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As an entrepreneur in the early stages of running your business, there's one surefire way to boost your revenue in a big way. Making your first hire. But that only happens if you make the right first hire. Get it wrong and it could cost you and your business big time. When I got ready to make my first hire, I didn't want to do it. I didn't want employees. As far as I was concerned, employees came late, left early, and stole while they're there. And then I met a guy named Russ Carroll who had the same heart for coaching people that were hurting with their money. He was there on a mission, a crusade, like I was. So Russ joined the team to be our very first hire over 30 years ago and coached people, counseled people, until he retired with Ramsey, many, many years later. He's an incredible man and he was an incredible hire. It's one of the smartest things I ever did. He coached thousands of families that I could have never gotten to. So when you're hiring, that's a lot of pressure. But that's why in today's episode, you'll learn exactly how to make your first hire the right way and make it a success. John Felkins from the Entrez Leadership Team is here to help you answer the three key questions that that'll set you up for success as you grow your team.
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82% of small businesses in the US are a one man show. And if you're one of them and you're thinking about expanding, the first question you need to ask yourself is how am I going to pay for this person? You need a clear path to revenue that covers their pay. And if their work won't bring in enough to cover their payroll, then you can't really hire them. Yet. If you have enough work for a team member and you can afford to pay them, you're ready to answer the next question, which is what role do I hire for first? For starters, you shouldn't create a nice to have position that isn't an urgent need. Instead, your first hire should be someone who can create ROI very quickly. In other words, they should help pay for themselves fast. This means either they're generating revenue directly like a salesperson, or they're generating revenue indirectly like an assistant who frees you up from admin tasks to so you can focus on the revenue generating work. Once you're locked in on the type of role you need for the hire, you're ready for the final question. How do you find the right person? Obviously you want somebody with the experience and A proven track record at excelling at the type of work they'll be doing in your business. But being able to complete a set of tasks should only be the starting point. That goes for any hire you make, especially the first one. That's because culture's fragile. At this stage of your business, one person can change the whole vibe. And a wrong hire early can tank your momentum, your morale. I think about it like a cruise ship in a canoe. A big business is like a cruise ship. You hire one crazy person that's going to cause a problem, but it's not going to turn the whole thing upside down. When you're a brand new business, you're more like a canoe. And if somebody jumps in that canoe and starts going crazy, everybody's going to get wet. You've got to be careful at this point. The bottom line. Your first hire should be qualified for the role, but they also need to be the kind of person you want to spend every day with. So how do you make that happen? Start by writing a clear job description. And as you get started with the hiring process, ask other folks in your industry what's worked for them. You can learn a lot. Then, once you start interviewing candidates, focus on making sure they fit the type of culture you want for your business. Simply caring about your culture at all is going to go a long way. And listen, you need to trust your gut. If something feels off in the interview, it's not going to get any better when they're on payroll. No matter what, your first hire is going to feel a little scary. That's totally normal. In fact, if you don't find it a little bit scary, that might mean you don't understand what's at stake. That said, if you do wind up making a wrong hire, it's not the end of the world. Just don't wait too long to correct it. But if you make sure you can actually afford the first hire, you design a role that will roi quickly and you hire for skills and culture fit. You're going to be way ahead of the game.
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Now, this is just a high level overview of what it takes to navigate the hiring process. The best way to ensure that you wind up with the right person is to follow the 12 step plan that we've been using at Ramsey for three decades. It's the exact process we go through every time we're hiring a new team member. And if you want to check it out, our team has written a free article that breaks it down from top to bottom. Just click the link in the show notes. That's it for today, so be sure to like and subscribe if you found this helpful. I'm Dave Ramsey, and this is Entree Leadership.
Podcast Summary: The EntreLeadership Podcast
Episode: 3 Key Questions to Ask so You Won’t Regret Your First Hire
Host: Dave Ramsey, Ramsey Network
Date: March 4, 2026
This episode focuses on the critical process of making your first hire as a business owner or entrepreneur. Drawing from personal experience and 30+ years of leading Ramsey Solutions, Dave Ramsey and leadership coach John Felkins discuss the top three questions every business leader should ask themselves before hiring their first employee. The episode blends practical strategies, real-world examples, and motivational insights to help business owners make informed and confident hiring decisions—ensuring growth without regret.
John Felkins outlines three essential questions to guide first-time hiring (01:24):
Acknowledge the Fear:
Recap of the Formula:
The episode blends practical business wisdom with relatable stories, using plainspoken advice, analogies, and humor to make sometimes-intimidating topics accessible for entrepreneurs at any stage.
To avoid regretting your first hire:
For a complete roadmap, check Ramsey’s proven 12-step hiring process (linked in the show notes).