product · 5 October 2026 · By Simon Berriman, Founder of Caddie Live

Every Round Deserves a Leaderboard: The Story Behind Caddie Live"

Every Round Deserves a Leaderboard: The Story Behind Caddie Live

Caddie Live was recently featured in The Maker Series, a set of interviews with independent makers run by 99helpers. It turned into a longer conversation than I expected — about why the product exists, what I have got wrong, and what building something on your own actually looks like when you are doing it alongside a full-time job.

You can read the full interview here. What follows is the part I think is worth repeating: not the origin story for its own sake, but the handful of decisions that still shape what Caddie Live is.

It started with eight friends and a spreadsheet

I have played golf since I was twelve, and the competitive side is the part I love. The problem is that outside organised tournaments, that feeling mostly disappears. You go away with a group, somebody keeps a spreadsheet, somebody else works out the handicaps, and nobody really knows who is winning until you are all back in the bar arguing about it.

That gap is the whole product. Watching professional golf, you always know where everyone stands — and knowing that is what makes a putt on the 17th matter. There was no reason an ordinary Saturday fourball could not have the same thing.

"The simplest version of the original idea is still: every round deserves a leaderboard."

Everything since has been an expansion of that one sentence. Scoring came first, then trips, then more formats, then bigger events — and once people started organising events with it, registration, payments, tee sheets and full society seasons followed. None of that was planned up front. It arrived because I kept using the thing myself and kept finding the next obvious gap.

Retain the power, remove the admin

The risk with that kind of growth is obvious: you end up with software that can run a national championship and is completely unusable for four friends on a Saturday.

So the principle I keep coming back to is this — retain the power, remove the admin. An organiser running a society trip should get registration, payments, tee sheets, formats and standings. A group playing a casual round should get a leaderboard and nothing else in their way.

"I've tried to make it powerful enough for organisers without making a Saturday round with your friends feel like you're administering the Ryder Cup."

In practice that means most of the work is deciding what not to put on the screen. The organiser's complexity lives in the organiser's view. The player's view is a scorecard and a leaderboard, because that is all a player standing on a tee actually wants.

The hard part isn't the screen, it's the logic

People assume the difficult bit of a product like this is the interface. It is not. Making a leaderboard appear is the easy half.

Golf is exceptionally good at producing edge cases. Handicap allowances, Stableford against stroke play against match play, teams, better ball, multi-round aggregates, countbacks to settle a tie on the back nine, then the back six, then the back three. Each is simple alone. Together they multiply, and they all have to agree with each other.

"A beautiful leaderboard that declares the wrong winner isn't particularly useful!"

That is not a hypothetical standard. When we scored the Markkleeberg Masters — a full club field, two formats in a day, a shotgun start and the standings up on the clubhouse screen — every one of those rules had to be right in front of people who would know immediately if it was not. A scoring product gets exactly one chance to be trusted.

It is also why real events have taught me more than any amount of testing. Something that makes complete sense at a laptop becomes baffling when somebody is on the 8th tee, it is raining, and three people are waiting behind them.

The uncomfortable part: distribution is harder than product

This is the bit I would most want another solo builder to read.

My instinct for every problem is to improve the product. Not enough sign-ups? Fix onboarding. Not enough rounds? Add a feature. Conversion looks wrong? Redesign the page. In a day job that instinct is fine, because there are marketing and SEO specialists handling the other half. On your own, there is no other half — you are the product manager, the developer, the marketer, the support team and the social media department.

"Eventually you have to accept that the button on screen three probably isn't the reason somebody hasn't downloaded your app."

They have simply never heard of it. I have spent money on advertising that achieved almost nothing, built features before anyone asked for them, and polished parts of the product that hardly anybody ever saw. At one point I made myself a rule: no more product work until I get real users. I have not been especially good at following it.

What has actually worked is unglamorous and slow — putting it in front of real golfers in real competitions and listening. Ten people who use it and tell me what annoyed them are worth more than thousands scrolling past an advert. The honest numbers from our first month came from exactly that, and so did most of what got fixed afterwards.

What success actually looks like

Freedom, more than scale.

Caddie Live launched in June 2026. It is bootstrapped, it is a team of one alongside a normal job, and the product is further ahead than the business — which is the accurate answer rather than the impressive one. I am not trying to build a company with hundreds of employees. I like making things.

What I would like is for Caddie Live to be something golfers genuinely know and use for their trips, societies and competitions, and for the things I build to eventually give me more choice over how I spend my time. A healthy independent business sounds considerably more appealing than a unicorn.

The full conversation goes further — into the stack, how I use AI to build as a non-engineer, the other projects, and the advice I would give someone starting out. It is on 99helpers: Simon, founder of Caddie Live — The Maker Series.

And if you would like to see whether the original idea holds up: put a leaderboard on your next round.

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