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I've done both - worked for 2 other people's startups, founded my own, worked 5+ years at Google, now founding another. My experience is that you learn something from both, but you learn different things from each, and which will teach you more depends on what skills you need to learn.

Working for someone else's startup, I learned how to quickly cobble solutions together. I learned about uncertainty and picking a direction regardless of whether you're sure it'll work. I learned that most startups fail, and that when they fail, the people who end up doing well are the ones who were looking out for their own interests all along. I learned a lot of basic technical skills, how to write code quickly and learn new APIs quickly and deploy software to multiple machines. I learned how quickly problems of scaling a development team crop up, and how early you should start investing in automation.

Working for Google, I learned how to fix problems once and for all and build that culture into the organization. I learned that even in successful companies, everything is temporary, and that great products are usually built through a lot of hard work by many people rather than great ah-ha insights. I learned how to architect systems for scale, and a lot of practices used for robust, high-availability, frequently-deployed systems. I learned the value of research and of spending a lot of time on a single important problem: many startups take a scattershot approach, trying one weekend hackathon after another and finding nobody wants any of them, while oftentimes there are opportunities that nobody has solved because nobody wants to put in the work. I learned how to work in teams and try to understand what other people want. I learned what problems are really painful for big organizations. I learned how to rigorously research the market and use data to make product decisions, rather than making decisions based on what seems best to one person.

Founding a startup, I learned the limitations of all of the above, and that even if you know in theory what can go wrong, it's quite a different matter to avoid committing those mistakes too. I learned a lot more technical skills; it turns out that no matter how well you prepared in your job, finding a workable startup opportunity requires that you do things that you don't know how to do. I learned how to talk to other people and gather information about the market from ordinary conversations. I learned to make decisions in the absence of firm information, knowing that I may be wrong but that I can't make any forward progress without trying something out that is almost certainly wrong. I learned how to take expedient shortcuts, and to un-learn many of the rigorous engineering practices that I learned working for people because they don't apply in this environment.

I've found many of these self-reinforce as well - I got farther on the first startup because I'd learned many of the basic technical skills from the two startup jobs I'd had before, then got into Google from the skills I taught myself founding that startup, then have a different perspective on what's possible for the second startup because of the work I did at Google. The overlap is less than I (or most people) would like, but one of the unfortunate facts of life you learn as you get older is that life is not a linear path of one move reliably preparing you for the next, and there are often twists of pure luck that throw a monkey wrench into all your plans.

This is a great comment, thank you!

> I learned that most startups fail, and that when they fail, the people who end up doing well are the ones who were looking out for their own interests all along.

Can you elaborate on this? How were people "looking out for their own interests", and how did it end up helping them? Could the founders have done things differently to make the outcome more equitable?


Also not the person you are replying to, but I have my own experience with this.

Basically the people who leave a failing firm early do better than those who stick around until the money runs out. They find better jobs faster because they're not competing with a bunch of their former coworkers, they don't have a gap in their employment to explain, and they don't have to answer the question of why they stayed when they should have known the company was failing. If you find yourself in this situation and you think that loyalty has any value, think again.

Not the OP but…

I took it to mean that you have a responsibility to yourself as well as the startup. You give them a lot of time and effort, sure, but you need to keep doing things like reviewing how the job is letting you develop, both technically and as a person, keeping up your tech skills by reading and playing, and building contacts and networks of your own.

The people who have done that (rather than just had their head down and working) have more to fall back on if the startup fails, and probably noticed things weren’t going so well earlier as well.

If you do not care about yourself, you may end up doing all that super important but non glamorous work that does not sound great when looking for another job. You will not have right checks and buzzwords on resume, cause you have been too busy doing useful "normal" work.

Consider also the latest "github is your resume" hiring fad. Do you think it is possible to crunch, give everything possible to your startup employer and have a pet project at the same time?

If you do not care about yourself, you will end up tired and overworked. Another potential employer will interpret it as a "lack of passion".

The issue is not limited to startups through. The same happen in established companies.

Not to speak for the comment you are replying to, but in my experience it likely means that those that worried more about the startup than themselves ended up worse off than those that looked out for there own best interests first.

I think the three reasons entrepreneurs so often give the advise to just "go do it" is that a) the biggest barrier they faced to their own success was the psychological barrier to actually committing to taking the plunge and b) the key to their success was in taking an unconventional approach to at least some aspect of their business and c) they no doubt set off in a bunch wrong directions that had to be corrected, and the only way to learn that was to make those mistakes.

The catch is that while by nature we are risk-averse, there is a degree of reflection that would definitely improve your chances of success. While big wins tend to require unconventional approaches, you can't just break rules at random: you need to understand the rules and the reasons behind them better than everyone else. Finally, mistakes are a key part of entrepreneurship, but learning from them is essential, and that second part is harder than successful entrepreneurs appreciate (because to be successful, you've had to put together a pretty impressive track record of learning from mistakes). Experience is key to interpreting events to learn the right lesson.

> I learned that most startups fail, and that when they fail, the people who end up doing well are the ones who were looking out for their own interests all along.

Pay attention to this.

It just confused me. How does anyone do well out of a failing startup? By jumping ship early? By going to a competitor? Surely there are no golden parachutes, right?

There definitely are golden parachutes. In my experience, when a startup is going to die, it will thrash around a bit before it quits living.

Most recently, the company was running out of money (~3 months runway), no significant progress was made on the large new funding round we were looking for, and a small round wouldn't do any good since there were big (expensive) milestones to meet. With about 2.5 months left, we laid off about 80-90% of the staff to extend the runway.

Most employees were let go with two week severance packages and about 1 week's worth of insurance. "Critical" employees stayed and were given sizable 'retention' packages with big bonuses if new funding was arranged.

For me, the applied skills I learned at a startup made me a much more attractive prospect. I can speak from experience about the relative strengths and weaknesses of machine learning models on real data, instead of the somewhat sterilized and over-used datasets often passed around in academia. It means a higher salary when I did jump ship into corporate-land.

Plus, it was just plain fun. Startups are the closest thing to the intellectual excitement and curiosity of grad school I've found in the private sector.

Still you get paid the whole time. You meet risk-takers. I've gotten almost every job for 20 years from connections I made at my first startup.

That's like asking "How does any do well out of failing?"

And the answer is surely the same: by learning from mistakes made.

I don't have as much knowledge to impart however I will piggyback. In my experience working for companies of different sizes and stages of growth can be eye opening. Seeing teams work through problems from different perspectives has given me great confidence when figuring out how to address new challenges and uncertainty.

I really like your introspection. I have read a lot of articles about startups (never started one, not even close). Given you summary here, I would definitely pay to read more of your insights.

Please write more down. I am sure I am not the only one who would wait in line to pay for it.

And do please fix the URL in your profile.

I come from marketing and working on my product all by myself now. Very well said. The journey to experience and learn is very personal. Even it can not always be monetized and is less possible to be fully got by others, it's still worth it.

Wanted to say I appreciate your in-depth reply. Quite nice hearing from someone who's had the experience and chose to introspect for us.

Very insightful. Compared to working in corporate or big org, startup can teach you a lot about yourself.

FYI, your url in your HN profile doesn't load (wanted to checkout what your new startup is).

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