How to Build a Self-Sustaining Business with Jason Duncan

December 01, 2025 00:15:59
How to Build a Self-Sustaining Business with Jason Duncan
Simple Wins
How to Build a Self-Sustaining Business with Jason Duncan

Dec 01 2025 | 00:15:59

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Show Notes

Are you feeling trapped in your own business, where stepping away means everything falls apart? You're not alone. In this episode of Simple Wins, America's Exit Coach, Jason Duncan, reveals the simple yet critical steps to transform your owner dependent companies into valuable, exitable assets—without needing to sell.

Jason stresses that relying on you, the founder, as the "hero" actually puts your business at peril. If you want true freedom and a predictable future for your team, you must shift your mindset and build a self-sustaining system. We dive deep into the first actionable steps you can take today, starting with mastering delegation and creating a reliable predictable revenue model.

Here’s what you’ll learn:

Jason Duncan is a TEDx speaker, bestselling author of Exit Without Exiting, and has helped countless founders reclaim their freedom by building businesses that can run without them.

Make sure to go visit Jason at therealjasonduncan.com

If you enjoyed this episode, please consider leaving a 5-star rating.

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Episode Transcript

Adam O'Leary (00:00.984) If you're business owner struggling to step away from the daily operations without losing ownership or profits, then our guest, Jason Duncan is about to give you a simple win you can implement today. The real Jason Duncan is a TEDx speaker, bestselling author of Exit Without Exiting, and America's exit coach who built a multimillion dollar business only to discover it was worthless because it couldn't run without him. Featured in Inc and entrepreneur magazines, He helped business owners reclaim their freedom by transforming owner dependent companies into valuable, exitable assets without the necessity of selling. So Jason, so glad to have you here. Really excited for this podcast. The Real Jason Duncan (00:42.092) Thank you for having me here, Adam. Adam O'Leary (00:44.204) Very cool. So I've heard you discuss how many entrepreneurs feel trapped in their business, unable to step back without everything falling apart. So why is it so critical for business owners to shift from being the hero in their operations to building a self-sustaining system? The Real Jason Duncan (01:00.942) Well, I think if we want to get real with one another, it's selfish. I mean, you could think about this. If you've had a business and let's say it employs 10, 15 people or maybe more, maybe a hundred people, yet the business relies on your heartbeat. Like if you don't show up, it doesn't work and you get hit by a bus, you've selfishly protected your own interest to the exclusion of taking care of all your employees and their families and all that. So not only do you and your family go through the suffering of you being sick or debilitated or dying, but now your company dies as well. And that's selfish. Now, I don't think anybody does that on purpose. I mean, you can look at the data and see that people aren't generally doing that where they're trying to put people's lives in danger because that business is too reliant upon them individually. But that nevertheless is the outcome. interviewed a guy on my podcast a few years ago named Dr. Sasha Becker, and he's a professor at Monash University. And he studied over, it was over 1500 founder deaths across like 73,000 companies. And what he found is that when the founder died, even when they knew that was going to happen, like you got cancer or something happened, it got sick. The companies, when the founder died, had a permanent degradation of revenue of 60 % and employee count dropped 21%. And even five years later, the companies that were the ones that still survived still weren't doing any better as compared to their counterparts whose founders were still alive. And that is all the evidence we need that we have to build companies differently if we want to take care of them beyond our own lifetime. Adam O'Leary (02:45.562) So let's say if I'm a founder and I'm looking to take the first step into trying to make my business run independently. What is that first step? The Real Jason Duncan (02:53.774) Well, the first step is going to be you have to get your mindset right because what you think about you bring about so if you think that you are the hero of the business and you have something I refer to in a book as hero syndrome, you know, you're the one in charge everything all the fires get put out by you all the damsels and distress get rescued by you like you're the Superhero that swoops in and saves the day if that's what you believe deep down that you are and that you always should be Well, you're going to operate that way continuously. So no amount of systems and processes and team building and hiring is going to fix that. So first of all, we've got to deal with your mindset that you cannot be the hero of the business because the heroes of businesses actually put businesses in peril. But practically, Adam, the first thing you have to do is you've got to learn how to delegate. You have to understand what that means and how to do it. And then once that's firmly a part of who you are, and it's probably not what you think it is, most people think it's something different, but once you firmly understand what delegation is, then we can move on to things like, well, now we got to look at hiring your support squad. Then we got to look at hiring your A team. Then we got to look at how do we put systems and processes in place? And then we've talked about how to create passive income through the business. And then we can talk about stepping away fully from day to day operations. Adam O'Leary (04:11.152) So what are some of those systems that need to be put in place? Like if we're looking at the operational side of things and say if it's a founder who might have a few contractors, they're not established business, what do you think is the first processes that should be put in place? The Real Jason Duncan (04:27.564) Well, I think it's going to be different really, truly for every industry, depending upon the number of contracts that you work on, whether it's B2B, B2C, it's going to be different based on whether or not you work in a certain geographical location. I will put that caveat out there. It really does depend. But I would say that every single one of us could agree that one of the processes and systems that have to be in place is a repeatable, predictable revenue creation model, otherwise known as sales and marketing. So we have to figure out how to get sales and marketing dialed in in a systematic way that it doesn't depend on a single person's input to make happen. And that's unfortunately a lot of it. That was my story. When I was, when I started my company in 2010, I started it as an unemployed school teacher and I had spent years prior to being a school teacher. I'd been in sales. I had also been a post oral ministry. So I've got four careers, but But I'd learned how to sell and I knew how to sell. So I was just banking on the fact that I could build a company because I know how to sell. I was the number one salesperson for years in my company, which is one of the reasons why we made a lot of money, but also the very reason why I couldn't sell the business even though we were making a lot of money because I was the number one employee of my own company. So you got to figure out how to put in place a predictable revenue model. Like how do you get predictable revenue where it doesn't require a single person, specifically the founder? Adam O'Leary (05:56.16) So I was literally just having this conversation with somebody today and I'm so curious to hear your thoughts on this. So most founders that I've seen is exactly the same thing. It's nobody can sell better than me. Okay, so how do you go about hiring those first one or two sales reps and making sure that they are able to sell in a repeatable way? The Real Jason Duncan (06:18.85) Well, you know, anybody is not an easy job. And that's one of the reasons why in my mastermind, we've partnered with a recruiting firm because we feel like that they're professionals. do this all the time. So we recommend, you know, people work with a recruiting firm because it just makes it easier. Yes. Is it more expensive on the front end for sure, but it saves you a ton of time that you pull you pull back later. So, but practically speaking and tactically speaking, if you're talking about that salesperson, You have to spend a lot of time. If you're the number one salesperson, you got to spend a lot of time putting and on paper, the process is documenting the process that you use to sell. So you can't just expect that your brain, the thing that goes on your mind, what you know how to do will automatically translate because even a great salesperson who comes in and sold millions of dollars, they don't know your system. They don't know your products. They don't know your, your, your methodology. They don't understand the vision. You have to. document that and give that to them and help them understand that. So I'm actually, truth be told, I'm going through the process of hiring my first ever salesperson for this company. Now I've hired dozens in the past for other companies, but for this company I'm in the process. And going through that process as I onboard this salesperson, what I have to do is I've got to spend a ton of time. So for example, I told the person when I hired them, I look, for the first month and we all, we're all remote. We all work from home. We have an office, but we don't use that as a meeting place or a work center. But I said, this first month, you could just bet on being in my home office five days a week, every single day for a month. And why? Because you have to, like, we're gonna need to be elbow to elbow for a while so that you can see what I do. You're gonna watch me take sales calls. You're gonna watch me on camera, just like what I'm doing with you on the podcast. I do the same thing with potential prospects. You're going to watch me do this. You're going to read my sales manual that I put down because I have everything listed, everything that I do. I've got a 21 page document on the script or template, whatever you want to call it, that I go through clients or potential clients with like you, there is a lot to do. So what I would say is you cannot halfway this or fill in with a blank, whatever you want to say. You can't do it halfway. You have to fully invest everything that you can. The Real Jason Duncan (08:41.422) in those first 30 days of that salesperson. And once they get it, okay, now they've got it. And then you're going to duplicate that. You're going to do that with three or four people as the company grows because you cannot rely on a single person. It can't be you. There can be no single points of failure. It can't be you. It can't be a salesperson. There's got to be multiple people handling that. Adam O'Leary (09:00.039) I love that it actually reminds me of when I first started sales the it was an online job remote job like this and What ended up happening is when I started so I was listening to way that he was doing stuff and what we ended up doing is we would loop the audio so we had like a room and we would loop the person's audio and we'd basically be on these rolling like 16 hour calls so he could literally listen in and give me feedback live as we were talking I mean, that's how invested he was into me And it allowed me to scale and be able to drive insane amount of money for them. So I really, really appreciate you saying that, Jason. The Real Jason Duncan (09:32.162) That's Good for you, man. That's awesome. That's a great system. Now Intuit of course has much bigger budget and many more leads coming in, but that's a great, that's a great idea. Adam O'Leary (09:43.726) Absolutely, no, a hundred percent. And so when you're looking at scaling these systems, so let's say if we go ahead, we don't have the single point of failure, we now have multiple sales reps, how do you go about, I guess, scaling this up? So we have the first two sales reps or first two marketing guys. What's the next step in that? The Real Jason Duncan (10:03.054) Well, so I think your question presupposes that scaling means exponential growth. We're just going to add more salespeople, add more, add more and more. Well, the reality too, I think that I found in my couple of decades as an entrepreneur is that you don't have to scale the way that Instagram and TikTok gurus tell you. That's not what's required. The hustle and grind mentality is so prevalent and so dangerous to healthy businesses. I'll give you a quick example of my point and then I'll answer your question. So we just had our mastermind retreat with my clients in the Smoky Mountains this past weekend and one of the people that was there, one of my clients, he got really emotional about the fact that he spent years building his business and lost two very important relationships in his life. And it's not my place to tell what those were or who he is, but nevertheless, It was very emotional and he turned and he looked at me and he said, this should be one of the selling points of your program because had I had your program before all this happened, I would still have those relationships in my life. He said, sure, my business might've been in a different place, but I would rather have those relationships than my business being where it is now. So I think this idea of scaling needs to be qualified. So, but your question is, How do you scale that? Well, again, I think it depends on what you're attempting to do. If you're running a potentially multi-billion dollar organization, you're going to have to have dozens, if not hundreds of salespeople on the phones or out in the, you know, feet on the ground doing that. And the scaling of that needs to be methodical. It needs to be planned and it needs to be on purpose because these are humans that we're talking about. These are not just dispensable things that we can come in and if it doesn't work, we throw them away. Too many companies and corporations do that. They'll They'll hire 50 people and they'll throw them at the wall like spaghetti and hope well, if they stick, they stick. If they don't, they burn out. That's not an integrist way to do things. I don't believe. So I think the scaling model depends on the level of company that you are, what you're trying to accomplish. But nevertheless, it needs to be repeatable. It needs to be methodical. It needs to be systematic. And it needs to be documented because that's what's going to make your company worth more if you end up selling it anyway. Adam O'Leary (12:22.085) So what you're saying is it's the documentation that is actually the saleable asset. It's not necessarily the individual. Is that correct? The Real Jason Duncan (12:30.338) Well, it's part of it because you can have it documented, but if nobody's following it, then that is going to reduce your valuation. But if you have a documented repeatable processes and those are transferable and the buyer, I mean, put yourself in the buyer's position. Let's say you've got a few million dollars and you want to put cash into a business and you go look at the business, you find out, yeah, the founder has three ring binders all throughout his office and everything's documented. Well, that's great. But if nobody follows that, nobody knows it. They're really not worth anything. But if he has all those three ring binders and you can randomly pull an employee out and say, Hey, what's the vision for the company or what's kind of the three step process for bringing customers on board or what's the blah, blah, blah. And they can answer at least semi coherently. That's something that you and I as an investor would look at and go, okay, this is worth something. Cause I'm not buying the job. I don't want to go in and buy a company just to buy a job on a buy company that runs itself. Adam O'Leary (13:26.125) Absolutely, and I guess for all the listeners right now, what would you say is one simple win that they should do today? Not this week, today. The Real Jason Duncan (13:33.518) today, pick one of your most important things that you do on a regular basis. Whatever it is, it could be sales, which we've been talking about. It could be accounting, could be finance, it could be administration, whatever. Pick one thing that you're already doing, not making stuff up, just one thing that you're already doing, spend 45 minutes writing down the process. Step one, step two, step three. You don't have to get super detailed. You could probably do it in 15 if we're honest, but just you know block out 45 minutes and then when your 45 minutes is up you're done just go away. It doesn't matter if you finish the document just walk away only spend 45 minutes document it every step of some process and see what you can find. I bet you'll find that this wasn't that difficult and now that you've done it for one you could probably do it for every doc every process in your in your business. Adam O'Leary (14:22.594) I love that. And what sort of results have you seen from your clients implementing these types of processes and where can people go to learn more about you? The Real Jason Duncan (14:31.224) So what I see when people do this, Adam, is they get the one resource that everybody wants more than anything, they get that back in droves, and that's called time. I'll give you a real example. I've got a client I work with who runs a very large insurance company. And just like most entrepreneurs, he's a workaholic, works a lot of hours, loves to work, loves his job. There's nothing about it that he doesn't enjoy. But as we sat and looked at his schedule, we found out he's working 60, 70 hours a week. And I saw, showed him what we could do if we started documenting things and worked on his focus management, which other people would call time management. And we looked at that and what we discovered through the process is that we found an entire eight hours of his week that he could get back if he just did this process. Eight hours, I mean, that's a full day of his life that he got back simply by documenting. So if I told you, could get everything done that you've ever done in the past six weeks, six years, but you could now start doing it four days a week, would that be interesting to you? Probably. So let's get on it. Let's do this. Adam O'Leary (15:44.578) I love that and what's the best website people can go visit you at? The Real Jason Duncan (15:48.312) So you can, if you just Google or you AI the words chat, if you go to chat.gpt, if you just AI the words the real Jason Duncan, you will find me anywhere and everywhere. my media kit's out there, my website, you can read my book, you can see me on social media, all at the real Jason Duncan. Adam O'Leary (16:06.998) Amazing. Well, Jason, so glad to have you on. Thank you. Thank you. Thank you so much for jumping on with me today. The Real Jason Duncan (16:12.204) It's been an honor. Thanks Adam. Adam O'Leary (16:13.923) Absolutely, well guys, thank you for listening and I will see you on the next episode of Simple Wins.

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