The Entrepreneurial Life Cycle That Will Make You Poor Or Rich (on DOAC Pt 2) | Ep 840
episodePreviously titled “The Entrepreneurial Life Cycle That Will Make You Poor Or Rich (on DOAC Pt 2) | Ep 866” — renamed by the publisher on Aug 2, 2026
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What is the entrepreneurial life cycle?
Welcome back to the game. This is part two of the guest spot on Diary of a CEO with Stephen Bartlett. This is a ton of fun. This second half, we talk about the entrepreneurial life cycle. It has six stages. You will be stuck in it forever until you break free. I was stuck in it for years. And I will say this, it does rear its nasty head multiple times. I have to fight it actively. This, I mean, this year I was talking about it last night. It's one of those pervasive things that I don't think you solve. It's something that you manage. On top of that, we talk about experimentation in the form of how you beat competitors and how to do that in a way that makes it harder for them to keep up with you.
And so the last thing we talk about, we actually zoom all the way out and we talk about work, life, balance, happiness, fulfillment. And I think it's one of the more clear moments I've had on a podcast in a while. I've got a lot of feedback from people from the last 20 minutes of this particular podcast, and it's, you know, three hour plus podcast. And so the fact that people got there, and then that was the part they were talking about, I think is good. But if you ever get criticized for how you work, how you approach life, you might enjoy it. So enjoy.
Well, I want to go through the four R's, but I also, I think that what comes before the four R's is knowing how to get customers in the first place, which was a tricky one. And actually, maybe even the thing that comes before that is being psychologically prepared for the toll and the rollercoaster that business is. I found this graph of yours.
Oh, God. Yeah.
And I think for any founder starting a business, it's important for them to understand this cycle. I think you call it like the crash-burn cycle or something. Because if you're not aware of this cycle, when you hit certain parts of it, you're probably going to think that there's something wrong with you. Yeah. But there's a certain inevitability to this crash cycle. I'll put it on the screen for anyone to see.
Yeah. This is the entrepreneur life cycle until you learn how to break free from it. And so there are six stages here. You have stage one, which is uninformed optimism. This is where you see your friend or you see something online and it looks like they're making money or it looks like there's some opportunity and you think, oh my God, that sounds amazing. And you have optimism because it looks great, but it's uninformed because you have no idea what it entails. So then you dive in and you say, okay, I'm going to pursue this thing, whatever it is, baking cupcakes, or I'm going to do lawn mowing, or I'm going to do crypto trading, whatever. Okay. Second step is you get into it and you're like, oh my God, I don't know.
There's so many things involved in this and this is significantly more complicated than I expected. So then you become an informed pessimist. You now know that it's hard or significantly harder than you expected. The third stage is you have your crisis of meaning or the valley of despair. So you're continuing to do this stuff. It's continuing to not work. And you keep working. And it keeps not working. And so this is the step. And this is the point of truth. And this is the cycle where the paths of the entrepreneur split. And the vast majority of people take this next step, which is they then say, you know what? There's that thing over there that my other friend's doing. Maybe I should do that instead. And so then they hop back to uninformed optimism.
And then they go, boom, to informed pessimism. And they just go around and around and around. And they live the same six months for 20 straight years. Now, the other path from the valley of despair is sticking with it. And so then you become an informed optimist because now you understand, you still understood all the bad stuff, but you also understand the good stuff and how to avoid the bad and maximize the good. And then once you're there, you stick on that path long enough and you end up achieving what you originally thought was really easy and fast.
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