If you wanted to get rich, how would you do it? I think your best bet would be to start or join a startup.

- Paul Graham

. . .

I started in the industry working at Amazon. But I was always enamored of startups. PG was one true god and working at startups seemed to be the only way to:

Get Rich Do meaningful work

And that’s all I want from my professional life.

So I left Amazon when my bullsh't threshold was reached after n’th re-org, worked with a friend on our own project for a while, took it to an alpha/proto stage, tried raising some money to support the development efforts. That hardly ever works out when you are trying to reinvent databases, without someone important vouching for you, or without enough traction. We had none.

But I wasn’t done with startups, they still seemed like the holy grail.

I ended up joining a cloud security startup. Joined as an early engineer (employee #15, and probably around 10th engineer).

Now let’s pause here and look at the promises of a startup as an early employee.

Fast career growth. It’s a small company, so you can grow easily if you work hard. Get rich quick in case of success. More learning. Small company, so you get to work on a variety of things.

That startup sold for 200 million dollars and, as the 10th engineer, I made ... 15000 dollars from that exit. Let me put that figure in perspective. That is the same amount a recent college grad would make at Facebook in 2 months.

Get rich quick scenario definitely didn’t turn to reality.

Well, what about career growth and learning?

In my experience, it’s harder to have any visible growth in a startup because well first, what do you grow to? There is no clear hierarchy, no promotion paths. The “no titles” thing is great in theory but unless you have a naturally dominating personality, it likely won't work for you.

"But I am sure, you learned a lot?”

I learned. But was it disproportionate to what I’d have learned in a BigCo. Nope.

The only thing startups prioritize is Shipping (probably the only word more abused that ownership in tech). Which is correct, that is what's keeping them alive. But you can’t have moonshot technical projects when you have only 6 months of money in the bank. Shipping is great, only when it’s not. In my experience, the deadline-driven culture crushes any scope for creativity and experimentation.

But here's another major problem: Founder's goals and your goals, as an engineer, will not be aligned most of the times. The founders, in your average startup, are thinking on a time frame of next 2 years at best. And a lot of times, they are figuring it out themselves. Which is fair, but where do you think an employee's, your career growth will fit into that plan?

The incentives are just not aligned.

Actual conversations (not verbatim, of course)

“Hey, I think we should experiment with Kotlin. It has lots of traction, Google officially supports it on Android and seems might help us write better code. Here is a PR showing how it’ll fit into our project.”

“Umm, engineers will need to learn a new language. We have other priorities right now. Let’s consider it later.”

...

“This needs a queue. This is literally is why queues exist”

“Ah, we don’t have queues anywhere else. We don’t want to complicate things right now. Can we just use a Postgres table?”

The second one is not necessarily a bad solution, just illustrates the point that in the absence of BigCo scale, you, as an engineer, might not get a chance to architect systems you might get at a bigger company

I am still not done with startups, though. I am onto my next one with the hopes of this being the startup dream turned to reality.

It hasn’t been. Yet.

Does that mean you shouldn’t work at startups?

No, but it makes increasingly less sense.

I’d have loved to be an early or even late engineer at AirBnbs or Stripes of the world. But I think these are a small subset of startups and a lot of things have to align for your startup experience, as an engineer, to be worthwhile:

Hopefully, it’s a consumer startup because enterprise startups run on sales and not on engineering. Which creates an extremely short term, feature, and deadline driven culture. The startup goes big ala Airbnb, or Uber and you hopefully get the work at scale because most application development is commoditized otherwise. You actually have enough equity to get worthwhile value out of your work. Or you just really care about the company mission.

You should at least have one or two of these things. Enterprise companies, for example, don’t generally see the scale, or engineering challenges of consumer companies, so you better have enough equity for it to be worth for you. (Note that enterprise companies make great business sense if you are a founder. But if you are, say, the 35th engineer at one such company, you might get the worst of many worlds and best of none.)

And if you don’t have #4, you should at least have #3.

Okay, so most startups are not great. You already knew that because most of them fail and failure isn’t great. However, to me, it’s dubious how many startup successes, especially in India, have been great for, say, 20th to 50th engineer at those companies. Swiggys, Olas and Paytms of the country are infamous for not giving good (or any, these days) equity to engineers.

What About The Big Companies?

BigCos have their own issues. Sheer politics will drive a lot of people crazy but there are areas where they do better:

Better scale and engineering challenges of problems More scope for moonshots, and if you can switch teams you can end up in one of them Better comp (and unlike startups, it’s not in a rosy future) Better Work-Life Balance. I have heard generally good things about the overall culture at Google and Facebook. Everyone I know at Microsoft/LinkedIn works practically 4 days a week. Amazon is a different story, though.

At the end of the day, what I am getting at is that with BigCos you know what you are getting into but with startups, only the best case scenario seems worth it. And the best case scenario requires literal aligning of stars.

Keep in mind that we aren't even talking about the worst of the startup world yet. We are not talking about how a lot of startups are just Ponzi schemes, existing to be sold.

You can literally get screwed in more ways than you can count. I have a friend who worked at a startup whose founders were plain abusive and should be in jail for frauds. I have a friend who worked at a startup whose founders are under investigation for hundreds of millions of crypto fraud. I was personally been shouted upon so badly by a founder at a company I interned at that I could have started crying if the other founder had not helped; to nobody's surprise they didn't pay the promised salaries.

Which is why I think that unless you really care about the mission of a company, working at startups makes increasingly less sense. The odds are just not in your favor.

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