around some crazy idea that might never work. I love being in the know about how things work and why people buy our product and all of that.

I used to want to work at Google. I have a few friends that do and the common thing I hear is that it is fun at the beginning but then it gets boring. Things move slowly, people are less excited about work and there's a lot of red tape. Not saying that it's inherently bad, it's just a tradeoff. I could see myself being into that kind of work at some point in life.

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One thing that people often miss in these conversations is that if a company is failing it doesn't take a long time to figure it out. If you join a startup and it's tanking or you think the founders are incompetent, you can quit and go try another one. That's more or less what happened to me. I stayed for 2 months at one company, 8 months at another, one company I almost started with some people but quickly realized we'd fail because none of us knew the problem space. Then I worked at a successful startup for 5 years and we all made money.

Another reason to work at a startup is if you ever want to start your own company. Starting a company consists of doing a lot of different things, so it helps if you have some prior experience with them. I learned a ton of random things working at startups, from interacting with lawyers to doing content marketing. I recently started a company and I talk to other founders a lot and I think people who worked at startups before are better prepared compared to people who come out of large companies.

I don't think the author is comparing apple to apples. Instead of contrasting joining startups and joining FAANGs, we should really compare joining top-notch startups with joining FAANGs. That is, just like good companies are scarce, so are good startups. Look back, and we can see that those who join square, pinterest, airbnb, uber (before early 2015), facebook (before its IPO) all did really well. By the way, Netflix circa 2008 was still in a sense a startup, as they were still being threatened by blockbuster and most doubted their streaming initiative and the company had fewer than 150 engineers.

Even those who joined Uber in 2016 or later got something back. Uber's success did give halo to its employees. As a result, many became senior managers or directors or staff engineers in other reputed companies, even though they had started their career only 3 or 4 years before.

The trick to land on a promising startup is taking sunken cost seriously. Switch to a different company decisively and swiftly once you are convinced that the company has a bad leadership. And trust me, there will be many signs. Take Uber after 2016, for instance, you would see 1. Head of HR reported to this hot-head VP, who was the buddy of the CEO; 2. CFO told employees that they RSU hold period was a year instead of 6 months and the reason is for employees' own good; 3. CEO told employees that he didn't want to go IPO simply because he didn't want the employees to check stock price all day. 4. Uber copies pretty much every policy from Amazon yet could execute well and everyone was launching project for promotion and the company had more than 800 services. 5. CEO forced managers to A/B test packages to see how low a package can go to hire people. 6. Company splurged 10s of millions hosting extravagant parties for 4 days straight in Vegas for bogus metrics like total number of trips; 7. HRs used number of people hired as the key metric to boast that Uber was the fastest-growing company.

See? When you see so much distrust from the top, you should just jump ship, and use the halo you get from UBER to land on a different top startup, whatever that is, and rinse (in case you ended up joining WeWork).