from Hacker News

The myth of the serial entrepreneur

by xachen on 6/29/12, 10:01 AM with 51 comments

  • by kator on 6/29/12, 10:53 AM

    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.

  • by adamt on 6/29/12, 10:40 AM

    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.

  • by tomblomfield on 6/29/12, 10:28 AM

    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

  • by technotony on 6/29/12, 10:30 AM

    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!!
  • by bfe on 6/29/12, 10:31 PM

    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.)

  • by dataisfun on 6/29/12, 10:12 AM

    This was extremely well written. A very nice change from typical meta-startup fare. Nicely done!
  • by slajax on 6/29/12, 10:32 AM

    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.

  • by cottonseed on 6/29/12, 1:37 PM

    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.
  • by srbufi on 6/29/12, 11:14 AM

    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.

  • by mik4el on 6/29/12, 12:32 PM

    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)?
  • by ragincajun on 6/29/12, 2:36 PM

    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.

  • by moron on 6/29/12, 1:45 PM

    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.