The Ai-Native Attempt

Turning a Side Hustle into an Ai-Native Business

Follow along as I build Ai-automations and systems designed to scale and grow my one-person side hustle.

Subscribe to receive the weekly videos, newsletter, and automation blueprints.

What is the Ai-Native Attempt?

AI is everywhere right now. It’s being sold as the magic solution to help businesses grow and scale. But, the companies I talk to are struggling to keep up and make it work inside their organization.

You don’t need more hype. You need a playbook — a practical, step-by-step look at how to take your systems and processes and infuse AI in ways that truly move the needle. That’s what the The AI-Native Attempt is all about.

Keith Moehring is documenting the process of transforming his one person side hustle—PlayThru, a live scoring system for golf events—into an Ai-Native company. He's sharing everything along the way (the wins, losses and automation blueprints) to help other business leaders scale and grow in the era of Ai.

Ep.
4

Content

In this episode, we are moving from strategy to execution. I’m going to walk you through the content generation automation I’ve built.

Watch This Episode
Ep.
3

Priorities

In this episode, Keith lays out the vision for what PlayThru will look like when fully Ai-enabled, defines agents v. automations, and prioritize the automations to build based on impact and readiness.

Watch This Episode
Ep.
2

Benchmarks

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.

Watch This Episode
Ep.
1

Teeing Off

AI is everywhere right now. It’s being sold as the magic solution to help businesses grow and scale. But here’s the truth: companies I talk to are struggling to keep up and actually make it work inside their organization. You don’t need more hype. You need a playbook — a practical, step-by-step look at how to take the systems and processes you already have and infuse AI in ways that truly move the needle. That’s what the The AI-Native Attempt is all about.

Watch This Episode

Subscribe to the Ai-Native Attempt

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.

L2 Digital Logo White Stacked

L2 Digital © All Rights Reserved 2025