- As a business owner with an INFJ personality and a brain wired for ADHD, I live in a weird mix of big-picture vision and day-to-day chaos. One moment I’m dreaming up a better system to serve our clients, and the next I’m halfway through three browser tabs and forgot what I was even doing. Sound familiar?
This blog series is for folks like me—business owners trying to balance innovation with overwhelm, clarity with clutter, and growth with sanity. I want to share our honest, sometimes messy journey of building an AI assistant in-house and shifting away from expensive, bloated cloud services to self-hosted tools we actually understand and control.
We’ll cover the good, the bad, and the “why did I even start this” moments. If you’ve ever felt like your tech stack is running you instead of the other way around—or like no matter how many tools you subscribe to, none of them quite fit—then you’re in the right place.
Why We Started This Journey
It began with frustration. Every month I’d look at our company’s software bills and feel that sinking sensation. We were paying hundreds—sometimes thousands—of dollars for tools that only sort-of worked the way we needed. And when they didn’t, support was slow, customization was limited, and we were locked in.
As someone who values efficiency, autonomy, and doing things the right way (yes, INFJ to the core), this didn’t sit well. Add in my ADHD tendency to hyperfocus on solving problems no one asked me to solve, and suddenly I’m spinning up a local server, testing open-source alternatives to our major platforms, and dreaming about an internal AI assistant named Jim Dandy.
Why Self-Hosting?
Self-hosting isn’t always easier—but it’s often more freeing. It lets us:
• Save money
• Customize our workflows
• Improve data security
• Avoid vendor lock-in
• More security control
But it also means more responsibility. We’ve had to learn, rebuild, break things, and sometimes walk away from a “perfect” open-source tool that just didn’t work in real life. We’ll talk about all of that in future posts.
Why Build an AI Assistant?
• Because we needed help—but not another SaaS subscription or chatbot that couldn’t actually do anything.
• We’re building Jim Dandy to:
• Answer internal and customer questions
• Set appointments
• Help with rescheduling and follow-up
• Eventually triage support tickets and take calls
Jim will have personality—charming but professional. He’ll work across roles and platforms, and someday, he might even answer the phone when you call us.
What to Expect from This Series
We’re going to share everything: the wins, the mistakes, the tools we love, and the moments we considered lighting it all on fire. We’ll also sprinkle in tips, ADHD/INFJ survival hacks, and some commentary on the weird world of tech as a small business.
Let’s take back control, one system at a time.
Stay tuned for the next post: Designing Jim Dandy: Building an AI Employee Who Actually Helps.
Curious about self-hosting? Check out Awesome-Selfhosted — it’s a massive, community-curated list of open-source tools you can run on your own terms.
