Episode 206: Start the Business or Stay Safe? The Decision That Changes Everything
Are you stuck between the desire to start your own business and the fear of losing stability? You’re not alone. In this episode of The Today Counts Show, Jim Piper Jr. and Winston Harris tackle one of the most life-altering questions aspiring entrepreneurs face: Should I finally start the business, or should I play it safe?
Together, they unpack the real tension between entrepreneurship and security, exploring what’s actually at stake—financial risk, personal growth, purpose, and long-term impact. If you’ve been waiting for the “right time” to launch your business, this conversation will challenge your thinking and give you the clarity you need to move forward with confidence.
In this episode, you’ll discover:
How to know if you’re truly ready to start a business
The biggest fears holding entrepreneurs back (and how to overcome them)
Practical steps to transition from idea to execution
Why playing it safe might be the riskiest move you can make
Faith-driven insights on calling, purpose, and taking bold action
Whether you’re a side hustler, a leader feeling stuck, or someone with a dream you can’t shake, this episode will help you answer the question: Is today the day everything changes?
🎧 Tune in and start building the future you’ve been putting off.
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Today Counts Show Episode 206
Preview
Winston: Let’s just say the person who’s, “No, I’m starting this business. I got this burning thing in my gut. I got to get it–.”
Jim: Yeah. “Shut up, J. I’m going to do my own thing.”
Winston: “I got to get it out.” And you slapped him in the face with that. Somebody just heard that and was like, “Wow, what a buzzkill. That’s unfortunate, but I’m doing it anyway.” What about the psychological or the emotional cost of not trying?
Appreciation of our Supporters
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Introduction
The Big Question: Should You Start?
Every great company started with one person who decided not to wait. But for every Bezos, there are thousands who lost everything. So, should you leap? Should you take the step? Should you start the business, pursue the dream?
That’s what we’re going to talk about today. My name is Winston Harris. I’m your co-host here at the Today Count Show, joined by the man, the myth, the legend, Jim Piper. How are we doing today, Jim?
Jim: Well, that always makes me insecure when you say that. Jim is doing well. It’s a lot safer to speak in third person. I think he’s doing well today. His pulse is fine. He has a good attitude. I think he’s okay for the day.
Winston: Looking good. Repping the Detroit Tigers.
Jim: Yes, I am. I got this for my birthday.
Winston: All right. Recently, happy birthday.
Jim: Happy. Thank you, sir.
Jim’s Entrepreneurial Experience
Who Should Even Talk About Entrepreneurship?
Winston: Recently celebrating a birthday. And speaking of birthdays and things that are being birthed, the desire for those who maybe want to venture out, maybe somebody’s listening or watching this and you feel like maybe you’re kind of stuck in the nine-to-five grind or you’re in a place where you think there’s more in you, or maybe you’re just kind of frustrated and want to kind of shirk off being led by other people and you kind of want to be the leader for whatever reason, and you have this desire to be an entrepreneur. We’re talking about entrepreneurship today.
And Jim, you have some experience on this. Why are you, of all people, qualified to even speak into this space?
Early Ventures and Lessons Learned
Jim: Well, the first thing that went through my mind is when you were talking about the nine-to-five, be your own boss. You didn’t say this, but you’re tired of working for somebody else’s mess. You might as well start your own mess, kind of a thing. A lot of it depends upon where somebody’s at in life and how they might track with our conversation today.
I mean, if you’re in high school, do you go work at Burger King or do you try to start your own thing? I’ve definitely got some opinions on that. But if you’ve got two kids and a mortgage and a family, it’s a little bit of a different conversation.
Winston: Yeah. And you’ve started some, a lot.
Jim: Yeah. I mean, who hasn’t mowed lawns? Maybe the kids today haven’t, but–
Winston: Shout out, Gen Z. Pow, pow.
Jim: Maybe that’s obviously below them. But the first true entrepreneurial effort that I did, if you push away the mowing of yards and raking of leaves and all of that, when you’re 12 or 10 or however old I was, was in high school. And it was a legitimate firewood business.
Winston: Wow. I don’t even know what that means.
Jim: Yeah. It’s a lot of sap on your hands and a lot of dumb mistakes, but actually you can make a lot of money doing that.
Larger Ventures and Turnarounds
Winston: And what would you say has been your greatest quote-unquote venture, or maybe largest, or most requiring the most effort? What entrepreneur venture have you come into?
Jim: Yeah, I would say that it was somewhat safer, but once I went through a period of being a business banker and learned a lot about business in general, starting and turning around businesses kind of became a forte for me, either as somebody with their hands a little bit off of it, as consulting, or somebody actually doing it. I’ve done both.
But to answer your question, I would probably say I entered into a couple of arrangements where they were turnaround situations, which is very similar to entrepreneurialism. If we failed, then I would have lost the time that I put into it, so not necessarily hard money, but time. But the reward was great because I received an equity in the company for turning it around and saving the company, if you will.
Autonomy vs. Business Reality
The Desire for Freedom and Purpose
Winston: Gotcha. I definitely have none of that experience. Not qualified to speak into it from that direction, but I hope to speak for maybe the person who is out there and, once again, they’re wrestling. They’re thinking about, man, what would it look like to start that business? Or maybe they’ve already kind of decided, but they’re looking for maybe some perspective about being an entrepreneur.
And maybe one space here to address is this desire for autonomy and purpose, this desire to kind of, you mentioned it already, be your own boss. I think there’s a lot of people out there that, especially we just did a podcast that’s already out about the culture of work and just getting stuck in this space of not really looking forward to the work that you get to do and not really looking forward to the environment that you’re kind of at some point feeling like you’re forced into. Maybe somebody wants to break out of that and create their own environment, create their own mission, have a little bit of freedom.
So what would you say to that person who is really driven by that idea, that reality that maybe the grass is greener on the other side and you want freedom?
Passion vs. Running a Business
Jim: No, that’s really great. It’s going to sound like I’m against you starting a business. I’m not. But boy, do I have all kinds of red flags and warnings and dumping cold water on you. I’ll give you some broad examples. A lot of times people confuse what they love doing with running a business. They are two different things.
Winston: So there’s a difference between a hobby and work.
Jim: Yeah. Hobbies can be very expensive, especially when no one participates other than yourself. Let me break it down to you in hard numbers. If I were to say that you started a business where you had 30% margins, which would be pretty high, meaning that for every $10 that comes in, you actually make $3 of profit. If you’re able to do that, that’s a pretty good margin after all is said and done.
So, in this economy, in this day and age, you’ve got to bring in about a million dollars to gross $300,000. That’s a lot of sales. One million dollars at 30% margin gets you $300,000 in gross income. So, do the math. It is not, “Oh, I’m just going to open up my stand and people are going to come running me over, throwing money at me, and I’m going to have that.”
But so my comment about mission versus running a business is that you might have a mission to save the world, but if you haven’t figured out how to run the business of saving the world, not only is your mission going to fail, but it’ll be self-destructive.
Can You Just “Figure It Out”?
Winston: So maybe I have the mission, but you’re telling me I need to figure out beforehand how to execute that mission. Is that right? Why can’t I just start it and kind of figure it out? I feel like you hear all these stories about, you just kind of figure it out. Are you discouraging that idea? Are you saying that I can’t just figure it out?
Jim: Well, you hear some success stories where everyone kind of, they’re trying to pretend all humble, and they’re saying, “Gosh, we didn’t know what we were doing in those days, and we just stumbled upon all these zillions of dollars.” And I just start vomiting about that time.
And I suppose that can happen, but I don’t. I mean, I’ll say this. I have invested significant money of my own in partnerships in entrepreneurialism and have lost every single dime. Just because something made sense to me doesn’t necessarily mean that the market agrees.
Market Demand vs. Personal Passion
Winston: So I can’t just, man, I really love gardening, and I can’t just open up my greenhouse? So you’re saying I have to actually consider the demand. I have to consider, do people really want this? I can be really passionate and really gifted. But that doesn’t equate to–
Jim: Yeah. What does the world need? What does the world really need? That’s one of the questions that somebody has to ask versus what do I like to do? In other words, if you have the right mindset, you might be able to run a business and be successful at it because one of the first things you recognize is there’s a big difference between what you like, what you need, versus what the market likes and what the market needs. And you have to differentiate yourself from that.
Detachment and Better Decisions
Winston: So if I’m hearing this–
Jim: Let me say it this way, Winston. To be a really good business person, you almost have to be agnostic to the product or the service in order to know whether it’s something that you should put effort towards.
Winston: Okay, that’s kind of messing me up. So, I want to double click on this. Are you encouraging me that I would be more successful if I was less attached to what I was doing potentially?
Jim: I would say you might make better decisions.
Lifestyle Business vs. Scalable Business
Winston: So, if I’m wanting to start a business, I maybe shouldn’t start a business around something that I am highly connected to.
Jim: Maybe, right? I mean, maybe. If you buy a franchise, if you decide, “I’m going to buy 10 franchises of ABC sandwich shop,” you’re probably doing that as a business decision, not because you love sandwiches that much.
Winston: But what about the person who really loves something? And once again, they’re working the nine-to-five job and they have this dream or this desire. Maybe they don’t want to be the biggest in their industry, but they do want to create essentially this level of freedom and autonomy in their life where work-life balance and all the things, where you want to create your own schedule and, once again, you want to be your own boss. That person, what do you say to that person?
When a Business Becomes “Just Another Job”
Jim: Yeah, that person needs to think about these kinds of things. One is that if you are starting a business, the limit of the business is simply going to take care of your economic needs. If that’s its greatest expansion vision and all you’re really doing is buying a job, right? And then when it comes to the autonomy part, maybe you’ve overestimated the autonomy part because if you want to go on a significant vacation, then who’s going to run your shop?
Winston: It’s not going to run itself.
Jim: It’s not going to run itself, and your shop doesn’t write you a check. You’re the one that writes yourself a check. And you only write yourself a check if you got money coming in. If you’re the one that’s making money come in and you go on vacation, there’s no money coming in. There’s no one to write you a check. So, at some point you have to think through scaling.
You don’t have to think about becoming the next Nike, but you got to think about, like I said before, if you build a million-dollar-a-year business and you want to live in upper-class, upper-middle-class America, that’s what you got to do. You got to bring in a million dollars a year. So, you need to think about that. Is it easier to make $300,000 in the corporate world or to start your own business?
Low-Cost Startups and Reality Check
Winston: Well, what about if we get into, we’ve done a podcast on AI now, and there’s all these resources and tools compared to previous generations where, in theory, and you see podcasts and you see all this content out there, it just seems like it’s pretty cheap to start a business, to start your own thing. So, why not? Why not take the chance and just jump in, especially if it seemingly doesn’t cost that much?
Jim: Yeah. You can go through the proof of concept yourself. Meaning, you could try something, and we call it bootstrapping, where you start with very low investment and you kind of do it on the side. But the statistics are just really clear that in order to launch something, it’s kind of an all-in type of mindset. In fact, to get to this million dollars, in most cases, and I would say to me, if you don’t see how you can bring in a million dollars a year, you probably shouldn’t start.
Winston: Wow.
The Harsh Economics of Business Margins and The Reality of Business Failure
Jim: I mean, that’s just my thoughts there. Depending upon the business model, but if you’re selling widgets, whatever those widgets are, or services, and you don’t have that strong built-in margin of 30%, because, for example, restaurant is somewhere between one and 5% margin, and you think about all the food that you got to serve to get to that percentage, and if you think that you’re living a certain kind of lifestyle owning a restaurant, you live at the restaurant, right?
But the sad commentary is that the majority of businesses fail. For example, I’m looking at stats right here. It says 20% fail in year one, 50% by year five. But let me qualify that. Fail means, in this definition, that they have decided to close the doors.
How many get past five years and all they’re doing is surviving? They hate their business, they hate their life, and it’s a constant struggle, but they don’t know how to get out of it.
The Cost of Not Trying and Failing
The Fear of Regret
Winston: So, okay, let’s just lean into that. Let’s just say the person who’s, “No, I’m starting this business. I got this burning thing in my gut. I got to get–”
Jim: “Shut up, Jim. I’m going to do my own thing.”
Winston: “I got to get it out.” And you slapped him in the face with that. Somebody just heard that and was like, “Wow, what a buzzkill. That’s unfortunate, but I’m doing it anyway.” What about the psychological or the emotional cost of not trying?
Jim: Yeah. Well, that’s a great question. And I remember saying when I was younger, “I don’t want to live a life where I would have said, gosh, I wish I would have tried that. I wish I would have traveled there. I wish I would have experienced that.” So I recognize that, and it’s going to sound a little bit like I’m contradicting myself, but entrepreneurship is a bit of a contradiction in so many different ways. It’s not the fast track to wealth, and it’s not the fast track to happiness. Maybe you get a rush, but there’s a lot of setbacks, a lot of exposure. If you are successful and somebody sees you as a threat and they’ve got the money to knock you out, knock you off, it’s easy to do.
So it’s like you’re a little fish in a big pond. Even though you might do something well. Well, I don’t know if I answered that. I don’t know if I answered that.
Can You Fail Well?
Winston: I think there’s something to be said for the person that would rather maybe have failed and can live with the fact that they failed. But I guess I would even ask, is it possible to fail well?
Jim: I mean, now let’s go back to those stories that we’ve talked about. Most of those successful entrepreneurs are not talking about the one attempt that they made that turned into millions. No, their stories are filled with, “Oh, I tried that, that failed. I tried that, that failed.” So I think the entrepreneurial lifestyle is that you have a resiliency to fail and you know that failing is part of the process of learning and succeeding.
Here’s my thing, though. A lot of us just don’t have much of an appetite for failing. And once we fail, we say, “I’m never going to do that again.” An entrepreneur is an entrepreneur. They’re wired.
Winston: There’s a personality–
Jim: There’s a personality.
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Reconciling Passion and the Need for Scale
Testing the Dream
Not everybody listening that is considering this is maybe not considering how they’re built, and maybe there’s a desire absolutely to venture out, but what would you say? What would you recommend for that person to maybe scratch that itch if it isn’t entrepreneurship, but they think it is because this is the only thing that they can reconcile? This is all that you see. This is all that you hear. “Oh, my friend started a business.” And they’re wanting to just maybe mimic what they’re all seeing, but how do you reconcile this?
Jim: Yeah. Now, let’s go back to that hobby part-time thing. Maybe that’s the way to do it. So, if you find yourself going out to the farmers market on Sunday morning or Saturday morning or whatever they’re doing it to sell the new jelly that you created or whatever, and then after six trips of doing that, you’re going, “Yeah, this is a pain in the butt.” And after adding it all up, I made $50. All of a sudden you lose interest in that dream of jelly. Well, you probably got your answer. You don’t have that burning desire to make this jelly empire, and you’re going to overcome it at all odds.
There’s a fond hearted approach, and then there’s the on-fire approach. Some of the best products and services that I’ve ever experienced have actually come from that fond hearted person who wanted to make the world better. Unfortunately, they just failed in business because they couldn’t figure out how to do it in a way where they kept the quality where they wanted it to.
Values vs. Scaling
In other words, they held on to the quality. And good for them, they didn’t sell it to the devil, so to speak, who knew how to get it out there and make more money. That’s not what they wanted because, gosh, if you study any of the stories, the McDonald brothers and Ray Croc, they fought about real milkshakes versus the powdered stuff. That’s a good example. The McDonald brothers fought to the bitter end. And then, of course, that story changed a little bit when Ray Croc had taken over that deal.
So there’s a lot of soul fighting that goes on, right, and what you want to do. That’s why sometimes there are folks who start their own business and they’re not interested in making $300,000 a year. In that case, they want to provide a good product, a good service. They want to be able to feed their family, and that’s what they see for themselves in life. That’s a wonderful thing. I just think that most don’t think that way. Most think it’s going to somehow magically grow bigger without a true business plan that can scale.
Building Teams and Raising Capital
Winston: And when you talk about scale, and you’ve kind of implied it in different ways, but with a person once again who is wanting to either serve people well, but also be really successful, how much of learning how to build a team and hiring appropriately–?
Jim: Debt and investment. The only way you can raise the money to do bigger things is either you have it, you borrow it, or you receive it and then you give back some of the ownership to it.
The Reality of Funding a Business
Winston: What do you mean by that?
Jim: The equity piece?
Winston: Yeah.
Jim: So, all right, let’s say that I find out that the jelly—it’ll go back to the jelly maker, or the jam maker. That’d be better. The jam maker finds out that, you know what, this is going to go. I believe it’s going to go. So they lease a little spot in town, and then they do some research on what it takes to buy manufacturing equipment. That manufacturing equipment costs them a half a million dollars, and they don’t have a half a million dollars. So how are they going to get a half a million dollars?
I can tell you right now, there’s no bank in the world that’s going to give them a half a million dollars. So they either got to ask Uncle Bob, grandma so-and-so, and all of that. And the family usually comes to the rescue on some level. But can they come to that? So if they can’t come to that, then they got to try to sell it to what you call angel investors. That’s not going to work, I’m going to tell you right now, because it’s too risky.
So what they’re going to do is they’re going to try to find partners, whether they’re silent partners or not, who, if they raise the $500,000, they give back a portion of the ownership instead of getting paid back. So, in other words, when you start writing checks to the owners, the people that you’ve given part of your company to are going to start receiving some of those checks.
Losing Control Through Equity
Winston: Wow.
Jim: And depending upon how much of the equity you gave away, you’re not going to be able to make these decisions in isolation. You’re going to have to make them as a team. Sometimes that goes against the whole idea of entrepreneurialism. Now you’re not in charge again.
Debt, Investment, and the Real Cost of Entrepreneurship
Hidden Costs and Early Learning
Winston: Well, I’m discouraged. But this is great because I don’t know how often we hear this side of entrepreneurship. We hear all the success stories, we see the status. We see what the young kids call flex, right? All of the benefits of the potential of entrepreneurship, but what is, on the other side of the token, the potential hardship of entrepreneurship? What is the real cost of entrepreneurship? What would you say?
Jim: Yeah. Well, let me go back to the beginning. So if you’re young and you’re not doing entrepreneurship because you haven’t made a decision whether you’re going to go the corporate way or whether you’re going to go the entrepreneur way, then, man, you need to get on it because when you’re young, that’s the time to do it. You have less to lose, and you’re going to learn a ton.
When you start learning how to run a business, you learn so much about just about every facet of life. You have no idea what you’re walking into. You also have no idea how expensive it is. Every time you turn around, somebody has their hand out. You can’t do that without a permit. Can’t do that without a license. You can’t do that without insurance, you can’t do that without a bond. You can’t do that. It just keeps coming.
Life Stage and Risk
So I would say that entrepreneurialism is, go ahead and get a job at Burger King for six months. You don’t need it for six. Go work for three months. You’ll get that. All right, then move on and try to start something on yourself. You’ll probably make more money than going and getting a job as an entry-level employee. If you have any kind of skill set, you will make more money doing your own thing than you will working for me and my sandwich shops.
All right? Now, as you begin to learn, if you start capturing some of that business mindset, watch out. You may move into that entrepreneurial mindset. Now, once you get more responsibility under your belt, you have a wife, you’ve got kids, you’ve got a mortgage that you’ve been able to afford through the corporate job, that’s when things get a little dicey because there’s a lot of things that corporations do to, we call them golden handcuffs.
Entrepreneurial Mindset vs. Starting a Business
You get your life to such a place where you don’t have to struggle so much. Now, you’re maybe not wealthy from an American perspective, but you’re wealthy. You don’t have to worry about paying your bills. Your bills are being paid, but now you’re talking about walking away and starting something new.
In most cases, that is not a bootstrap. That usually comes from people who have learned that there are things called private equity. There are partnerships. Now you’re taking your life savings. You’re playing a bigger game. And if you don’t have a coach, an experienced coach or consultant to help you along with that, then I’m scared for you in doing that.
There’s an entrepreneurial mindset that you can apply in corporate America, which maybe this particular episode isn’t going to address, but I would say there’s a difference between starting a business and being an entrepreneur, having an entrepreneur’s mindset.
Fractional Work and Alternative Paths
Winston: What do you mean?
Jim: Yeah, it’s a great question. An entrepreneur’s mindset thinks in terms of seasons, projects, hills, goals, things like that. And they’re not so bound to the company store. This is kind of a new thing. Once that whole loyalty to the employee and to the employer kind of got blown apart, I would say somewhere in the 1980s, it’s been a whole different world.
So if you’ve got a skill set, you might run into an entrepreneur who’s at stage four in their development and they see your skill. If you’re a smart entrepreneur, you’re going to be employed by that person, but you’re not going to be a W-2 employee. You’re not going to get a paycheck. You’re going to get a check, but it’s not going to be a paycheck coming with benefits because you’re kind of running your own show and it’s a separate deal, separate contract on the side. You are going to bring these skills, these products, these outcomes over the next six months, and it’s going to cost that company this.
The Fractional Work Model
So, that’s another way of thinking about entrepreneurship. I think there’s a term for it, too. It almost sounds like entrepreneurship, and I can’t remember the name of it, but it’s really when you recognize that your skill set doesn’t have to be owned by a company. You can sell it to a company.
Winston: Wow. So is that the same as a side hustle, or talk us through your thoughts even on—
Jim: Yeah. Depending upon how fractional you are. What I mean by fractional, for example, if you scroll through LinkedIn occasionally, you’ll see somebody describe their role as fractional CEO, fractional COO, fractional CIO, et cetera, et cetera. And what they’re saying is they’re giving a percentage of their time to that company in that role because that company doesn’t need someone full-time to do it, but you can sell it at a premium.
Let’s say that that role pays $300,000 a year. You might sell it fractionally for $150,000, even though you’re only working 20% of the time. And if you do three of those gigs, now you’re doing $450,000 a year and you’re still working 30 hours a week. So it’s a different kind of mindset.
The Mindset: Running To Something
Escape vs. Purpose
Winston: There’s so much to try to unpack, and I know there’s going to have to be another episode where we get into the real practicals of, okay, this person who is listening or watching is like, no, I’m doing this. How do I do it? And so we’ll address that in a coming episode.
But I kind of want to land the plane here with just some honesty. How do I know if I’m pursuing something just to run away from my current situation, if I’m just trying to exchange environments, or when I’m truly feeling like I have something that is going to be of value, I have something that is worth pursuing?
Jim: Yeah, I read something, I think the book is Unreasonable Hospitality, and that’s the first time I actually heard that phrase: Don’t run away from something, run to something. And it seems like a paradox, right? I can’t quite figure that out because to run to something, you’re running away from something.
But I get the idea, right? I think it’s like you’re quitting because you’re disgusted with it. You’re tired of it. You think it’s stupid. You think you’re being taken advantage of, et cetera, et cetera, so I’m leaving. And the leaving is desperate. So the leaving takes what’s in front of them and naturally sees that as a better thing.
Clarity Before Leaving
So, I think you nailed it. I think that is a really good question to ask. If you’re going to leave—I mean, I talk to people almost every week where someone says, “I am so sick of my job. I’m getting out of it.” Okay, that’s fine, right? That’s fine. That’s fine. But I’ll ask questions like, “What are you going to do?” Right? And often the answer is, “I don’t know what I’m going to do. I’m just not going to do this.”
Yeah. That’s not a good answer. For example, I’m bringing back another episode in our podcast, Winston, with Richard Morales, who was imprisoned for over 20 years. And what he learned is that when you ask people in prison what they want to do when they get out, if their answer is, “Man, I don’t care. I just want to get out,” it’s the wrong answer because those exact same people come right back into it.
Stress Testing Your Plan
But if they have a clear vision for what they want to do when they get out, their success rate goes way up. So I would say that’s almost the same thing. It’s like you feel like you’re in prison, and you just want to get out. You’re going to need to work on that.
Stress Testing Your Financial Assumptions
Here’s another good thing. So let’s say you’re penciling it out on a napkin and you say, “All right, Jim says I can make a million dollars. Okay, I have to make a million dollars to make—I don’t believe that. I think I can make $300,000 a year.” Okay, well, you’re stupid, but go ahead and believe that anyway. But if so, if you think you can make $300,000, then what I would challenge you to do is cut that in half because that might be the reality. So if your gross income is going to be $150,000 and your margin is 30%—
Winston: Why is it 30%?
Jim: Well, that’s just general. Like I said, restaurant, 5%.
Winston: Depending on the industry.
Jim: Depending upon the industry. Thirty percent is a really good margin. In fact, everyone that’s got any kind of business degree, they’re yelling at me right there going, “Thirty percent? Nobody makes 30% margin.” Well, yeah, they do. It kind of depends, but some of my biggest clients, they are fighting to get 10%, right? And the bigger you get, the harder it is. So the more your top line—top line means money coming in, revenue—the more revenue you come in, it’s amazing what it takes to do that expense-wise. And then what you have left over is what we call margin.
So, stress test your finances. If you say you can bring in $150,000 and you do a 30% margin, that’s $45,000 a year. If you can live on $45,000 a year and you’re happy, then okay, go for it. So, I think that’s a really good idea, actually, is stress testing it that way.
Risk Tolerance and Team Thinking
I would say the other thing is even though I’ve come down hard on this, I think you know that I am an entrepreneur. That’s just how I’m wired. I just hate seeing people be so idealistic because I’m a bit analytical as well, and I have failed in entrepreneurism, but my batting average is pretty good. I think others who have a better batting average than me do because they have more tolerance for greater risk than I do.
Winston: Really good.
Jim: Yeah. And so you just got to give them credit. I have a low tolerance for high-risk situations. So, did I do anything in one year where I made a million dollars in that first year? No. That’s not the case. Now, when I say make a million or two million or three million, I always think we. So I tried to put together—and this really wasn’t part of our talk—but when I think about entrepreneurialism, I still think team.
Winston: Wow.
Jim: Because I want to take certain people with me if they want to go. And so we’re not simply talking about one million. We might be talking about the first three years, first five years, or something like that. But if you can start with a team, wow, that’s muscle.
Final Reflection
Serving Real Needs vs. Personal Passion
Winston: Yeah. I think what I’m going to walk away with here is, there’s a lot here, but for the person who is thinking about wanting to start the business, maybe a question to ask is, am I serving my biggest problem, or am I serving the biggest problem I know others have? And if I can answer that question well or confidently, that might give me the pathway, peace, clarity, vision, predeciding, okay, what is this going to be when it actually launches? When it actually starts.
Learning the Business Behind the Passion
Jim: Can I add something to that? What I’d like to say in absolute love is that if you listen to the brightest minds, which I don’t think I’m part of, but if you listen to the brightest minds when it comes to business, they would not discourage you to start something that you like doing. They would just say you might want to brace yourself that you’re going to learn a lot while you do that.
But what you’ll learn is entrepreneurialism is less about a product, less about a service, and more about meeting a need and learning how to run a business to do that, to create a machine to do that. And then just enjoy what you like to do and keep it in that bag. Let that be something that you like doing.
Or like we talked about before, one other example I can give about using your strength, using your gift to market to businesses is if you are really good at organizing sales, if you’re really good—we used to call it, I don’t know what they call it anymore—but if you’re really good as a sales manager, you can sell yourself fractionally in multiple places at one time. It kind of feels like a job, but if you don’t think your entrepreneurial venture is going to feel like a job, then that’s where you need to smell the salt.
Takeaways to Carry Forward
Winston: Well, man, I know there’s so much here that I’m walking away with. Those of you who are watching or listening, I’m believing that you’re walking away with something as well. And if you know anybody who is either already an entrepreneur or is considering, please share this with them and let’s spread the knowledge and information that’s necessary to make people successful.
Until next time, we’ll see you on the Today Count Show.
Outro
Thanks for spending part of your day with us on the Today Count Show. If today’s conversation encouraged you, challenged you, or helped you grow, share it with someone in your circle because we’re better when we grow together. And be sure to subscribe, leave a review, and stay connected with us on Instagram, YouTube, LinkedIn, and Facebook. And remember, real change doesn’t happen someday, it happens today. Until next time, keep showing up, keep building, keep making today count.
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If this episode stirred something in you, don’t ignore it. The tension between security and purpose is real—but clarity comes when you lean in, not back. Take the next step in your journey with these powerful resources:
- Episode 201: Kingdom Principles, Corporate Impact: Jesus’ Influence on Business: Deepen your perspective and discover how faith and purpose shape impactful leadership in the business world.
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If you’ve been waiting for the “right time,” this is your reminder: clarity comes through action. The real question isn’t just whether to start the business or stay safe. It’s what you’re going to do next.
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