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Why "Entrepreneurship Is Just Luck" Is the Dumbest Take on the Internet
14th November 2025 • Repeatable Revenue • Ray J. Green
00:00:00 00:15:35

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A viral tweet calling entrepreneurship "just a lottery" hit my feed last week, and I had to respond. The author claimed successful entrepreneurs are lucky players who pretend their success was skill, and thousands of people ate it up. In this episode, I share my original reaction, but more importantly, I break down a powerful story from Alex Hormozi's $100 Million Leads about "The Many-Sided Die" that reframes the entire conversation. Yes, luck exists—some people roll green faster than others. But the real insight is this: you win by continuing to play. Every roll improves your odds, builds your skills, and gets you closer to success. The only guaranteed way to lose is to quit and blame your failure on everyone else getting lucky.

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Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green.

About Ray:

→ Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more.

→ Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses.

→ Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com

→ Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.

→ Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com

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Transcripts

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Have you ever seen a viral tweet that made you stop or, you know, Facebook post, whatever that made you stop mid scroll? And not because it was profound, but because it was so confidently wrong that you could feel your response, like actually welling up inside. That was me last week. Like, I stumbled across this tweet, and it's from a guy who's got a few hundred thousand followers and he's basically calling entrepreneurship nothing but luck.

It's all random. The winners are basically just lottery players who got lucky once and built an entire career on, you know, trying to pretend that it was something other than luck. It's basically all just one big scam. That tweet went mega viral and it was all over my my feed. I had a ton of people who were drinking the Kool-Aid like, hey, like nodding their heads like, yep, you know, it's complete bullshit.

You know, I tried my hand at it. You know, like most people on on social or bullshit. Um, and, you know, the other half are like, nah, dude. Like, I'm playing the game. I'm winning the game. I'm, you know, I must be good at playing the lottery, so I couldn't resist. Like, I, you know, I had a I wrote my own response, which I stand by and I'll share that with you.

But after sitting with this for, for a little while, I realised like there's an even better way to respond to this. There's a better way to think about this. And in my view, the best response to this mindset, it actually doesn't come from me at all. It's actually a quick story that Alex Ramos shares in $100 million leads, and I think that it perfectly captures the mindset gap between the people that succeed in business and the people that don't succeed in business, and the thought process that they have that leads them to the outcome that they that they get luck or not involved.

If you follow this with me, I guess follow up follows through. I'll share the tweet response and then this story, what I what I think it will do is help you reframe like the idea of of luck and the the challenges and the obstacles that are natural and come up in business And also reframe how to think about, you know, what it's like when other people are winning and you don't feel like you're making progress.

As far as like all of that comes together. In this in this video. So what I'm going to do here is I'm going to start with the actual tweet. Okay. So I'm going to read the original tweet to you. Is it still called a tweet when it's on when it's on X. Anyway I'm going to read this. The original message to you that actually made me stop mid scroll and create this.

Imagine your Twitter feed only showed people who won the lottery every day. You only see posts from people who won big. Within a few weeks, you'd start thinking winning the lottery is normal and you'd probably start playing the lottery yourself. At first you would lose, of course, but then one day you'd get lucky and you'd win your first hundred bucks.

And since you're seeing daily posts of lottery winners, you would think this is proof that the lottery is working. I just need to learn how to play it better. Then you'd meet a community of full time lottery players. Every time you you have a small win, they'd support and boost you. You're on the right path.

Path, bro. You're going to make it, you know. So you so you quit your job. You focus 100% on the lottery. You still see posts about other people who win big every day, and you're sure it's only a matter of time until you get your turn. It's. But months go by and you're still only winning 100 bucks here and there.

But you know, one time you win 10,000 bucks after spending 20,000. It's crazy. And you think finally, you finally figured it out. But the next day you're back to losing now. The years go by, you still see the daily stream of winners celebrating on your feed, and you're still nowhere as successful as them.

And you start wondering, why am I not winning? Is there not something? Is there something wrong with me? Am I stupid? But there is nothing wrong with you. You just made the mistake of believing the algorithm. The algorithm which gives 100 times more visibility to the winners and makes it seem like everybody but you is winning.

But the truth is, 0.1% of people win anything significant at the lottery. Most people fail, but you'll never see or hear about them because of the algorithm. There's nothing wrong with you. You're just a normal person who didn't win the lottery. Like basically 99% of the people on earth. Your perception that you should have Won was just a fantasy driven by social media algorithms, and his realisation makes you feel sad for a while.

But after a few days you feel liberated. You stop thinking there's anything wrong with you for losing at the lottery and you, you know, start coming back to your real life and you look for a job again. You're just a normal person and that feels good. No need to win big. Just just build a good life. Once you start realising this.

You try to warn the other lottery players. You tell them about the reality, but they don't listen. They're too addicted to themselves. So they dismiss you as a loser who gave up too quickly and cast you away. But in reality, you just woke up to the fantasy and tried to help them. Indie hacking is a cult. Indie hacking is, you know, just a form of solopreneur entrepreneurship.

And I, you know, I do a little digging. I realised this is actually a guy who, um, you know, tried to start a few businesses, uh, built up a really big following on X, didn't work out, went back and took a sales job, and now has the, you know, feels like I'm going to go out and warn people about the, the the challenges with entrepreneurship or indie hacking, whatever the hell it is.

oldest. I had an emotional response because it's really frustrating to hear, not only because of my own entrepreneurship career, but having worked with a ton of entrepreneurs, I know that is their lecture. I know how much work is going into this. I know that there are winners, that it's like, I know all this, right?

And so I respond, now, here's here's my original response, which I, which I stand by. But then I'm going to share the story that I think puts this all together and makes it make sense. So my original response is this this metaphor is empty. And anyone who's truly tried their hand at entrepreneurship knows why.

Lottery winners don't invest 60, 70, 100 hours a week for months. For years. Buying a ticket at the 7-Eleven doesn't require the courage it takes to bet on yourself. No one calls you a loser when you lose the lottery. You don't call yourself a loser, either. But here's the real difference in my opinion. Lottery players who lose.

Walk away with nothing. Show me an entrepreneur who's been at it for five years with nothing. A show, no money, no skills, no wisdom, no relationships, no audience. I put a hum because this person has built up hundreds of thousands of followers to tweet to. So nothing to show for it. And I'll call BS, which is why it's basically impossible to invest in yourself and not see ROI.

Even if the business fails. You can't say the same for playing the lottery. Yes, survivorship bias is real. Yes, bullshit influencers exist. But calling people who've built real businesses lottery winners, it's damn near offensive and dismissed and dismissing their work. As luck says, everything about your mindset, not ours.

One obviously not a lottery game, right? There's a lot more effort that's involved in saying that. It's the same as people going and buying a ticket is complete bullshit. If the amount of effort that you put into building your business is close to what you would in playing the lottery, well, then it's probably the reason you lost, right?

Or if you thought it was luck to begin with, or if you thought it was just purely about the riches. Also reasons that you may not have won at the game, but ultimately there's no way to walk away with nothing, right? Like, if you play the lottery, you've done nothing except develop a bad habit and a shitty bank account if you invest in yourself.

If you are building a business, if you are developing the skills, you are guaranteed to win something. Even if the business doesn't become a multi-million dollar business and make you filthy rich. So I stand by all that. However, there is, in my view, a story that summarises all of this really well, and it's from Alex Romo's book, $100 Million Leads, which I which I have right here.

And it's, it's at the very end and I'm just I'm going to read it to you. Word by word that I've got here. It's called the many sided die. And what he writes is imagine you and a friend playing a dice rolling game. You're each given one die. One of the die has 20 sides. The other has 200. On each die. Only one side is green and the rest are red.

The point of the game is simple. Roll green as many times as you can. The rules of the game are as follows. You can't see how many sides you have. You can only see if you roll red or green. If you roll green, one of your red sides turns green and you get to roll again. If you roll red, nothing happens and you get to roll again.

The game ends when you stop rolling, and if you stop rolling, you lose. So what do you do? You roll. When you roll red, you pick up the die and roll again. When others roll green, you pick up your die and you roll again. When you roll green, you pick up the die and roll again. You keep telling yourself one thing.

The more I roll, the more greens I get. At first you roll green once in a while, but as more red sides turn green, the green happens more. With enough rolls, hitting green becomes the rule rather than the exception. What does your friend do? He rolls a few times and hits red. each time he sees you roll green and complains that you must have a die with fewer sides, he says it's the only way that you could have rolled green before, and although you did, you rolled many more times.

So which is it? In either case, he rolls a few more times in frustration and hits a green, but then he complains about how long it took. He spent more time watching you and complaining than he did actually playing. Meanwhile, you've hit your green streak. It's so much easier for you, he tells himself. You get greens every time the game is rigged, so what's the point?

He quits. So who got the die with 20 sides? Who got the die with 200 sides? If you get the game, then you see, once you roll enough times, the die you're given doesn't matter. Die with fewer sides. Might roll green sooner, die with more sides. Might roll green later. But a die with a green side always has a chance of rolling green if you roll it.

Every die hits a green streak when rolled enough times All of us get a mini sided die. And looking at the other players, you have no idea if it's their 100th roll or their 100,000th role. You don't know how good other players are when they start. You can only see how well they do now, but if you understand the game, you also know it doesn't matter if you begin playing early.

Others begin playing much later. The rest sit on the sidelines complaining about how lucky the players are. I guess so, but they're luckier because they play. And when they hit red, which they do, they didn't quit. They rolled again. Learning to advertise is a lot like a game of mini sided die. You don't know if it'll work until you try.

And when you start advertising, you probably hit red on your first rolls. But if you try enough times, you will hit green. And when it works, you have a better chance of getting it to work again. The more you do it, the easier it gets. You begin to understand the game. No matter how many players there are or the number of sides that you're on the die that you're given, you start to see the only two guarantees one, the more times you roll.

The better you get two. If you quit, you lose. This is the definition of an infinite game. You keep playing, you will win. You win by continuing to play. Is luck involved? Sure, there's some luck. Some people will roll the read more. Some people will roll the green more, or some people roll the green faster.

Some people will get ahead. Or at least what you see as ahead or perceive as ahead faster. All of those things are true, but at the end of the day, you're playing the game to win for yourself. You're not playing a game. That's comparison to other people. You're playing the game to win for yourself, and you win the game by continuing to play the game and you continue to play the game, your probabilities get better, your bets get better, your skills get higher.

You have you have more. You have more experience to leverage as it goes on. You get more greens. You get luckier. You get luckier because you continue to play the game. But the really important lesson to me here is as you go through the process, you're going to hit like walls, you're going to hit obstacles, you're going to hit challenges.

You're going to have to change markets. You're going to have to change a product. You're going to have to fire somebody. You're going to have to start over on something. You're going to think, this shit doesn't work, and you're going to roll, read, read, read, read, and you're going to say, fuck it. I'm just going to get a job.

For many people, that is perfectly fine. This is not a judgement on whether you quit and go get a job like that's like that is not like. But if you want to win in business, if you're determined to win in business, then what you do is on a streak of reds. You roll again and you keep going and you recognise along the way I'm just rolling.

Red's like there is a green. As long as there is a green on the die, you have a chance and you can keep playing. And at least for me, like I'll say this for myself, recognising that is the best mindset hack that that I have that I can think of, because there's no way to play this game without some hardship and without some frustration, without some risk and without some losses.

But when you recognise that that is part of the game and that hitting those things is not a reflection of you losing the game, but it's a reflection of you simply playing the game and making progress, knowing that there is a green around the corner, then you're in good shape. So that's something that hit me kind of hard.

The original message I read to you, uh, hit me pretty hard. And the response? Um, when I, when I had I can still stand by it, but I think this encapsulates what I really want to say and what the real lesson and what the real takeaway is, is that you keep playing. There's no way to lose if you keep playing, even if your business doesn't win or turn out the way that you want to, you will be a better person and develop skills and develop, um, experiences and things along the way that are going to be useful in other places and in other ways, however you choose to apply those.

The single worst thing that you can do, in my view, is Quit and attribute your loss to other people being scammy, other people being, you know, lying to people, other people simply getting lucky to me. If you quit, if you choose, if you're tired of rolling, Red's fine, like, okay, you know what? I'm gonna go get.

I'm gonna go get a job. I'm gonna get a paycheque. If you do that, I mean, even if you go that route to me, the the least healthy thing that you could do is walk away and let something like that be your excuse and your rationalisation and the energy and the frequency that you bring to to future conversations.

So that's my take on this whole thing. Um, I hope it helps or resonates in some way, shape or form. Uh, if it has subscribe to the channel. And if you want to hop on my weekly newsletter, there's a link in the description below. Feel free to do that. Send out sales tips, growth tips every every Sunday, and I'll see you there or in the next video.

Adios.

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