Business advice from my pirate uncles

• ~600 words • 3 minute read

A few weekends ago I went out to the same family reunion we have most years on the McKenzie River in Vida, Oregon. We spend the time acting like happy animals; socializing, grazing, sleeping and looking for pockets of shade in the summer sun behind the old, charmingly dilapidated cabin my grandparents built and retired in decades ago. It's been a tradition since I was a small child; something I look forward to as a way to recharge, especially over the past four years or so as I've expanded my web development business and found the opportunities to vacation few and far between. Summer never officially begins in my heart until I've dipped my toes in that river, watched the deer walk through the yard at night, eaten seven kinds of pie and soaked-up just ever-so-slightly too much sun.

Like most families, we have a variety of characters making regular appearances. There's are school teachers, a judge, an etymologist and two engineers, but my favorite interactions have to be the business advice I receive from my two, wildly disparate uncles. I call them my pirate uncles for obvious; one has a gray beard, a ponytail, a pet parrot and spent a good amount of money one year pulling together an authentic pirate costume for Halloween, right down to having a real sword. The other... Well, the other guy is a pirate. He builds scale-model pirate ships about the size of a small sailboat, complete with miniature, working cannons.

To put it in perspective, one is a Silicon Valley veteran who came out of retirement to work at Google in its startup days because it "sounded like fun", writes and publishes books about science experiments you can do in the home and has an automated business that sells science kits online. The other spent time working on boats in southern LA, living above his shop, driving his motorcycle and (I'm fairly sure) worked as a bouncer at some point. He's a very gifted mechanic and woodworker, able to fix just about anything with his hands. On the surface, and quite a bit deeper, they are very different people, and needless to say I love them both. Perhaps also needless to say, my two pirate uncles dispense very different kinds advice, though they're both proponents of the 4-hour work week in their own strange way.

Realizing this gave me a great idea — I should write a book called "Business Advice from My Uncles". Each chapter would alternative between the two men and the different lessons and wisdom they've imparted on me. I can see the chapter titles already:

  • Automating your business through outsourcing
  • Collection payments with a sledgehammers and threats
  • The importance of generating original content for your website
  • Ways to not let the man screw you
  • Turning your hobbies into a business case study #1: cooking and chemistry
  • Turning your hobbies into a business case study #2: bootleg hooch

And maybe I could start each chapter with some choice quotes, like this one:

...So I take my sledgehammer and walk out to the dock. I walk in front of his yacht and take my shirt off and tell the guy “Buddy, I can swing a sledgehammer under the water like you wouldn't believe. I'm either leaving this dock with my $9,000 or I'm taking it out of your boat.”

I'll leave it to you to figure out which uncle provided fodder for which chapter titles and the quote up above.

Man, I wish I was back up the river already.