

Are you in a startup career path or are you one and done? - adityakothadiya
http://www.gabrielweinberg.com/blog/2010/11/are-you-in-a-startup-career-path-or-are-you-one-and-done.html

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tptacek
Strongly recommend, if you're interested in startups as a career, that you add
"taking a job at a startup and working your way up to a key role" to your to-
do list. I know a couple people who have tried to make startups their career
by serially founding go-nowhere companies; that's the wrong way to do it.

(My rule of thumb, which I've back-rationalized onto my career, is not to
start back-to-back companies).

~~~
gfodor
I totally agree. The reason this is so important is it makes it possible for
you to see the ways companies fail without bearing the burden yourself.
(Because, odds are, the startups you join will fail.)

It also shows you that there is more than one path to success. I've worked for
several startups and each one taught me a different way of thinking about what
are the important things to focus on, what kind of people to hire, and what
problems are worth solving.

~~~
mscarborough
Agree with you and the GP. Both well said.

It wasn't until my fourth start-up job that I found one that I loved and stuck
with for more than 1.5 years. Luckily, that one worked out and I was rewarded
for it. Not as a founder, but as the GP recommended: work at it and find a key
role. Work up from there and get your efforts recognized.

You won't make millions this way but you will learn a lot about business--
mainly, how to recognize the good and bad things in your environment, and how
to navigate those issues. You also don't have to risk your savings or
livelihood. Unless you have a clear or novel idea about what you want (which I
didn't), it is a great learning environment.

One thing that I have always known is that I'm not a natural business-type
person. After having the safety blanket of learning through 6 years of funded
start-ups, rather than on my own dime (and thinking I could do it myself
"because it's so easy"), it really helped my long-term prospects of running my
own business. One day I will but not yet.

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dasil003
I'm not sure how I feel about phrase "startup career path" as concept. Not
that I disagree with what Gabriel is saying here, but be careful not to box
yourself in conceptually.

I definitely consider myself an early-stage startup guy, and I am extremely
hesitant to work for a large company, however I've actually only been in a
true startup for 3 years out of a 12-year career. Before that I worked for a
public University, a new media agency, and a bunch of small freelance gigs. In
all of those circumstances I was able to do great work, meet great people, and
learn a lot about business (yes even at the U).

Now it's true that nothing matches the ambition or intensity of a true
startup, and it's definitely a place I like to be. Conventional wisdom in
silicon valley evolves quickly, but it's very inbred, and it tends to create
bubbles of competition around sexy concepts, where hundreds or thousands of
the very smartest people in the world are working 18 hour days on some
specific concept that doesn't even have a market yet (eg. Check-in-base mobile
apps). Meanwhile, out in wider industries you find huge markets with huge
inefficiencies due; billion dollar markets that are ripe for disruption, with
reasonably small barriers to entry for someone with a little inside
information.

If you bring your technical and execution skills to one of these markets you
have a much greater chance of success, and with an established market you also
can be sure there's something really there. Spending a couple years in an
established company could be the seed to a brilliant startup. Likewise,
working on yet another social widget just for the sake of being in a "startup"
could land you with obsolete skills when app-fatigue turns to backlash, and
silicon valley moves onto the next hot thing.

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jmilinovich
Gabriel, I really like your article because all too often to we get short-
sighted and get caught in the "get rich quick" mentality. I think it is
critical to balance this long term approach with a firm belief that your
current project will make it BIG.

Without this belief that what you are working on will be the next sliced
bread, it can be easy to get discouraged or, as you mentioned, move on to the
next project.

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sayemm
One of the best startup posts I've read yet - big kudos to @yegg, he's the
man.

Thinking that you're going to win by just playing one or two hands is dumb. I
also don't like the view that entrepreneurs do it because their personality
naturally gravitates towards risk, that's just not smart business.

Only way to win is to take advantage of high EV moments in life, but to also
maintain a long-term view and mitigate risk along the way so you can keep
playing the game for as long as possible - survival goes before anything else.

Max Levchin failed 4x before he hit it with PayPal. No one becomes a great
entrepreneur overnight.

~~~
ruang
Using investment as an analogy, this is like a barbell strategy. Put most of
your portfolio into bonds and put 10% into pure speculation like out-of-the
money options.

~~~
sayemm
No, it's not. It's more like the Kelly strategy:
<http://en.wikipedia.org/wiki/Kelly_criterion>

Be ready to seize opportune times, but never risk disaster. The world's
greatest entrepreneurs and investors didn't get to where they are today with
diversification strategies.

They did it by concentrating the bets they made in life.

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Jd
I think there are lots of ways to go about startups and only some subset
qualify as the yegg's "startup career path." Which is to say, there are a fair
number of things that are startups and can be done with a couple coders and
some ramen over a couple months -- often not evening needing a "marketing"
guru -- while there are lots of other problems which require more specialized
domain knowledge (either with respect to technology, market, or both).

In this case, what you need to succeed depends largely on having the right set
of skills to succeed within your specific domain, assuming you have one. I'm
generally of the opinion that there is much lower risk in these areas
(assuming you know your market well) since presumably all you have to do is
match an existing need with a product, the primary barrier being your
competence.

How do you acquire the skills necessary? This too depends on which side of the
ball you are on. Larger startups need people in different roles. Rather than
getting in on a little startup and being part-time coder, part-time cleaner,
part-time ramen cook, get out in the would and be the most excellent in
whatever facet you excel in. Heck, you may decide that making the world a
better place in whatever capacity you are best at (usually also what you
enjoy) you is better than attempting getting superrich and retiring at 30.

In other words, my advice to all "startup" people out there is do what makes
you tick, do it as best as you can, and let your startup, _if_ it arises meet
a need that you know is real. This may be a problem that people don't realize
is a problem (like limited and often unintuitive course management software)
or it may be something bigger and better that only a few people will
understand (e.g. a cure for Multiple Sclerosis).

Anyways, I've nothing against serial entrepreneurs if that's what makes you
tick. More important though is do what you love.

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erikstarck
I wrote a blog post about this a few months ago, the cloud or the ladder:

[http://blog.opportunitycloud.com/2010/05/07/the-cloud-or-
the...](http://blog.opportunitycloud.com/2010/05/07/the-cloud-or-the-ladder-
choosing-a-career-strategy/)

"Cloud" in this context is an opportunity cloud, the sum total of all the
positive things that can happen to you at one particular moment. It is what
happens when you position yourself to be in a spot where good things happen,
not knowing exactly what.

This is a different strategy than the "ladder" strategy which basically is
about climbing a corporate career ladder.

When you're in "startup mode" you constantly try to expand your opportunity
cloud but you don't always know the direction. It's a completely different way
of thinking compared to the ladder.

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geophile
I joined my first startup 20+ years ago because I liked creating software,
being at the researchy end of the product spectrum, the informality and speed
of a small company, having a lot of responsibility, and of course, the
prospect of a big payout was attractive.

I've been exceptionally lucky in all of these aspects, so I've been doing
nothing but startups since then (except when I found myself at a big company
post-acquisition).

If you're going into it _just_ to get rich quick, you are definitely doing it
wrong. And your motivation is sufficiently off-course to pretty much guarantee
that you won't get what you want.

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schumitsch
I respectfully disagree. A start-up is hard. If you're doing anything other
than putting maximal effort into your current endeavor odds of success go
down.

~~~
epi0Bauqu
I think you can certainly be successful in that mode. I was--working in almost
complete isolation, and afterwards I still wasn't really a part of the startup
community (since I didn't really know many people in it).

What I missed though and what I've realized since is that if you actively
engage in that community you end up meeting people that end up helping you
that you would otherwise never meet because you can't justify meeting them
with your head down all the time.

So it ends up being sort of non-intuitive, and hence the post. I think if you
do relax that mode a bit your chances actually go up. Of course there needs to
be a balance though.

~~~
dasil003
I'm three years into an ambitious and promising startup now, and feel the same
way. I gotta get out and get in touch more with the community.

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iuguy
I'm doing my current job for now, but there's plenty of other stuff I could be
doing afterwards. I imagine that I'll probably take a break, but sitting at
home growing olives and playing tavla isn't something I could do forever.

