A while ago, I found myself the only customer at a hotel bar, sipping some amber liquid and thinking about making money in general and income investing in particular.  My thoughts meandered to a question – What road-weary stranger would I most like to sit down at the bar next to me and strike up a conversation?

Three Guys With Stories To Tell 

I decided I’d like that guy to be Warren Buffett, glossing over the fact that he wouldn’t be all that road-weary since he travels on his own jet.  I got a kick out of thinking about swapping war stories with such a seasoned and successful investor.  I’m pretty sure I could keep the conversation going since I’ve read the Snowball biographyand remember some of the juicier parts about his life.  Maybe he’d even ask what path led me to this bar and I’d get to tell some of my small stories.  I just have a feeling he’d ask.

Then, with ol’ Warren sitting next to me in my thoughts, I wondered who next I’d like to see come in and join us.  Bruce Springsteen popped to mind.  I’ve never seen him in person but I’ve sure listened to many of his rocking thoughts and that gives me a sense that he’d be pretty cool to talk with.

I may have ordered up another bucket of the amber stuff and continued sipping because I couldn’t help myself thinking about who I’d like to be the last to sidle in and join us old guys at the bar.  I decided I’d like my next drinking companion to be Brett Favre, the quarterback that never wanted to retire.

Usually sipping that stuff I was sipping makes me a little less reserved and a little more loquacious but I’m pretty certain I’d still take a back seat and mainly listen to those guys.  Even though there’s almost 40 years difference in age between the youngest and the oldest of that trio, they are all at or toward the end of their careers in their profession and they all would be considered big money earners during their careers.

So What Would They Say? 

You know what I thought those accomplished, rich guys wouldn’t talk about?  Making money.  I bet they wouldn’t talk about that even if I’d like them to, just a bit.

I bet they might talk a bit about their greatest failures, like Warren’s misplaced bet on some derivatives years ago or Bruce’s “Queen of the Supermarket” song or Brett’s six interceptions in one playoff game.  Maybe they’d chat about some of their successes, like Warren’s philanthropy or Bruce’s “Born to Run” or Brett’s beating the Patriot’s in the Super Bowl while tossing two TDs and running for another.

But the thing I’m guessing they’d most talk about wouldn’t be the highs and lows of their careers but the fun they had along the way.  The failures and successes that others recognize would be part of that fun they remember but it wouldn’t be the major part.  After all, Brett spent a lot more time on the practice field than he did playing NFL games and Bruce spent much more time practicing and hanging with his band than he did in concert and Warren spent a lot more time digging into numbers and doing his homework than he did basking in the glow of an acquisition announcement.

They might talk about the roads they took to get where they are and maybe even some of the roads not taken.  But most of all, my guess is that they would talk about loving what they did and wanting to get up every morning and getting to what they loved.

No, I don’t think they’d talk about making money.