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.
> 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?
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.
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.
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.
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.
Pay attention to this.
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.
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.
And the answer is surely the same: by learning from mistakes made.
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.