Ship Ugly: The Four-Fingered Portrait That Taught Me AI
Everybody I meet is “evaluating” AI. Reading about it, attending the webinar, waiting for it to settle down. Meanwhile a smaller, quieter group is just… using it badly and getting better fast. Guess which group is winning.
The Four-Fingered Portrait
Let me show you what “using it badly” looks like, with a real example I’m not proud of. I needed a portrait of myself for the Resistance Wine site. I asked an AI image tool for a simple pen-and-ink sketch. The first version gave me four fingers. The second dropped me into a Tuscan vineyard wearing a hat I have never owned, standing like a man unfamiliar with his own legs. The third looked like Seth Rogen and Carrot Top had a baby. I have a dozen more saved. They are genuinely upsetting.
That afternoon taught me more about what AI can and can’t do than every article I’d read combined. Because reading about AI gives you opinions. Using it gives you instincts — and instincts are the only thing that compound.
Reps Beat Research
This is the trap founders fall into: we treat AI like a major capital decision. Research it, scope it, pick the perfect tool, roll it out. But AI isn’t a forklift. The tools change every ninety days, so the “perfect” one you spent three months selecting is a fossil by the time you’ve trained everyone on it. The skill you actually need isn’t tool selection — it’s the muscle memory of pointing AI at a messy real problem and wrestling a useful answer out of it.
You only get that muscle one way: reps. Cheap, slightly embarrassing reps. The founder who’s had fifty ugly failures with AI is now dangerous. The founder who’s still reading think-pieces is exactly where they were a year ago, just more anxious.
Your Assignment This Week
So here’s your assignment, and it’s deliberately small: take the one task you hate most this week — the proposal, the email you rewrite five times, the spreadsheet — and hand it to an AI. Let it be bad. Then fix it. Then do it again tomorrow with something else. You are not trying to be impressive. You’re trying to get your four-fingered portrait out of the way early.
I keep mine, by the way. They’re a useful reminder that everyone who looks like they “get” AI mostly just embarrassed themselves sooner and kept going.
Final Thoughts
Why It Matters: AI competence isn’t a document you can buy or a course you can finish. It’s reps. The gap between the doing and the studying widens every quarter — and it compounds.
What to Do: Pick the task you dread most this week and let AI do it badly. Fix it. Repeat tomorrow. Collect your four-fingered portraits.
Coming Up Next: How a found hour a day turned into the foundation of an AI-first company — starting with the least dramatic origin story you’ve ever heard.
Disruption with a side of humor — Kirk Drake, signing off (until the next post).
I tell the four-fingers story (with slides — you have to see them) when I speak. Book me here if your people need permission to stop studying and start shipping.
