Thanks for the feedback :). I'm terrible when it comes to design, and I totally agree that there's an opportunity to go somewhere with the BreakStreak concept -- back to the drawing board :). For now, though, I'm pleased with the experiment!

Let's take the following hypothetic example, which by the way isn't so hypothetical:

Your company decides it wants to build its business on mobile phones. You go out and hire the best iOS developer you can find, and she builds the app. Then, once you have a few thousand users, you realize that actually this app should be a website. You pivot the company to become a website before an iOS app. Now you have an expert iOS developer and nothing for them to work on. You'd be in a better position to have a super awesome programmer who can (and has interest to) learn new things.

The above example happens all the time. The earlier a company is, the more likely they'll make big pivots.

Alex - I agree with the above example, but my definition of a generalist is someone who knows a little bit of everything - engineering, sales, marketing etc. An awesome programmer is still a deep expertise in my opinion. But I get your point.

I've never been able to find the time or motivation to do side projects, probably because I'm more of an all-in kinda guy. But I agree that side projects could be a good way to scratch the startup itch and have a great time, too.

Do you think you'd have the time and motivation to do a side project if you worked at a big company?

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.

I've worked at big companies before and I could never go back. I'm not a 9-5 kinda guy, which is what I meant by "all in."

Stress is something that comes with doing exciting, scary things. Sure, having a comfortable day job and working on a side project on the side might be fun, but it's probably not scary and big, unless of course the side project becomes something big. At which point you'll be stressed again.

Very good point. I suppose I've only worked at startups that have done very well (Redfin, Cloudera), hence the bias here. While we're here, though, could you share some of the negative parts of working at a (failing) startup, apart from the obvious: you're out a job?

There are plenty negatives! but such is life when things didn't go your way right? (^_^)

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.

It might be wasted time & money, but i think most people who are willing to join startups probably believe in the idea and hopefully are passionate about it. Thus they're doing something they love and are hopefully happy, during the time the startup isn't falling apart at least. And also at startups (if run correctly), you can learn a lot in a short amount of time - technical stuff, responsibility, dedication, how to start a company, acquiring users, etc...

Also, you can learn a lot from you failures.

So while you may lose out on time and money, you gain other things too. Depends on if that trade-off is worth it.

I'm not so sure if young people believe in the idea more than they just want to work in a start-up because the media (and HN) have been painting the negative picture of BigCo/establishment and positive, bright, and exciting pictures of start-up.

It's almost as if people will get jeered/booed for working in establish companies.

What do people love? Building software? you can do that anywhere though, doesn't have to be in a start-up. I think people tend to be choosy these days: they want to work in a company that is young, hip, quirky office layout/design, get a lot of attention, and use cutting edge (sometime unproven) technology.

Don't forget that there are plenty people out there that build software on their free-time (i.e.: side projects).

I'm having a little bit difficulty to understand of what you can learn in a short amount of time that you can't outside start-up. If the start-up moves too fast, you're bound to cut some corner, you're bound not to use the best-practices, you're bound to "hacked it up". I think we all have been exposed with the Mythical Man-Month book that explains some of the properties of software.

And if it moves in an even faster speed, I'm not sure how you can learn so much more as you'll get tired and just go to sleep after work.

Yes, you can definitely learn a lot from failures, assuming you know what went wrong. Not a lot of people know what went wrong though. Some people would stick it to "bad luck" as oppose to "we don't have enough skill to pull it off".

There's some truth to the old wisdom of learning from failures, I'm not dismissing any of it. There's that difference between actually experiencing the failure and learning from other people's failure. Sometimes it instils discipline and better work ethic.

If you were trading salary for equity and the startup fails you're out that. You're also out time which you could have been advancing at a different company.

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.

Early in your career, trading salary for experience is a smart move. In my case, I turned down a Google offer to work at a startup after college (taking a 15%-30% pay cut) and my equity ended up being worth less than I paid to exercise it. But, in the two years that I was there, I learned way more than I would have at Google, and got a much bigger network, both of which helped immensely when I interviewed for my next position.

I agree, working for peanuts is dumb. But 20%-40% less than what Google offers is hardly poverty -- it's still much more than what most non-engineers make out of college.

Second this. Right after school I passed on a higher-paying job to work at a startup. It didn't do well, but I learned a whole lot about what is involved in running a startup correctly, from the perspective of a mid to late stage employee.

Forward many years, and I have my own thing going and I appreciate the failed startup experience because it gives me some framework on which to base my decisions. And I hope I'm doing things better... (and that a few years from now that junior dev we just hired will do a better job with his/her company!)

Your point #5 about transparency may not be true all the time. Strict policies force consistency and some level of transparency at big companies while the ad-hoc nature of start ups makes it really easy to hide information. In a badly run startup it doesn't take long for founders/leaders to mislead the engineers with false information.

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.

Just some off the top of my head, from my own experiences when I was still naive and ignorant (and I still am), and from observing others.

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.

I'd hire you if you were a good engineer but not a good interviewee :). My hope would be that a good interviewer can see through an interview in the same way that a good teacher gives good grades to good students, not good test takers.

If you can tell that a bad interviewee is a good engineer, you've cracked the elusive interview code that everyone has been trying to figure out for decades.

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

Hiring a good engineer that is a bad interviewee is the responsibility of the interviewer. A sufficiently good interviewer should be able to pull the necessary info out of a bad interviewee.

You couldn't be more right about what's going on between my cofounder and I. He loves New York. I love San Francisco. But still, I expect there are clear differences between the two tech scenes, for example meetup sizes, general candor, how willing a VC is to meet with you, etc.

I've lived in Brooklyn for eleven years, Manhattan for three years before that. I grew up in Chicago, went to school in Pittsburgh and have spent significant time in Sydney and San Francisco.

I don't think you can do wrong by coming to NYC, but I also don't think you'll necessarily do better here than in SF or Pittsburgh or Austin or wherever.

Assume your startup fails entirely: where do you want to end up living? NYC is great, but you'll definitely burn through cash faster here (or in SF) than in a cheaper city. SF has a lot going for it, but will you really be there or in the Valley?

Rather than ask people to justify why one city or another is better, why not list the criteria you're using to make your decision?