Illustration by Mr Seth Armstrong

EPISODE 24: Oliver's Army

Not long ago Nicholas came down with a bad case of "middle manager-itis". The symptoms, even in an eight-year-old boy, were quite apparent and incredibly distressing to a father who fancies himself an iconoclast even though on close inspection he is just another card-carrying member of the bourgeoisie.

"Dad, guess what? I've been asked to join this army at school. My friend Oliver is the president, and I'll be the vice-president," Nicholas announced one morning as I was putting on a starched white shirt and a blue suit for the office. "The pay is a dollar a day. We're going to be opening some car washes called, 'Oliver's Car Washes'."

While being a member of Oliver's Army has a nice ring to it - especially to a decrepit Elvis Costello fan such as myself, this was no laughing party. I was both annoyed and concerned with how easily the heir was willing to subjugate himself to another man.

"Why aren't you president?" I asked. "And why isn't this army-car wash business called, 'Nicholas' Army'?"

"I don't want to deal with paying everybody and all the problems of running everything," he replied. This is a line I've heard countless times, but not usually from a second-grader. Usually it tumbles off the slurring tongue of a fellow salary man after a big boozy steak dinner in which my colleague has outlined a brilliant concept for his own start-up and then uses the mortgage and his children's private school tuition to talk himself into staying put.

It is just that I hate to see a boy who is so fantastically bright and charismatic under the sway of a classmate whom I find to be so fantastically average

It is not as if I base my parenting style on dynasty-builders such as Joe Kennedy or Kim Il-sung, who was not only North Korea's Eternal President of the Republic but also the father and the grandfather of the next two rulers of the "hermit kingdom". It is just that I hate to see a boy who is so fantastically bright and charismatic under the sway of a classmate whom I find to be so fantastically average. But how much should I interfere? And how could I be sure that I wasn't merely foisting one of my demons onto my son? (Undoubtedly these are the sorts of touchy-feely dilemmas that kept Kim Il-sung up at night as he debated whether or not to invade South Korea.)

I should have seen Nicholas' willingness to settle for vice president coming. When he started playing soccer, I purposely did not push him towards one position or another. He was naturally drawn to fullback (my old spot). I had secretly been hoping he'd want to play in attack rather than defence. When he started playing tennis with a regular doubles partner, he naturally volunteered to play the backhand side (my forte).

In a few years' time, if he were to start a band, I live in fear he'd end up playing bass guitar. Sure, The Who's "5:15" wouldn't be a quitting-time anthem without The Ox's bass solo, but Nicholas will be entering a work force where oxen get slaughtered and entrepreneurs rule.

Nicholas is still too young for me to have a chat with him along the lines of "You don't have to follow my advice but just please learn from my mistakes". One of those mistakes has been to run for the cover of a promising gig in a prestigious company instead of going with the higher risk-reward ratio of a start-up. Over the years I've dutifully sat through so many management classes and human resources seminars that I now know the correct way to discuss an underling's body odour problem without putting the corporation at risk of litigation. All the flavour of my once tangy office persona has been drained to the point where I'm as exciting as a slice of Wonder bread.

Thankfully, the deus ex machina arrived at Easter lunch in the form of my brother-in-law, Nick. Aside from sharing the same first name, Nicholas and "Uncle Nick" are very similar. They both like the good life - even if Nicholas' definition of the good life is a thin-crust pizza and Uncle Nick's includes a single-malt, a smoke and some high stakes backgammon in his best Henry Poole. Uncle Nick is also the sort of character who will press a hundred dollar bill into my son's hand on his birthday in lieu of yet another educational present. Every boy should have an Uncle Nick.

First and foremost, Uncle Nick is an entrepreneur. That means he isn't a vice president. He is his own boss. There is no Oliver. It is Uncle Nick against the world

By trade, Uncle Nick is a distressed real estate investor, meaning he buys large properties out of complicated bankruptcies and uses his own army of white shoe lawyers to extract hidden treasure from the wreckage of the 2008 meltdown. Lately, he has been working on a couple of deals in Puerto Rico which have captured Nicholas' imagination - one in particular involving a small island. Uncle Nick spent part of Easter lunch soliciting my son's ideas on how to make his Puerto Rican properties better.

"You have to make them really fancy so people will want to live in them, then once people are living in them you secretly raise the prices," was one snippet of advice I overheard. On the drive home from Greenwich, Connecticut, I sensed an opening to point out that Uncle Nick would never settle for being an adjutant in Oliver's Army.

"Dad, did you know Uncle Nick is a millionaire. His office is bigger than yours. He orders pizza whenever he wants, and he owns his own island in Puerto Rico. He doesn't have to deal with ice and snow."

"Nicholas, your Uncle Nick is many things..." At this point, a much less secure father might have filled in a few of those things, but instead I grabbed a hold of the teachable moment. "But first and foremost, Uncle Nick is an entrepreneur. That means he isn't a vice president. He is his own boss. There is no Oliver. It is Uncle Nick against the world."

"Oh," said Nicholas, and I could hear the wheels turning in his head and wondered whether I might not be reading in the FT some time soon about a restructuring at Oliver's Car Washes.

To read Mr Brodie's previous columns, click here. Follow Mr Brodie on Twitter @jbrodieny

Commanding Style

Richard James
Suit
Charvet
Shirt
Drake's
Tie