

The myth of the serial entrepreneur - xachen
http://swombat.com/2012/6/29/serial-entrepreneur

======
kator
Really good article, at first I started reading on the defensive because I am
a serial entrepreneur. For 28 years of my life I never had a payroll check
from anyone but my own companies. It was amazing and painful at the same time.
I thought about starting my sixth company and I got a chance to be an SVP at a
very large public company. I did that for a while and really enjoyed it and
actually moved on to a new company now were I'm an executive and get to do a
lot of cool stuff.

I often debate on going back to start company six, and many saturdays my
circle of friends hold "startup circle" where we pitch ideas and push a couple
small projects forward and debate on quitting our real jobs and going back to
building another company.

I would say the best realization of this article is that entrepreneur is a
state of mind. A willingness to create from nothing in the face of extreem
adversity. I have been a developer for close to 30 years now also and it's
very much like that first couple of hours when you stare at the blank screen
thinking about the 100,000's of lines of code needed to build whatever system
it is you're about to build. Except it's more addicting then that because the
scale is so much larger and your "vision" collides with "reality" and becomes
something you can influence but often you end up along for the ride.

I personally would bet it's the same reason professional bull rider's ride
bulls. Most of us look at them like they're insane but they have this zen
approach to managing risk and the randomness of the bull trying to kill them.
And when they beat the other guy the "high" must be quite insane.

Entrepreneurs suffer from the same sort of bold blindness. I have spoken with
many people over the years who ask me "how can you do that, how do you get out
of bed every day and just push forward" and I tell them I just like the
challenge. To them they see me risking my family, my house, my car and my
career to do something that scares them to death. To me I see the opportunity
to express something that burns in the core of my soul and make something from
nothing on a scale that should scare me but really just excites me!

I think the saying "40 years of work in 4 years" is a bit unfair, the reality
is if you love what you do and are passionate about it you can work like this
in a company that already exists or a mid-term C round start-up and have a lot
of fun and potentially be well rewarded. That part is just the workaholic that
might give an entrepreneur slight edge and a chance to ride the bull just a
bit longer then the next guy.

~~~
aortega
It's amazing how you people really believe all this. I don't mean to offend
anyone, but I hate when people think of themselves a beautiful butterfly.
Common people, employees, plumbers, etc. also have ideas, also have "bold
blindness", they also have a willingness to create from nothing (who think
created the thousands of open-source apps that are part of GNU and/or Linux,
entrepeneurs?) is not that what separates you from them. You have disposable
money and instead of a nice boat or car you put it in a business. And you know
how to talk people into putting money in your idea, and you probably live in a
country so terribly full of money that people are willing to risk it. That's
it. Unless you are an entrepeneur living in some hellhole african country, in
that case, respect to you, bold african entrepeneur.

~~~
krschultz
Success or failure has a large component of luck that people don't like to
acknowledge. Especially counter-factual luck. My parents are very lucky to
never have had to deal with serious illness, injury, accident, etc. I'm sure
if there was a terrible car accident that killed my family, I wouldn't exactly
be as focused on my work and therefore less 'succesful' as an entrepreneur.

But there is an element of uniqueness to dive into the entrepreneurship game
at all. Plenty of people have ideas and _do nothing at all with them_. If you
don't actually dive into it, quit your job, and work at it, it's impossible to
build a business. Most people (the vast majority) don't have the balls to do
that.

Hard work and taking that risk are necessary but insufficient conditions for
entreprenurial success. You also need luck. But that doesn't discount the
amount of risk taken or the amount of work put into it, and most people can't
stomach that.

~~~
aortega
I agree with all you said, but consider that humans in general are terrible at
estimating risk. I believe being an entrepeneur is not that risky, and being
an employee is not that safe either. The main problem that I see about seeing
entrepeneurship as unnaturally bold, risk-takers, creative intelligent people,
is that you dehumanize the no-entrepeneur person, in such a way that's very
easy to exploit them, because, they are like cattle, non-risk takers, and
deserve it, right?

~~~
swombat
Funnily enough, I covered exactly this point in an earlier article, though
this one wasn't so popular with the hn crowd..

<http://swombat.com/2012/6/18/entrepreneurship-safest-career>

------
adamt
I agree with a lot of what the author says, but I am not sure I agree with the
main premise in his title.

Luck and timing often play a big role in setting up a business. I think there
are some people who saw an opportunity through being in the right place at the
right time and created a business out of it. Often these evolve into being
what people call lifestyle businesses. In my mind these people don't fit into
the 'compress 40 years of work into 4 years' camp and are non-serial
entrepreneurs.

To me, the mark of a serial entrepreneur is someone who has started a business
up, got it to the point where it's been successful, and then having had the
option of staying on very comfortably with either a lifestyle business,
working in a bigger company, or early-retirement has decided that they want
the buzz and excitement of a startup again.

A good serial entrepreneur is by extension of that someone who can do this
more than once successfully. To create a single business that works out can
often involve a lot of luck/timing; to do it 3 or 4 times is something else.

~~~
swombat
That's an interesting angle, though I would argue that what you're defining
here is a very successful serial entrepreneur, rather just a "serial
entrepreneur". I'd say that someone who willingly jumps into startup after
startup is a serial entrepreneur - successful or not. Max Levchin was clearly
a serial entrepreneur already after his 6th company, even though he hadn't
started Skype and Slide yet...

~~~
loceng
We could look at through a different lens and state that if you aren't jumping
into startup after startup - successful or not - are you even an entrepreneur?

~~~
swombat
Well, that's sort of my point... serial entrepreneurs are the norm. Perhaps we
should come up with a term for those rare entrepreneurs who are satisfied with
a single attempt at the business game...

~~~
loceng
I would just say it's something entrepreneurial they are doing, doesn't per
say make them an entrepreneur - perhaps it does though; If you're learning a
musical instrument, are you not a musician? Maybe not a professional.
Professional Entrepreneur vs. Amateur? :P Serial Entrepreneur has a better
ring to it, though it really is just someone who is an entrepreneur IMHO.

------
tomblomfield
I can't help but feel that there's some sample bias going on here.

Each example given is an person who is _currently_ well-known for being an
entrepreneur. By definition, they haven't moved on to something else.

There's a tonne of people who've succeeded as an entrepreneur and then gone
onto something else; venture capital (in fact most VCs partners are ex-
entrepreneurs), politics or philanthropy, for example.

The point is that these people are now known for something other than
entrepreneurship, so they don't spring to mind as examples of one-time-
entrepreneurs.

/rant

~~~
swombat
Can you name a handful? I don't argue that there are no such people, but I
don't think there's a tonne of them.

~~~
KingMob
The very fact that you don't know them could support the point. In science,
this is known as survival bias.

It's a mistake to argue that the entrepreneurs you read and hear about must be
representative of all entrepreneurs. It's quite likely that the ones most
likely to become serial entrepreneurs will remain visible, and the ones who
stop after a successful exit are less likely to remain in the field.

~~~
lrobb
Quite right. There's a lot of people that just start one business and then
stay with it for the rest of their working life. Then there's a lot of people
that start something, decide that it's not for them, then go back to join a
company. If your news only comes from techcrunch and venturebeat, you're
missing out on these stories.

------
technotony
Great quote to finish: "It means you should not burn relationships, piss off
people, take damaging shortcuts - because you're in this small world of
entrepreneurship for a long time to come. It means you should always act as if
your behaviour as a founder will be with you for the rest of your career -
because it will." so true. Thank you!!

~~~
chegra
And even if you did[burn relationship, piss off people, take damaging
shortcuts ], you will find the more intelligent people are apt to forgive.
Making mistake in the past is no reason not to try again.

~~~
dsirijus
tit for tat with room for forgiveness

------
bfe
Great essay, though I don't think it's precise in how it characterizes pg's
status as a serial entrepreneur.

There's no doubt YC is a second startup, but it's still sort of a unique case
or meta-startup that serves pg's prior stated interest, as quoted in the
essay, in not fully facing the risks and schleps of a normal startup. I
believe I remember pg writing somewhere that he didn't want to repeat the
giant risk of a normal startup, and he saw YC as a way of taking a diversified
portfolio approach to startup involvement, of smoothing out the risk (and
schleps) of a startup.

So, I don't think the essay is precise in simply characterizing pg as saying
he shied away from doing another startup until he changed his mind and did one
anyway. Instead, he came up with a kind of startup that he could get into that
didn't require changing his mind about his approach. (At least, that's how I
understood it.)

------
dataisfun
This was _extremely_ well written. A very nice change from typical meta-
startup fare. Nicely done!

------
slajax
I enjoyed and agreed with most of this. I've never understood the term "serial
entrepreneur" beyond the idea that it solidifies the fact that a certain
individual has sold ( if that should be their goal - not mine ) more then one
company.

Ultimately all entrepreneurs come from the same cloth of success driven
business (value) invention. Some want to follow the hollywood IPO story. Some
want to bootstrap. It's all a matter of preference beyond those details and to
some it's not about being defined as a "serial entrepreneur". Personally I
wouldn't sell my company just to start another until I met my professional
goals.

------
cottonseed
I'd probably be described as a "normal" entrepreneur. I worked on five
startups, the last of which had a reasonably successful exit. I haven't
started another company since. A company isn't the only "laboratory of ideas",
and money let me explore some other options. I'm in a PhD program in
mathematics now. I didn't avoid starting a company because it is hard work. I
agree, starting a company had an addictive intensity that is hard to find
elsewhere. Will I start another company some day? Maybe. Would I ever have a
"normal" job again? No way.

------
srbufi
Isn't a serial entrepreneur any entrepreneur that hasn't created a company as
large as Google or Apple or Microsoft?

In tech, it's possible to iterate indefinitely until reaching such size that
it no longer requires a completely new company to be motivated to go on.

------
mik4el
Another perspective; can you call yourself a true entrepreneur if you haven't
had more than one entrepreneurial endevaour (I'm not talking that you need to
have IPOd a tech company before but rather had a lemonade stand as a kid and
vice versa)?

~~~
mindcrime
When I read a question that gets into what or is not a "true entrepreneur" all
I can think of is:

<http://en.wikipedia.org/wiki/No_true_Scotsman>

which suggests to me that debating over labels like "true entrepreneur" (or
not) or "serial entrepreneur" (or not) is a waste of time.

The same discussion also smacks of a sort of elitism that I associate with the
idiots to run around talking about what metal bands are or aren't "tr00 kvlt".
None of this strikes me as very productive.

------
ragincajun
Great article. It's hard enough to choose one idea from all of the great ideas
"I think" I have.

If I'm successful on my first venture, there is no doubt I'll try again with
something new.

------
moron
I'm trying to go the other way. I'm trying to decompress 20 years of work into
40. I'm not much of one for schleps, I guess.

