Our Best Investment

We made our best investment 13 years ago.  Now don’t pay any attention to the featured image.  It was not our house (Really?  You think I would be talking about our primary residence?). Or any other piece of real estate for that matter.  However, like a rental property,  it required constant attention, knowledge, and a little bit of luck.  Our best investment was one of those complicated deals.  The original draw seemed minimal at first but we knew there would be periodic calls from time to time.  A hundred here, a thousand there.  The duration of these calls was unknown at the beginning of the term .  So was the total ask.

Crazy, huh?

I know this doesn’t sound like the usual careful investing espoused here on DiverseFI.  But we were young and heard good things from most of those who got involved with this outfit in the past.

Doubling Down

Those first few years were rough.  We saw the value of our holdings rise and fall.   There was quite a bit of anxiety about losing everything.  We certainly went many nights without sleep.

It wasn’t just the money involved, but the work.  We found that we were anything but passive investors in this deal.  Our input was sought at every turn.  We streamed through reams and reams of data, articles, behavioral manuals.

And then inexplicably, the tides turned.  We felt the tea leaves were forecasting in a positive direction. Our due diligence was paying off, and the dividends were piling up.  This was easy money.  What could go wrong?

So 10 years ago, with our confidence brimming, we doubled down on our investment.  We had plenty of cash reserves.  Our careers were in overdrive.  Our other investments, properties, and index funds provided a safety net for this risky venture.

Mo Money, Mo Problems

We should have known.  It only is fitting that the more involved we became, the more work that would be required.  Now substantial share holders, we were expected to determine the voracity of our investments.  Decisions were dumped on us from all directions.

A little here, a little there, too much here?  Should we walk away from that allocation or focus more heavily on this one?   As the portfolio expanded, it became harder to keep up.

My wife and I often daydreamed about what life was like before we jumped into this firestorm.  We remembered lazy Saturdays sleeping in, and lounging about the house unencumbered.

Those days are long gone now.  We find ourselves rushing about like chickens with our heads cut off.  So much to do and so little time.  We have aged along with our investment.  The portfolio size has become inversely proportional to the amount of hair on the dome of my head.

Let’s just say that I’m balding fast.

Life Intervenes

My wife and I were in the middle of a heated shareholders meeting the other day.  Usually on the same side, we now found ourselves face to face on the opposite end of an argument.  My teeth gritted and the minuscule tufts of hair on my head clenched in my hands, a small tapping came from the boardroom entrance.

The bedroom door opened.

Daddy were hungry!

It was the ten year old investment.  Apparently her and the thirteen year old needed to be fed.