Real-world stories from running a full-time AI assistant.
Saturday I board a nine-day cruise to Alaska. The office comes with me anyway. It just doesn’t need me. Every morning my AI assistant has already been through the overnight logs: server health, backups, website uptime, what the email brought in. The digest is waiting on my phone when I wake up, wherever the ship…
I recommend Amazon KDP to students who want to get their books in print. These days, the publishing industry is a mess and doesn’t do the marketing for you anyway, so you’re better off being in control of your own fate. Amazon KDP is free, and it’s straightforward to get your book published. I teach…
Anthropic and Google are now watermarking the text their AI models write. Invisible statistical fingerprints baked into the prose, so anyone with the right detector can prove a paragraph came from a machine. Plenty of writers cheered. Finally, a way to tell machine prose from the human kind. I think the question is already aging…
My web server froze for the fifth time in ten days this morning. Each time, my AI assistant’s health check caught it within a minute and rebooted the box while I did other things. This morning I finally told it to alert me when it does that. I’d rather know. Five freezes is enough. Rebuild…
A client’s search tool was quietly returning every listing in the database to users in five states. Nobody complained for weeks. Type your zip code, get nearby results. Standard stuff. But for certain zip codes, you got everything. Not an error. Not empty results. The entire database. Which looks correct if you don’t know what…
I pay $1,200 a year for my AI assistant’s brain. No usage meters, no per-token charges, no surprise bills. A year ago that sounded impossible. You rented intelligence by the token. Input tokens, output tokens, cache tokens, each priced separately like a phone bill designed by a casino. Three things changed. Open models caught up….
Andrej Karpathy posted something last week I’d been doing for months without a name for it. Long, rambling, voice-dictated prompts work better than carefully constructed ones. You talk. The AI sorts it out. Your mess gives it more signal than a tight prompt. 2.5 million impressions. Because everyone who’s tried an AI assistant knows the…
192 em-dashes to convert. 13 chapters opening with “I was.” 400 words to trim from one chapter. Two characters who needed more texture. One scene that needed dialogue after the disaster. Twelve revisions across 32 chapter files. Each one simple. Together, a week of keyboard work. I’d gotten developmental notes on a manuscript. The kind…
I have 152 students in one of my courses. Until last week I had no idea who was actually watching the lessons. My AI assistant found a complete progress-tracking database on my course server. Lesson-level data, watch position, completion percentages, timestamps. It had been quietly collecting for months. Nobody was reading it. So I said:…
Installing an AI assistant takes 20 minutes. Making it useful takes longer. Phase 1 is mechanical: install the software, pick a model, connect it to a chat app. Phase 2 is tools: API keys for WordPress, Dropbox, email, image generation. An hour, maybe. Phase 3 is the part I had to figure out myself. I…
The cost of running a full-time AI assistant snuck up on me. Not the server. The tokens. I run two AI assistants on my server. They handle email, social media, course management, infrastructure monitoring. Around the clock. The conversation context for a persistent agent grows to hundreds of thousands of tokens. Prompt caching is what…
Every course platform I’d ever used was built for the platform’s benefit, not the student’s. Teachable. Thinkific. Podia. They all look the same: a list of courses on the left, a cramped video player in the middle, progress buried in a database you can’t see. Customize anything? Support tickets. Want to understand what students are…
OpenAI recently shipped computer-use for Windows. Every tech influencer is posting clips of an AI as it moves a mouse, clicks dropdowns, and fills out spreadsheets. It looks like magic. But mouse-moving is a terrible way to run a business. When you automate a task by pantomiming a human, you inherit every bit of friction…
Twenty-two scanned memos from 1983, sitting in a folder for years. Primary sources for a book I’ve been meaning to write. Typewritten, faded, a few with handwritten notes in the margins. I’d tried processing them before. Got through three, then something more interesting came along. Last Saturday I pointed my AI at all 22. It…
If you’re running your own AI assistant, you’re probably wondering when you’ll get access to Mythos — the new, far more capable class of AI model Anthropic is starting to roll out. Ethan Mollick got early access to the first one, Claude 5 Fable, and his writeup is worth your time. But “when do I…
My self-hosted AI assistant was quietly burning money on every cold start, and the culprit was tools I never used. Here’s how OpenClaw works under the hood: every tool the assistant can call ships its full JSON schema into the system prompt. Parameters, nested objects, enums, the works. On a fresh start, all of that…
I’ve been running Amazon book ads for a few months. Tweaking bids, checking dashboards, the usual. I asked my AI assistant to pull the actual search-term data and tell me what was going on underneath. 194 search terms over 30 days. The AI pulled them through the Amazon Ads API, ranked every term by impressions,…
Ethan Mollick made a webpage this week addressed to AI agents, not humans. The idea stuck with me, so we built our own version the same afternoon — and the reason why is more interesting than the novelty. Here’s the shift nobody’s pricing in yet: increasingly, when someone asks “what should I read about AI?”…
I had a 47,500-word manuscript sitting untouched. Forty-four chapters. I knew the structure needed work but couldn’t see where. Fed the whole thing to my AI assistant in one session. It restructured the book into 29 chapters, merged seven covering the same ground, and flagged a five-chapter stretch that read like a résumé instead of…
For 18 months my business websites had no real analytics. Cloudflare rounds to the nearest 10 and can’t tell bots from humans. Never got around to fixing it. Last week my AI ran a monthly marketing review. Traffic down 30%. Funnel converting under 1%. Then it pulled the raw data: April had been inflated by…
A developer’s AI assistant ran up $8,000 over a single weekend. The code worked fine. The loop just didn’t have an exit condition, so the AI kept re-invoking itself thousands of times. Nobody noticed until Monday. Seven months running my own AI assistant, and I’ve never had a runaway cost event. The architecture won’t allow…
Most people interact with AI the same way: type a question, get an answer, close the tab. My AI runs a team. Twenty scheduled tasks run on my server: blog posts, email triage, website audits, newsletters, social media. Each one spawns a separate worker and picks the right AI model for the job. A blog…
I noticed one blog post had its featured image missing. Just gone; the post looked normal otherwise, and you’d only catch it if you compared it against a newer one. My AI assistant traced the problem in about ten minutes. A CSS snippet buried inside a WordPress plugin was hiding the featured-image banner on every…
Most people send a marketing email and check one number: did anyone open it. Then they move on. The email did its job, the report looks fine, and a pile of free information sits untouched in the sending platform forever. I send a monthly newsletter. Last week I asked my AI assistant to pull the…
A friend called with a problem. He runs a national association of wedding DJs with members spread across every state. He wanted to add a feature so that the public could search his site for members. As it was, a bride planning a wedding in Tulsa couldn’t find a DJ in Tulsa. The membership list…
I gave the same 42-chapter manuscript to Claude and ChatGPT without letting either see the other’s work. They agreed on the biggest problem. They disagreed on the fix. Both caught the same flaw: the book opened with backstory when the strongest material was in chapter 21. Both flagged chapters that restated what the scene just…
I have two websites. One gets all my attention. The other one I basically forgot about. My AI assistant runs a weekly traffic review — pulls analytics, compares both sites, flags what I’m missing. This week it surfaced something I’d been missing for years. The forgotten site gets more traffic. 18,000 weekly views vs. 17,000….
I spent this afternoon teaching my AI assistant what my writing sounds like. Not by telling it. By showing it. I pulled 34 of the strongest passages from my most polished book and ran them through a pipeline inspired by @Jaytel’s taste.md concept: two different AI models analyzed each passage independently, focusing purely on craft…
You spend months on the product. Then you hit publish, and a different to-do list appears: the ad campaign, the website update, the email sequence, the sales tracking. I published a book on Amazon last week. Within 48 hours, my AI assistant had: Created an ad campaign—17 keywords, tiered bids—through Amazon’s advertising API. Updated my…
Originally posted on X — view the original post. Everyone’s still obsessing over how to write the perfect prompt. Meanwhile, the real leverage has moved somewhere else entirely. Dharmesh Shah (HubSpot co-founder) just coined a term for it: “context engineering.” The idea is simple but the implications are massive. Instead of optimizing how you ask,…
A startup called Hark just raised $700 million to build a personal AI assistant. They have 70 employees, a $6 billion valuation, and no product yet. I’ve had mine running on a $20/month server for over six months. Hark’s director of design told TechCrunch he “hasn’t seen anything that really helps the normal person.” He’s…
A newsletter in my niche has 2 million subscribers. I wanted to know what they’re doing right that I’m not. My AI assistant broke down their post-signup flow — a 10-screen quiz funneling subscribers toward a course. Each screen has a job: name your frustration, reveal what you spend on tools (price anchoring — you…
AI assistants manage email, publish content, analyze financial data. To tell yours something, you type it with your thumbs. I added voice to mine. My assistant built the whole thing in a day. A web page with push-to-talk. Press a button, speak, and the assistant processes it with access to my files, tools, and six…
Writing a book takes months. Outline, research, draft, revise—it’s a grind that stops most people before page one. I needed a comprehensive guide for a product I sell. 18 chapters covering setup, workflows, troubleshooting, advanced features. My AI started with competitive research—tools, integrations, projects I didn’t know existed. That research reshaped my outline twice before…
Everyone assumes the expensive part of running an AI is “thinking hard.” I pulled my actual cost data and the breakdown surprised me. Context management—the AI organizing its working memory—is 75% of the bill on heavy days. All output including reasoning: 3.4%. Local work (voice synthesis, audio processing): $6/day. Deep collaborative conversation: $100/day. Conversation length…
150 lessons across 5 online courses needed narrated video. The usual way: weeks of studio time. My AI cloned my voice from existing recordings and narrated all of them. It wrote the scripts from my course material, designed the slide decks, and assembled the videos with timed transitions. My part: review the scripts. A few…
Every time you start a fresh chat with an AI, you’re talking to someone with amnesia. You explain your business, your preferences, your history. Again. Brilliant contractor who forgets everything overnight. My AI assistant maintains its own memory: curated knowledge files it reads every session. One file stores permanent facts: people, projects, credentials. Another stores…
Most business owners start their morning checking a dozen apps: email, social media, analytics. Half an hour gone before real work begins. I start mine by reading a single message. Every morning at 10 AM, my AI assistant delivers a briefing to my phone. Industry news filtered for relevance. Flagged emails needing decisions. Task reminders….
Most people use their AI assistant alone. Private browser tab. Nobody sees it work. Today I brought mine into a business meeting with 20 people. My AI assistant spoke through Zoom—its own voice, a British accent, answering questions in real time. I was in Vancouver. The room was in Orlando. Someone asked a question, I…
Last week my website went down in the middle of the night. By morning, my AI assistant had already rebooted it, added more memory to prevent a repeat, and set up monitoring that checks every five minutes. I found out from its daily status report. Which is one of about 20 tasks it runs without…
Writing a good book takes time and many, many revisions. My latest book, Harnessing the Machine, has been in the works for several months and has gone through 19 major revisions. Once you have material you’re happy with, you still have to make sure it’s all arranged in the right order and properly formatted. That’s…
We had to give my AI assistant its own voice — because people in meetings couldn’t tell us apart. Last week I set up my AI to join video calls. It transcribes in real time with 100% accuracy and speaks back through my speakers — using a clone of my voice. People on the call…
Most business owners know their website needs work. They’ve been putting it off for months. My AI assistant redesigned two of mine in a single day. New typography, a cohesive color scheme, hero sections rebuilt from scratch. One site got a 27-book cover grid organized by category. The other got course thumbnails replacing placeholder icons….
My AI assistant had incomplete memory for weeks. I had no idea. OpenClaw boots with context files — project notes, past decisions, infrastructure details. My main memory file had grown to about 25,000 characters over months of daily use. There’s a config setting that caps how much of each file loads at boot. Default value:…
I’d been putting off migrating my web servers for 18 months. Not because I was afraid of breaking things. I was afraid of the week it would take to fix them when something went wrong. 10 WordPress sites on 2 servers, both running years-old pre-packaged software. Yesterday, my AI assistant moved all of them. One…
An upgrade yesterday uncovered tasks from seven months ago still running on my AI server. Not causing problems. Just never cleaned up. When AI software upgrades, it needs to drain: finish pending work before restarting. Those old tasks blocked the drain. 5 cascading restarts. Broken config. Server that couldn’t stay up. The fix came from…
My 29 books have been on Amazon for years. Until last week, 7 of them had ads. The other 22 were invisible. In one session, my AI assistant built 9 new ad campaigns — every remaining writing book, each with custom keyword research and negative keyword lists built from scratch. The travel writing campaign got…
Right after sending our monthly newsletter to 11,000 subscribers, the email platform suspended the account. No warning. Just a wall. My AI had the diagnosis in about 10 minutes. We’d migrated 3,400 contacts from a previous platform last fall, loaded them directly onto Brevo, and sent to them without any warmup period. Those contacts had…
A viral post this week says you should ask Claude to audit its own instructions and delete whatever it flags as unnecessary. I tried the opposite approach. Here’s why it works better. I’ve been running an AI assistant full-time for 3 months. It manages my email, runs my marketing, posts to social media, sends my…
1 new customer in 5 weeks. That’s what my funnel audit found. My homepage had a category page in the middle of the path to purchase. The idea: let visitors browse by topic. What actually happened: that’s where they stopped. My AI traced the full purchase flow and cross-referenced the traffic data. What it flagged:…