How to start a 1-person business with AI (ask these 3 questions)

I've built multiple successful companies starting with nothing but one person and AI. Some of them are already making millions in revenue. But did you know that over 600 businesses fail every single day in the United States? Most don't fail because of bad ideas or bad marketing. They fail because they didn't ask the right questions before they started. So before I start any one-person business, these are the 3 questions I ask AI. So the first one is what to sell. Everyone starts an AI business the same way. They see AI do something super cool and then they try to build a business around it. That's completely backwards. And I was doing the same thing way before AI was even a thing. I started building companies when I was 17 and I went almost a decade completely failing. My first 2 companies, I asked the wrong question. First company was a vacation rental site. My dad had a cottage and I wanted to learn some new technology. Instead of building a business, I built technology. And then the guy who owned atthecottage.com, he kicked my butt. Then I decided to build another company, a hosting company. Why? I thought, well, I'm paying somebody else for hosting, I should own the hosting. Web hosting is like selling salt. I'm sure somebody out there is making a bazillion dollars selling salt, but back in 1999, I wasn't that guy. And both died because I started with the question, what do I wanna build? Then I changed the question. What problem are people already paying someone else to solve? That one question allowed me to build Spheric Technologies, my first real company. Because instead of starting with the technology, I went to find out who was already paying for solutions. And I discovered there was a whole bunch of companies paying other companies to build what was called enterprise portals, these internal intranets. And because I followed the money, I found out where the pain was. I asked who was already paying to solve this problem. That allowed me to find the customers. That allowed me to find my partners. My partners brought me into deals. As a 24, 25-year-old, I was selling to Fortune 500 companies all because I asked the right question. And only 4 years later, not only did I sell the company, I became a multimillionaire. Same person, same knowledge, same skill, but a different question. Now, today, I never start another company without asking this question first. Every single company starts with the market. The market tells me where it hurts. They show me what they're already paying for. Then I get paid to build a solution. Today with AI, it allows you to get even deeper, quicker without trying to guess. And I'm gonna show you how to do that today because there's only 2 types of businesses. You're either a vitamin, nice to have, or you're a painkiller, a must-have. One of them can make you some money, the other one will get you rich. When I think of vitamins, I think of things that like could make my life better, tools to help me stretch or productivity apps or insurance for a problem I never experienced, but maybe it could happen. I don't need them. I don't have an acute pain. But when I think of painkillers, this is a pill. That solves an acute problem. These are tools that help people make more money, get more leads, retain their team, hire quicker, because most people have like hair-on-fire problems and we need to get them the painkiller to solve those problems. I call this a frustration list. When budgets get tight at a company, the first things to go are the vitamins. The last thing that's gonna go is anything that makes money, which is usually a painkiller problem. So a lot of people ask me, okay, well, Dan, well, how do I find painkiller problems? Well, the first thing is we have to develop the muscle. We got to see all these frustrations that are happening around us that sometimes we just go through life and ignore. When people start businesses, they usually struggle with finding good ideas. I have the problem of saying no to a lot of great ideas. Why? I've developed this muscle. These are the steps to develop this skill. So what I want you to do is tomorrow, as you go through the world, I want you to write down anything that frustrates you. I'm talking about simple things like why do I have to plug my phone in? Why do I always have to open and close my garage door? Pretty much Anything that makes you go like, ugh, every day. As you build this list, what you'll develop is the skill to see opportunities. 'Cause people only pay for 3 things. They pay for money, things that'll make them or save them money. They pay for time, productivity. How do I get my time back? It doesn't matter if I'm a CEO or I'm a manager or I'm an entry-level employee. And then they pay for status. How does this thing make me look? If you miss all 3 of those, then you haven't built a painkiller, you've just built a vitamin. The point is to develop volume and write down as many things as you can to develop the skill of seeing potential ideas that become painkillers. And the way I see it is million-dollar businesses aren't built on $10 problems. You have to have serious problems that solve serious pain for somebody out there that's hurting. If you got a migraine and I got a pill and it's $100 to get rid of that migraine, you're gonna buy it from me. And here's a crazy hack for this. Call the consulting companies already working with those companies that are getting proof through what they're paying for to solve those problems, because those are the services that they sell. They wouldn't sell a service if there wasn't demand for it. So that's how we do it manually. But here's how we use AI to accelerate things. I use Claude, but any AI can work. We gotta find the pains. So write this into your Claude: I wanna start an AI-first business in— and insert your industry— that's where I already spend my time and it's where I want to build. That means it's something you know. So give me 10 this is key, observable and nuanced pain points that people in this industry deal with every single day. Not the obvious stuff everybody already knows, the specific ones you'd only catch if you were actually in the room. Only give me pains that are getting worse, not better, and rank them by how much people are willing to pay for them to be solved. And ask me any question you need to get clarity. So this is the exact step that I use to make sure that it's bulletproof. By definition, if you ask the AI a generic question, you will get a general response, which will get you a very basic business. So we want to be very specific around the pain points. With this, you'll get real specific problems people will pay for. So now we figured out what we should sell. That's a painkiller, not a vitamin. Here's what you're going to ask AI. Question number 2, find your edge. Finding a painkiller is just the start. Question number 2 will help you figure out how to solve it in a way that only you can. For example, when my brother started building homes, he had an idea. How about I build the cheapest home? Because if it's the cheapest home, then everybody's going to buy it. Obviously, people had to pay and they wanted to buy a home, but he built the wrong thing because he didn't figure out what his edge was. And it's why it didn't sell for almost 9 months. He realized his edge was working backwards from the customer and building something they wanted. He was willing to do something nobody else in the home industry at the time was doing, which is market research. He decided to grab all the potential buyers, go look at the dozens of different open houses on a Sunday, and ask them what aspect of those homes do they like? and took the best ideas and put it into a new design. And he didn't then just go out and build the 3rd and 4th home. Instead, he designed it, he got renderings for it, and then he pre-sold 16 homes with deposits before he ever put a shovel in the ground. That's what allowed him to scale to be one of the top home builders and now real estate developers in Eastern Canada. The other thing he realized is that it takes them on average less than 100 days to build those kind of homes. So what he decided to do is make a commitment to his customer, a promise. Of building the home in 99 days or less. And what's funny is I remember the first time he did a home show and other builders would walk by his booth with his 99-day promise and they would say like, that's not that impressive 'cause we do the same thing, but they weren't willing to claim it. He figured out what his edge was. Early on for me, my obsession and passion for just writing code and building software and building any tool that anybody found useful, that's what I love. Now I wanna teach you how to do this for yourself. For you, it could be your skills, it might be time, it might be relationships that other people don't have. You got to mine what you have to figure out what gives you an edge in the market. The reason why I was able to help my brother go through this process is because it's something I had to figure out the hard way. And it's why I teach other people the same way that I did it. And oftentimes it's teaching business owners how to integrate AI into their business. So the question you got to ask yourself is how do you figure out what your unfair advantage is? Essentially, what do you know how to do better than almost anybody? One of the things that my brother had that most homebuilders didn't have back then is a dedicated architect. And because most people building homes just buy plans off the internet, especially if it's a spec home, and then just build it, there was no advantage. How do you compete in a red ocean like homebuilding to create your own blue ocean, which is one that doesn't have competition, where you can differentiate and you're better? This one's about you. It's what's unique to you, the thing that nobody else can do. And the hard part oftentimes is you can't see your own advantage because you're too close to it. It's really easy for you. So you just assume everybody knows how to do this. You don't realize how special it is. So it's easier to get an external source to tell you, which is where we bring in AI. So here's what we need to do. The first step is you got to connect everything you have that it can use for research. I'm talking your Gmail, your Slack, your calendar, your social medias. Make sure that it knows everything about you so that it knows you better than you know you. For example, my AI has access to everything. I'm talking meetings, transcripts, trainings, all my financials, my whole life, all the decisions I've made for the last 15 years. I've slurped it all in so that it knows everything. So in that same chat where we already have our painkiller identified, here's what we write: Based on everything you know about me, where do I have an unfair advantage? What can I do better than 97% of people? And the second step is, if you need to give it more context, make it interview you. This is where you write, now interview me about the last 10 years of my work, 10 questions, one at a time, then tell me what my unique edge is. And like, here's the pro tip: use your voice. It's way faster and it provides more context. So I use a tool called WhisperFlow where it asks the question, it prompts me, and then I can reply talking to it. It transcribes it, enter way quicker talking. Now once you get an answer, the third step is to make sure it fights you on the answer. Essentially, you don't want it to just be a yes man. So this is where we write, be brutally honest. Is that actually rare or am I overrating myself? Where would someone who's done this their whole career actually crush me? You wanna make sure that it's not just making you feel good. Now you cross-reference those answers against the first question. You've got the painkiller we picked and the edge we just found. Where do they overlap? Gimme the one place where my edge is the reason this problem gets solved better than anybody else could solve it. If they don't overlap, say so. So pain alone is a market. Edge alone is a resume. Where they cross is actually where the business is. And that's the reason somebody will pick you over everyone else selling the same thing. For me, my edge is helping other business owners use AI to scale so they don't build a business they grow to hate. Why? Because I went through it personally and I know the pain that I felt and how hard it was to figure out the path forward. It's why I teach so many people to do it, which is why I built my AI Company OS, full playbook on how to integrate AI into every department of a business. I'm talking marketing, finance, delivery, all of it. And if you want it, just find me on Instagram and DM me AI business and I'll send it over. When I work backwards from a real pain a customer had to figure out what I need to sell, and then I added my unfair advantage, which is the fact that I would do this for free, then I had an edge that made me successful. Which brings us to our 3rd question. We have to find real buyers and test the market. Question 1 told us what to solve. Question 2 told us how we stand out. But unfortunately, neither one of those get us paid. The only thing that actually makes it worth it is getting a stranger to part with their money. We need to get a wallet, which AI can help us get. As you build a business, people will tell you, that's such a great idea. You should build it. Come back when you're done. I'll use it. I'll pay you for it. I'll be your first customer. And I will tell you, they're lying to you. They don't mean to, but they're not being honest because if you actually ask them for money in that moment, they wouldn't give it to you. That's why we have to do this test. When I started my 4th company, Flowtown, I wanted to know if they would actually pay for it. So what I did is I created a landing page. I had them go through the whole signup, go through all the different screens, and even put in their real credit card to validate and confirm they're willing to pay. And guess what? 20% did. That number told us everything. And then I would just say, unfortunately, our servers are overcapacity and we're not able to take new customers on. But here's the deal. There were no servers overcapacity. There was no product that was even built. That simple idea. That's why I call it the Wizard of Oz. The man behind the curtain. I simulated the real transaction to validate, to ensure a customer was willing to pay with a credit card before I built anything. There's nothing more expensive than building something that nobody will pay for, and that's just something I've done in every company I've built since then. We've launched 12 companies in the last 18 months, and we've done this process with each one of them. We wanted to test before we built. Did they have a painkiller problem or a vitamin problem? Question 3 for me is both validating that there's demand for what I want to solve and for the way I've solved it. It's not would somebody pay, it's would they pay for it the way I'm solving it? And an even better question is how do I get a real payment over the next 7 days? Here's what you need to understand. You need to prove it before you build it. This is why we need to figure out— people fall down the path all the time. I got to register my Instagram account. I got to build the perfect design. I have to have a logo, a business card, all before they ever even find out if anybody wants this. So the right question is, does anybody want this enough to pay me right now? Because here's the way I look at it. Certainty brings currency. You sell before you build every single time. This is how we use AI to test even faster for our third question. And there's 4 parts. First, we have to ask the cheapest possible test. We don't want to spend a bunch of money to validate anything, so we need to figure this out. So the prompt is this: based on the painkiller and the edge we landed on, design the cheapest market test that gets me one real payment within the next 7 days. No preexisting website, no brand, no logo or business registration before I spend hours building anything. And then number 2 is have it write the offer. So ask it, write the one-page offer, a clear promise, timeline, and price. Nothing else. Third, make it build the actual path for a payment. So write this prompt. Now give me the 10 people I should contact first, the exact message to send, and the follow-up to ask for the money. Not a call, not a demo. Cash. Number 4 and the final step, then make it find the hole before the market does. So we want to write, why would some people say they want this and never pay? Ask it, what is my riskiest assumption and how do I test for that one first? Now it's given you a cheap test. You've got the offer and you bulletproof it so you know they want it. Send that message that it gave you the offer out today and take deposits from whoever's willing to lean in. Now, here's an important thing. We want to go manual before we start automating anything, before we even know what people are going to say. So we do the first 10 by hand before automating a thing. And I know with AI you might want to start automating or even scaling this up. You're like, 10, I can do 100. Stop yourself. If you scale things up too quick, it's the wrong move. So for test, we have to pre-sell. So now we know what we're selling. It's a painkiller. We have an unfair advantage on an edge and we're pre-selling to get people to pay us with money to prove they actually want what we have, the way we're going to solve it. Now, here's the thing. You could do all those 3 things and do them perfectly and still walk away with nothing because there's 2 mistakes that kill all of it. The first one I was guilty of for the first 7 years. Number one is you fell in love with your solution. I wanted to build stuff. I was interested in the technology. What I should have did is fell in love with my customers' problems because that's what I needed to learn. I needed to understand exactly what they felt was a painkiller and how they wanted it solved, not what I wanted to do. Theory and ideas will tell you what could work. A real person opening their wallet tells you what actually does. That's why we go through this whole process, so we're not delusional. So the first time you go through it, make sure that you're not lying to yourself and you really test your assumptions. Because the second thing is we got to make sure the AI doesn't lie to us. Because as great as AI is, it is world-class at being a people pleaser. It will sit there and tell you you're smart, And you're awesome, and it'll be a cheerleader for you, and you could do no wrong. It doesn't want to tell you that your idea is dumb. It would never say that. Instead, it's going to tell you to go do it. It's going to tell you exactly how to do it, even if it's not the best one. That is a trap, and you don't even notice that it's happening because you never question it. And everybody wants AI to agree with them. Everybody needs— especially in the early days when we're starting business, we're just like so fragile that any negative feedback could derail us, and we just decide not to do it. But please don't allow yourself to fall prey to this. You have to push back on the AI and ask it to be a ruthless critic. Be brutally honest. That's the language I use in my prompts. And that's why for every single answer, make sure you give this to it. You got to flip it back. Now push back on me. Tell me why this fails. Where am I kidding myself? In the military, they call it red teaming. You essentially attack your idea or your plan based on what you think the enemy will do and make that a habit and do that as often as possible. You have to put yourself on the other side of the coin. You have to say like, why won't this work? How do I think about it? And then from that, you can actually do the things that are going to protect you. So doing those things will help you not only find the right thing to buy and give you your edge, but it's going to allow you to validate so you don't waste a bunch of time and energy building something nobody wants. Now, here's what I've learned building companies for the last 30 years is essentially realizing that my whole life is the byproduct of questions, questions I ask myself. The quality of my questions dictate the quality of my life. And I want to encourage you to be more curious, to seek continued growth, to decide that a properly timed question, even a question you repeatedly ask yourself, on the backside of that is potential for you to become even more. So out of those 3 strategies, figuring out what you want to sell, your edge, or how to test it, which one did you like best? I need you to leave me a comment below to let me know that you picked that up, because the next time you start your business, because it may not be your first time, you're going to use that strategy to avoid making that mistake. And remember, if you want my full playbook on how I integrate AI into every department of my business, just DM me AI Business on Instagram and I'll send you the Company OS. And if you want to learn how to make your first $100K, click this video next.