Entrepreneurs: should Techcrunch’s Michael Arrington be your cheerleader?

Bill Gates and Michael Arrington

Michael Arrington wrote a humdinger of a post this weekend, titled “Are you a Pirate?” It almost universally was cheered by entrepreneurs.

But 24 hours later I’m left with a bad taste in my mouth.


1. Pirates steal, but don’t create value.
2. He just told his team to earn his respect by starting a company and not working anymore for him. Is that good strategy for someone who wants to build a lasting brand?
3. He was made rich, at least in part, by the efforts of others. AOL bought Techcrunch, in large part, because of his great conferences. Those were done by other people. Plus, I’ve seen the hard work others put in behind the scenes at Techcrunch. Mike hired well, but now seems to be spitting at people who’ll work for other people.
4. Great things require teams. While Arrington is praising the “pirate” who leaves normal society to “run a company” he forgets that a baseball team with only a coach isn’t very interesting at all.

Believe me, I know what he’s talking about. I left a nice cushy job at Microsoft to join a small startup (Podtech) that no one had ever heard about. It’s the fourth startup I’ve been a part of in my life.

I remember the thrills of closing deals, and hiring people, but I also have lots of battle scars after that, too. Guess what, the scars tend to stick around long after the wine celebrating the successes has been drunk.

But there is something in Michael’s post that rings true. I like people who build things. I don’t call them pirates. I call them innovators. Inventors. Geeks. Coders. Developers.

My favorite memories are when I get to hang out with them and study what they are building. I remember that lunch where I invited Albert Lai and Michael over to have lunch with Bill Gates. It’s one of my favorite memories. Why? Because Gates had already built an interesting company and I knew Arrington and Lai would do something interesting in their futures. Why? They are builders. Not pirates.

Lai went on to found Kontagent. You can see him here:

But back to Arrington’s post and whether or not he should be your cheerleader?

I love how he says entrepreneurs don’t need to be rewarded for risk, because they get utility out of the risk itself. That’s bull. I don’t see Mike handing back his check from AOL, for instance. If there were no possibility of getting freaking rich there would be far fewer people who’d take the leap.

It is a hard leap to take, too. On my wall is a poster from the latest Techcrunch party. It is by my friend Hugh MacLeod. It says “I’m not delusional. I’m an entrepreneur.” The act of leaving a cushy job at a cushy company like Microsoft or Google or Facebook and heading somewhere that there’s not a certain outcome +is+ delusional and it’s not done for any one reason.

Hugh's art: I'm not delusional. I'm an entrepreneur.

But there are some good reasons.

1. You want to build something that your company isn’t letting you build. I’ve heard this over and over. Steve Wozniak told me how HP and Atari didn’t let him build the personal computer that he wanted to build. Look at the pain that drips out of the reasons that Lars Rasmussen gives for leaving Google and joining Facebook. I think this reason trumps the “living the pirate’s life” that Arrington gives.
2. You want to have a bigger impact on the industry. Let’s face it, if you stay at a big company the chances that you’ll get to somewhere you can control a big budget, thousands of people, etc, are pretty small. Yes, it happens. But usually it takes decades, a lot of hard work, a lot of luck, and probably a good pedigree (you’ll note that most of the people at Microsoft in power positions actually started companies at some point in their past). If you join a startup that gets big you’ll have a bigger impact on industry. Here, who has more impact? Tristan Walker, who’s doing business development at Foursquare? Or someone at level 51 at Microsoft (that was my level, seven levels down from Ballmer)? Believe me, it’s easier to become the next Tristan Walker than it is to get to level 54 and usually it’s the level 60’ers who have a world impact at Microsoft. Yes, I know, I broke the rules, but how often has that happened at Microsoft in the four years since I left?
3. You want a better lifestyle. Believe it or not, I’d rather work at SmugMug than at ANY big company. Why? Dogs are allowed (watch my video tour of the company). They have hand-made meals every day. And everytime I visit there folks are having fun. Or, go around the corner from my house to GoPro. Now THOSE guys have fun! They take their cameras surfing and skiing and their founder started the company out of a VW van. Most of the small companies I’ve worked in were more fun (for both the pirate reasons that Arrington gave, as well as the other ones that Rasmussen talked about) then big ones.
4. You want to work with people you LIKE. Ask Tony Hsieh, founder of Zappos, about this one. He sold a company in the 1990s because he hired people he didn’t like. They all went to Microsoft. When Tony started Zappos he made sure he hired people he liked. Would he last long at a big company where he didn’t have control over who he dealt with? No way.
5. Control of your destiny. This doesn’t come automatically, even at small companies. At Podtech I and another executive had huge disagreements over strategies. One of us was wrong and one of us should have gotten fired. But those disagreements caused life to not be fun for either of us. In the end I think they contributed to the lack of success that company saw. At great companies I see everyone rowing in the same direction. I now look at strategy of companies I join and look for whether everyone is pulling in same direction. It’s a HUGE quality of life decision and worth leaving any company over if you can’t have it.

Anyway, back to the question I posed. Entrepreneurs, is Michael Arrington really the guy who want cheerleading you?


1. He’s had great success. I can’t argue with his bank account.
2. He’s built a great team and a great company.
3. He changed the world.
4. He got to work with people he liked and got to get rid of people he didn’t.
5. He kept control of his life and his strategy.


1. Pirate is a horrible metaphor for someone trying to build something of value. Pirates steal, the best entrepreneurs build.
2. Changing the world takes a team, not just a leader.
3. I know many entrepreneurs who find a way to balance real life and their work, Pirates can’t.
4. Entrepreneurship isn’t an elitist club. I joined that club in high school in Junior Achievement (I was so happy I met the CEO of Junior Achievement at Davos — aside, great organization that helps tens of millions of kids get into entrepreneurship). Arrington makes it sound superior to other career choices. It’s not. It’s just different.
5. Risk should be faced as a team. Pirates face risk alone and force their teams to deal with the consequences of that risk. The best entrepreneurs I meet face risk as a team. Jim Fawcette, for instance, asked us all to take a salary cut one year to help avoid layoffs. He took that too. A pirate’s approach would have been to cut staff and damn the consequences.
6. Pirates don’t work with other ships, but entrepreneurs do. Think about all those folks working in big companies. Foursquare did. They just got picked up by Zagat’s and Starbucks. By folks working in non-pirate modes. How? They worked as smart entrepreneurs, looking for win-win. Great entrepreneurs don’t denigrate the efforts of those who didn’t make the same career choices they did. They celebrate them, in fact. If no one was working at big companies there wouldn’t be anyone to make deals with.
7. Pirates hide their loot under ground. Great entrepreneurs look for ways to put money back to use to help make their companies bigger, better, or to invest in other companies and people. I’d rather hang out with Chris Sacca, for instance, than someone who wanted to be a pirate.
8. Great entrepreneurs want to build great companies and look to successful companies as models. I’ve walked around great companies with some great leaders and I notice the most successful ones take notes. Listen to Rackspace’s chairman, Graham Weston, talking with Tony Hsieh, founder of Zappos, after Graham got a tour of Zappos. Guess what? Success is usually big companies. Pirates poopooh studying big companies, but great entrepreneurs don’t.

Anyway, Arrington is a friend of mine, but as the industry cheerleader I’d rather go with Brian Chesky of AirBnB. He is the entrepreneur I wish to be someday, you should watch his speech at YCombinator’s Startup School from a couple of weeks ago.

I don’t want to be a pirate. I want to be someone who keeps building until I find a way to please customers.



25 thoughts on “Entrepreneurs: should Techcrunch’s Michael Arrington be your cheerleader?

  1. Entrepreneurs are risk-seeking, but for the reasons Mike articulated. The payoff is not the adventure or the thrill of taking the risk (that may be part of it), but the payoff is the chance to build the next Google/Facebook. Plus, there is always the option to go back, in case things do not work out.


  2. Well now I’m feeling a little sheepish for retweeting @arrington’s piece on being a Pirate. You make some great points about Pirates being low-down dirty thieves, but somehow I don’t think that was what the author meant when he declared himself and other true entrepreneurs as worthy of the title. Maybe we can embrace the positive aspects of pirating – willingness to leave the comforts of dry land for the adventures of the high seas and general restlessness when being stuck in one place too long, and be sure we each are not following the less-than-desirable aspects on our own journeys. After all, the treasure can be the process, not necessarily the payment.


    1. Yeah, Arrington is an entertainer. He knew that using that metaphor would be more interesting to us than some geek sitting in front of two screens changing the world.


  3. Well now I’m feeling a little sheepish for retweeting @arrington’s piece on being a Pirate. You make some great points about Pirates being low-down dirty thieves, but somehow I don’t think that was what the author meant when he declared himself and other true entrepreneurs as worthy of the title. Maybe we can embrace the positive aspects of pirating – willingness to leave the comforts of dry land for the adventures of the high seas and general restlessness when being stuck in one place too long, and be sure we each are not following the less-than-desirable aspects on our own journeys. After all, the treasure can be the process, not necessarily the payment.


  4. I love your post and I still enjoy Mike’s metaphor. His title was engaging and his article kept us intrigued. His duty is to inform and entertain. I do agree with you on Brian from AirBnB…love his story. I hope to be on that stage one day!


  5. This is one of your absolute top drawer posts. I wonder, though, if Mike’s use of “Pirate” isn’t a reference back to Steve Jobs’s old quote “I’d rather be a pirate than join the navy.” Remember Mac was developed under a pirate flag—inside a corporation.


    1. Yeah, geeks like anti-establishment metaphors. Especially useful when you are trying to change an organization from the inside out and when you are trying to pave a new path no one else sees.


  6. Robert, I think you’re as one dimensional as you accuse Arrington of being with this article. I’m not gonna debate your knowledge of pirates, but I will argue that pirates were freedom fighters to some extend. And I really find your cons to be rather uninformed, at least from where I’m standing.

    And the part about pirates not being a team – that’s just utter BS. Not one great captain would stand out in legends if they did not have the backing of their crew. If you’re defining “pirate” as a Johnny Depp character, no doubt you’re well on your way to make an uninformed post here.

    Than again, I feel as though you missed the essence of the Arrington pirate post. The essence is that it’s a cutthroat business and you’ve got to be in it to win it. In the days of pirates, the common folk suffered, the royalty lived like kings. The only way you could actually make something of yourself as a nobody was to become a pirate.

    And the part about pirates putting loot underground… such non-sense. The majority of pirates shares out the loot after raids. The tales of buried treasure could be argued to be absolute equal to VERY successful entrepreneurs who’ve suddenly made such much money they dont know what to do with it!


    1. Kenneth: from my studying of pirates, they were willing to enslave their crews to get their work done.

      Freedom fighters? One guy’s freedom fighter is another guy’s terrorist or thief.

      I might have missed the essence of his post. Fair enough. And your point is correct, if you want to be an entrepreneur you better do something you love because you’ve gotta give everything to it.

      Glad to have you here. I still don’t like the metaphor.


      1. I think one of the downfalls of this entire setup, from you and me both, is probably a lack of understand of pirates and the times they lived in. I think we can safely say that neither of us are actually able to completely empathize with/document the inner workings of a crew member on a pirate ship no matter how hard we actually try. And as such I don’t know if we’re really qualified to actually say if being a pirate of the high seas build any real value, and if stealing could just be compared to what we today call marketing?A Marxist might even argue that today big business with your marketing schemes and entrapment campaigns are just as much stealing as anything. It’s simply how you get to the swag that is different. By knowledge or by brute force, it could merely be considered a difference in time line positioning on the great scale of the world history. Having said all that. I do think you’re right in saying that maybe Arrington isn’t the best “cheer leader” for entrepreneurs. I think we all find our own heroes on the battlefield. I’m personally very much in awe of someone like Tony Hsieh. And I feel as though I must add – when I read and forwarded Arrington’s post yesterday, I did so because it reminded me of a “rally call”. A moment of inspiration if you will. A kick in the ….. to all the people who still live in fear of actually getting out there and doing it. Personally I’m just starting out in this world of entrepreneurs, and when I see someone like Arrington do a post like that it just fuels me to keep pushing.


  7. He should be one of our startup cheer leaders. We can afford to have hundreds if not thousands, no two alike. Each startup and it’s founders have their own way of imprinting their imagination on the world around them. Enjoyed the post Robert.


  8. If by Pirate, Arrington means someone who is ceaselessly restless, and has an almost irrational thirst for adventure, the unknown, the unexplored, then it’s an apt metaphor.

    When looking for inspiration in the early days of our start-up, I came across this excellent book: A Pirate of Exquisite Mind: Explorer, Naturalist, and Buccaneer: The Life of William Dampier.

    At one point, having barely managed to outrun the Spanish navy, having just sailed around Cape Horn in a massive storm, only to become beach wrecked on the Pacific side of South America, the crew, after only a few days of resting and licking their wounds, would grow restless again, and egg each other on to sail up a river they had never seen before, just to see what was there (and yes, plunder).

    I’m always in awe of that unbridled spirit of adventure and risk taking that some seem to have.


    1. I’d rather go with Christopher Columbus for that kind of cheer, then. Pirates just are out to take other people’s wealth. Not something I can cheer about, even if it’s taken from unjust royalty.


  9. Great post, but I think you are putting a little too much emphasis on the pirate stuff and then diving headfirst into a discussion of pirate pros v. pirate cons. I don’t really know anything at all about pirates, was just using it as a way to get my point across.


    1. That’s fair. I figured you were using it for the entertainment value rather than a value judgment. It let me enter the conversation with my own points, though. 😉


  10. Robert,

    Loved the article, but you seem to using the term ‘pirate’ as if there’s some sort of membership out there that defines people as either being one or not. Truth is, there’s a full scale between people who have never pirated a thing in their life to those that do it on an hourly basis.

    The act of downloading copyrighted material has done just about as much good as it has bad, which couldn’t have been said for the old role of ‘pirate’. If it wasn’t for the masses flocking to file-sharing technologies like Limewire and BitTorrent; the iTunes store would still be another 5-10 years away, and you can forget about Hulu.

    While these ‘pirates’ might have been in the wrong, the fact is we owe them a lot- If it wasn’t for them we’d still be scheduling time to watch reruns on TV, or paying thousands of dollars per year to have walls of DVD’s, not to mention Blu-Rays and/or the next media format.

    The reason we’re where we are today is partially because of the acceptance and even romanticism of piracy. Arrington was applying this to entrepreneurship- and all the more power to him if it has the same effect on startups as it did on media.


  11. Great Post, I really like your insight into level 51. Having real “Impact” and “Controlling ones Destiny”, would be the main reason I would leave a stable job to throw myself into a start-up or my own company. You can work for others and enjoy a good lifestyle with great people, but your are rarely in control of your destiny.


  12. Dunno Pirates can be cunning entrepreneurs to in a legal fashion Bill Gates and cohorts pirated a sweet deal with IBM. The loot needed for that needed some cunning incentive for MS to become well one of the biggest company ever. Pirates have their nifty ways to let people react better to illusion after all the biggest loot got to be control and growth right.


  13. Like both of your posts for the points they make regarding startups and businesses.
    But I don’t really mind Mike’s use of the pirate metaphor – it worked for the ideas he was trying to convey. But like any metaphor, it breaks down when you push it too far.
    Hopefully this one doesn’t devolve to hygiene… Pirates don’t tend to shower all that often 😉


  14. I’ve been doing computer engineering for 40+ years, and have been following tech writing for the last two.

    Michael Arrington hurts my head because I can’t figure him out. At the very least he’s inconsistent, one minute brilliant and successful, the next a jerk and loudmouth. Is “always leave them guessing” his schtick? Why does he make it so hard to understand him? What’s the point?

    I saw him do an interview one time with John Gruber and if he had asked me questions like that I would not have been so polite and answered his questions by asking him what was the point of being an ass?

    One thing is clear. He doesn’t seem to care what people think of him, and he doesn’t seem to care about being consistent. Yeah, those things take effort. Is he lazy?

    He CREATES ACTIVITY, that’s for sure. Look at your post and the comments — and unnecessary activity in my brain.

    There’s too much going on in our industry, and I’d rather read the writings of John Gruber, Horace Dediu, Jean Louis Gassée, Federico Viticci, Matt Drance, Daniel Eran Dilger, Marco Arment, you, etc. and just chuck anything Michael Arrington has to say, knowing I’ll be able to get along fine without him and rely on the others to help me sort out what’s happening.


  15. I liked Michael’s post for some of his points, but I would agree that Pirates is the wrong metaphor.

    But, I do think there is a difference between someone making his millions in joining Google in the early days and someone making it via building and selling his company.

    Yes, it takes a team, but a team without a driver is not a team.


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