CEO-OS: How I Built an AI Assistant That Keeps Me on Track Every Day

Imagine: An assistant that never sleeps, never forgets — and honestly tells you every evening whether you really worked on the right things. Not what you think you did. But what you actually did.

I built exactly that. And in this episode, I'll show you how you can too — even without coding skills.

What This Is About

Imagine having an assistant that never sleeps, never forgets, and tells you every evening whether you actually worked on the things that move your business forward. Not what you think you did, but what you really did during your working hours. I built exactly that, and today I'll tell you how I did it so you know how to build something like this yourself — or have your IT team build it.

My name is Jan Koch, I'm the CEO and co-founder of KoBra Dataworks. We've been building AI solutions for two years, primarily in the transport and logistics industry, though we're expanding into various other sectors.

The Challenge

The challenge I face — and you surely know it too — is juggling too many things at once. I have a young company, a small team, and as CEO I'm basically the jack-of-all-trades. I manage about 15 projects in parallel, sometimes 10, sometimes a few more. It's easy to lose track in the daily chaos: the phone rings, emails pile up, everyone wants something. You know the drill as a business owner.

So over the holidays at the end of 2025, I thought about how AI could help me focus on what truly matters. What I built is an AI assistant I can chat with — and soon I'll be able to have voice conversations too, sending and receiving voice messages.

This AI assistant has access to everything happening in our company day-to-day. My typical day starts early — I begin working around 5 AM, simply because the phone doesn't ring yet. I have peace to work from 5 to 6:30 or so, then my family wakes up and it's family time before work resumes.

Throughout the day, you feel busy. You have your task list, you try to work through it, but then a client calls, an email arrives, something's on fire somewhere, team members have questions. Before you know it, your plans are out the window.

At the end of the day, you've had a super busy day, you feel like you were productive — but were those the things that actually move the needle? That's exactly where AI helps me now. Too often, urgent things crowd out truly important things. Too often, I jump into client projects and have no time left to build systems, work on strategic initiatives.

Without this feedback system, you only notice when it's too late. A real team would have a CFO telling you daily "we're burning too much money in area X," or a COO saying "this process Y is totally inefficient." But as a solo CEO, I don't have anyone telling me that. My freelancers and employees are focused on delivery and customer support — they don't have visibility into the bigger picture.

The solution is what I call CEO-OS. I defined my north star: I want to build a company that can outlive me, with the freedom to fully live with the people I love. Every decision becomes relatively simple — does this bring me closer to or further from what I want?

I defined three work categories: Building (creating systems, improving processes, multiplying output), Marketing (growing the company — this podcast, customer acquisition, networking), and Delivery (client work that pays the bills). The art is balancing how much time I spend in each category, which depends on how the company is doing.

If we have cash flow problems, Building is probably less important — maybe 10-15% of my time. Then it's about Delivery and Marketing. The AI assistant tells me this too, based on bank statements, open invoices, and running projects.

What the AI Assistant Does

Every evening, this AI assistant looks at my completed tasks in ClickUp, sees not just what I worked on but how long (we track time there), and each task is assigned to one of the three categories. It automatically calculates my time distribution and honestly — or rather, emotionlessly — tells me whether how I spent my time aligns with the goals I set, or whether I need to shift focus.

What's brilliant about this: it doesn't let me make excuses. The self-deception that was previously possible is eliminated. This is an incredibly important productivity improvement that simply wasn't possible without an AI agent.

My evening routine: I open Telegram, ask for a daily summary, and get my Daily Review. It shows my habits (deep focus work, planning tomorrow, first task before email, family/personal time), tasks completed vs. created, and alignment with my north star across Building, Marketing, and Delivery.

Then I plan the next day with the AI — it shows what's scheduled, and I can chat back and forth about optimization. "What happens if we reduce Building from five hours to three? Will we still hit our weekly 30% target?" This back-and-forth helps tremendously with prioritization.

At 1 AM automatically, the AI moves all overdue tasks to 9 AM the next day. No more huge backlog of overdue items — everything is planned for the day with a clean list.

The AI actively asks me about habits and planning steps every evening. That accountability is key. Calendar reminders to "plan tomorrow" that I'd set for myself? I'd skip them. But because the message comes from another system, there's somehow more psychological commitment. And if I don't do it, the system holds up a mirror the next morning.

How I Built It

It started with Claude Code — available at claude.ai. Comparable to ChatGPT at $20/month to get started, but significantly better at programming. In December, Claude Code ran over 305 hours for me — the equivalent of two full-time developers, and I'm on the highest tier at $200/month. Incredible ROI.

I chatted with Claude Code just like I would with ChatGPT, described what I wanted to build, explained my challenges, and specified the data sources: tasks in ClickUp, bank statements via CSV, emails in Outlook, calendar also in Outlook, open invoices in our accounting software. Build me an AI agent that keeps me on track as CEO.

The simplest start: Install Claude Code, get a $20/month license, and say: "You're helping me build an AI assistant for me as a CEO that helps me structure my days efficiently and stay on track. Ask me all the questions you need to get the information required to implement this system." Claude Code will guide you through the entire process.

You don't need to code — Claude writes the code. You don't need expensive tools — it's $20/month. You don't need a complex system — just start and iterate. Build function one, test it, build function two, test it, and so on.

The Honest Result

I've had this AI assistant for one week. Exactly one week. And the honest result is: I don't want to work without it anymore.

I have absolute clarity. I know every day in advance that my tasks are planned to lead me to my long-term goals. I have no more self-deception — the numbers don't lie. I get a brutally honest summary every day of what I did, how I spent my time, and can adjust the next day accordingly.

The revelation: I thought I was spending 15 hours a week building systems. It was actually only five. The system tells me uncomfortable truths that I need to hear — and that no human employee would dare to say.

Remember: you don't need a team to get feedback. You need a system. And AI makes that possible for everyone today. Build yourself this assistant. I only regret not doing it sooner.

Key Takeaways

• Building, Marketing, Delivery: The three categories to structure your work time around
• Eliminate self-deception: An AI assistant honestly shows you where your time actually goes
• No coding skills needed: With Claude Code (from $20/month), anyone can build a personal AI assistant
• Connect data sources: ClickUp, Outlook, bank statements — the more context, the better the recommendations
• Accountability through systems: You don't need a team for feedback, you need a system

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