Business Owners Will Respect You If You Do These 5 Things I Joseph Cabrera - AO 55 I

Are you constantly getting rejected by owners?

In this solo episode of **American Operator**, we break down the **five things that actually earn trust and respect from legacy small business owners** — the kind of owners who’ve spent decades building something with their hands, their name, and their reputation.

Because here’s the truth:
These owners don’t sell to spreadsheets.
They sell to people they respect.
This episode covers:

• Look the part — show up like a normal, grounded human being
• Earn the right to shoot straight — build real rapport before talking shop
• Shoot straight — honesty over polish
• Business is personal — these companies are family, not assets
• Humility through action — respect what they’ve built, don’t just say you do

We talk about instinct-driven operators, old-school owners who “feel” their way through decisions, and why respect matters more than ROI in many succession conversations.

If you’re pursuing small business acquisitions or hoping to take the torch from a retiring owner, this is step one of understanding what they’re actually looking for.

They don’t need to like you.
They need to respect you.

Join the Movement
Tactical insights and behind-the-scenes stories from America’s operators:

• Website: www.americanoperator.com
• AO In Action: https://www.youtube.com/@AmericanOperator
• Instagram: https://www.instagram.com/theamericanoperator
• Newsletter: https://americanoperator.substack.com
• Locally Owned and Operated: https://www.locallyownedandoperated.org/

Transcript

00:00:00:00 - 00:00:18:23
Unknown
All right, team, welcome back on this episode. Just me this time, but I want to cover something that has a lot more urgency. I think especially for those of you out there looking to potentially get into the owner seat. We tour all across this country, from the west to the east coast, all the way up to North Dakota, all the way down to South Texas.

00:00:19:01 - 00:00:43:03
Unknown
And one thing we learn over and over again is how owners think and what they're looking for in their successor. There's a lot of things involved in that, and often a lot of things you're not going to learn in a textbook or an MBA class or any of those things. And if you really think about it, to a lot of you all mean, well, I've had a lot of stories of folks go, hey, I had all my ducks in a row.

00:00:43:04 - 00:00:57:21
Unknown
I studied everything about the industry, but at the end of the day, I felt like I walked out and the owner just wasn't feeling it right. And then just moved on to somebody else and more importantly, maybe even moved on somebody else and didn't end up getting the highest price, right. A lot of this thing is not about price.

00:00:57:21 - 00:01:32:23
Unknown
So what we're going to do today is cover the initial, what I would consider like more of the instinctual, intuitive kind of the raw nature of what it takes to build rapport and give yourself a chance for a second conversation. Before we get into that, there's going to be some really good things that we covered today, and I hope that'll be beneficial to you, but do me a solid in order to help a bunch of Americans out there, either getting in the owner seat or that are currently in the seat and just keep feeling inspired to continue building what we do here in this country, which is the backbone small business.

00:01:33:01 - 00:01:50:08
Unknown
If you're watching us right now, please like and subscribe. And if you're tuning in via audio, leave us a review. Leave us a rating, read all of it. It's super helpful to us. And most importantly, it gets the word out. It helps us get the word out to other folks who need to hear these things so they can continue doing what they do best.

00:01:50:10 - 00:01:51:13
Unknown
We just keep this country moving.

00:01:51:13 - 00:02:08:08
Unknown
All right, so let's get into it. Let me paint a picture. First of all, of who these owners are. Some of you've met them. How many you maybe haven't. Some of you are them. And so but I really want to just paint really clearly what these owners are all about, how they tick.

00:02:08:10 - 00:02:31:13
Unknown
And maybe it'll give you some context before we get into five things that I ultimately think you should be thinking about in order to get second or third, and maybe you go the distance on these meetings here, to ultimately become the new owner of the business. If you go back to think of a plumbing company, you think of, you know, an electrical supply, think of a septic company, you think of anything, right?

00:02:31:13 - 00:02:56:09
Unknown
Skyscraping, cleaner, skyscraper cleaners, whatever those things are. Just if you think about any business, zoom back 30 years and think about this young guy or gal who decided that they're going to start this business. Never done it before. They don't even know where the money's coming from. Maybe the economy's down. Maybe they just had a newborn. Maybe they just got out of the military, or maybe they just got kicked out of the house.

00:02:56:11 - 00:03:02:23
Unknown
And they don't really know where they're going to go to next. But all they know is they gotta go figure out how to make something happen.

00:03:03:01 - 00:03:27:23
Unknown
This individual built their entire business out of thin air, pushed a rock up a hill for years and years and years without a paycheck, often doesn't have a college degree. Sure as heck. Probably not an MBA or a PhD or nothing. Some of them. I met a guy the other day, runs probably one of the most premier racing organizations out there, never even graduated high school.

00:03:28:01 - 00:03:42:13
Unknown
And so if you think about that, education doesn't matter to them. It's more of this like school of hard knocks out in the real world. They make it happen. They will things into existence. And if we've ever met somebody like that, we all probably have an uncle that's like that, or an aunt or something like that. Just gritty.

00:03:42:15 - 00:04:17:05
Unknown
That's who they are. And so if you understand that, that's how they tick and you understand that they're not really in or impressed with what your resumé says, or that impressed with your big words, I think you'll really understand more and more and more just how it is to start earning their trust and building rapport. And so the thing that when you're when you're thinking about meeting these owners and when you're thinking about really trying to understand if there's an opportunity here and if this is a way that you can potentially take the torch, recognize that these owners, they're looking at you as like a complete gut check.

00:04:17:11 - 00:04:37:00
Unknown
They're not using any math. They're not they don't have a checklist. They don't have a matrix. They don't have a project management board. None of that stuff. They're sitting in there I and you'll find most of them aren't going to even talk for the first few minutes. They're just there to to size you up, figure out if you're worth continuing to talk to or not.

00:04:37:02 - 00:04:59:14
Unknown
And so what I want to do is kind of spend the remainder of this time we have together to really just highlight, I think, five key things that if you can just keep top of mind and do it genuinely, it's going to give you the opportunity to continue the conversation and at the very least, just build good relationships and connective tissue with somebody who's built something real.

00:04:59:16 - 00:05:09:15
Unknown
And so the first of the five things here, I just want to be able to talk through, which is going to sound like I'm probably picking at some of y'all, but I'm not, is look, the part number one.

00:05:09:21 - 00:05:27:18
Unknown
These owners, if you've never met them, I don't even know most amount of suit and showing up. It might be an old school thing. You go to a 9 to 5 corporate job where I go, wear your best suit, go buy your grandfather's tie, go shine your shoes. And I'm talking about 80% of these businesses, right? They're blue collar.

00:05:27:18 - 00:05:45:13
Unknown
They're gritty. If you show up looking like that and you're wearing your slacks and your loafers and you're coming in and you're even if you're the nicest person in the world, they've already made up their mind about you right there. If you're not one of them, right? So you're not one of them. And therefore it's going to be hard for them to trust you.

00:05:45:15 - 00:06:01:16
Unknown
The way I like to think about it is if you ever get a chance on a Sunday and say, if you go to church like on a Sunday, go to a rural town and go in to one of the services and just watch how the guys are dressed and the gals. But specifically, I'm thinking about right now, like I'm thinking about this particular owner right now.

00:06:01:16 - 00:06:21:01
Unknown
In my mind, what you'll find is that these owners are the most dressed up. They get is they get the pair of jeans that doesn't have stains on it. They might of iron them. They got the cleanest pair of ariat or, whatever boots they're wearing, just ins or whatnot. If they're lucky, or maybe save up some money.

00:06:21:01 - 00:06:39:08
Unknown
They got a pair of cases, but most and most, you know, they're just using the cleanest work boot they got. And it's part of the work boot that eventually is going to turn into actual work boot. But it's the one in the in the lineup in the rotation right now that's the cleanest. They're probably wearing a poncho outdoors fishing shirt that's like dark and somewhat clean, or a polo shirt.

00:06:39:09 - 00:06:59:06
Unknown
These guys will typically wear a t shirt or something pretty rugged. A Carhartt vest most days. This is what this is like getting dressed up for them. So if you come into a meeting with them and you meet them at their place of business and you look more than that, they already are going to have you pegged as somebody they're not really quite sure you get them.

00:06:59:08 - 00:07:19:12
Unknown
And so I know it sounds like a nitpicky thing, but if you really want to earn the trust of these folks and start to at least have that be a nonfactor look the part, it'll go a long way after you look the part. Then what you want to do is earn the right to shoot straight. And what I mean by that is you're right.

00:07:19:12 - 00:07:37:16
Unknown
You're going to talk about number three as a spoiler. Number three, shooting straight. But you want to earn the right first. A lot of the times I've seen it quite a bit. We've done all our homework. You know, we get this idea. Maybe you're a, a family member. Maybe you're somebody who's never met this owner before. But you graduated from a top notch school.

00:07:37:16 - 00:07:55:10
Unknown
Maybe you're a corporate burnout. You're tired of your 9 to 5. Maybe you're somebody serve their country, whatever it might be. You're in this position now to talk to this owner about this business, about their business, and about potentially being the next owner of it. And what ends up happening is you immediately get to the brass tacks right off the bat.

00:07:55:11 - 00:08:17:23
Unknown
You just start getting in the numbers, picking about their pal. All these things and all of it is not wrong. Getting an understanding that stuff. You must do that to know what you're getting into. But you haven't earned the right yet. You haven't earned the right to actually go out there and ask the tough questions. You haven't earned the right to even ask them what's going on here, just haven't earned the right.

00:08:18:05 - 00:08:36:10
Unknown
Think about the business as like a family member, right? When you meet somebody, family member, think of this owner has a son or daughter. And let's say you're hanging out somewhere at a coffee shop. You are going to ask them, let's say the scenarios you're talking about their kids and they're playing sports you're going to recognize are certain things you're going to talk about.

00:08:36:10 - 00:08:52:03
Unknown
Right? You're going to talk about what sport they're playing, what position, how they do it. The last game all these things. What you're not going to do is, oh yeah, tell me about your son's, like ACL injury. It sounds really interesting. I notice he's got a little limp. Like you're not going there first, right? Maybe eventually. Right. Once it opens up, you want to know this?

00:08:52:03 - 00:09:10:04
Unknown
Potentially think of the business is the same thing. You got to earn the right. And the way you earn the right is literally by just being a good think about just being a good friend to somebody you've never met before, but you've gotten maybe somebody to vouch for you at a coffee shop, right? Hey, I know Tim for years.

00:09:10:04 - 00:09:26:09
Unknown
I want you to meet Jared. And you're going to catch up. Just think about what that relationship would be like. You're going to do the same thing. Maybe find common ground, right? Maybe you're both into a certain football team. Maybe you both like being in the outdoors, maybe all went to the same church, whatever it might be, right?

00:09:26:09 - 00:09:48:17
Unknown
You find some common ground and you spend as much time as you can just building trust, building connective tissue until it becomes effortless. And the way that I the way that, you know, you've earned it is that there's usually some banter, there's some humor, maybe they're teasing you back on something. Once they start doing that, then people start getting warmed up.

00:09:48:19 - 00:10:03:18
Unknown
And for those of you've done this before and talk to owners, they're tough folks. They're usually just going to stare at you for a while. So it's going to it's going to be awkward at first. A lot of the time they're just going to stare at you. They're usually people, not many words, and they're just going to see kind of what comes to be.

00:10:03:20 - 00:10:22:07
Unknown
But once you've earned that right to shoot straight, then you move on to the third step, which is shooting straight. You see, these guys and gals built a business on handshakes, looking people in the eye and trust in their friends, in their community. And so all they want you to do is tell them that, like, just tell it like it is now.

00:10:22:12 - 00:10:43:14
Unknown
Telling it like it is also means not being insulting, right? There are direct ways to be able to ask a question, and that is probably an entire other episode about how you deliver something is as important as what you deliver. But just for the purposes of this kind of let's call it intro into rapport building with these owners and understanding what they're looking for.

00:10:43:16 - 00:11:07:02
Unknown
Just recognize they just want you to be honest. Like they ask you, hey Joseph, you ever run a plumbing company before? And you answer, well, you know, my uncle is a plumber. And, you know, I got I was in the home at my favorite island, Home Depot is, you know, is the plumbing section. They're like, okay, this guy's just starting to like, give me a runaround instead of going, no, sir.

00:11:07:02 - 00:11:24:00
Unknown
I've never run a plumbing company before, but if you're willing to teach me and if I have some time, I'm pretty good at picking up things fast. And I notice that learned in my life that the best plumbers in the world, the best managers and best leaders in the world, are often not the best plumbers in the world, or the best specific skill set in the world.

00:11:24:05 - 00:11:51:03
Unknown
And I my skills to help those people do their job the best. But I still got a lot to learn. That's shooting straight, that's being honest, and that's just telling them off the bat. You've never done plumbing before. They'll respect that way more than somebody is giving them the runaround, because as soon as you do that, they're like, okay, I know these guys because you're reminding them of a bid they put out that this owner never got back to me, said they were going to, and now they have all this money tied up in this project they thought they were going to do or this vendor who said they could pay him on a net

00:11:51:03 - 00:12:01:03
Unknown
30. But now they're saying, well, maybe it's got to be a net 15. And, you know, they're used to these folks in their towns that they don't trust that. Well, or big vendors that have given them

00:12:01:03 - 00:12:09:11
Unknown
bad experiences that bring them right back to that point. And so when you're in these situations, what you want to do is spend time

00:12:09:11 - 00:12:11:16
Unknown
just shooting them straight and making sure that

00:12:11:16 - 00:12:20:20
Unknown
that you answer the question I know is obvious is that sounds. But the more that you can answer the question and the more direct you can be, the more they're going to appreciate that honesty.

00:12:20:23 - 00:12:34:01
Unknown
Now, you're also going to find that a lot of these owners are making an assessment about you also just in your body language. Right. And so shooting straight also means communicating in a way that.

00:12:34:03 - 00:12:53:20
Unknown
Bears the most honest version of yourself. Case in point, I think this takes a little exercise and self-awareness. Probably another episode as well. But one of the things that I've noticed that these owners, it's a little bit like being out in the wild, right? It's almost like an animalistic nature. If you're kind of a goofy person, you just know who you are, then just be goofy.

00:12:53:20 - 00:13:10:18
Unknown
It's okay. You don't have to like, I mean, look the part, but like, if you got a kind of a, you know, just a certain way that you sit or whatever the case might be, trying to force yourself not to do that, they're going to just see that's even more awkward. And so if they call it out, or maybe you get ahead of it and say, hey, look, I know I'm a little bit off right now.

00:13:10:18 - 00:13:32:15
Unknown
It's just something. I'll admit, I'm a little nervous. I got a lot of respect for what you got doing. I just want to make sure I do this right. They're going to see that way more. As good thing than you can ever imagine. So shoot straight. But remember, you got to earn the right to shoot straight. All right, number four, what you have to understand about these small businesses is that the business and the personal are not separate.

00:13:32:17 - 00:13:53:09
Unknown
They are one thing. One thing all the way down, like the pickup truck. Like they pick their kids up from school in the same truck that they go out there and install a water heater. It's literally no difference. They host their Christmas parties, which are also the same things. They, the same locations or same spot that they'll have a wedding in the backyard for one of their employees.

00:13:53:09 - 00:14:04:17
Unknown
Like, none of these things are separate. And the reason you have to understand that is allowing you to just tread softly in these questions. Ask. You're asking as you're asking these questions.

00:14:04:17 - 00:14:23:02
Unknown
Case in point if you're out there and you find something, let's say you've earned their trust and you start to get to this point where you're starting to kind of dig into some of these initial questions about, you know, how they're ordering is going, or truck deliveries that maybe haven't showed up on time or tariffs or whatever those things are.

00:14:23:03 - 00:14:45:16
Unknown
Just recognize that these owners and their towns and what they do in their community are all in one same. So when they when they answer you, when they give you an answer, they would break your brain, because that would never happen in the corporate world. Just recognizes what small business is all about, what they do with their families, what they do with their communities, and what they would do with their business is all in one bucket oftentimes.

00:14:45:18 - 00:15:06:04
Unknown
And so understanding that you kind of have to show some reservation here, right? You might change it. You might do something different when you take over if you get the chance to take over. But this is probably not the time to start beating them up about why they've categorized things the way they did. You have time later to do that, but for right after this initial like, can I get a second conversation?

00:15:06:06 - 00:15:28:09
Unknown
You want to just take it easy and you want to just understand that business and personal are one thing for these folks, as it should be the real blood, sweat and tears and went into this business and this is what this is just what it is. This is truth. All right. Number five, last thing. I think this is something that I can't harp on enough, but it is showing humility through your actions in not three words.

00:15:28:09 - 00:15:31:12
Unknown
I've seen a lot of.

00:15:31:14 - 00:15:50:05
Unknown
Well-intended folks come out there and they just talk a lot. They just go out there and they're just like, oh no, I love what you've built. I respect this or what. You know, they're just they're given all this praise and almost sometimes too much. And the owner's probably never used in his entire life getting these many compliments in like five minutes, let alone the last 50 years.

00:15:50:07 - 00:16:13:08
Unknown
And you're just it's just a lot. And so what you can do is show humility through your actions. And it comes out in small ways. For example, the owner shows up often with their spouse if they're married, sometimes with their eldest or whatever. But it isn't uncommon to be at these meetings when you're meeting these owners and they're bringing their family along, you better show respect to their spouse.

00:16:13:10 - 00:16:28:16
Unknown
That's just something. You better talk to them. Hi, ma'am. Good to meet you. Sounds like you got build a great business. And I'm sure it couldn't be done without you. Right. Can you tell me a little bit about what you do day to day here? And, you know, maybe some things that I can learn because I recognize I'm not going to have you around.

00:16:28:18 - 00:16:47:07
Unknown
And every great household and every great business runs with a really strong team. And so anything you can do to help me understand just how you played a critical part in this would just help me make sure that, you know, let's say I'm married, make sure that my spouse is working. You're willing to step into that as well, or just I know what I'm potentially going to be missing and where I need to cover down on my gaps.

00:16:47:09 - 00:17:02:09
Unknown
Those actions, right by just talking to the person, shows that owner. Okay, is guys paying respect to the guy, or gals paying respect to the most important thing in my life outside of this business. That's humility. Or you know, the other day we were out at, at a visit

00:17:02:09 - 00:17:08:10
Unknown
one of the spouses came in a little later and even a little thing, like, just everybody standing up and offering your chair.

00:17:08:10 - 00:17:30:14
Unknown
There's no chairs left. And even though you could just say, well, right now it's a business meeting, just doing that little thing shows them because they're all old school. And so they just shows them that you care. Now, hopefully you genuinely mean this. I think it's just good practice period. But doing those things, believe it or not, even if you're in the midst of like some really great juicy information, you're going right through deal terms, whatever.

00:17:31:16 - 00:17:40:00
Unknown
If you don't do that stuff, you're going to find yourself wondering why you didn't get invite back, even though you felt like it went well. Right? It's just little things,

00:17:40:00 - 00:17:46:18
Unknown
you know, we left a meeting there recently, and, we had a lot of food left over. We had bought lunch for each other and kind of hung out.

00:17:46:20 - 00:17:56:06
Unknown
We spent the last ten minutes cleaning up, and the owners kept saying, no, no, no, don't worry about it. But let's just wouldn't ask. People say they said, don't worry about it. What's your action? Are you actually going to go clean up?

00:17:56:06 - 00:18:01:18
Unknown
And I'm probably telling you all this and you're probably thinking, Joe, something like, I don't understand how any of this stuff can matter.

00:18:01:18 - 00:18:30:09
Unknown
We're talking about deal stuff right now, and I'll go all the way back to the beginning. When these owners started, they had nothing. They had to figure out how to make something out of thin air. And every single day, like their word is bond and what they do and what they built. Even these companies that are worth seven, eight figures, whatever they are, these are people who have never forgotten where they came from because they recognize, like because it's so, like embedded in their DNA.

00:18:30:09 - 00:18:54:19
Unknown
They don't know how to be anything else. And so having these five things top of mind, again, all of it is just to allow you to earn the next meeting to earn their respect, to earn their trust. This is what they're built about. This is what they're all about. And if you can actually continue that in, let's say you get the great fortune of being able to take the torch of this business and carry it on in the next few decades or 50 years, or whatever it might be.

00:18:54:21 - 00:19:12:11
Unknown
I'd say, don't forget those things, because that's probably what's going to allow that, that that probably won't allow you to, like, run the business as successful as they did because they're doing that type of stuff every single day. If you just watch these owners, if you ever get the privilege of just like letting them take you around what they do day to day, you'll learn that a lot of this stuff just instinct.

00:19:12:11 - 00:19:28:12
Unknown
It's just the way they treat people, the way they talk to people, the way they like, even to the end of the little thing. Like you'll see an owner put their arm around one of the employees. It's just the way they are. It's a very much like a family. It's very much like this, like intense team. It's very much like the animal kingdom out there.

00:19:28:12 - 00:19:53:02
Unknown
There's just like this tribe that operates in this very like instinctual, intuitive nature. You don't want to lose that. You want to just make sure that. Yeah, sure. As you're kind of beating up CRMs and figuring out how to automate emails and all this stuff that you're doing and not forgetting to do these other things. And so just as a recap, just because I know we covered quite a bit of stuff there, if you're not, if you don't do anything else after this, just remember these five things and just sit with it.

00:19:53:04 - 00:20:08:01
Unknown
Just sit with it and just let it put it in your brain. But again, number one here is look the part dressed the right way. I'm not asking you if you never wore cowboy boots in your life, like you don't have to show up that I'm just saying, like, look normal, like just like a regular human,

00:20:08:01 - 00:20:15:02
Unknown
Second, earn the right to shoot straight. Spend the time just building rapport, talking about everything else except for shop.

00:20:15:04 - 00:20:41:19
Unknown
And then three shoot straight. And number four, I think is one of these things that I can't like. This is more of not an action, more than just to keep a mindset which is business and personal or the same thing. And if you understand that, then you understand what these businesses mean to these folks. And then lastly, humility through action, not words, do the things that show that you truly respect what they've built, and it will go a long way.

00:20:43:00 - 00:20:57:21
Unknown
I left a meeting one time where the owner basically didn't say anything the whole time. He had a lot of his teammates say things and whatever, which was great. He had a lot of questions, a lot of productive things. But the whole time I was trying to read and go, like, is this is kind of an old cowboy, you know, kind of looking dude.

00:20:57:22 - 00:21:20:11
Unknown
And at the end of it, he goes, I'm impressed. And then how much sage is impressed and he goes, yeah, this was this is what I, this is, this is he goes, the way I feel right now is what that is, is where I had hoped. This ended up. And basically I'm feeling all the right things. It's a feel thing.

00:21:20:11 - 00:21:37:17
Unknown
You look at this guy's a multi-millionaire, right? And he's like, he's feeling his way through business. It's kind of odd, right? Because every business meeting you've ever been in, there's no feelings. It's just ROI numbers. So just take this with you. I hope it's helpful. I hope you find it as we continue to like, do series or do conversations like this.

00:21:37:17 - 00:21:53:05
Unknown
Just take this is part one how you build rapport, what owners are looking for and how you earn their trust. How you earn their respect. If they respect you, they don't even need to like you. They just need to respect you. If they respect you, then it will allow for a much more fruitful conversation to go with or go forward with.

00:21:53:07 - 00:22:12:04
Unknown
All right y'all, that's all we got. Thanks again for tuning in again. If you enjoyed this content and conversations we've had with guests and other folks, we just greatly appreciate you helping us get the word out. Please like, subscribe, leave us a review, leave us a comment. It all matters. And at the end of the day, let's just get to work and keep America running.

00:22:12:04 - 00:22:37:06
Unknown
Thanks for tuning in to the American Operator Podcast, where we celebrate the backbone of America small business owners and operators like you. If you've enjoyed today's episode, be sure to subscribe so you'll never miss out on more of these stories and insights from people who keep our community strong. Until next time, keep building, keep operating, and keep America moving forward.