@joshthacker

Founder @SearcherOS 🔎 (https://xitter.cf/t.co/GV77G3iVzi) Building portfolio of autonomous assets SMB • Real Estate • SaaS • Syndications Writing about AI and cashflow

 Folsom, CA
joshuathacker.com
Joined December 2009
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In August 2025, I walked away from a lucrative 15-year career as a tech executive. Not a leap of faith. An allocation decision. 1/7
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I slept on a green canvas army cot for 6 years as a kid. We didn't start out that way.
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That's probably why I stopped using net worth as my North Star. When I left my corporate role in August 2025, I built for cash flow first. 14 sources now: self storage, apartments, short-term rentals, private lending, and yes, mobile home parks. (The irony isn't lost on me.)
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That cashflow ballast is what lets me build software startups with AI. We moved the family from San Diego to Sacramento. Family nearby, a 30% drop in costs. I miss the weather. But I sleep much better at night. After 6 years on a cot, I don't take that lightly.
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Howard, my AI chief of staff, flagged a $1,500 charge on one of my cards back in August. He couldn't classify it and couldn't find a receipt in my email to match it. I didn't recognize it either. So I called Chase. Confirmed fraud, new card issued.
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"Let's look at the data. In November 2024 you had the best muscle mass and body composition of your history, and the 3 months before that show 5x5 Olympic movements. Why would you do anything other than recreate that same routine?"
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Hard to argue with that. It's the routine I'm running now. He holds my business, my money, and now 5 years of my health, which is why he catches what I'd scroll past. Health was the one I felt weird handing over. I did it anyway.
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Here's why I'm not migrating to dots, Muse or Grok Bot. I've built my own company brain: 3.5 million words, with dozens of agentic processes tied to it. Migrating the tasks the agents do is fine. The problem is actually the memory.
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The bigger issue: your most precious information, the context about your business and your life, lives with the vendor. It compounds over time, and the cost of switching gets too great. I send my vault through ChatGPT and Claude too. But the canonical copy lives with me.
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My brain is just text files, about 5,200 of them. So when the next super powerful model comes out, I hand it the whole pile and say, Hey, here's everything about me. I don't want to give that up.
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