Startups are like short-handed sailboats, and vice versa

Markham Nolan
6 min readFeb 21, 2023

You gotta do it all

Hi, folks. I don’t publish much here any more. To follow my writing, do please sign up to ‘Oscillations’, a Substack newsletter I’ve created. Why call it ‘oscillations’? I explain it here. (This piece is a crosspost)

I’m embarking on my fourth startup adventure. I’ve been involed in three different startups in the past, all media, always in a senior leadership role. This time is different, for two reasons. The startup is non-media, and I’m a co-founder. NOAN is a global accelerator platform for small business, combining a proprietary strategic roadmap for business-building, a marketplace of top-tier consulting talent, and (in the medium term) generative AI solution to create all the strategic and marketing content small businesses need to go to market.

Since starting this newsletter, I’ve kept a list of potential topics, and a note at the top saying: Startup founders as solo sailors? Dinghy sailing as startup life? Feels like it’s time to explore that.

Even in the short time I’ve been sharing the helm of this new startup, it’s clear 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 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, constantly communicating. There isn’t a moment where you’re not engaged in the race.

Random aside: I’m told this pic (which I shot) was, bafflingly, used as a frame-filler on the set of Desperate Housewives. I have people checking.

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. 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 less 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 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 essential. You can’t get around the course safely or successfully without them on your team. 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 now hit plenty of rocks. Not sure how many more hits it can take.


It’s not hard to guess which scenario I prefer — I’m a fan of small boats and small crews, or of being at either the front or back end of the rail. If you’re in strategic leadership or running a startup, it’s unlikely you’re a ‘middle person’. During my forays in the corporate world, I’ve never been content to sit quietly in the middle of the rail. It was nice to have the comfort afforded by 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 see if I could help make it go faster.

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. My co-founder is an ambitious surfer & climber — two sports where the effort is a risky, singular, solo affair so he’s of a similar mindset, and understands what it means to own the success or failure in its totality.

Over nights and weekends, we have built the initial product for our new startup — NOAN — working ourselves using no-code tools, so we are intimately in touch with the systems. We’ve pivoted since we started, correcting as conditions changed — the emergence of ChatGPT being a big change & source of opportunity for what we’re building. We’ve brought customers onto our platform and adjusted based on their activity and feedback. We are running the marketing (Sign up! 📬), the engineering, the fundraising. (WE ARE RAISING — read to the end for more). We’re laying out the strategy and doing our best not to be distracted. We’re set up to profit from chaos, because our business leans into the secondary effects of layoffs and recessions. We’re in business to help people build businesses — and we know there’s a lot of talented people with time to think and severance money in their pockets right now. We think they’re going to be launching a lot of new businesses in the coming months and years.


Of course, the thing about startups like ours 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 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. 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? Well, two things.

One, is how we plan to build our team. We want to create a startup that can scale to high performance. To that end, I’d much rather hire fewer, better people with the same mindset of ownership that I share with my co-founder. I don’t see there being room for many middle-of-the-rail folks. Everyone needs to be comfortable being a decision-maker.

💵 Two, is the obvious fact that we’ll need money to hire the best, lightest crew crew and build the best, lightest boat. We’re going out for fundraising and have a limited number of slots for friends-and-family investment. If you or someone you know might be interested in investing in building a global accelerator for small businesses — do please send them our way — we’re at



Markham Nolan

Co-founder @getnoan || COO @ Recount Media // Priors: @WWE @cbsnews @storyful @vocativ @metroUK // ‘Ask not for whom the web trolls, it trolls for thee’ //