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What's the most expensive mistake most business owners make early on? It's not pricing, it's not marketing. It's not even their product. It's their first hires. In fact, who you hire and when you hire them will either make or break your entire business. So today, Entree Leadership's head coach John Felkins is going to walk through who your first three hires should be, the order you should hire them in, and the biggest hiring mistakes that trip up. Most business owners get this wrong, and you can stall out before you even get going. But get this right, and you'll build momentum fast. Let's get into it.
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Thanks, Dave. When you first start in business, you're overwhelmed, you're exhausted, and you need somebody, anybody to help. So what do you do? You bring on someone you know or the first person that responds to the job posting, and it feels like help for about five minutes. Then the wheels start to come off. This person maybe shows up late all the time, or they miss deadlines or they tick your customers off. So now you're not just trying to run a business. You're having to clean up somebody else's mess. The problem is, many business owners hire on how they feel in the moment, but you've got to be intentional about it, not just grab the first person who can fog up a mirror. So let's start with your first hire. In the beginning, you're the one wearing all the hats. You're the chief everything officer. You're taking the calls, you're doing the work, you're fixing the problems. And for a while, that does work. But eventually, you're gonna hit a wall because there are only so many hours in the day. And as demand grows, you don't have the capacity to meet it. No matter how hard you work, you become the lid on your business. At the same time, you probably don't have the margin to go and hire a full team yet. So the first person you bring on needs to pay for themselves as quickly as possible. Let's call them the revenue driver. For example, Dave's first hire was another financial coach who could take on more clients for you. This could be another technician or another stylist. Maybe another person mowing lawns. And if you're thinking, wait, I can't afford to hire another version of me yet. Hold that thought. We'll come back to that in a little bit. But the goal with the first hire is to get another set of hands that can bring in more money asap. Now, once you've got someone to help you do the work and the money starts rolling in. Something else happens. You get buried. Not just in the work that grows the business, but also in the logistics that keep it afloat. Emailing and scheduling, refilling the coffee machine, all the little ankle biters that eat up your day. And suddenly you're spending your whole day doing minimum wage work when your time is worth way more than that. You need to find margin to work on your business, not just in it. So your second hire needs to be the margin finder. This is someone who can handle things like bookkeeping or taking calls, scheduling or other day to day operations in your business. They don't need to be an expert in your business. They just need to be reliable and organized. Someone who can keep the train on the this rule may not bring in money directly, but they free you up to focus on the work that does. And look, our friends at Belay exist for this exact moment in your business. You just heard me talk about the margin finder. The person who helps you maximize your time and find margin in your schedule for the things that matter. Belay helps you do exactly that. They connect you with qualified US based executive assistants, marketing assistants and accounting professionals so you don't have to wear 50 different hats. They take ownership of your scheduling and communication and day to day operations so you can protect your time and actually lead. Because your role as a business owner isn't to do more. It's to set the strategy and put the right people in place to execute it. And if everything runs through you, you don't own a business. The business owns you. And I'll tell you this. I know the team at Belay. They truly want to help you. So don't wait until you're burned out to fix it. Download Belay's free resource the Freedom Framework by texting ENTRE to 55123 that's ENTRE to 55123 so once your revenue is up and you've got more margin back in your day, you now have the ability to handle more business. Then and only then can you bring on the third hire. The growth engine. This is your salesperson or your marketing person. Someone to get the word out about your product or service their job. Simple. Get more business. That includes generating leads and following up with clients and turning interested people into paying customers. This is how you build something that can grow without you having to physically be there. So those are the first three hires. Revenue driver, margin finder, and a growth engine. But many business owners don't hire in that order. They either hire an admin first because they're just overwhelmed, or they hire a marketing person because they're desperate to grow. But if you want to keep up with demand, that growth will actually hurt your business. It's like pouring gasoline on a fire you can't contain. So remember, if they don't increase your revenue, your capacity, or your reach, you, you probably shouldn't hire them. Now this is just part of the problem. Even when you know who to hire, you can still mess things up by how you hire them. So let's talk about the biggest mistakes people tend to make when they're starting to hire. Mistake number one, that's hiring too early. And I get that this is tricky because you need the help, but if you hire before you're financially ready, you can just make matters worse. You don't want to try and train someone while you're stressing about being able to pay them. So let's go back to that question from earlier. Can I even afford to hire someone? A better question to ask is, am I going to be able to afford this person six months from now? If the answer is no, you're not ready to hire them today. Because payroll is your biggest expense and every dollar you spend on hiring should produce a return. Now, if you're sitting there thinking, well, I guess I can't afford to hire someone yet, not necessarily. One option is to put them on commission, but you need to be up front with them and say, hey, I can't pay you a full salary right now, but I can offer you a base salary plus a percentage of whatever you bring in. For example, a car mechanic would only get paid when there's actual cars to be worked on. If the business is making money, they're making money. And if things start to slow down, you're not stuck carrying a payroll you can't afford for the right person. There's a real upside here. They're not just taking a job, they're helping you build something. They're getting in on the ground floor. So as the business grows, their income grows and their role grows and they get to be a part of what this thing becomes. You could also hire a contractor, someone who's only committed to a project or a season. That way you're not taking on a full time risk before the business can support it. The point is, you don't have to rush into a bad hire because you need help you can be wise about when you build your team. But on the flip side of that is mistake number two, which is hiring out of desperation. That's not a good place to hire from because it means you're willing to ignore the red flags and hire the first Joe Schmoe who walks in the door. You think, yeah, this person isn't great, but I need the help. Trust me, that decision will come back to bite you and you may learn exactly why they were free to work in the first place. One bad hire can cost you money, wreck your reputation, and set you back more than you think. That's why here at Ramsey, we take our time hiring. We're picky about who we let in this place. So even if you really need help, slow down and be intentional about those first people you hire. That said, the most dangerous hiring mistake is number three, hiring without a plan. This happens all, all the time. You finally hire someone, but you haven't thought through what winning looks like for their role. You don't know what they're actually responsible for, what results they should produce, or how their role actually moves the business forward. So what happens? They show up on the first day and then constantly interrupt your own work to ask for instructions. And at the end of the week you're not really sure what they accomplished. You're still doing everything just now with more payroll and that's frustrating for everybody. Don't bring someone on just to figure it out as you go. Take the time to get clear on the role first before you even post the job listing. So let's wrap this up. As you start hiring your first team members, make sure you're financially ready. Be intentional, not desperate, and have a clear plan for how that person is going to add value. Do that and you'll build a solid foundation to keep growing your team the right way. And if you want a step by step breakdown of how to hire, well, we put together a guide on the 12 components of a good hire and you can find that in the description below.
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Your first few hires don't just help your business, they shape it. They shape your culture, your standards, and how the company operates moving forward. So don't treat hiring as a quick fix. Treat it like a long term decision. It is. Because when you get the right people on your team, you. You can build something that lasts. And if you want to make sure your next hire is a good one, go watch this video next on how to attract the right kind of people you want on your team. If you enjoyed this episode, be sure to like and subscribe for more great leadership and business content. I'm your host Dave Ramsey and this is Entree Leadership. If you're a business owner who's serious about growth, you've got to be at Entree Leadership 2027 Summit is our world class leadership conference where you will learn from the people. People who have influenced the way we lead at Ramsay. You'll also connect with like minded business owners who are facing the same challenges as you. To get your tickets for May2027, go to entreeleadership.com summit to reserve your spot today. That's entreeleadership. Com summit to reserve your spot today.
Date: June 10, 2026
Host: Dave Ramsey
Guest: John Felkins, Head Coach at EntreLeadership
This episode dives into one of the most critical (and costly) early decisions business owners face: who to hire first, in what order, and how to avoid the expensive hiring mistakes that cripple many companies before they scale. Dave Ramsey and John Felkins break down the ideal hiring sequence, tangible steps for small business owners, and key pitfalls to dodge. Their advice is based on decades of business success, leadership principles, and real-world lessons from the Ramsey organization and its coaching clients.
"Who you hire and when you hire them will either make or break your entire business."
John Felkins establishes a clear hiring sequence for entrepreneurs:
Hiring Sequence Recap (05:59):