In this YouTube video, seasoned angel investor Nick Kugelman explains how artificial intelligence has transformed his investment approach and offers a step‑by‑step playbook for viewers. He begins by urging a mindset shift from wealth preservation to wealth creation, arguing that money should be actively deployed rather than hoarded. Kugelman then shows how to use large language models (LLMs) to uncover hidden deals by prompting them to map second‑ and third‑degree winners and losers, identify obscure companies, and analyze market signals. He provides concrete prompt templates for industry trend scouting and emphasizes running the same prompts across multiple LLMs to catch different insights. The next phase is “red‑team” testing: using AI to generate worst‑case scenarios and ten potential failure points for any investment thesis, then evaluating whether each objection can be answered. After a deal passes this stress test, he recommends building an AI‑driven live dashboard that monitors all assets in real time, sends alerts on significant price moves, and produces daily cash reports. Kugelman outlines three essential filters for any investment: (1) personal knowledge advantage, (2) willingness to pay attention, and (3) long‑term relevance to future trends. He illustrates the framework with a recent investment in Hark Labs, an AI‑powered robotics sensor company, confirming it meets all three filters. Throughout, he intersperses pro tips, personal anecdotes, and a promotional call‑to‑action for his “AI Company Operating System” (YouTubeOS) available via Instagram DM. The video concludes by urging viewers to apply AI to their own portfolios and share their plans.
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AI has completely changed the way I invest my money, and it's not the way you think. I was voted number one angel investor in Canada and have personally invested in dozens of companies with founders of Google, even Jay-Z. And now with AI, I'm making way more money by investing in the right things and staying away from the wrong ones. So in this video, I'm going to show you the exact playbook on how to use AI to invest your money, starting with the very first move you need to make. Don't preserve it, create it. Wealth preservation sucks. Wealth creation is super fun. Preserving wealth is like building a wall around your money. It blocks other money from coming into your life. Your dollars are like little soldiers that should be out there on the battlefield working to make you more money. Because when the money's working for you, then you'll get to a point where you don't need to work for the money. Most people are stuck penny-pinching and preserving and couponing, and I'm like, what? How about we go invest to create more? So once you decide you're going to let the purse strings go a little bit and deploy your dollars, the next question is where do you actually deploy them? You got to spot what others don't. You can use AI to find deals other people miss, things that nobody's talking about yet. You want to find the opportunities where everybody else is not even looking, but it makes sense. And that's where AI can help you in a big way. The real wins are not in the stuff that's obvious. Buy Google, it's asking yourself what's the second and third degree plays that that unlocks? If you can figure out those two, lots of money to be made. I like to invest in real estate, so I have an agent whose whole job is finding those hidden gems, running the whole financial analysis, and all I have to do is approve it. That's how I use AI to find shit that other people are just too busy or not going to find because they're looking for the easy stuff. So for example, I asked the AI to come up with the 7 top research papers on where the world's going. I then had it analyze the trends that it found that's common across all 7 papers. I then correlated that with my thesis in my current business of what I'm building and had it define the areas I should go invest in. That is how I choose the companies to invest in in my life. I just use the AI to do it for me. So here's how you can use AI to find opportunities to invest in. First off, open up your favorite LLM. I'm talking Claude, Gemini, ChatGPT, and then run these 2 prompts. These are things you can do. Just ask it, I wanna invest in this industry or trend that you like. Map out the second and third degree winners and losers. Who are the suppliers? What are the adjacent industries and the companies that are gonna get disrupted? Now gimme 10 names I wouldn't think of. Prompt number 2, now run an analysis of recent trends and market signals around those names and show me the second and third degree winners and losers that could be real opportunities. For example, if you told it to investigate the AI industry, it's not gonna tell you to invest in Google and Nvidia. It's gonna talk about the energy use and the electricians that are gonna have to install that. Let the AI keep doing the digging for you. The pro tip is only investing in what you know. If you don't live in biomedical engineering, then don't ask it to do that research for you because you won't have an information advantage. By the way, if you're a business owner, you should already know your best investment is in your business. That's why I built my full AI Company Operating System. It has everything you need, the master prompt templates, the workflows, the frameworks to integrate AI into every department in your business. If you want it, just find me on Instagram and DM me the word YouTubeOS and I'll send it right over to you. Now, finding great opportunities, that's a great start. But before you put your money in, you need to know you won't lose your money. You got to red team it with AI. AI, if you prompt it properly, is the best red team you'll ever have. Red teaming means you purposely try to tear your idea apart. I want AI to have no ego, no agenda, and just tell me everything about my thesis that might be wrong. Because guess what? If I know everything can go wrong, then I can figure out all the steps I can make it right. And that way I have a higher probability of not losing my money. So we should always pressure test the deal before we put money in. Most people just skip this step and then they pay for it later. That's how money gets lost on stuff that look great that you should have never touched. I was about to invest in a personal finance AI tool. Then the AI told me about two things. One, the GDP Val for AI. And 2, the concept of economic value creation with tokens. So I found a great opportunity. I was excited about it. I actually know a lot about it. And then when I red teamed it, the AI explained to me, you could, but there's a large probability that the big AI companies are going to launch something in that space. You might not want to compete. I literally could have lost millions of dollars making that decision. So here's how we use AI to battle test and red team our ideas. First, just write this prompt. I'm about to invest into this company or asset. Let's play out the worst case scenario and give me the 10 reasons why I would lose all my money. Now, be honest, be brutal, don't be nice. Now you take those 10 objections and ask yourself, do I have an answer for each? Right? They just become the hit list to make sure you overcome it. Because if you can't with high confidence, then you pass. Do they have a low chance of happening? The AI doesn't know this. You're going to have to know this. You're going to have to make a gut decision. But you can use AI to get you there a lot faster than trying to do it on your own. So here's a pro tip, is run the prompt against 2 or 3 other top AIs. Different models catch different things. The best deals I've ever done are the ones I almost made but didn't. It's where I made the most of my money. So now let's say we red team the investment, it passes the test, and we decide to move. Now what? Let AI monitor it. AI's got this really cool ability of building dashboards for you and monitoring in real time. And the cool part is kind of like set it and forget it. You just sit down, you build a stock portfolio,, and then you have it monitor it. You can even say if it moves up or down 10%, send you an email. I do this for all my investments, all my real estate, all my vehicles, all my stock, all my companies, all the valuations. It's all in one beautiful dashboard and it was built with AI. So instead of like calling people or jumping into one platform and another platform, it's all over the place, you have it in one spot. And it's fun because AI can pull all the updates and give you red, green, yellow for all your stocks, little sparklines to tell you if it's going up. And then even set up alerts in case you gotta get rid of some stuff. Paying attention to where your money goes is how it grows. Long time ago, I was trying to teach this to my friend and I asked him, "Well, how much money do you have in your business?" He's like, "I don't know, about 70 grand." I'm like, "About 70 grand?" Like, I can tell you to the penny how much I have today because I monitor it. I teach this thing called the daily cash email that I now have AI do every day. So if you want your money to grow, have the AI analyze, monitor, and give it to you. It's like Peter Drucker's quote, "What gets measured gets managed." If you wanna make money, you gotta manage it. So how do we do it? First off, we have to list every investment you own. Anything you have your money in, anything that has value, anything that's an asset, make the list. Second is open up your favorite AI and prompt it. Build me a live dashboard that tracks, paste the list, for each one of them, show me how healthy it is. Look for price movements based on the valuation of the market. And then flag anything I should look at, right? Look at the market trends, look at the key signals. And then third, tell it what matters most to you. You gotta tell it your goals so it has a direction for how it should guide you towards those goals. And then last, pick a day where you sit down and you review it. I like to do mine every Monday when my mind is fresh and I've got all the data for the previous week and I look through. If everything's green, I'm pretty good. If it's yellow or red, I gotta dig in. And here's a pro tip. If you're using Claude, you can actually ask it to build an interactive artifact in the chat so it's easy to visualize. All right, before you go out and spend money on a bunch of investments, I need you to hear this last thing because all this can go to shit if you don't follow a simple rule. Stick with what you know. The richest people invest in things and people where they have an unfair information advantage. AI can change a lot, but it doesn't change what humans know and what you know AI can't do. I'm an AI guy, So if I see some AI tool that I start paying for, then I go, hey, is this a public company? Is this a stock I could buy? You just have to go, how do I use AI to battle test my concepts? I made the mistake 15 years ago to buy homes in Detroit. I spent $100,000 buying a bunch of homes for $8,000. And about 18 months later, I realized I was in a world of shit because these homes were literally ready to burn down. They had homeless people in it. The guy that I was working with never rented them out. They didn't do the value add. The whole concept didn't work. Why? I invested in shit I didn't know. If I had been a real estate guy, I probably wouldn't have done the deal. Sometimes pain is the perfect teacher. I had a little pain, I learned a lesson. I'm going to teach it to you. Stick in what you know. The biggest risk isn't losing money. It's wasting it on things you don't understand. So there's only 3 filters. These 3 have to pass. 1, do I know about it? Do I have an unfair advantage? Is it in the information flow of things that I naturally pay attention to? 'Cause number 2, which is the filter, is will I pay attention to it? Oftentimes I won't make an investment because if the amount that I gotta put in is not big enough for me to care, then I know I won't care, which means I'll probably lose my money. So I'd rather do less deals, bigger number, bigger focus, what I focus on expands, than doing a bunch of little tiny deals. And number 3 is will it be true in the future? I don't wanna invest in things that are gonna have high turnover because I wanna invest in things that are aligned with where the world's going, long-term, 10 years, so that I don't have to always be redeploying my money. And AI helps me battle test my portfolio through that lens. One of the most recent investment I made is in a company called Hark Labs, which is creating an embodied model. It's this new AI to essentially power the robots of the future. The founder of Figure, which is one of the top robotics company, is the lead investor and founder. So do I know it? It's AI. Will I pay attention to it? I wrote a big check. And third, do I think the world is going there? Uh, fuck yeah. The future is AI-powered sensors. Everything that's electrified will be cognified, and that model is literally going to power, not ChatGPT. So yes, yes, and yes. Buffett doesn't invest in tech, and I don't invest in oil. Know your edge and stay in it. And here's the crazy part, is the next 10 years, it won't reward the best stock pickers. It's going to reward the system builders, the person that can collaborate with AI, can use it to track its money, to battle to test it, to red team it, to ensure that it's not just being forgotten about, but it's focused on. I believe that my money should be out there working as hard as I'm working for it. So if it's not, I got to fix that. And AI is a great tool to do it. So let me know below, how are you going to use AI to get to your next level? And remember, if you want my full Company OS, the AI workflows and resources I use across all my businesses, just DM me the word YouTubeOS on Instagram and I'll send it over for free. And if you want to know what AI businesses are worth starting in 2026, click here. I'll see you on the other side.
