Startups are like short-handed sailboats, and vice versa
Originally published as part of my newsletter, Oscillations. Want posts like this in your inbox as they publish? Sign up here.
Why’s it called ‘Oscillations’? I explain it here.
I’ve been involved in four different startups to date, always in a senior leadership role. The most recent one is different, for two reasons. Of the four, it’s the only non-media startup, and my first as founder.
Since starting this newsletter, I’ve kept a running list of potential topics, and a note at the top saying: Startup founders as solo sailors? Dinghy sailing as startup life? So let’s explore that.
Being a co-founder is a lot like racing a small, short-handed boat.
Most of the time, on dinghies or other short-handed boats, there’s just you, or you and one other person. Everything comes down to the decisions you make, so success means understanding every aspect. You have to know how to prepare the boat, rig the boat, and set it up to perform in the conditions you face. You have to know all the systems well enough to set them up for success, and fix them if they break. You are responsible for setting out strategy, breaking that down into tactical decisions, correcting as conditions change. You work all three sails. The whole shooting match - it all comes down to you. You own it all. You are immersed, and always in action. You are constantly calculating and ideally constantly communicating. There isn’t a moment where you’re not engaged in the race.
This 2001 photo ended up on Desperate Housewives. But that’s a different story.
Big boats are different. You might be among as many as 12 people on a crew, maybe even more. Unless you’re sat at one or the other end of the boat, where the decisions are consequential, you’re not making calls, you’re following orders, adhering to process, watching metrics. Your job is more specialized, and it’s likely only in demand at certain times. You might trim one sail only. There may be long periods where you’re waiting to be called into action.
This is the corporate world for many people. There’s a little more room to hide a lot of the time, it’s a little more comfortable, you might get less spray in the face and work up less of a sweat, and for many folks that’s exactly what they need.
Of course, you own a smaller share of the wins, when they come. You’re slightly more of a passenger. You’re rarely, if ever, driving. You might make it to one of the business ends of the boat on occasion, but if you’re mostly in the middle, you spend a lot of time wondering what the next order is going to be.
Big boat sailing includes long periods of sitting quietly on the ‘rail’, for most of the crew.
And let’s be clear, for boats or businesses set up a certain way, or at a certain size, those people in the middle are absolutely essential. You can’t possibly perform without them on your team – when you need them it’s essentil they’re there. Twitter is a great example of a company that grew to rely heavily on its middlefolk. Elon Musk clearly thought he could shed almost all of them, but his new boat has hit plenty of rocks. Not sure how many more hits it can take. The US in general is firing its entire rail at the moment.
LESS IS MORE
I’m a fan of small boats and small crews, or of being at either the front or back end of the boat. If you end up in strategic leadership or running a startup, it’s unlikely you’ll ever ben content to be a ‘middle-of-the-rail person’. During my forays in the corporate world, it was nice to have the benefits of that bigger corporate boat, for sure - larger teams, better equipment, even some perks. But I always worked my way to the business end where the action was more constant and the decisions made were more directional & meaningful. I wanted the spray in my face. I wanted to actively make it go faster and in the right direction.
It is very much a way of thinking, I believe. You either want to run the boat or you don’t, you either seek out that accountability and opportunity and the risk that comes with it or you’re happy to have someone else take that heat. You have to believe you should have your hand on the tiller.
SMALL BOATS BECOME BIG BOATS
Of course, the thing about startups is that the successful ones have a habit of becoming larger companies. How does the small boat analogy work as you scale to a bigger boat? Top-class competitive race boats, even the big ones, keep things lean even as the length of the boat grows.
They restrict their crews to the minimum viable number, opting for pure professionals, because more people means carrying more weight, more baggage. The highest-performing offshore racing boats these days, in the 60-70 foot range, often have no more than 2-4 people on deck (the average amateur 40-footer would typically have 8 on deck).
If you look at the skippers who have won the Volvo Ocean Race, the vast majority, particularly in recent iterations, have been ex-Olympians or otherwise world-class dinghy sailors – they have small-boat roots. They have small-boat attitudes.
Paul Cayard. Torben Grael. Ian Walker. A handful (Franck Cammas, Charles Caudrelier) were top-class solo offshore sailors - and again, they started their careers in smaller boats where all the decisions rested with one or two individuals, who took full responsibility. All of these pro skippers will have done some time in bigger, bulkier boats along the way - comparatively sluggish boats with large crews, whose speed is restricted by their weight and drag. But when they want to feel competitive, get the spray in their face, when they want to win against the best, the dinghy mentality returns, regardless of the size of boat.
What’s the takeaway here?
How you build your team is important. I seek out the same kind of people in boats all the time. Calm heads, rational folk. People who can focus on their role and own it, and delegate well. Economic communicators. Realists. I end up sailing with the same people again and again, and the way I communicate with them all is always the same. We share the same understanding of what’s important and how decisions should be made. We can practically finish each others’ sentences.
Whether you’re a rail person or an either-end person or a small boat person, what’s important is you at least know what you are so that you can find your crew. You want to fill your boat – whatever size it might be – with people who share your mindset, your concept of ownership & communication.
