Here’s the exact 3-step system I now run before a dollar leaves my account.
Step 1: Find the deals everyone else is missing
The money isn’t in the obvious play. It’s not “buy Google.”
It’s in the second and third-degree plays. If this trend is real, what does it set off next? Who supplies it? What gets disrupted? Answer that and there’s a fortune sitting there, because nobody’s looking.
Here’s how I do it for real. I asked AI to pull the seven best research papers on where the world is heading, find the trends common to all seven, cross-reference them against the business I’m already building, and tell me where to invest. Not a hunch. A map.
Run a lighter version today. Open Claude, Gemini, or ChatGPT:
Prompt 1: “I want to invest in this industry or trend. Map the second and third-degree winners and losers. Who are the suppliers? What adjacent industries and companies get disrupted? Give me 10 names I wouldn’t think of.”
Prompt 2: “Analyze recent trends and market signals around those names, and show me the second and third-degree opportunities.”
Ask about AI and it won’t say Nvidia and Google. It’ll point at the energy load, and the electricians installing all of it. That’s the layer everyone’s too busy to find.
For my real estate, an AI agent hunts the hidden gems, runs the full analysis, and hands it to me. I just approve.
One rule: only invest in what you know. If you don’t live and breathe biomedical engineering, don’t send AI off to research it. You’ll have no edge when the answer comes back. And if you own a business, your best investment is usually the one you already run.
Step 2: Red-team it before you fund it
Finding the opportunity is the fun part. Before your money goes in, make sure it won’t come back in a body bag.
So red-team it. Prompted right, AI is the best red-teamer alive. No ego, no agenda, no feelings to protect. Show me everything that could go wrong and I can figure out how to make it go right.
Here’s what it saved me from. I was about to invest in a personal finance AI tool. Excited, and I knew the space. Then I red-teamed it, and AI flagged two things I’d underweighted: GDPval, and economic value creation with tokens. The verdict was blunt. The big AI labs will likely launch straight into this, and you don’t want to be standing there when they do. That one prompt probably saved me millions.
Run this before you fund anything:
“I’m about to invest in this company. Play out the worst case and give me the 10 reasons I’d lose all my money. Be honest. Be brutal. Don’t be nice.”
Turn those 10 into a hit list. For each: do I have a real answer? Are the odds actually low? AI can’t make the call, that’s your gut and your edge, but it gets you there faster.
Pro tip: run it through two or three models. Each one catches different things.
Some of my best deals are the ones I almost did and didn’t. Passing is a position too.
Step 3: Let AI monitor what you own
The deal clears the red team, you move. Now hand the watching to AI.
Every investment I own lives in one live dashboard: real estate, vehicles, stocks, companies, valuations. Red, yellow, green. Sparklines showing direction. If something swings 10%, I get an email. One screen instead of five platforms.
Attention is how money grows. Years ago I asked a friend how much he had in his business. “I don’t know, about 70 grand.” I can tell you what I have to the penny, because I watch it. What gets measured gets managed.
Build your version:
- List every investment you own. Anything with value. Write it all down.
- Prompt your AI: “Build a live dashboard tracking [your list]. Show me how healthy each one is, watch price against valuation, and flag anything I should look at.”
- Give it your goal so it knows which way to steer you.
- Pick a review day. Mine’s Monday. All green, I’m good. Yellow or red, I dig in.
In Claude, ask for the dashboard as an interactive artifact right in the chat. Easier to look at, so you actually will.
The rule that protects all of it
You can run every step perfectly and still blow it if you break this one.
Fifteen years ago I bought a pile of homes in Detroit. A hundred grand, about eight thousand each. Eighteen months later: falling apart, some with squatters, none rented, zero value-add. A total zero. Why? I invested in something I didn’t know.
Stick to what you know.
The richest people invest where they have an unfair information advantage. AI changes a lot, but it can’t change what you know, and what you know is the one edge it can’t hand your competition.
So everything runs through three filters. All three have to pass:
- Do I know it? Do I have an unfair advantage? Is it already in my line of sight?
- Will I pay attention to it? If the check’s too small to care about, I won’t watch it, and I’ll lose it. Fewer deals, bigger, with real focus.
- Will it still be true in 10 years? I want investments aligned with where the world’s going, not high-turnover bets I keep re-deploying.
Take Hark Labs, one of my most recent. They’re building an embodied model to power the robots of the future, led by the founder of Figure. Do I know it? AI, yes. Will I pay attention? Big check, yes. Is the world heading there? Everything electrified will be cognified, yes. Three yeses.
Buffett doesn’t invest in tech. I don’t invest in oil. Know your edge and stay in it.
Where this is going
The next 10 years won’t reward the best stock pickers. They’ll reward the system builders. The people who use AI to find the deal, red-team the deal, monitor the deal, and keep their money focused instead of forgotten.
My money should work as hard as I do. If it isn’t, that’s my job to fix. AI is the best tool I’ve got to do it.
So what will you point AI at first? Finding your next opportunity, or pressure-testing the one you’re already sitting on?
-DM