I’ve built a lot of things. This chart explains why some worked and most didn’t. After building 100+ products in my career, this chart is the closest thing I’ve found to a cold, honest explanation of how people actually get to one million dollars online. It shows you why a few of my projects took off, why most didn’t, and why the price, the buyer, and the path matter more than whatever clever idea you start with. I’ve always liked that this chart starts with the salary paths. Earn fifty thousand a year for 20 years. Earn one hundred thousand for 10 years. Earn two hundred fifty thousand for 4 years. They’re steady, they’re real, and if you’re working for someone who believes in you and you believe in them it can be one of the cleanest ways to build a great life. But even good jobs come with risk now. Teams get restructured, priorities shift, AI automation creeps in at the edges. I love this path for lots of people, but you’ve got to be aware of the ground you’re standing on. The rest of the chart shows the other routes, the ones where you design the path instead of relying on someone else to define it for you. The next part of the chart looks almost childish at first glance. 2,000 people buy a 500 dollar product. 1,000 people buy an 83 dollar monthly subscription. 300 people pay 278 dollars per month. But hidden inside those lines is the real blueprint. The numbers look interchangeable, but they push your business in completely different ways. A 200 dollar product puts most of the pressure on distribution because you need many buyers and a steady stream of new attention. A 500 dollar product puts more pressure on perceived expertise, since people only spend that much when something feels tailored to them. An 83 dollar subscription puts pressure on ongoing usefulness, because customers have to remember why they are paying you every single month. And a 278 dollar monthly offering puts pressure on outcomes, because people paying that amount expect a clear and meaningful shift in their lives or business. Every path needs trust and retention and value, but the center of gravity changes depending on which line of the chart you choose. This is where most founders drift off course. The problem isn’t that they choose “bad ideas.” It’s that they choose ideas without understanding the path those ideas place them on. A subscription idea puts you on a path where you have to deliver value every month. A 200 dollar offer puts you on a path where distribution becomes your main constraint. A premium service puts you on a path where the real work is selling, not building. The idea still matters, but the path matters just as much. When you choose an idea, you’re choosing the physics you will live inside, and too many founders make that choice without realizing what comes with it. If I had to make one million dollars, I wouldn’t pick an idea in isolation. I would look at the chart and decide which path fits the way I actually operate. Then I would choose an idea that works inside that path. The idea and the physics need to match. Most people pick the idea and discover the physics later, and that’s when they get stuck. AI shifts the conversation in a quieter way than people admit. Ten years ago, exploring one of these paths meant building an entire supporting structure around the idea. You had to shape the story, package the offer, design the touchpoints, test the funnel, gather feedback, and refine the pitch. None of that was rocket science, but it was slow because every piece required a different person (and lots of cash). Now the bottleneck is no longer talent or tooling. The bottleneck is whether you can make clear decisions. If you can, you can generate every piece of the experiment yourself and run multiple versions side by side. When the overhead disappears, the smartest move is no longer to plan the perfect idea, but to run a few controlled tests and see what actually has energy behind it. Clarity is the moat. If I were building toward a million today, I would treat the chart like a menu. I would test the 200 dollar path with three different ideas and push them through social channels to see if any spark. I would test a 500 dollar path by creating a simple offer that solves a painful problem and pitch it directly to people who already feel it. I would test an 83 dollar subscription path by launching ten onboarding variations until one sticks. I wouldn’t protect any of these ideas. I wouldn’t fall in love with any of them. I would watch which one shows upward pull and drop the rest without hesitation. This is the operating system I see in the best builders. Path. Prototype. Publish. Proof. Pick a path. Prototype something simple. Publish it in the wild. Look for proof in speed, clarity and response rate. If it hits, you focus. If it doesn’t, you walk away immediately. The arrogance is in holding on. The wisdom is in momentum. AI didn’t just make building faster. It removed the emotional cost of trying. You don’t need six months. You don’t need permission. You don’t need the perfect idea. You just need to run more experiments with cleaner thinking than the people around you. When experiments are cheap, the winners are the ones who iterate the fastest with the least ego. The point is to choose a path you can actually sustain, a price you can actually justify, and an idea that fits the way you like to work. When those three line up, the business stops feeling like a gamble and starts feeling like something you can grow for years. The million dollar paths have always been simple. They just used to be out of reach because each one required so much time, money and coordination. Now you can explore them quickly enough to see which one fits you instead of forcing yourself into the wrong one. That is the real advantage. You are no longer betting your life on a single idea. You are running small, honest tests until the right idea and the right path finally meet. Getting to a million still feels like pushing a boulder uphill. This doesn’t make the hill smaller, it just keeps you from pushing the boulder in the wrong direction for five years. Most of the pain comes from climbing the wrong mountain, not from the climb itself. Note: enjoy the free workshop from my co-founder of Ideabrowser on building a startup live with AI agents (from ideas to build) on Nov 20 while seats remain here #1
The scale of YouTube is hard to even understand. It's one of the greatest place to build internet audiences even today. 2% of human time?! That's wild. #2
Be careful who you "grab coffee" with or "brain picked" from. Your time is your most precious resource. #3
I talk a lot about building organic audiences/community but paid should always be in the mix ONCE you find the organic content formats that are working. This was a reminder that scaling with paid is a beautiful thing. #4
There is no perfect timing and no perfect idea either. You can grab ideas at Ideabrowser.com if you're looking for inspo. Thank you for reading Greg's Letter. I hope you it got your creative juices flowing. You can forward this email to a friend that might benefit. Until next time. Be well, © 2025 Late Checkout LLC
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Free startup ideas and frameworks to help you win on the internet. The weekly email written by Greg Isenberg that gets 100,000+ people's creative juices flowing.
I’m hosting a private 2 day workshop in South Florida called Offline Mode. There are only 5 seats left. Because so many founders need some time "offline" to think, get real feedback, and a clear plan for 2026. We'll spend 2 days together in a 20,000 sq ft mansion working through the systems my team uses to run a $10M+ bootstrapped portfolio: AI, content, distribution, and simple products that scale. We will teach you everything. Price is $5375. January 23rd-24th 2026. Fort Lauderdale, FL....
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Two things you might be happy to hear... I convinced my team to do a black friday sale for Ideabrowser. You get $500-$1000 off plans until Dec 2 or until we run out. Grab it here. I'm doing a free workshop on Sunday at 3p EST called commit 2026: building a cash-flowing startup with AI. I'll share frameworks, startup ideas, tools I use. if you want get serious about building a cash-flowing startup with AI in 2026, join me this Sunday at 3p ET and let's learn commit. RSVP for free here. 2026 AI...