A short YouTube monologue advising solo entrepreneurs to externalize decision-making by role-playing key stakeholders using 'empty chairs' (customer, investor, employee). The speaker recommends speaking out loud to simulate stakeholder questions—illustrated with a pricing example—and argues this reveals new considerations, communication needs, and risks (especially for irreversible decisions).
Chapters
As a solo Entrepreneur, you're making 99% of your decisions just in your head, okay, this is what I'm going to do. This is how I'm going to do it. And you're thinking about your customer, your investors, you're thinking about your employees, but you're thinking about it in your head. And you think you're thinking about them, but actually you're not. You're really thinking about you, your company, your solution, and your next milestone and accelerating scale. And so by default, you're thinking about your company outwards, out to your customer, out to your investor, out to your employee, out to your other stakeholders. And the easiest way to actually make sure you're truly thinking about it is to essentially make sure you have two empty chairs. Empty chair number one is your customer. Empty chair number two is your investor. Empty chair number three is your employee. As you go through your decisions or the things you want to make, you turn to that chair and you role play. And I get it, it's a bit weird. But doing it out loud, not in your head out loud, and talking about it will open up net new questions, net new things that you need to think about. Net new ways you might communicate it. You want to increase your price, you turn to the customer chair, hey, we want to go, you know, increase our price 20%. The customer is going to say to you, what? Why? How are you going to communicate it? How much time do we have? You know, are you creating more value? Am I going to get more features? And as you think about the questions the customer is going to ask, you can think, okay, that's a good point. How do I need to communicate it? How do I need to talk to it? How do I need to make sure that I'm being fair to my customer? Are my existing customers going to be given legacy pricing, or is this just for new customers? It allows you to role play and simulate, which by default, which will help you think through the idea better through the eyes of the customer. And I get it. You're thinking, really, am I going to just sit and talk to a mirror and an empty chair and actually role play? And the answer is yes out loud, not just in your head. You will find very, very quickly net new opportunities to make better decisions, to better communicate your decisions, and to think through the impact of those decisions. This is especially true if some of your decisions might be irreversible. Look, if the decision is something that you can change and pivot quickly, if you make a mistake, cool beans. But if it's a decision that's going to have, you know, lasting or one way impact. I think Jeff Bezos called it a one way door, a two way door. Have those two chairs turn to your investors. We're going to raise our price. What are the investors going to say? Some of them might say, fab, maybe you make more money. One of them might say, well, are you creating sufficient value to do that? Should you consider keeping the price the same and instead focusing on more users? I'm not saying that you don't know these answers. I'm just forcing you to go through the role play because doing it out loud is a game changer and will help you. A bit weird, but will help you, I promise. Good luck.
