Knowledge Systems Engineer — Build Our AI Second Brain in Obsidian (Experimental)

**This is not an AI-slop-job ad.** **Read or waste your credits.** I'm Tyler, Chief of Staff at InsideSuccess.TV. We're a TV production and streaming platform building the Netflix of Business TV. (Insert hype startup lingo, rapid growth, disruptive, etc.) I'm seeking someone driven who wants to learn and grow with me. I don't care about where you went to school, or your Upwork profile that claims you are great at everything. I care more about your mindset and how you think. I'm looking for someone whose only limitation is finding the right environment to do their best work. **Disclaimer** This is an intense, high-expectation work environment. It is NOT for most. We have high turnover. You will be thrown into a fire and expected to solve problems. Many will see this job ad and be rightfully irritated. But if you have a similar growth and entrepreneurial mindset, you understand these challenging environments tend to be where opportunity comes from. **About the Role** Most companies have AI sitting on six disconnected documents in six disconnected tools. Nobody builds the layer underneath. So the AI never actually knows the company. We're building that layer. Every decision, every transcript, every project, every piece of context. Connected to everything else. One brain for the whole company. That's the moat. Competitors can buy the same models. They can't buy this. You'll build that in Obsidian. Not because we told you to. Because you already think this way. This is an experimental role. Idk what it looks like exactly. It's whatever you build that makes the whole system smarter. We are looking for someone who could not help starting this for themselves already. **Requirements** 1. Systems thinker — look this up if you aren't familiar with the term. This is the main requirement. 2. Already building your own second brain — not planning to. Already doing it. Months not days. 3. OpenClaw/Hermes — you should have at least tinkered with a bare minimum set up. Please don't waste your time applying if you don't know what this is. 4. Prompt engineer 5. Context engineer 6. Tinkerer 7. Passion for AI **Job Details** Rate: $7/hr Important: This is a work trial. My goal is to get you a raise. I want you to make as much money as possible. But it needs to be justified by value added. Hours: Mon-Fri, 9:00 AM to 5:00 PM EST. Those are the required hours. You can work more if you want, as the rest of us do. **How to Apply** Just answer the questions below. I'm not reading anything AI-generated. **Questions** 1. What is your dream job? Be specific. I know most of you don't know. So just pick something. No wrong answers. And don't say what you think I want to hear, because I promise you don't know. One sentence. 2. What is 1 thing you enjoyed learning about this week? Doesn't need to be work related. One sentence. 3. Why are you better or different than the other applicants? One to two sentences. 4. Share 1 favorite quote. Don't use AI. I'd rather you make one up and quote yourself. 5. What is the thing you've built that you're proudest of? Doesn't need to have made money or any impact. One to two sentences. Include a link. 6. Who are you? Like why would you apply to a job like this? Don't say family or money, like what makes you tick? One to two sentences. 7. Tell me one thing you discovered about AI that was surprising, annoying, humorous, or insightful. One to three sentences. 8. Have you connected your knowledge system to AI in any way? Describe exactly what you built and how it works. If you have not done this yet describe how you would approach it. 9. How long have you been building your own second brain or personal knowledge system? Describe it. How many notes, what structure, what makes it yours. If you do not have one be honest. 10. Anything else you want to share? Optional. **Interview Process** One 20 minute interview. 5 minutes casual conversation. 15 minutes you will screen share something you have built and I will grill you on it. I don't care about the impact of it, but rather your thought process while building it. If selected, ideally you can start within a week or two or ASAP. Thanks, Tyler