I've been building solo for 6 months. Some days I feel like I'm making progress. Other days I'm just... blank. Last night I spent 3 hours talking through a major decision with ChatGPT. About a personal LinkedIn channel where I express my view on things in my domain. I added a lot of context. Like, a lot. I tightened the prompts. I was in flow. It was one of those conversations where someone finally gets your context. They understand your constraints. They're challenging your assumptions in ways that actually help. I was making progress. Feeling a little relief, even, that I can talk through the intricate bits with someone. Then: "You've reached the maximum length for this conversation." Everything gone. All that context. All that understanding. I stared at the blank window and it hit me – this wasn't just inconvenient. It felt like loss. Like my advisor just quit. Like I was alone again. I feel like I have to make so many decisions a day and I have nobody to sanity-check them with. No board. No mentor who knows my full story. Just me, a blank ChatGPT window, and this constant fear that one wrong move could waste the last 6 months. Here's what I'm thinking: what if there was an AI that actually remembered your journey? Not "here's generic startup advice" but something that knows your specific constraints, challenges your blind spots, and doesn't forget everything you told it 375 messages ago? Some kind of architecture that works with the latest LLMs but significantly expands how long you can talk to the AI without session limit or hallucination. Very strongly worded system prompts - system prompts, not user prompts - that give you the best, most concrete advice for your immediate next step? Catches my productive procrastination - “avoiding doing the right things because they are scary” Catches my inverted work ethic - “being busy, busy, busy all the time but getting nowhere” I am trying to build this for myself. Real question: How do you all handle making decision after decision? And would something like this actually help or am I solving a problem only I have?