Why Your First AI Project Should Be Embarrassingly Simple

And why that's exactly what will make you successful

If you're thinking about diving into AI automation, you're probably dreaming big. Maybe you envision an AI agent that handles your entire sales process, manages customer service, and writes all your content while you sip coffee on a beach somewhere.

Here's the hard truth: That's exactly why most people fail.

The "Go Big or Go Home" AI Project Trap

Chase Hannegan, a former Marine pilot turned AI builder, sees this pattern constantly in his consulting work. "I think right next to not being able to define what they actually want, the second biggest issue I see with clients is trying to bite off way more than you could chew," he explains.

Picture this: A client walks into a consultation and rattles off 20 different things they want their AI to do. Chase's response? "That's great. If I could build that, I'd be worth a hundred million dollars. Let's start at number one."

The reality is that simplicity should always be the name of the game, especially when you're new to AI workflows and agents.

What "Embarrassingly Simple" Actually Looks Like

So how simple are we talking? Here's a real example from Chase's clients:

The Two-Step File Transfer Agent One client wanted an AI that would automatically take files dropped into Google Drive and upload them to YouTube. That's it. Two steps. The client admitted "it arguably didn't even save him time," but for him, it provided enough value because he processed enough videos to make the automation worthwhile.

Other examples of winning "simple" agents include:

• Email classification: Automatically tagging and sorting incoming emails

• Basic content generation: Taking a topic and creating a simple social media post

• Calendar scheduling: Finding available time slots and sending meeting invites

• Document summarization: Turning long PDFs into bullet-point summaries

The Personal Assistant Foundation Strategy

Chase recommends that everyone in his community starts with the same project: a personal assistant AI agent. Here's why this approach is brilliant:

1. It Creates a Foundation You Can Build On

Unlike a one-trick automation, a personal assistant gives you a base that can grow. You start with basic email capabilities, then add calendar functions, then internet research, and so on. Each addition teaches you new skills without starting from scratch.

2. It Teaches Core Concepts

Building a personal assistant forces you to learn:

• How AI agents make decisions

• How to connect different tools

• How to write effective system prompts

• How to troubleshoot when things go wrong

3. It Provides Immediate Value

Even a basic personal assistant that can send emails or check your calendar saves time and gives you confidence to keep building.

The Psychology of Small Wins

There's a deeper reason why starting simple works: you need early victories to stay motivated.

As Chase puts it: "You have to get yourself a couple easy wins off the bat." When you attempt something too complex on day one, you'll likely hit walls that feel insurmountable. Those failures are demoralizing and often lead people to quit entirely.

But when you successfully build that "embarrassingly simple" automation and watch it work? That's addictive. Suddenly you're thinking, "What else could I automate?"

The 80/20 of AI Impact

Here's something that might surprise you: most of the actual business value in AI comes from simple automations, not complex agents.

Chase notes that "for most of my clients, most of the work I do is not fancy AI agents. It's simple automations that save time and are low hanging fruit."

Many of these time-saving automations could have been built 10 years ago with basic scripting, but people didn't know they were possible. AI tools like ChatGPT have simply made people aware of what's achievable and given them the tools to build without coding.

Your Simple Start: The 5-Minute Test

Before you build anything, try this exercise: Can you explain your AI project to someone in under 5 minutes, and would they immediately understand what it does?

If the answer is no, it's probably too complex for a first project.

Good first projects sound like:

• "When I get an email about sales, it automatically tags it and drafts a response"

• "When I upload a document, it creates a summary and posts it to Slack"

• "When someone fills out my contact form, it adds them to my email list and sends a welcome message"

The Path Forward

Starting simple doesn't mean thinking small forever. It means building competence systematically. As Chase emphasizes, "You always have this baseline you can go back to and you can really teach a lot of different fundamentals based off that template."

Your embarrassingly simple first project is actually the foundation for everything more sophisticated you'll build later. Master the basics, then expand.

Remember: every AI expert started with something simple. The difference between those who succeed and those who give up isn't intelligence or technical skill—it's the wisdom to start small and build momentum.

What's your embarrassingly simple first project going to be?

Ready to build your first AI automation? Start with something so simple you're almost embarrassed to call it AI. That's exactly where you want to be.