With Ai, context is key. So I figured some context about the business we are taking from side-hustle to Ai-native would be helpful. This episode lays the groundwork for the AI-Native Attempt by unpacking what PlayThru is, how it began, where it stands today, and where the biggest opportunities lie.
With AI, context is key. So in this episode, I thought I'd provide some context about the side hustle we are transforming into an AI-Native organization. Specifically, what is it? Where is it at today? And, what are the opportunities existing for Ai and automation?
PlayThru is a live-scoring system for golf events — a web app that makes scorekeeping simple, fast, and accessible. There’s no app to download, no logins to remember. Organizers set up their event, add golfers, and share a short link or QR code. Golfers open the link, select their name, and start entering scores.
The design philosophy is what I call “stupid simple” — as in, so simple anyone can use it. If you’ve ever tried to get a group of distracted golfers (especially those not fond of tech) to use a digital tool, you understand why simplicity isn’t optional — it’s survival.
That simplicity, paired with the fact that PlayThru is free to use, has been key to its growth. Organizers can create unlimited scorecards and add unlimited players without paying a dime. Revenue comes from upgrades — premium features like custom branding or enhanced scorecard options. This model allows for viral exposure: every event introduces the tool to hundreds of golfers who might later bring it to their own outings.
The idea for PlayThru started in 2010, after a painful one-stroke loss in my family’s annual Atwood Open. Post-round scorekeeping revealed a math error that would’ve changed the result — I should’ve tied. That sting sparked a vow: we’re never manually keeping score again.
The first version was a glorified Google Sheet that automatically tallied scores. It worked — and made the event more fun and competitive.
By 2015, I was bored at work and wanted to learn how to code. So I turned that family spreadsheet into a web app. Around the same time, our family hosted a 130-golfer memorial outing. I tested the prototype there — and to my surprise, 80% of golfers used it. That was the turning point. People could see live scores. The competition got more exciting. And best of all, it worked.
That’s when I realized: there’s a real business opportunity here.
After several years of tinkering, PlayThru started gaining traction. By 2020, it was adding around 20 new accounts a month. Then COVID hit — and golf became one of the few socially acceptable group activities. Growth exploded.
Organic search was the main driver. As a digital marketer by trade, I had optimized the site to rank for every relevant golf scoring keyword. For a while, it worked beautifully.
In 2024, a user asked, “Can this work for a mini golf course?” The answer was yes — with a few tweaks. The feature set was simple: scan a QR code, generate a digital scorecard, and play.
The feedback was overwhelmingly positive, so I built a dedicated version called PlayThru Mini. That decision unlocked a whole new market. The B2B opportunity with course owners was much larger than the B2C event space. Since then, mini golf has become the company’s biggest growth driver.
To start the AI-Native transformation, we need a baseline. Here are PlayThru’s key performance indicators today:
Not bad for a one-person side business — but at roughly five cents an hour, not sustainable.
PlayThru has always been a nights-and-weekends project, run entirely by me. Every support ticket, update, email, and product fix lands on my desk. The platform serves many nonprofits and charity events, which I love supporting, but the workload isn’t scalable.
The goal of the AI-Native Attempt is to change that — to offload repetitive tasks, automate key workflows, and turn PlayThru into a self-running business that continues to grow without consuming all my time.
These are the friction points I’ll be targeting with automation.
Despite the slowdown, PlayThru’s upside is massive:
If the automation foundation is built right, there’s no reason PlayThru can’t become a six-figure business — and eventually a seven-figure exit.
Now that you’re caught up, the next episodes will focus on prioritizing automations — identifying which tasks have the biggest impact and are most ready to automate.
This journey is being documented in real time — no sugarcoating, no filters. If you’ve got ideas, feedback, or questions, jump into the comments.
Because this isn’t just about PlayThru. It’s about showing how any small business can become AI-Native — one automation at a time.
Follow along as we transform my side hustle into a fully Ai-native business. Hopefully we all learn a few lessons along the way and I'll be sharing the plans and automations I'm building.
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