Before I came to Commerce almost a decade ago, I had a secret life. If you’ve read these Startup Blogs for any length of time, you know that I was an entrepreneur and small business owner before joining the state. But as you can see by the headline, I am also a pirate.

Not a real pirate, mind you. I am still very much anchored to reality. I’m not the Johnny Depp cartoonish kind of pirate either, swaggering around, wondering why the rum is gone. I am an entertainer who dresses up as a rogue of old to entertain at festivals, fundraisers and the occasional bar. Over the last 40 years, I have had the good fortune to travel all over the country and the Caribbean to perform on someone else’s dime.

During this time I learned a ton about business without even knowing it. Convincing a well-known CEO that you can ghostwrite his future bestseller is a cinch compared to getting an event planner to pay you and 10 of your friends to do a corporate gig on the beach of an all-inclusive resort in Puerto Rico. Talk about being a pirate.

Here are some lessons I learned that may help you think more like a pirate less like one of the King’s Navy (to steal a line from Steve Jobs):

Lead by example

Few are born leaders. But leadership is a skill you can and should learn. A good place to start is a mentor or boss who was a great leader. Take what you learned from them, blend in some other things you’ve learned on your own and create your own leadership style.

I had to learn this the hard way. The “crew” I took with me on my many adventures weren’t even employees. Most didn’t even have to follow me and could have mutinied on me at any time, leaving me high and dry. They were there by choice, not obligation. But even when things were going horribly wrong (and believe me, they did), I always made sure that the crew came first. I do the same with my team today. If there is dirty work to do, they will find me in the midst of it. If they are having a bad day, I am there for them. In return, they perform far above their pay grade and over the last 10 years, I’ve only had one person jump ship, and that was for a position elsewhere that offered more skill growth.

Stay on course

No one wants to be part of a team or project with no clear direction. Everyone should be able to see that point on the horizon your business is heading towards. Sailing hither, thither and yon in search of a destination is not only a waste of time, but your mates will jump ship. Remember that your adventure is not aboard some luxury cruise liner looking for a port of call. You are aboard a ship that must be ready to go to war at any time.

Stay battle ready

Even when there wasn’t a ship in sight, a pirate vessel was always ready to do battle. Business isn’t playtime. It’s war. You need to keep everyone on their toes, ready to duke it out in the marketplace when an enemy shows its face. Pirates don’t get participation trophies. They seize the prize. If you aren’t in fighting form, get in shape now. Believe me, your adversaries are spoiling for a fight, and they’re going to hit you when you least expect it. This includes your seemingly friendly competitors.

Be well armed

No pirate ever lost a battle because they had too many cannon on board. Make sure you’re armed to the teeth with the latest data, a well-oiled marketing machine, attractive pricing, top-notch service and a loyal following. If you bring a peashooter to a slugfest, you’re never going to come out on top.

Step in, step up

Aboard a ship, every crew member knows at least one other role. If one person is out of commission, another steps in. If the navigator falls overboard, someone else tells the guy at the wheel where they need to go. Can you imagine a ship that loses its navigator, and the captain says, “Well, I guess we should go back from whence we came. No point going on.” Cross-train your crew and switch them around from time to time to keep their skills sharp.

Check from stem to stern

A small leak can be easily fixed if found early enough. But left unattended to, it can sink a ship over time. As you run your business, make sure you check to see that everything is shipshape. If you are bleeding money, time or efficiency, fix it. Leaving it as it is will only slow you down in your plan for growth and profitability, and over time, you could find yourself – and your business – completely underwater.

Give ‘em shore leave

No one can work 24/7, certainly not in the times we are in now. Break up work-life monotony by encouraging shore leave (vacation or comp time). Even the King’s Navy allowed their crew a wee bit o’ rum now and then. Driving people too hard will only drive them out. And in a world where there is more work than crew, even your most loyal members may be tempted to jump ship if you don’t give them some well-deserved shore leave. Give them grace, and they will follow you to the ends of the Earth.

Have a trusted second

Every great leader needs a second. You can’t do it all. On a pirate ship, the captain is only in charge when engaged in battle. The quartermaster handles all other functions. He commands the crew and the entire ship, from the rations to the course that is set. Find a good second who can handle the day-to-day so you can focus on strategy and the big picture. As the captain, you shouldn’t be spending your valuable time swabbing the deck or mending the sails of your company.

Finally, remember that the voyage is never a straight one. Even if you have a particular goal in mind, you will need to change course now and then to get there. No ship can make port if it only sails into the wind.

Somewhere north of the Emerald City, ready for battle, but only if there’s a good Italian restaurant nearby,

  • Robb