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Business, Bourbon & Cigars
One Trust Decision. One Right Person. How a Nine-Figure Empire Gets Built
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I want to tell you about a conversation that happened at a local Starbucks here in Louisville, Kentucky. Two people over one cup of coffee, maybe 60 minutes, give or take. That conversation eventually led to a nine figure business exit. This didn't require an advisory team or a strategy deck. There was no six month planning process, was just a friend asking another friend who had been where he was trying to go. He just asked him one direct question and one piece of advice that turned out to be the entire game. I was one of those two people and I. And I have to tell you, when I think back on that conversation, the thing that still gets me is how simple the answer was. Not complicated, not sophisticated, but it was just right. And my friend trusted it completely, even before he had any evidence that it would work. That trust and what he did with it is what today is about. At the end of this episode, I want you to think differently about where the real leverage is inside your business. It's not a new marketing strategy or a better sales process, but a person, the specific person in a specific seat whose presence changes what your entire organization is capable of producing. I'm going to walk you through the full story of what happened from that Starbucks table to a multi nine figure exit. Then I'm going to give you four things that can sharpen how you identify that person. Put them in the right position and actually get out of their way once they're there. That last part is a lot harder than it sounds. Or hell, everyone would be doing it right. But I'm going to explain exactly why. Welcome to business. Bourbon and cigars. I'm your host, Scott Joseph. Three decades of building, acquiring and scaling companies across multiple industries has given me a very specific view of what actually moves the needle in a growing business. And one of the most consistently underestimated levers that I've ever seen is the talent decision. I'm not talking about, you know, hiring in general, right. I'm talking about the one hire, the specific person in the specific seat that changes the math on everything else. That's what we're getting into today. You know, I think the clearest way that I can show you what I mean started with a simple phone call from a friend. And I'm going to give you the full version because the details are what make it real, you know, then we'll get into what actually makes this kind of decision possible inside your business. And more importantly, right. What gets in the way of it more than anything else. You know, a friend of mine called me one day and he asked me If I had time for a quick coffee, you know, he was already very successful at this point. He accumulated a lot of wealth, you know, built some solid things, collected his hobbies, he collected vintage Porsches and love cars. But he had an opportunity in front of him that was a different scale than anything that he had done up to that point. And he wanted to talk through it with someone who had been in that world. So we meet at a local Starbucks, you know, and he walked me through what he was looking at. It was a business that was significantly underperforming, at least relative to what it, you know, was capable of, was a low volume retailer, but was it was in a huge market and had a huge upside. The type of store we all looking for, right? And one of the things I love about my friend is up to that point he had never been involved in that industry before. But it didn't stop him from looking and acting on it. He called me because he wanted to know what he was really getting himself into, you know, before he just signed on the dotted line and committed that type of capital because it was going to take a lot to get the deal done. And this is exactly the kind of opportunity that looks obvious, you know, when you're looking back in hindsight, but it's nerve wracking in the moment. He didn't know the industry, but he believed in the opportunity. He just wanted a straight answer from someone who navigated it before, you know, he committed. So he asked me, you know, what do I need to know going in for me to get this right. And I gave him a few things worth being aware of, but my number one piece of advice, and I was direct about this and it was about one thing and it really came down to hiring. I told him the business itself, it's really not complicated once you understand the fundamentals. It's actually a pretty straightforward operation. You know, the only hard part is what makes it easy and that's finding the right person to run it day to day. You find that person, the right one, not just a good one, and everything else becomes considerably easier. You don't find them and there is no amount of your personal involvement that fixes what's broken underneath. So he listens, right? He asks a few good questions, we finish our coffee. Within 10 years, that man went from never being involved in the industry to owning 19 of those retail locations. By the way, it's auto dealerships. He created his own brand, his own niche, which was ultra high end luxury. He understood exactly who those buyers were, you know, what they expected. And he believed he could serve them better than anyone else in the industry, let alone his market. And he went all in on that conviction. You know, the first business he acquired was doing about 90 units a year at the time he'd bought it. By the time he sold it, that same location was doing 910 times the volume. And when he exited the full portfolio, the number was multiple nine figures. You know what made it work? My number one piece of advice, he hired an incredible operator to run the business. Someone who is still overseeing those locations today, years after the exit. You know, he also made it a priority, I should say early on to hire the right financial leader, someone he could trust completely, who knew exactly what they were doing. He put the right people in the right seats. He gave them the authority to do their jobs. You know, and then he focused his own energy on building the next thing and the thing after that, instead of staying buried in the day to day of the first one. That's the whole story. A conversation at a Starbucks that included one clear answer. One leader who trusted it, acted on it. And without second guessing the process to death, I want you to write this down. It's important. Most leaders hire for the business they have today. The ones who build something lasting hire for the business they're committed to building, and they do it before they think they can afford to. And here's the thing that gets me every time I tell this story. That first hire, that operator who's still there today, didn't just make the first location run better. He created the foundation that made the second opportunity possible. And the third, and eventually 19, compounding from one decision made early, made correctly, and then trusted fully. Let me give you four things that sharpen the process. Because identifying the right person is one challenge, and actually letting them do what you hired them to do is a completely different one. First, you have to identify the single role in your business where the right person produces disproportionate return. Every business has one. If you're lucky, you get two or three of them. The role where the difference between a good hire and the right hire isn't incremental, it's exponential. So for my friend, someone told him, clearly, you know, what the role was before he even started. Most leaders, they either haven't named it explicitly, even for their own business, or they've named it, but aren't treating it with the urgency that it, you know, it deserves. Really, that requires. Here's the question I'd encourage you to sit with. In my business, which single Role, if held by exactly the right person, would change what I'm capable of producing. Most significantly, not is important, not who's currently in the role, not who's available right now. Who would the right person actually need to be and what would become possible once they were in that seat. When you can answer that clearly, everything about the search gets sharper because now you know what you're actually looking for and you can hold out for it rather than filling the seat with, you know, whoever's closest to available. The worst mistake you can make is to settle or to sell yourself on a candidate that never works out. And we've all done it. The second is to hire for where you're going, not where you are. And this is one of the most consistent errors that I've watched people make. And I have to tell you, I have made this mistake more than once. You hire to solve a current problem, right? The candidate can handle. They come in, they do a good job, they can handle what's on the plate right now. The scope fits what their business, what your business needs today. And then six to 12 months later, the business starts growing. The scope expands, and the hire that solved yesterday's problem is now the ceiling on tomorrow's opportunity. They cap your potential and growth. My friend didn't hire an operator for a 90 unit business. He hired someone who could operate at a standard that was well beyond 90 units because the goal was never 90 units. Right now, you're juggling every decision, putting out fires, and trying to grow your business on your own. Every day feels like a grind. And no matter how hard you push, the breakthrough you've been chasing seems like it's just out of reach. You don't have the right perspective or maybe the network to see the opportunities waiting for you. The Business Bourbon and Cigars Leadership Retreat is your chance to change that. Imagine being in a room with entrepreneurs who have already overcome the challenges you're facing. Leaders who have scaled, innovated, and found the clarity you're searching for. Through our Mastermind Style sessions, you're going to gain actionable strategies and the opportunity to connect with active Me plus Ultra members. These aren't just networking contacts. They are entrepreneurs who think strategically, spot opportunity quickly, and can provide insights that accelerate your growth. This experience allows you to see firsthand how high level leaders solve problems, create momentum, and unlock opportunities. So you can leave the retreat not just with a plan, but with a network that expands your possibilities faster than you ever thought possible. The first five people to apply at me+ultra.com BBC50 is going to receive 50% off their ticket. Don't wait. Secure your spot now and step into a space where real business breakthroughs happen. It's funny, you know, I talked to him after he had grown the business to the 19 locations. He said, you know, the hardest part early on was making sure his superstar operator, you know, didn't leave out of boredom. He continuously had to reassure him where they were headed, not where they were. The goal was a business worth holding for a decade and exiting out of multiple nine figures. The hire had to match the destination, not the starting point. Before you know your next significant hire, I want you to ask yourself honestly, is this person built for where the business is going in three years, or are they built for where it is right now? Those are not always the same person. And the gap between them is what you know eventually will become your next ceiling. The third. And this is where a lot of leaders quietly sabotage the hire that they worked hard to make. Not easy finding the right person. And that is, you got to actually give that person the authority that matches their responsibility. Finding the right person's half the decision. The other half is letting them do what you hired them to do. This is genuinely hard, especially for founders and operators who kind of built everything themselves. It was hard as hell for me. You know, when you've been the one who figured everything out, stepping back and trusting someone else to carry, it feels, it's almost, it's. It's unnatural, at least at first. But here's the reality. Someone hired for a season year role needs the authority to make the decisions that role requires. They need access to information that shapes those decisions. They need the ability to act without routing every call back through you. Most top people are compensated, you know, at least in my business, some way, you know, on the bottom line. How can you expect to retain top talent if you pay them on the bottom line? But then you're the one making all the key decisions on how to get there. When you don't allow people to make the call, you don't get what that person's capable of. You get a fraction of it, and eventually you lose them. Because talented people don't stay in situations where they're held responsible for outcomes they don't have the authority to control. You know, another thing I want you to write down, this is important. I believe in writing things down. It's easier to remember. You cannot hire someone to lead and then manage them like a follower. The moment you do that, the hire is already failing. You just haven't seen it yet. The fourth is to protect the relationship long enough for the compounding to show up. Great hires take time. The first 90 days, they're almost always about learning the context, you know, the culture, the relationships. There's unwritten rules of how the business organization actually operates. Transformational hire does not transform in 30 days, expecting that as a setup for both of you to fail. You know, the operator my friend hired, he's still in those locations today. Like I said, years after the exit. That's not luck. That's what happens when a leader finds the right person, gives them real authority, and it builds a relationship that makes that person want to stay most of the time, you know, retention of the right people isn't a compensation problem. It's usually a trust and clarity problem. When somebody knows, you know, what they're building toward and they believe that they have the authority to build it and feels genuinely valued for the specific contribution that they're making, they stay. And the longer they stay, the more the compounding works in your favor. The cost of losing the right hire and replacing them, it isn't just in the recruiting cost. We all have that number, right? It's the accumulated context, all that momentum, the institutional knowledge that lives in that person and nowhere else. Protect it the same way you'd protect any other high value asset in your business. Because that's what it is. The right person in the right seat when they're given enough time and enough trust, doesn't just solve your current problem, they solve the next three you haven't even named yet. A three dollar cup of coffee at a Starbucks, which, that's what I think they cost. One honest conversation, one direct answer about the most important thing to get right, and a friend who trusted that answer completely, hired accordingly, gave that person the authority to lead, protected the relationship, and stayed focused on building the next thing while the right operator ran the current one. Think about that. 19 businesses in 10 years, multiple nine figure exit built over a decade. I'm not telling you this story because it's dramatic. I'm telling you because it's repeatable. The principle behind it works in any industry, at any revenue level, in any kind of business, as long as the leader is willing to do two things most people find, you know, harder than they expect. You gotta name that role that actually matters most and then trust the right person to own it. That's it. That's the whole game. The question I want to leave you with, and I want you to actually think about this one, is this in your business right now, do you know exactly which seat that is and do you have the right person in it? If the answer to either of those is no, that's your most important priority. Not the next strategy, not the next initiative that if today's episode got you thinking about the talent decisions inside your business, who's in the right seats, where the gaps are, and what becomes possible when you finally have the right people around your biggest opportunities, I want to tell you about something worth being part of the business. Bourbon and Cigars Leadership retreat is where this kind of conversation happens at a completely different level. A small group of high level operators. It's two and a half days of structured, honest working sessions, not presentations and common speeches. Actual problem solving with people who are running serious businesses and they're willing to be straight with each other leaders. They leave that retreat with clarity that they couldn't generate alone and in relationships, you know that they gain with people who are doing things at a level that makes every conversation genuinely useful. The next retreat is October 13th through the 15th. This is 2026 in Louisville, Kentucky. I want you to visit me +Ultra.com BBC 50 that way you can claim 50 off your ticket. The spots are limited and they fill for a reason. I am Scott Joseph. This is business. Bourbon and cigars. Go build something we're talking about. Cheers everyone.