

Ask YC: Why would someone leave his/her cushy job to join a startup? - popat

what personality / characteristic make that person to take risk? its definitely not the money or comfort ...
======
fallentimes
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.

~~~
Prrometheus
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.

------
abless
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).

------
grahamr
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.

------
edw519
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?

~~~
tptacek
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.

~~~
edw519
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?

~~~
tptacek
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.

~~~
ericb
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_.

~~~
webwright
Brilliantly put.

------
truebosko
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

~~~
tptacek
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.

~~~
richardw
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 :)

~~~
tptacek
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?

~~~
richardw
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!

------
ivankirigin
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.

------
richardw
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.

~~~
0x28aa1f185a6b4
That's about as good an answer as you could get.

------
ccwu
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.

------
tptacek
Ego. Not kidding.

------
seshadripv
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

------
iamelgringo
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.

------
alex_c
For me, it was getting sick of this cycle:

[http://thedailywtf.com/Articles/Up-or-Out-Solving-the-IT-
Tur...](http://thedailywtf.com/Articles/Up-or-Out-Solving-the-IT-Turnover-
Crisis.aspx)

------
LostInTheWoods
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.

~~~
tptacek
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.

~~~
angstrom
"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'.

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

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

[http://www.amazon.com/You-Need-Be-Little-
Crazy/dp/079318018X...](http://www.amazon.com/You-Need-Be-Little-
Crazy/dp/079318018X/ref=pd_bbs_sr_1?ie=UTF8&s=books&qid=1209748282&sr=8-1)

Cheers

------
pierrefar
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.

------
marrone
probably the same motivation that makes people jump out of planes

------
KirinDave
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.

~~~
blader
Hi Fayram, fancy seeing you here.

~~~
KirinDave
I see you, Mr. Chen.

------
Hates_
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.

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

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

~~~
optimal
This you?

[http://www.arlingtonva.us/Departments/Police/news/printartic...](http://www.arlingtonva.us/Departments/Police/news/printarticle.asp?ID=546)

------
falsestprophet
restlessness, ambition and greed

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

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

~~~
jdavid
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.

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

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

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

------
merrick33
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

------
NonEUCitizen
to avoid meetings with pointy-haired managers.

------
ideas101
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.

~~~
tptacek
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.

