The 13 Troublemakers You Meet in a Startup

Don Rainey of Grotech Ventures writes a pretty good VC blog entitled VC in DC.  He covers the usual topics and provides a lot of insight into Grotech and their investment process.  Don also pens some amusing posts every now and then.  Two of my favorites are The 7 Troublemakers you meet in a start up and 6 More Troublemakers you meet in a start up.  I have worked in three different startups over the past 25 years and find Don’s tongue in cheek assessment rather accurate.  I’ve lifted rather liberally from Don’s posts and combined them into one post.  You should read the original posts and comments to get the full description of these personas.

1. Ms. Strategy

This capable, driven, articulate young lady will meet any requests for tactical execution with a discussion of strategy.   In a start up, everyone is close to both the strategy and the supporting tactics.  Some people can’t help themselves from knowing better about either or both.  Plus, talking is a lot easier than doing.

2. Mr. Big, Hollow, Pipeline

He made $300k at Cisco before taking this job.  Now he has a huge sales pipeline of brand name companies with massive revenue potential and no disciplined approach to characterizing possibility of closing them.  Ask him how a 30% likelihood of close defers from a 70% likelihood of close and he will talk about people and conversations rather than steps and actions.  I now assume that Cisco pays all failing salespeople $300k.

3. Goldilocks

The ever changing roles and challenges of a growing start up provide an endless set of opportunities to try new jobs and responsibilities.  Most people love being stretched and many discover or develop new skills or interests.  Not Goldilocks, however, as this individual tends to be too heavy for light work and too light for heavy work.

4. The Big Time Scaler

No sense building any system today that won’t scale to size of General Motors.  Yes, every start up organization has plans and dreams but sometimes you need to sell one house to get another, larger one rather than live in a mostly empty, expensive one along the way.

5. Mr. Artiste – the programmer

He is creating software (sometimes the company’s core product/hope of future success) and he isn’t limited by the contents of the requirements document.  He isn’t limited by it because he isn’t reading it.  He is creating, damn it, and brings his own vision.

6. The Holiday Maker/Union Rights Leader/Salary Surveyor

Yes, a long title, but its a big job.  First, this person will seek the addition of incremental holidays to the company calendar.  What no Veteran’s Day?  We don’t get off the week between Christmas and New Year’s?   Friday before Easter or the Monday after?  Well, you get the idea. . . .This contributor will also “represent” the feelings of employees to management without consulting many of them first.   There’s no who in this group, its a group of “everybody”. . . Finally, this person usually investigates and shares salary data for the purpose of fomenting general dissension within the company.

7. The Angry Support Person

I can never figure out what makes them, or keeps them angry, but they can be the Energizer Bunny of anger.   Maybe the line of work, or being the starting point of a feedback loop for whatever is going wrong with the product or customers, but in any case, the Angry Support Person can create a special kind of crisis

8. The IT Support Guy/ Flannel Bob

He’s busy but he is working?  Does every computer need to be taken apart?  And how come you can never make a point that he doesn’t already know about like “Did you see the next version of this has that? or “I saw they’re coming out with ….”  Answer is always, “Yeah, I saw that.”

9. The New Marcom Manager/ Captain MoonRocket

He is much cooler than you. He dresses better.  And he has come up with a new campaign to re-position the product and company.   You just don’t know how a picture of a rock in a bed of sand does that.  It makes sense to him.   Just not to you.  Or anyone else.  But boy he is convinced and it is as if he needs to reach across the time/space dimensions to reach you.  He can really talk with his hands and his framing gestures are intended to create breakthroughs in your understanding.  Where did he get those glasses?

10. Joan of Accounting/ Defender of the Realm

New customers and, worse troublesome accounts receivable, just make more work for her.  If good accounts don’t make it through her screen, it is just less work. Since the collection of bad debt will inevitably fall to her, she sees her primary job as the prevention of bad accounts that will become work for her later.

11. The Time Traveling Middle Manager

Always ready to visit in your office and spend some time, he is ready with insightful commentary, nay advice, related to everything that HAS BEEN done by you or anyone else.  If you had that advice AND a time machine, you would really have something

12. The Triathlete Production Assistant

She arrives at the Monday morning staff meeting to describe an extreme fitness weekend which included a 48 hour race with running, swimming and cycling.   She got almost no sleep at all.  She looks ok.  And she will be fine for the next couple of hours.  Then she begins to fade.  Completely fade.

13. The Project Manager

It can be dis-spiriting to create fabulous GANTT charts for unfabulous goals. All the start up organization’s dysfunction in a walking, talking person.  He is characterized by his unanswerable questions –“How can the developers lose more than one week in their completion date, when only one week has passed?” or “Couldn’t we have known that people will take off work on Christmas day? or “Why does our one and only Q.A. staff need a month notice when they’re going to test the company’s only product?”


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16 Comments

  • Reply DGentry October 29, 2009 at 12:16 pm

    I believe the Angry Support Person has bee inadvertently duplicated (or perhaps is twice as damaging as the rest). I’d suggest a replacement for one:

    The Great Facade
    He knows everything about every topic in computer science. He is always the smartest person in the room. Presented with a problem, he comes instantly to the optimal solution… at least, thats the impression that he’s desperate to make. If it so happens that he says something which might, in some sense, be ever so slightly off the mark, he becomes belligerent and insists that the question was imprecisely phrased. He’s also give to “proof by emphatic repetition,” substituting bluster for facts. He may not always be correct, but he’s _never_ uncertain.

  • Reply Mark Silver October 29, 2009 at 2:12 pm

    RT @Don_Crowther: Laughed when I read this: The 13 Troublemakers You Meet in a Startup. I've met them all, even been a few http://ow.ly/xond

  • Reply Chris Carnduff October 29, 2009 at 5:16 pm

    The 13 Troublemakers You Meet in a Startup | spatially relevant http://bit.ly/2KYsL8

  • Reply anonymous coward October 31, 2009 at 9:48 am

    LOL great article. I used to work at a startup when I was fresh out of college, and all of these people were there. I’m more experienced now and I don’t do it any more, but back then, I was Mr. Artiste.

  • Reply Joanna Lord November 2, 2009 at 4:06 am

    RT @kyleplacy I'm loving this post from @spatially The 13 Troublemakers You Meet in a Startup http://bit.ly/1FBlQ

  • Reply alibabaoglan November 2, 2009 at 4:08 am

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  • Reply David...only better! November 2, 2009 at 4:11 am

    RT @kyleplacy: I'm loving this post from @spatially The 13 Troublemakers You Meet in a Startup http://bit.ly/1FBlQ

  • Reply ProStar Warsaw November 2, 2009 at 4:11 am

    RT @kyleplacy: I'm loving this post from @spatially The 13 Troublemakers You Meet in a Startup http://bit.ly/1FBlQ

  • Reply ProStar Indy November 2, 2009 at 4:11 am

    RT @kyleplacy: I'm loving this post from @spatially The 13 Troublemakers You Meet in a Startup http://bit.ly/1FBlQ

  • Reply Chris Reed November 2, 2009 at 4:15 am

    RT @kyleplacy: I'm loving this post from @spatially The 13 Troublemakers You Meet in a Startup http://bit.ly/1FBlQ

  • Reply Lorraine Ball November 2, 2009 at 4:40 am

    Met these people RT@GloveBoxGourmet RT@kyleplacy: Loving this post from @spatially 13 Troublemakers U Meet in a Startup http://bit.ly/1FBlQ

  • Reply JulieGrice November 2, 2009 at 6:33 am

    RT @kyleplacy: I'm loving this post from @spatially The 13 Troublemakers You Meet in a Startup http://bit.ly/1FBlQ http://myloc.me/1iURG

  • Reply Kyle Lacy November 2, 2009 at 7:04 am

    It is scary that I am seeing myself in some of the caricatures… time to start changing. lol good stuff. 🙂

    • Reply Jon Gatrell November 2, 2009 at 2:55 pm

      I think I’m in everyone, glad mecke wrote this one.

  • Reply Kyle Lacy November 2, 2009 at 7:04 am

    caricatures – characters

  • Reply Lorraine Ball November 2, 2009 at 7:53 am

    I think I might have been Ms. Strategy once upon a time… and may fall back into that habit every now and then

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