Working at a Startup vs. a Big Company (opens in new tab)

4) You can also be removed from your role a lot faster and be forced down if the team (or worse, the investors) feel you're not ready and they feel the company requires adult management. For some people, it's true. But in some cases, you can get really buried because of petty issues, or in worst-scenario cases, forced out and left hanging to dry. You may come out of the experience having learned a lot, but you may also come out of the experience very bitter. See recently submitted article about Khalid Shaikh, regarding YouSendIt, Noah Glass of Twitter, Eduardo Saverin of Facebook, etc. Yeah, all of these guys probably made big mistakes and probably didn't deserve to be one of the senior guys. But the point is that they also didn't get a lot of help to develop themselves, whereas at a big company, the structure is in place to help develop people who need it (not always, but more often than in startups where everyone has to pull their own weight or die). Another recent alleged example is Naveen Selvadurai of Foursquare, though that guy has done a good job of taking the high road if it's true: http://www.businessinsider.com/naveen-selvadurai-tried-to-fi...

5) The level of transparency and all the good stuff that comes with it is all dependent on the level of integrity of the startup's leadership. There are lots of stories of founders who lie, mislead, and misuse the startup's money.

6) You can help shape environments, but it is also a natural psychological event that your environment shapes you. If your founders are domineering, arrogant, and generally assholes, it will be hard for you to influence the company, especially since most of the early hires will either be similar or easily cowed into groupthink. If you're not up to the task of standing up, you either become one of the cowed sheeple or get pushed out. It's sad if an startup's (or any organization's) culture is like high school, but it can happen.

7) I'd say it really depends on the leadership's philosophies. If it's a business type who's like "I'm the CEO, this is my leadership group, and you guys are just code monkeys", I'm betting you probably won't see this kind of culture where everyone can be involved in the hiring across the entire organization.

8) Already addressed somewhere in these comments.

9) Politics can exist in smaller companies too. And when the group is as small and tight-knit as startups are supposed to be, if the politics exist due to poor leadership and poor culture, it will be an even more painful experience than in a big company. After all, in startups, you can often spend all your time with the team when it's crunch time. In big companies, more often than not, you have the option to go home and leave work at work. It can become a lot more personal in a startup if the culture is bad.

It takes toll psychologically. There's that nagging feeling that "had they listen to me, we wouldn't fail this bad" for a while depending on how slow/fast you can move on.

Wasted [time & money]: you lose money, you lose time. Could've done something else, build a career, street-cred, resume, and do something else as well.

The positive part of working at a failing start-up is about opening your eyes that start-up isn't as glamour as what people perceive it to be. It makes you not wanting to work for a start-up ever again unless it is yours. So I'm not saying it kills your entrepreneurial spirit, but it does kill your youth-risk-taking-high-flying mind.

However, because working at a startup is gambling, you have to treat it as such. If you can't live with losing out on salary you could've made at another job, you shouldn't work at a startup.

At a startup my friend worked, he was one of the best engineer on the team and thus the founders wanted him to take on more work in return for a bigger bonus. In the end they did not make enough money to pay the promised bonus .. turned out the founders knew this all along but still kept mentioning the said bonus.

You may not need to prove yourself technically as much as someone who comes in cold, but you always need to prove that you're a good cultural fit for the team.

A teacher has an ongoing relationship with a student, so time is on their side. An interview is the opposite.

I'm also curious to see how stressed you were working at a start-up. If you're getting as much stress as the founders without the potential upside, it seems like in many cases it may not be worth it.

At 75-100k you're not losing that much happiness and stress wise if you take a pay cut at a start-up.

If you have an offer of 40k at an established company and are taking a lower salary (30-35k) to work at a start-up, that will hurt significantly in terms of your happiness, stress, and your ability to pay your bills.

Also, most startups use a little trick: they tell you that your equity is enough to make up for the difference in salary. Some of the clever ones will even do this using the valuation at the last fundraising event. VCs will agree that startups are a risky investment, and they seek 10x return on their investment because most of their investments fail. If you know that most investments fail, then you should really be compensated at a risk-adjusted amount of equity (ie: you should get waaay more equity at the current valuation than the discrepancy with the market rate to compensate you for the risk that the equity will be worth 0.) Additionally, there is the chance that after starting employment you discover the personality fit isn't there or you otherwise have to leave before the first year is up; if you don't reach your one year anniversary you take a 100% loss on the income discrepancy because you have no equity. To add insult to injury, you ARE NOT BEING GIVEN THE AMOUNT OF STOCK IN YOUR PACKAGE; an "option" is just the right to purchase at a set price. So really, people are "paying" you the difference between the current valuation of the company and its future growth, so you are getting a much worse deal than the last round of investors.