Morph of a Nerd CEO – First Sole Practitioner

If you’re a nerd like me with executive office ambitions, quickly ask yourself why.  You won’t get to write more cool stuff because you’re the boss.  You’ll be too busy being the boss.  You won’t be able to take cool vacations whenever you want because there is no one to tell “I’m outta here; deal with it.”  For good reason nerds are generally held in higher esteem than CEOs and, on a day-to-day basis, are usually more useful.  Girls may prefer CEOs so that’s a plus but you’re likely to end up in real trouble if all the women you meet work for you.  (I’m not being sexist.  There are great woman nerds and great woman CEOs; I just don’t know what it’s like to be one.)  It’s also unlikely that you’ll become Bill Gates.

Maybe you just don’t like anyone else being boss.  That reason’s OK for starters but once you’re out on your own, you’ll find that bosses actually do more stuff than you think – and a lot of it may be stuff you don’t want to do and aren’t good at.  Sales, for example.

In 1969 I was nominally Systems Programming Manager (a nerd job if there ever was one) in a startup funded in the software bubble of the late 1960s.  Unfortunately, since we didn’t have any customers for our facilities management business, we didn’t have any computers for me to be the Systems Programming Manager of; and so I was being rented out as a consultant at $300/day.  Since all nerds can count, I realized that not all of this money was going to pay my $25,000/year salary.

So I quit and started my own consulting company - Solutions.  I had arranged funding through American Express – my green card.  I also had a Diners Club Card for backup.  I had a couple of weeks untaken vacation that I got paid for when I quit so that was my personal nest egg – and I was single, a good thing when you’re being irresponsible.  I did have one consulting assignment at McDonald’s subcontracted from a former boss who was doing management consulting and who was, fortunately, willing to pay me faster than he got paid.  I quit in order to be able to take what was at least two weeks’ work.

The gig at McDonald’s was fun.  The corporate headquarters in Oak Brook, Illinois was the latest thing in office design – cubes!  They were brand new then.  Because no one had a private office, conference rooms could be booked so you could still carry on office politics and talk behind people’s backs.  There was real fear that the lack of privacy would drive people crazy so the architect included a think tank – a room with padded walls shaped like the inside of a flying saucer (or perhaps a hollow Big Mac), mood lighting, and surround sound – from records, of course. There were red and green lights outside that let you know if anyone was inside.

When executives used the think tank, they were suspected of either dalliance or incipient madness – so executives stopped using the think tank.  Non-executives were expected to be in their cubes during working hours.  So I slept in there a lot during the twenty-four hour days of getting the flawed new payroll system up and running.

Then, one day, the parallel runs succeeded; the job was done.  Learned a lot about how sacred “meeting payroll” is.  I thought about it with satisfaction on the flight back from Chicago to New York until I realized that I had no more work lined up.  Panic!

None of the other Systems Programming Managers and MIS executives that I knew from industry conferences wanted to engage me since my specialty was cleaning up what MIS screwed up.  Somehow I didn’t manage to pitch this as a benefit to them.  Maybe I didn’t even think of doing that.  OK.  Got to sell to the level above MIS.  Trouble is I didn’t know anyone with those jobs.  OK.  Make cold calls.  Once I got through to the CEO of a large utility.  My pitch was written out: in an audit of MIS which “we” would perform at no charge, we would identify huge cost savings opportunities which we would implement at no risk to them since we would only charge a share of the savings actually achieved.  Of course, there would have to be a small advance.  But I was so surprised to get through to the executive and so unprepared to make cold calls that I just hung up when he picked up the phone.

I still can’t do cold calls.

Luckily for me, my ex-boss got a new assignment from McDonald’s which again included me.  The company I’d quit gave me a small assignment.  An ex-customer of my fomer company became a customer of mine.  Yet another ex-boss got a job where MIS reported to him and did see the benefit of hiring me to straighten out a pretty shoddy operation.  Since MIS didn’t quite see things this way, I was forced to develop a modicum of tact in this assignment.

The lesson in all of this is networking, not that I would understand that until many more years went by.  I had left prior jobs on a friendly basis and that turned out to be crucial in making my new business work.  At this point I was a good nerd, not a good businessman.  I got repeat business because I did good nerd work for my clients.  I got new clients when individuals who were used to using me moved on to new companies and introduced me there.

Especially for nerds it’s good advice to be your own boss before you try to be anyone else’s.  Here’s where you find out whether you can sell and market or whether you’d rather “outsource” that to a boss.  Here you find out whether you’d really rather have a regular paycheck that someone else worries about than doing the worrying yourself.  And it’s easy to step back from here.

Also, happiness for you may be as a sole practitioner.

This post is now available as a podcast.

If you’ve decided to hire other people (or are thinking about it), please read this post.

And here are some negotiating hints and here something on selling.

I’ve blogged some hints for CEOs on managing programmers here, here, here, and here.

Just to evenhanded, I’ve also blogged on how programmers can manage technical and nontechnical CEOs.