What Made Bezos Walk Away From Millions (To Build a $2 Trillion Empire)

What if you could know with mathematical certainty, what life decision that you should make about the job, about the relationship, about where to live, about who your friends should be, there's a way to do this. So I want to talk about something that Jeff Bezos uncovered early in his career. His story and thought process that he went through to leave his incredible job and to build Amazon a thought process that we should all go through. But let me tell the story first. So in spring of 1994, Jeff Bezos was 30 years old. He was senior vice president at a Wall Street hedge fund. He had a seven figure salary. He had a Manhattan penthouse, the American dream. Basically, he'd achieved all of it, right? 30 years old, million dollars a year. And he was about to throw it all away for his startup idea, selling books online, right? Not writing them, not reading them, selling them on something called the internet that most people at the time couldn't even understand or define. He came up with this five minute mental exercise prompted him that pushed him to start Amazon. And it really just turned him from this hedge fund VP into the world's richest or one of the richest men. And this mental exercise, something we should all do because it's going to help you make better decisions. If you aren't going through this mental exercise that Jeff Bezos went through, even at a smaller scale, there's a really good chance that you've been making the wrong decisions your entire life. Now back in 1994, Bezos worked at DE Shaw and Co. Now it was one of these Wall Street firms just prints money and he prints money using math, right? It was a trading firm and they used algorithms to figure out, you know, what to buy, what to sell. And his boss, David Shaw was a former Columbia professor who figured out how to use computers to beat the market. Think about it like legalized money printing, but with algorithms. Now Bezos was Shaw's golden boy, right? He was the youngest senior VP in company history. He was on track to make tens of millions before 40. And one day, while he was researching opportunities for the firm, he found this incredible stat. Internet usage was growing at 2300%, not 23%, not 230%, 2300%. Nothing really grows that fast. And he couldn't stop thinking about it. That number, 2300%, 2300. He saw a massive opportunity. So what did he do? Well, he's like, how do I use the internet? How do I leverage the internet? And he made a list of 20 products that could be sold online on the internet. And out of the 20 products that he listed out, one, why? It was very simple math. Three million books existed in print. The biggest bookstore could only hold 150,000 at a time. Biggest bookstore in the world, the internet. So why not sell books on the internet, the fastest growing phenomenon at the time. But he had to tell his boss. So he sat down with Shaw and Shaw said, Jeff, let's take a walk. And this was their thing. Whenever there was a big decision to be made in the firm, they took walks through Central Park. And it helped them think, right? So they walked for two hours, and Bezos told Shaw his idea. And Shaw understood immediately that it wasn't just about books. It was about the future of how humans would buy everything. And after the two hour walk, Shaw spoke. And he said, this is a brilliant idea. It would be an even better idea for someone who didn't already have a job. Basically, what Shaw was saying was, you're about to become filthy rich here. At my company, why are you risking it? Shaw told Bezos to take 48 hours, think it through and make a rational decision about leaving his firm and just starting this startup. In that night, Bezos went home and he developed this framework. Instead of making lists or calculating the odds of success, like a lot of entrepreneurs do, he imagined himself as an old man. He projected himself forward to 80 years old. He asked himself questions to minimize the number of regrets that he would have as his 80 year old self. And this later became known as a regret minimization framework. So he asked himself three questions. He asked himself, how will I feel about this decision in 10 minutes? How will I feel about this decision in 10 months? How will I feel about this decision in 10 years? How will I feel about leaving Shaw and Co and my job, my very high paying job, and starting Amazon in 10 minutes, 10 months in 10 years? And in 10 minutes, he'd be terrified because he'd be walking away from guaranteed millions in 10 months. He'd either be building something new or he'd be begging for his job back. And in 10 years, well, this is where this mental model, this thought process, he knew in 10 years, 50 years that he was not going to regret having tried to build Amazon. He was not going to regret trying to participate in this thing called the Internet. He was not going to regret leaving his job and starting this startup selling books online. He knew that if he failed, he wouldn't regret it. He wouldn't regret trying. But he also knew that the one thing that he might regret is not ever having tried and that that idea, the thought of not ever having tried would haunt him every single day. So the decision suddenly wasn't about success versus failure. It was about two different flavors of regret. The regret of never trying, the regret of trying and failing. And if he tried and failed, there would be no regret. That the main issue was if he didn't try, never tried and always wondered what if that version of regret hasted much worse than the other. And Bezos quit the next day. He loaded his entire life into a beat up Chevy Blazer. His wife, Mackenzie, drove while he typed a business plan on his laptop using his knees as a desk. He left directly for Seattle. Why? Because it had the most book readers per capita in America. And he got everyone else on board. His parents invested their entire retirement savings. That was $300,000. When he explained the Internet, his mom asked, what was that? I don't get it. But didn't matter. Their family. They put the money in any ways. They weren't investing in an idea. They were investing in their son. Bezos set up shop in his garage. He built desks out of doors from Home Depot because real desks cost too much for him. So he was in full startup mode. The company was originally called Kadabra, like Abra Kadabra. And then his lawyer misheard it as Kadabra on a phone call. And Bezos immediately changed it to Amazon. And that was the beginning. One of the biggest companies in the world. Bezos never second-guessed leaving Wall Street. Not once. And the reason why is because he went through this regret minimization framework in his head. He asked himself the right questions. He took that lead to less regret. He took the path that made sure that at the very minimum, he tried to do the thing he wanted to do. It worked out. Today, that calculation, that bet, that chance, that him leaving his Wall Street job. Yeah. He left a couple of million bucks on the table. But you know what? It made him. It made him billions and it made a company worth trillions. Now, when Bezos went through this mental exercise in his head, when he was thinking about if he should take the jump or if you just say it as Wall Street firm, and he went through the exercise of imagining himself at 80 years old and what would the 80-year-old Jeff Bezos regret or not regret. He accidentally discovered something that scientists would actually prove later is a very powerful mental model. Cornell psychologist Thomas Gillovich spent 20 years studying what people regret and his findings changed everything that we thought we knew about decision making. We regret what we didn't do twice as much as what we did. And what's really interesting is that it gets worse over time. Things that you do, so actions that you take that you regret, you start to forget about them. They fade, right? That business it failed. Five years later, you're going to be telling funny stories about it at dinner parties. The relationship that crashed and burned, eventually you're going to laugh about it and you're going to say, you know, what was I thinking and just move on? But the things that you didn't do, they grow. They compound like interest on a debt that you can never pay off. They become these ghosts that haunt you at 3am when you can't sleep. So when Gillovich surveyed thousands of people about their deepest regrets, he found that 76% of the deepest regrets were things that people didn't do and only 24% were things that they did. What gets really dark is that this pattern intensifies with age. So 20 some things they have equal regret for action and inaction. 40 some things twice as much regret for inaction. You're over 60. You have three times as much regret for inaction. And then if you're over 80, you almost exclusively regret inaction. So think about what this means. The older you get, the more you regret the chances you didn't take. Not the chances you took and failed. And the science gets even more interesting. So neuroscientists at USC put people in brain scanners, MRI machines and they watched what happens in your brain when you experience regret. Your brain processes a missed opportunity exactly like an actual loss. So neurologically they're identical losing $10,000 cash and not making $10,000 that you could have. Your brain can't tell the difference. But when you actually have a loss, you actually lose that $10,000. You have closure. It's done. You lost. It's over. The game is ended. You process it and moved on. The missed opportunity it never closes. They create these open loops, these mental processes that they never they never complete. They sit in your brain, consuming energy, running in the background like an app that you can't force quit. So your brain will constantly be thinking about, I've lost $10,000. But because you didn't actually lose it, it was just a missed opportunity. Your brain will never stop processing that idea. And in northwestern researcher Neil Rose found this pattern in every culture, American, European, Asian, African, everyone everywhere shows the same pattern. The regret of inaction compounds like interest. And on the flip side of that, there was another research from Hamburg by Stephanie Brasin. And she studied people who aged well, people who stayed happy and sharp and satisfied into their 80s and their 90s. And the one thing that they all shared is that they weren't people who succeeded at everything. They were people who tried everything that mattered to them. Their brains had literally rewired around action instead of avoidance. They trained themselves decision by decision to be the kind of person who acts. And that made them happier. So Bezos didn't know this. But what he was doing, he was doing this mental math. He was doing this calculation. And he was and he did make the decision 80 year old him would be happy with. So when he was standing in his Manhattan department, running this mental calculation, he wasn't just making a decision about leaving Wall Street. He was choosing which kind of life he wanted to have, which kind of brain he wanted to have at 80, the brain of someone who acted, the brain of someone who wondered. And the beautiful thing is that his framework isn't some corporate secret locked away in Amazon's headquarters. It's not proprietary, it's not complex. And it's really something that you can use right now today for any decision. Because remember all those successful ages that Bracen studied, they didn't have special genes. They didn't have special unique circumstances. They just had a pattern of choosing action over avoidance and minimizing regret. And that pattern starts with a very simple framework. This is the exact framework that Bezos used. It's a same mental model that took him from a Manhattan penthouse to a Seattle garage to the everything store. He called it the regret minimization framework. And it really just takes five minutes to run, five minutes, that's less time than you spend scrolling on social media while you're avoiding the decision that you should be making. And it's five minutes that could literally change the trajectory of your entire life. And remember that we just learned from the research, your brain is plastic, it can rewire. Every time you use this framework and you choose action, you are literally restructuring your neural pathways. You're training yourself to be one of those people who ages without regret. Basically, you're building the brain of someone who tries and does. So this is the framework. Step one, make it binary. First thing you need to understand is that your brain hates gray area. It's literally designed for yes or no, fight or flight, stay or go. So what you need to do is convert your decision to a clear yes, no question with a specific deadline. So let me give you an example about what I mean. Here's the bad version, the way that most people frame their decision, right? They'll say something like, should I think about maybe changing careers someday? Now, that's terrible. It's ambiguous. It's not specific. There's no deadline. A good version of a decision that they have to make and the way that you should frame it is, will I quit my job by March 31st to start my business? Now you see the difference, right? Specificity forces clarity. vague questions are going to produce very vague lives. Every word should be specific, including dates, including actions. So you make it impossible to misinterpret. Step two, you need to set time horizons, okay? Set a timer on your phone. You're going to give yourself 90 seconds per horizon. You're going to write without stopping. You're not going to edit. You're not going to think too hard. You're just going to write. So there's going to be three time horizons, 10 minutes, 10 months, 10 years. The first time horizon right on the page, 10 minutes from now, ask yourself, how do I feel? What am I dealing with immediately? What stories are running through my head? What are the immediate consequences that I'm facing if I make the decision 10 minutes from now? Then you move on to your second horizon, 10 months from now. You're going to ask yourself, what does daily life actually look like? What problems have gone away? What new problems exist? What does Tuesday afternoon feel like? Be very specific? Free, flow, write, don't edit. Just put your ideas on paper. I want you to be specific about the mundane details. Finally, the third horizon, 10 years from now. This is the big one. You're going to ask yourself, what story do I tell myself about this decision? What would I tell my current self 10-year in the future self to travel back in time to this moment? How do I describe this chapter of my life? And the most important thing when you're writing for the 10-minute, 10-month, and 10-year is that you are writing from the future looking back. Don't write, I will feel scared. You want to write it like this. I felt scared for about two weeks, then it became normal, then dot, dot, dot. So write as if you are already the 10-minute, 10-month, and 10-year version of yourself. This is going to force you to think like yourself in the future. It's just very much a self-awareness exercise. After you finish step two, this is a self-awareness time horizon exercise. After you finish that, step three, I want you to do some math. Pure Bezos, I want you to make it quantitative. So I'm going to give you three scenarios, and I want you to rate each scenario on a scale of 1 to 10. So the first rating is the action regret. If I do this and it fails completely, how much will I regret it in 10 years? And I want you to give it a number from 1 to 10. There's no right or wrong answer, just put whatever makes sense. The second rating is inaction regret. If I don't do this thing, how much will I regret it in 10 years? Another number from 1 to 10. And now you can actually write these numbers down because you've gone through the exercise already, and you know what you will feel like in 10 years from now. After you write these numbers down, this is the key, you are going to take your inaction regret number, and then you're going to subtract it from your action regret number. You're going to get results. If you get a positive number, that means you have to act. If you get a negative number, that means you're not going to act. And if you get zero, that means you're not being honest with yourself, or you need more data. So let's do a fake calculation based on what Bezos was thinking about in his Manhattan apartment before he started Amazon. So his action regret, say it was a two out of 10. So if Amazon failed, he figured, well, at least I tried something that I wanted to try. And his inaction regret number was a 10 at a 10. So he knew that if he did not do this, he would think, well, I watched from the sidelines as the internet revolution happened. So the difference between his action and inaction, or rather his inaction and action was a plus eight. That is an overwhelming signal. Now, after you've gone through this, step four would be to do a pre-mortem. So if you're differential between the inaction and the action number was positive, the mass says act, then assume you will act. But no, and this is important. I also want you to assume that you're going to fail. This is the immunity that you're building to failure. If you assume you're going to fail, then you're going to identify how you're going to fail, and then you're going to prevent it. I don't want you to skip this step. This pre-mortem assumption of failure is what really separates just reckless action from calculated courage. It's the difference between jumping off of a cliff and bungee jumping, both involve a lot of falling, but one has a plan for landing. So you will pre-meditate all the different things that could possibly make this unsuccessful, which means that you are increasing the likelihood of it being successful. And after you've gone through all of this exercise, all of these different ideas, the last step is to burn the ships. So within 24 hours, and I mean this, not next week, not when you feel ready, but within 24 hours, you need to do something irreversible that's going to force you to act. It means you send the resignation letter, or you pay the deposit, or you tell everyone who matters what you're doing, or maybe you book the ticket, or you register the domain, or you sign the lease. Whatever it is, you do something that you can't. This is actually based on the story of Hernan Cortez. The burn, the ships burn the boat story, right? When he reached the new world, when he was an explorer, he was traveling, he reached a new world, he burned his ships. Because if you burn your ships, there is no retreat. The way to go home was burning. It's up in flames. Him and his troops, they could either go forward, they could conquer, or they'd die. Now that's extreme, but you get the analogy. Now Bezos did something similar. He told his parents, he told his boss, his parents knew that he was quitting Wall Street to sell books on the internet. His boss knew he was quitting Wall Street to sell books on the internet. There's no going back. You've burnt the ships. Now this is really the framework that Bezos took to radically change his life and ultimately build a trillion dollar company. But what most people don't understand about this framework, that it doesn't just help you with that one next decision. It helps you with all decisions going forward. Because if you don't make a decision, like we spoke about the inability to act compounds, but also the beautiful part about this framework is the courage to act compounds. So every time you make a decision, even with this framework, the next decision, the next action is easier. Every time you choose to act despite the fear, you are rewiring your brain. You're becoming the kind of person who acts. So Bezos didn't just use this framework once. He used it for everything. AWS, Amazon Web Services, his executive said it was crazy to let the competitors use their infrastructure. Would we regret not trying? And now AWS makes more profit than the entire retail business. Everyone said it would bankrupt them, right? Why why not try it now? Half of American households have prime Alexa, space exploration, healthcare, same question every time. Would we regret not trying? And the framework became a philosophy and the philosophy became a culture and then the culture became an empire. So right now, as you're listening to this podcast, you're sitting on a decision. You know it, you might be pretending that you don't, but you do. It's been eating at you for weeks or months or maybe years. It's a thing that you think about in the shower. It's what keeps you up at night. It's a conversation you have with yourself when you're alone in the car. You've made lists, pros and con lists that go on for days. You've asked everyone your friends, your family, your mentor, strangers on the internet. You've researched yourself into complete paralysis, but you haven't run the framework. And you know why? Because you already know what it will tell you. This is what Bezos understood that most people don't get. You're not actually afraid of failure. Think about it. Failure is just an event. It happens. It hurts. You recover. You are afraid of the space between now and potential failure, the temporary discomfort, the awkward conversation, the period of uncertainty. Your 80 year old self doesn't care about temporary. Your 80 year old self has perspective. Your 80 year old self knows temporary discomfort is, and your 80 year old self only cares about one thing. Did you try? Not did you succeed? Did you try? Bezos could have stayed at DE Shah. And if he'd stayed, he'd be worth hundreds of millions today, maybe a billion. He'd be safe, comfortable, successful by any measure, but he wouldn't be Bezos. And you choosing safety, you're not becoming you, you're becoming a shadow of who you could be. The every decision that you delay is a vote. It's a vote for who you were instead of who you could become. Every day you don't act is a choice because you're choosing your past over your future. That 10 minute version of you wants comfort. Of course it does. That's natural. The 10 month version of you wants security and that makes complete sense. But the 10 year version of you, the 80 year version of you, the 10 year version of you wants stories. The 10 year version of you wants to know you try. The 10 year wants to respect the person in the mirror. So what you're going to do today, not tomorrow, not after you think about it more. Right now is you're going to open a document on your computer, grab a piece of paper, you're going to write the question, the real question, you're going to make it binary, make it specific, include a date, you're going to run the calculation. And then you're going to think about how you'll feel in 10 minutes, 10 months, 10 years, you're going to rate your regrets, you're going to do the math, you're going to do the framework that takes five minutes. Remember, the regret lasts forever because without making a decision, you are choosing one of them right now in this very moment, whether you realize it or not. And every moment that you don't act is a choice. And just know that your 80 year old self is watching you make or not make that choice at the end of the day. What life do you want to live? What story do you want to tell? What 80 year old version of yourself do you want to be?