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Ask YC: Why would someone leave his/her cushy job to join a startup?
23 points by popat 3487 days ago | hide | past | web | 79 comments | favorite
what personality / characteristic make that person to take risk? its definitely not the money or comfort ...

One day you realize that you only have x days on this earth and y of them are already gone.

You don't want to waste any more of your remaining (x-y) days refactoring the same poorly written crap for the eighth time, answering the same 84 inane emails, drinking the same lousy coffee, looking at your watch through another pointless walk-through meeting, and listening to the idiotic pontifications of a boss who you would never talk to in a million years if you weren't here.

You know you can do better. You know you have it in you. You know you can make a difference. Then you know you have to. So you get out your calculator, work your finances, and when you have it all figured out, you turn in your notice and enjoy the best day of your life.

Did I miss anything?

The part where you spend two years on your magnum opus, your hit the end of your runway, your company goes out of business, and your IP becomes the property of investors who will never (a) use it in any way or (b) allow you to use it in any way.

We only talk about the most successful startups. Most companies --- most of the 1 in 8 YC companies that get A-rounds, even --- fail. We don't talk about them.

So you're saying I shouldn't leave the cushy job I hate to do what I really want with the one live I have because there's a possibility of failure?

No, I'm saying that when you leave the job you hate, you should consider options other than the one least likely to succeed. And I'm saying "consider", not "do", and I consider that an antidote to your flowery evangelism --- no offense intended, the world needs both flowery evangelists and cynical assholes.

Your counter-argument has merit, but I'd like to add that, at least in my case, failure adds a small amount of regret, but not trying adds TONS.

Brilliantly put.

I have experienced tons of regret from putting too much into a dying startup. It is more than possible.


I've been accused of many things, but "flowery evangelism"? lol More data to support the argument that creativity can come from misery. I was using language to try to convey the level of misery I have endured in "cushy" jobs.

You are absolutely right about the odds. But I don't care. I am aware of them, but at a certain point, I just put them in the back of my mind and plow on. In my case, keeping those odds in background just makes me work that much harder.

The world also needs both illogical achievers and comfortable conformists.

Hey, I hear you; I'm 3 years into the last company I founded, and the only BigCo I've ever worked for bought the 10 person startup I had been working at. I see the attraction. But startup life has also kicked the shit out of me for almost 15 years.

People are not logic-driven automatons. We do things because feel it "from the gut" or simply because we like the sound of something. We don't make all of our decisions in a calculated, mathematical way.

Humanity would not be as advanced as it is if people worked in the way you suggest. We wouldn't have landed on the moon, made it to the South Pole and, I suspect, have barely made it out of the cave..

What does this even mean? Plenty of advancements have come from large companies, well-run and not.

I was talking, like you, about personal decisions. Admittedly I should probably have used "thought" rather than "worked" in my last line, as it perhaps implied working in a corporation limits risk, which isn't true.

You said "I'm saying that when you leave the job you hate, you should consider options other than the one least likely to succeed."

You are talking about a personal decision. My comment was about why people do not rely entirely on logic for personal decisions (and why they shouldn't), not about the contribution of corporations to society.

refactoring the same poorly written crap for the eighth time

Which part of this is different in a startup? The refactoring, or the quality of the code?

It seems to me that while working at a startup is a good way to guarantee that you'll never have time to refactor your code, it does nothing to ensure that your code -- or that of your cow-orkers -- will be any good.

If I have to change a diaper, I'd rather have it be my own baby.

You do realize that you get paid to change diapers for other people, right?

Even if you don't get paid, look at the grandparent/aunt/uncles' position: have some fun with the baby, change some yucky diapers (ok not so fun), but in a short time you will be handing responsibility back to the parents, who will have to wake up in the middle of the night, night after night...

As both a repeat startup founder and a repeat parent of infants, I'll attest: the diaper-changing aspects are similar. You're doing it for love, not money or enjoyment. =)

Not too far off the mark. Once you get your head on straight, you can exploit any salaried job of at least some intrinsic worth as your own tool for business experimentation and even peripheral market research/experience.

So you're obviously not a parent, since you're not understanding that every parent sees your comment, agrees and thinks: Yeah, but I'd rather be a parent. :-)

Actually, I am a parent and both of us, while we love our children and love to see them grow, are still tickled to be done with diapers. And when I hear a kid whine or a baby cry (out in public), it is music to my ears; That is not my kid crying, I don't have to do anything about it. A bit selfish yes, but an honest and natural feeling.

Fair enough. I can certainly sympathize. :-)

I've always approached those stressed out midnight feedings and diaper changes with enthusiasm though. Every time I take a look at my crying son I think: these are the times I'm going to remember when he graduates, gets married and has a family of his own.

Makes things much more bearable, I think.

If you really get stressed out with the crying and sleeplessness, just take some video or pictures being "cranky". That's what I did. It became a significant stress reliever.

Upmodded, and also, pretty sure parent commenter is high. ;)

Yes, and that's called a "maid." Do you want to be a maid a or a mommy?


I might rather be a maid than a housewife. Tough to say. My wife codes for my startup.

I think the point is that at a startup, ideally you're working on something thats interesting and exciting.

In my case, you missed the part where my employer's stock value dropped to $2 and the whole company was sold at wholesale to a group across the street.

If I gotta be connected to those kinds of risks, I want more control and more freedom.

And then you missed the part where your years of career development enabled you to walk the other direction down the street and pick up a job almost immediately making approximately the same amount of money, continuing to contribute to your IRAs.

BigCo's fail too, but no amount of dissembling is going to make BigCo tech careers as risky as startup tech careers.

The job market here in NYC for financial techies is not as you described. You clearly believe too much in startup tech centers because the risks involved with finance are as risky as start up tech careers. Riskier in some. Not as risky in others.

Why do you think Bernanke and Paulson had to get involved when Bear collapsed..?

> The job market here in NYC for financial techies is not as you described.

I suspect that this will be a short term effect based on so much upheaval due to the mortgate securities collapse.

Then again, if I were in your position right now, I doubt I would find that particularly comforting, so I understand where you're coming from.

I'm going to respond to this by pointing out that my company's offices are at 44 Wall and in the Loop in Chicago. I'm not a financial techie; I just get paid by them.

Fair enough. The job market is really screwy right now for financial techies. I'm on linkedin and my phone rang like crazy the day Bear collapsed. It's been ringing with people from UBS looking for staff. I've been told people are running out of UBS like crazy. The computer security market will probably get a boost from this actually. JPM's security has been boosted as they take over Bear's stuff and attrition potential isn't clear.

Come to think of it... you might want to cold-call JPM and see if they need help!

I'm sorry for being snarky about the NY-FI market. I can see why it's scary right now. I was reacting to the "irrational faith in startup tech centers". Startup tech centers are a scam. It's 2008! You're building web technology! You really think your location matters?! UR DOIN IT WRONG.

From one new yorker to another, you've got that right! I live here because I love the city. I work in financial tech because I like the excitement of working as fast as possible to solve problems. I also dig the bonuses. :)


Hi, I'm Dan.

We just got accepted in to YC Summer 2008 this past weekend. Before this past Wednesday, I worked as a financial analyst at a small due diligence firm where I could wear what ever I wanted to work, had relatively flexible hours, got paid pretty well and loved my coworkers.

Let me take you to that Wednesday: Bossman called me in and said he was pleased with my performance since December and gave me a promotion (essentially a 10-20k raise). He also added that some final details needed to be worked out before it would go in to effect.

After nodding and saying thanks, I told him to hold off as I had just received early stage seed funding and would be moving to Boston June 1. He was at a loss for words ...and so I was. It was awkward/hilarious. After what seemed like a minute pause, we started a conversation. He shared with me his regret for not trying to make it as a major league baseball player (he was a stud ballplayer at a Division I University) while I shared with him how much I had enjoyed working at his firm. At the end of our conversation he gave me his full support and definitely understood why I was doing it.

Dissimilar to many of the people out there, I don't hate my job or loathe my coworkers, I just wanted to try something different - something I'm excited about every time I wake up in the morning.

Trying to launch a startup while having a real job (and in my case another side business) is just too much. I was spread too thin.

So I guess to formally answer your question: the urge to try something different and work for yourself regardless how good (or not so good) your current situation is.

My boss wanted to be a photographer, or run his own mortgage company. A) seems out of the question for him at this stage in life but B) might still be possible.

I see it like this: I can always go and work for a big company and make good money. But right now, that's not what I want to do. I want to explore, I want to take risks, I want to be a little crazy. I am not really afraid since the worst that can happen is gaining experience. I am so incredibly valuable and smart and strong and [...] that I will get a high-paid job anytime I want. It's there, I just need to collect it. But I don't want to. Not yet.

So I guess the most valuable personality trait must be self-confidence (read: overconfidence).

The reason I left a cushy, high-paying job was that I think I can always get another cushy, high-paying job even when I'm older. On the other hand, my mid-twenties are years when I can afford to take (calculated) risks and do all the things I know I will have regretted not doing when I'm in my 30s and 40s and have more responsibilities.

I was also surprised how many people at and above my level in a big company seemed envious that I'd go to a startup.

It's about doing what you want, taking a risk, and not being afraid. To me, it's about having creative freedom and enjoying your day. Every morning I wake up and am ready to go to work, 9-5, sometimes much longer.

Sitting on my butt doing little to improve my self or a company (ie: being some corporate tool) would kill me

If you want a friend, buy a dog. If you want creative freedom and enjoyment, start an open source project on the side.

There are ways to mitigate all the BigCo problems without gambling 2-5 years of your life on a longshot.

What's wrong with "gambling your life on a longshot"? There are rewards for taking that risk, and it's not like you suddenly won't be able to get a job back in the corporate world. The world is desperate for good developers, so basically as one you have the freedom to do whatever you want.

There are ways to mitigate the risk of starting up, as well. The process of starting your own business is exceptionally rewarding.

(Edit - I see you've done some of that. Maybe you're jaded with startups, I'm jaded with BigCo :)

What are these ways of mitigating the risk that you speak of?

Also, tell us more about what you found rewarding about your startup. I think: winning is rewarding. Being fully exposed to wins is rewarding. In a BigCo, closing a $100,000 deal feels good. At a startup, closing a $100,000 deal feels fucking awesome.

But: losing feels really fucking bad. Flirting with debt feels even worse.

Who's to say where it ends up on balance?

Well, I was worried about leaping into it feet-first and the application was emerging and needed lots of massaging. So I got a contracting gig that requires 1 or 2 days a week but lets me work full-time if I need to. I choose when to work on what, depending on what needs it most. Now that it's getting somewhere and I'm happier to take more risks, I'm spending some money on other people doing stuff for me.

What I love about it: Feedback. Really nice feedback. Meeting people I'd never interact with in my day-job. Not throwing the code away when the project is finished. Each bug fixed is one that matters a lot to me. Payments while I sleep! Lifehacker links that set the server on fire. I didn't work for them - they just arrive.

I finally did it. Who knows how it'll work out, but after a long time of killing myself for projects I got limited benefit from, I finally dragged an application from idea to release under my own steam and it's making money. That's a great emotional boost!

Because the worst case scenario of a failed startup is going back to the status quo of the cushy job.

That's why I decided to take the plunge.

Because when I die I want to know I tried. Sure I might make mistakes but the feeling of just sitting there not trying is worse.

That's about as good an answer as you could get.

Because it will make you happier, if the cushy job is not making you happy that you are seriously thinking about leaving for a start up then you probably should. Note if the start up will put you in REAL poverty, not decreased living standard, but serious poverty or risk (i.e. lack of health insurance, something catastrophic happens).

Studies show that material gains beyond a certain point do make much difference in happiness. Note that diminished relative status can contribute to decline in happiness, so take the ego comment seriously too. You better have one if you go startup.

Ego. Not kidding.

Some people suck at doing even the easiest of things when they are told what to do. They tend to do much better when they can choose what to do to solve a problem or create a solution.

If you are in a corp environment doing things the way you'd like or want means you have to be a senior level IC or some sort of a team leader. But getting to that in the best of corporate cultures would mean you have you 'do' what you are told for 3-5 years - the same thing that you hate and would like to stop doing.

You would have 2 primary options#.

Go through the motions for abt 3 years and then hope you can get in to a meaningful position and do things the way you'd like...

Or, join a startup that works on something that thrills you and instantly start doing things the way you'd envision it. (You have the added incentive of having a shot at becoming really rich through a buyout or an IPO)

# - Other factors like family, current financial condition, the "real" scenario at your current place of work etc, are likely to add weights to the 2 options

I think that there's a distinct bias in your question. The question pre-supposes that the default should be to get a job, sell your time to someone else and get cash in exchange for money. Why does that have to be the default position. You could rephrase the question, "Why would someone stay at their soul-sucking 9-5 job making money for someone else, when they could try and solve the money problem once and for all by making money for yourself instead?"

Job vs Startup, the issue is the same: you're trying to solve the money problem. It's two different solutions to the same problem. Many of us on hacker news think that the smarter way to solve the problem is by starting a startup/business.

Now, you also mentioned "join" a startup. I wouldn't leave a company to work for someone else's startup. I will leave my job to start my own company, however.

A pink slip ... after 5 long years of loyal service and hard work. It is at times like that when you realize that working at a fulltime job is something you should do ONLY if you have absolutely no alternatives.

If you've managed your career, when you get a pink slip, you should be less than two months away from restoring or even enhancing your income.

If you're committed to startups, and your current startup craters, you could be 9-18 months from revenue.

It's just a fact: for any reasonable definition of "wealthy", more people reliably become wealthy by carefully saving and investing the income from a well-managed career than by any get-rich-quick scheme.

Don't do it for the money. You're not going to make any.

"Don't do it for the money. You're not going to make any."

Agreed, but I would temper that with 'hope for the best, be prepared for the worst'.

For me, it was getting sick of this cycle:


Same answer to the question, "Why take LSD?" If you have to ask, you don't understand.

Because when you wake up in the morning, you don't say "Damn, I do want to go to my 9-5 job". That's a sign for you to jump.

probably the same motivation that makes people jump out of planes

Recommend Barry Molttz's "You Need to Be a Little Crazy: The Truth about Starting and Growing Your Business":



It can be money, with the chance of big financial reward over financial stability. Sometimes it can just for the excitement, challenge or freedome of being your own boss and calling the shots.

You are far, far more likely to prosper in a solid, successful corporate career than as a startup entrepreneur.

Not for the money?

People seem to confuse small-scale financial success with google-style massive money. Even if your company doesn't take off, if you can secure a round of funding you can pay yourself fairly well.

And consider that it's a long-term investment in your career as well. A former startup founder is probably worth more than another similarly skilled person for a given task, even a given engineering task. It's like a college degree in that it implies a certain level of dedication that is difficult to gauge otherwise.

Hi Fayram, fancy seeing you here.

I see you, Mr. Chen.

It's safer than my hobby, which is robbing banks without a mask.

restlessness, ambition and greed

There's few things in life that feels as good as signing your own checks.

this almost feels like a reason to post a blog entry and link back, answering the question, "Why are we entrepreneurs?"

so, here is my mini-post of why I am an entrepreneur.

I had a number of things that led to the decision, but after my first startup failed, there was little doubt in my mind that THERE WAS NOTHING ELSE I WANTED TO DO MORE. In high school I had a few experiences, were going against the flow not only provided me with experiences that I could not learn in textbooks, but I also found financial benefit from them too.

One such experience, was when I was working at Omni Grocery Store, and I had a string of quick promotions from doing something of core value to me, but it was out side of the scope of my job. I started as a stock boy to learn the store, but when they found I was helping the customers, they thought that I was both too slow at stocking selves, and too helpful to let go, so they promoted me to check-out. Next, at check-out I caused disruption by being friendly. I would ID and card all women buying alcohol, and I would try to remember all of the customers names. With time I started greeting them by name. Again, I had lines when other checkers were waiting for customers, and my scan rate was much slower than theirs, so again they wanted to promote me to customer service, rather than let me go, they offered me another pay raise. With 1 week of customer service training and no work, the Union was getting insistent of me joining. Having a core disbelief in the function of Unions I avoided the issue again, only to find that the store wanted to promote me to manager as that would be the only way to keep me and not join the Union. It was an odd circumstance, but it gave me a tremendous confidence in being different and going my own way. I started the summer earning $4.25 an hour, and by the end of the summer I had been promoted to $6.xx an hour, and management would have brought me closer to $7. I had my goals in school and on the football team, and with manager they wanted me to work 18 hours a week, and from my estimates I could only afford 12 hours of work and still meet my goals. So, I asked for reduced hours, and they were insistent, so I quit. A week later I was shopping in the store, and the store offered me a scholarship if I would come back and work for the store. They just wanted 2 years of me after college. I declined, I had earned plenty that summer for the fall, winter and spring.

Next summer, it was time to get another Job, but this time I had won a few competitions from my independent studies in engineering graphics (drafting), and in the summer is I started interviewing for drafting jobs that were offering $35k a year. After a little help, and a few interviews I landed a job at $9 an hour as an engineering intern. I was proficient enough at my job that I often had dead time, but because I was working at a startup consulting company in house, they gave me random projects, like programing and technical recruiting work. The programing was fun, and I latter realized that I was being billed at $50 an hour and being payed $9 an hour for my time. At the end of the summer I was awarded a $3,500 bonus, which felt good. I also loved being able to work 10 hours a day with over time being billed at 1 1/2. In my time there, I did several large drafting projects, called about 500 people, placed 5 at $.5 million in business for our consultancy, and I programmed 2 databases. It was a ton of fun, and I earned a ton of cash that summer for college.

The following summer I asked for a raise, enough for me to live on my own, I was shot down, so I stayed up at college that summer.

The next summer I had a huge corporate job, at a fortune 500. The company had no problem paying me to sit around all day, but then at 4pm on friday, also had no problem asking me to work over time till 10pm, when the Alaska consultants would !be done with the next release of the code. My Bill Lumburg boss was always very upset with me when I did not want to cancel a date on friday night. He also hated it when I would work on projects to help the efficiency of the company in dead time, and when I would read the engineering spec to things like USB 2.0 for fun(again during dead time). So after you combine the 45Hz lighting with the 56Hz CRT monitor, the boring, hurry up and wait work, with the poorly managed employees, I developed a sort of habbit to come home at 4pm, sleep till 9pm, and then go to the bars from 9pm till 2am only to do it all over again the next day. I was so depressed, to think this is what I have to look forward to to graduating.

Upon graduating, I had a consulting job working on a custom software project, and at first it was great earning more than my just graduated peers, heck I had plenty of experience under my belt, but then again I had experience under my belt and I KNEW that the project was being miss managed and that it would not get done. I kept trying to get the team to do things in off hours to get it going in the right way, but the team lead was not happy with me. It ended up as a confrontation in the server room, where he tried to play me in to complacency, and said "its either my way or the highway." His plan had convinced the other folk to stick around and continue to pay their mortgages, and car payments; but felt it was more important to tell him to change his ways. I ended up quiting that day, and ended up putting more time into one of my side projects that turned into a very educational but very expensive lesson for me. Not only did I spend most of my cash, but I lost friends in the process to not knowing how to manage a full business vs. just a software project.

After that first business failed, I knew that I would rather fail 10 more times if it meant 1 success, than to work at another corporate job where I had to have another stupid boss. Now working for that startup consulting business in high school, was the second best job in my life. Second to my current startup, where I think I have been doing a much better job than my first startup, but I now know that I need to react faster to lessons being learned. So for me, I think it's an innate feeling of wanting the freedom to try things, life learning, stay active, and leading people to a better solution. To me making something beautiful is of so much more value to me, than making person gain for it.

Upmod for having the audacity to call this a mini-post.

Hey, I understand where you are coming from. Good luck!

In the final analysis, the wild roller coaster is so much more fun to ride than your average jetliner :) Go figure...

You've got to have a little gamble in you.

to live a more sane life, for the excitement, the unlimited growth potential, the ability to solve the problems you want to solve how you want to solve them, for the financial freedom, for the ability to work when you want to

to avoid meetings with pointy-haired managers.

Creating something from scratch is very exciting, also working in a small but well focused group gives you satisfaction of achieving something meaningful on daily basis and this could be a big plus. Apart from that if you are passionate about the idea/product then nothing else would bother you anymore.

That's what Marty Roesch was thinking when he started the Snort IDS project, as an open source project, on the side, with no real hope of turning it into a company.

SourceFire went public with Snort last year.

There are ways to do this without going for broke.

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