The myth of the serial entrepreneur

http://swombat.com/2012/6/29/serial-entrepreneur

by xachen • 14 years ago

156 51 14 years ago

swombat.com

dataisfun• 14 years ago

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

tomblomfield2• 14 years ago

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

swombat7• 14 years ago

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.

technotony2• 14 years ago

Mitt Romney (who founded Bain capital), Bill Gates, Pierre Omidyar to name a few

tomblomfield2• 14 years ago

Marc Andreessen, Ben Horowitz, Robin Klein, Bill Gates, Silvio Berlusconi, Michael Bloomberg, Niklas Zennström

prof_hobart• 14 years ago

I know more than one person who's quit their day job, started up a business, made a few million pounds and then retired. They won't be anyone that you, or I suspect anyone else on here, knows. They are simply people I've worked with.

And that's the thing. The ones that become mega-famous are typically the ones who have been around for an extended period of time - either through having spent the time building a single successful company (Bill Gates, Zuckerberg etc), or people who become well known for starting up multiple companies. If Bill Gates had retired 4 years after starting up Microsoft, how many people would even know his name now?

Rather than trying to identify people who've famously walked away after a few years and comparing them to the number of famous people who didn't, a far better measure would be to find random 20 entrepreneurs who have only been doing it for a couple of years and see how many of them are still doing it, either with the same company, or with a new company, in 10 years time.

KingMob• 14 years ago

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.

technotony2• 14 years ago

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• 14 years ago

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• 14 years ago

tit for tat with room for forgiveness

kator4• 14 years ago

Funny I thought the same thing, I've been in business for almost 30 years now and I can still call people I worked with 25 years ago and they will work with me in an instant. The number of times I have looped back around and ran into the same people over and over is funny. Especially considering over time I have moved through many different industries.

The golden rule applies to to entrepreneurs too. Karma is a bitch and worth paying attention to in life as in business.

slajax• 14 years ago

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.

adamt• 14 years ago

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.

swombat7• 14 years ago

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...

loceng2• 14 years ago

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?

guth• 14 years ago

Skype?

Dn_Ab• 14 years ago

This is a great point. I also think it is worth noting that by the third or fourth time, even if they were peniless, the person would be starting from a far better position than a first timer. Networks and Reputation are a powerful form of currency and more useful than money if you want to do hard things.

Confidence from repeated success - do not underestimate pressures from family and self doubt in their contribution to start up cave ins.

vannevar• 14 years ago

...to do it 3 or 4 times is something else.

Doing it 3 or 4 times is in fact much easier, which is why so many entrepreneurs who are successful the first time go on to have further success. It's much easier to raise money with a track record, you have connections with skilled people on both the technical and financial side, and you have your own experience to avoid pitfalls and give you confidence. If entrepreneurship is a marathon, it's a marathon where every mile gets easier and easier as you run.

In such an economic race, it's no wonder there is a growing disparity between the leaders and the rest of the pack.

kator4• 14 years ago

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.

bedris• 14 years ago

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 agree with this. I came across the following definition of an entrepreneur, which I also really liked: "[the] definition of an entrepreneur is someone who makes things happen despite not controlling the resources necessary to achieve them."

Source: http://www.tcpinnovations.com/drugbaron/?p=242

aortega3• 14 years ago

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• 14 years ago

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.

nuaccnt• 14 years ago

Resentment won't help your cause, whatever it is.

drx• 14 years ago

It's not as zero-sum as you seem to imply.

saraid2163• 14 years ago

Why the diss on Africa?

j_baker• 14 years ago

Whether I agree with you depends upon your definition of "you people". HN certainly has its fair share of startup circle jerkery and idealization, but the grandparent didn't come off as being a part of that. Rather, it sounds like they were just trying to share their experiences on the subject of the OP.

kator4• 14 years ago

What's is a amazing is I started my first business with $486.00 in the bank. Don't berate people because you don't understand how it's done. Several of my companies were partnerships with other people for funding.

As bedris quoted: "[the] definition of an entrepreneur is someone who makes things happen despite not controlling the resources necessary to achieve them."

It's not always about rich people having fun.. most of the time it's about people following their passion and pushing every limit to make stuff happen.

And most of the time it's about complete and utter failure and learning from that so you do better the next time. :-)

heretohelp• 14 years ago

Create from nothing in the face of extreme adversity?

You're an entrepreneur, not an infantryman. Don't kid yourself, nobody's preventing you from going and making something.

saraid2163• 14 years ago

The extreme adversity isn't necessarily from other people.

srbufi• 14 years ago

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• 14 years ago

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• 14 years ago

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.

cottonseed• 14 years ago

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.

moron• 14 years ago

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.

ragincajun• 14 years ago

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.

bfe• 14 years ago

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.)

The myth of the serial entrepreneur

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