EP 28 – Bringing a New Philosophy to Sales – Dale Dupree

Presentation of the episode

On the 28th episode of the Virtual Selling podcast, our guest is Dale Dupree, Founder & CSO of The Sales Rebellion.

He explains how he brings a new philosophy to sales and why he encourages teams to live intentionnaly as a sales person.

About Dale Dupree

To learn more about Dale Dupree and The Sales Rebellion click on the links below :


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Hi, I’m really happy to be with Dale Dupree, who is the founder of Sales Rebellion. Hi Dale, how are you doing today?

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I’m good Gabriel. I appreciate you having me on.


Yes. Great. And could you first tell us about your story and how you came to sell? 


Yeah, absolutely. So I date my story back to the founding of my father’s company, actually in 1984, he left the big box store, selling copy machines and actually decided for himself that he wanted to do it differently, more structured on a level that served people.

More respectfully than the company that he worked for. And so, because of that, he took a massive risk, and left a job where he was the number one sales rep to go and just do it on his own. And, I was born a year later in 1985. And people like to say that toner was running through my veins. And what’s funny about that is that in the copier industry, most businesses are actually family owned and operated to some extent whether it’s father, son, mother, daughter, maybe an aunt or an uncle, a cousin, I mean, there’s family inside of the business.

So from the moment  my dad started this copier company, there was destiny that somebody in my family was gonna end up being there at some point. And actually most of us worked all of my siblings some of my aunts as well, too. Most of us worked for my father at some point which was awesome. But for me personally, I decided it wasn’t necessarily the right thing for me.

And that was about the time I was 17 years old when my band that I was about to start touring with got signed to a record label, which eventually became a major record label Warner brothers. And I ended up spending time on the road touring and playing every night for a bunch of strange kids. But what my rec my realization was inside of those days was that man, I’m doing sales every night. I’m playing for a bunch of strange people. I’m trying to get them bought into my performance so that they’ll buy a CD or a t-shirt or a sticker, maybe all three at the end of the night. And, I slowly started to learn the identity of influence and over persuasion, the identity of community over commissioned checks and, and the concept of how to build a legacy inside of what it is that you’re doing, that you’re passionate about and what you intentionally want to accomplish. Because of that, I learned the foundations of sales, and so when I decided to leave the band and come and work for my father, to sell coffee machines of all things, the most boring thing on the face of the earth. I brought a lot of differentiation with me because I was this dude that was very creative that was a musician that was jumping into a stale and generic industry where the sale was very just black and white. And I colored the rainbow as they say, in those moments and that sales foundation that I started, you know, as a musician and as a creative carried into my  you know, copier life and, and, you know, painted me bright red. And for the next 13 years, I had a massive amount of success and eventually founded the sales rebellion where I work today. 


Great. And where did you call your company sales Rebelion? 


So we decided that to name the [00:04:00] rebellion after probably like, you know, two dozen names, just like anybody else goes through. But what we realize is that the thing that we’re building, isn’t just a company or an organization. It’s a movement, it’s a movement against the brainwashed sales world today that thinks that somehow money is the most important thing. And that’s why sales exists and, and having a sales career exists, but we don’t believe that.

Period. We believe that sales is service. We believe that impacting communities, organizations, and people is much more important than a commission check. We believe that legacies can be built through sales and because of the way that the typical sales world thinks, you know, you walk into a sales leader’s office and they have a picture of the Wolf of wall street and a quote from the movie behind them. We recognize that we’re going against the grain and doing these things in a rebellion seemed most appropriate. 


Yeah. Great. And so you are really against those, this philosophy about sales and money and and more into the human part of it.


Yeah. And, let me clarify that I made a ton of money selling copy machines of all things, right.

People when people see, you know, my financial success, even inside of that industry, they’re like, you can make that kind of money and copy yourselves. What am I doing over here in SAS or whatever they’re selling. Right. You know, so I still agree with the identity of sales, being a very lucrative job to begin with because there’s a massive amount of sacrifice.

There’s a massive amount of just very, a myriad of things. I should say that are money related at the end of the day, and that is still important. And, and listen, people want to pay you. That’s another piece of it, right? Nobody’s sitting around going, oh, I just wish I could have all this stuff for free. People are working hard to build their own businesses and transacting with others. They’re very happy to meet somebody that can bring that extrinsic and intrinsic value to the table that’s worth them. You know, leaning toward and committing to and purchasing with money, cold, hard cash, as they say, and you making some, so we’re not against profits, we’re not against the identity of what revenue is, because we believe that that money can change the world just the same as well if we’re [00:06:00] using it for the right things, the reason that we focus on. The identity of purpose and mission and vision, and the values that sales can bring to the table is because if we start there, it’s much easier for people to then have the money conversation. It’s much easier to be truthful and honest than having to be deceitful, or just trying to win the deal to just try to hit quota, to just hopefully make a commission check this month.

There’s that scarcity mindset that’s also created, you know, from money that we’re trying to keep people away from and, and build out abundance. And, the best way to do that is by recognizing that sales is a team sport and not like you and your folks and, and friends in the bullpen, I’m talking about you and your customers, the people that buy from you are part of your sales journey. And, the more that we can really look at it from an altruistic approach, the more it changes. 


I totally agree with you because the baseline of sales deck is team and deal. So it’s really about teaming with your buyers and creating a bond between buyers and sellers. And that’s the purpose of the solution is really to team and deal. That’s great. Today you are out of the copier business. What type of company do you help in selling? What type of product?


Yeah. Good question. So, yes, the sales rebellion is a training coaching development organization. And we help all kinds of different verticals from manufacturers to people that are selling actual products, tangible products. Whether that be even, you know, software or SAS all the way down to copy machines as well, all the way to L E D lights. You name it, we’ve been in it. And then also, you know, from a service standpoint, so people that are in like financial services, for example, whether it’s you know, somebody that is an advisor or they work in a bank, we’ve had a myriad of different verticals come through our organization and our bread and butter is based around for us. Like our ICP. The things that we look for are. Not necessarily the vertical itself. So whether it’s fashion and design or, you know, whether it’s a brokerage firm, we’re, we’re not too concerned about what you’re selling. We’re more concerned about where’s your heart at and what do you wanna accomplish? Are you interested in giving experiences to people that are undeniable and that cause curiosity and that interrupt the typical patterns and that change the game. Are you committed to the identity of a rebellion inside of your organization from that perspective of purpose and hope and really living intentionally as a salesperson. And if people can buy into that side of things, it’s much easier for them to then take what it is that we’re teaching them on all aspects from prospecting to pipeline, building to the actual framework of their sales process and adapt those things believe in those things and see them come to fruition from a success standpoint.


And so how do you transmit this rebellion spirit? What is… It’s only training or what do you break into the people’s mindset for them to change? 


Yeah. So to just to give you like an identity or an overview, I should say what it is that we bring to the table from a product standpoint is we are, we’re a full service firm, boutique firm.

So we have online curriculum. We have customized one-on-one coaching for teams and individuals as well, too. And so what we do is we take people through their rebel journey. Right. And we teach ’em the rebel way as we call it. And we start with the identity of basics and foundations or roots, if you will, of a sales professional’s career, where we talk about, what is your mission? What is your vision? How do you structure a day, even? What are the baseline and basic functions that you are committing to as a salesperson, to be able to win a deal in the first place, or find a prospect to begin with. And we teach the identity as well, too, of having a reason inside of your prospecting efforts, which translates into what we call the living pipeline, which is this concept of an ecosystem that we sell into and not just a rusted old leaky funnel that most people are shoving their prospects down in the first place. Doesn’t sound like a very nice place to be. If I’m a prospect and then the framework side of sales, right, we call it the rebel invasion. Which goes through the whole identity of how do you, how do you identify and qualify a prospect? And then how do you also walk them to the finish line with you arms locked instead of pushing them or dragging them to that finish line, which then helps us to translate the other side of sales, which is, you know, what we call the rebel gym, which is an attitude mindset and really just the idea of how are we relating to people? How are we communicating with people?


Are we empathetic? Are we being mindful? Are we genuine? Because we believe that’s a huge piece of the puzzle of sales and nobody really teaches it. Instead, people just teach, like here’s a sequence, follow it, do it every day and you’ll get some sales. And does that stuff work? Absolutely. It works. Okay. But what is it? Does it actually keep people working at that organization for 15, 25, 30 years and clients coming back over and over again and happy to do business with those people? The answer is no, quite simply. It’s easy for, it was very easy for the copier warrior, which was my alias inside of the copier industry. As my personal brand. It was very easy for me to go and win business that people had been supporting for 20 plus years because the sales world is stale. It’s generic, it’s bland. It doesn’t bring anything to the table. It doesn’t build relationships. Instead, it just nurtures money over and over again, it nurtures the transaction, and those are empty places.

And I was leading with a completely different revolutionary concept inside of my marketplace with individual people. I sparked something and sure. It took time. It took me a couple years to really, you know, lay the gauntlet down and create consistency, but that time is worth it. And any salesperson that’s playing a short term or, you know, Quick win outlook of their sales walk is gonna lose 100%, especially if they’re up against people like the copier warrior or like the rebels that are in our system.

You know, that really the, the idea for us at the end of the day is how do [00:12:00] we help people that are going through our courses to be better people, right? Not just better sales people, but better people. And because of that, because of that focus, we cause people to change a lot of things in their life. Not purposefully, right. It’s not like our agenda to come in and make you do all these things different. We watch that slowly happen from the choice of the seller, the choice of the team, the choice of the sales leader, because they start to slowly recognize, wow, I can do it this way. And it’s just as effective. If not better. And it also makes me feel more complete as a human and I have better, you know, responses from people. We call it the, when we prospect, we call it, get the best no you’ve ever gotten. That’s what we say. Where in most cases people are like chase the no, to get a yes. Right? We’ll have somebody write you an email and go, wow. That was the best prospecting method I’ve ever seen in my life. But unfortunately we use our brother-in-law and we can’t really fire him. Right? Like that’s the kind of conversation that you should be having as a salesperson. We believe it, we teach and we breathe it every day. 


And can you give us some examples of a story of one of your training making this journey?


Sure. Great question. So one that comes to mind right now is a young man out of Australia. I can’t say the name of the company you know, NDAs and all that stuff, but the organization that he worked for put him through the training really had they believed that he could be better than what he was now. Their quota for setting appointments monthly was four. Now they were going after really big organizations as well, two billion dollar banks, right? Like massive organizations. And so what happened in the process of us coming into the fold and helping this young man, an individual contributor in his role is that he went from that four appointments a month to setting upwards of 20 on a monthly basis. Now, what he did though, is he adopted one of our favorite concepts, which is what we call it, interrupt marketing. And so we have a thing called the rebel letter campaign. It’s [00:14:00] easy for anybody listening, just to Google the crumpled letter and you’ll find a whole page and breakdown of what it is, but it’s a four part sequence concept that builds out conversation with others instead of just pitching them on product and trying to find pain and poke at it or whatever else, you know, people do with that. But instead it gives the person a very unique experience. It does highlight some of the illnesses they might be affected by from a business standpoint, but it also talks about some of the pleasures they might want to enter into as well based on product service and offering without selling on the advantage and benefits. Instead, it tells a story, right? It tells. Builds this narrative, and it’s very creative. For example, one of the letters that has a big coffee stain on it. And when you open the letter up, you know, it says that here’s a coaster. And when you open the letter up and you start reading it, it says, Hey, 90% of the sales and marketing you get is trash. And it’s probably gonna go in the garbage anyway. So we thought it would be mindful and a better use of your time to be able to repurpose this letter into a coffee coaster. So every time you’re sipping on that morning, Joe, you can think of me. And because we interrupt that mindset and we, and we hit something that a nerve, right. That’s very common. It’s very familiar. Like, yeah, I do get a lot of sales garbage. Right. Thank you for this coffee coaster. It makes it much easier for that rep in Australia to call and say, Hey, this is so and so calling with this company, did you get my coffee coaster? Hey. Yeah, I did actually. That was very clever. And, because we can sequence those letters as well, too. And we have more than one. We’re not relying on this one, hitter quitter concept that so many sales people fall victim to instead we’re looking at something from a long term perspective, and we’re trying to build that relationship. Gain that trust and credibility from people, cuz that’s the first thing that sellers need to be focused on.

And if people like what’s happening to them bonus, right? If people like you, when they’re talking to you bonus and if all those things fall into place, it’s much harder to lose that sale. It’s yours to lose as we like to say inside of the rebellion. [00:16:00] So now we’ve seen, we’ve seen instances of that. We’ve seen instances of entire teams writing 250% of their yearly quota annually, we have gotten some pretty significant wins in our book to include reps, you know, selling their products to giant organizations like Bank of America or Papa Johns all over the United States. There have been a myriad of different wins that the rebellion has experienced that are bar none.


And what is your tip when it’s not a good day, you have a lot of no and a lot of door closed. How do you find the moral to find back the patient and to be again lively with your next customer? 


So what we recommend is a proactive approach, right? We, what we tell sellers to start thinking about is less about, I gotta make 80 calls today because that’s my call quota and more about how do I have fun with this? How do I mix it up? How do I create conversation? And so if proactively, we started that place, even if we’re not getting in a lot of connections or we’re hitting a lot of voicemail or, you know, we’re talking to people, but they’re not the decision makers, those folks aren’t in today. It allows for us to have a lot more confidence instilled in those moments, because we are breaking through to other people inside of the organization, or we’re building that repetition of doing something differently and doing it differently enough that we can always be pivoting around the perspective of like how we’re calling somebody, for example, because the definition of insanity is to do the same thing over and over again, and expect a different result. Right? So if we can, as sales people, if we can focus in and zoom the lens in around this idea of proactively just starting with interrupting patterns, telling people when they pick up the phone. Hey, you know, I’m sorry, this is a sales call, probably the last thing you wanted today, but Hey, good news. I’m not pedaling any kind of timeshares and I’m not calling about your car’s extended warranty. Would you like to roll the dice and see what I do have? And if we do, if we do things that are a little bit [00:18:00] non-traditional to the typical approach, we get better conversations with people. And so for me, it’s about that proactive mindset, because when you are talking to people, if you can make them laugh, feel a connection, have a great conversation, gain some earned knowledge that you pull out of those conversations with folks decision maker or not. Then at the end of the day, if you didn’t set an appointment, that’s okay because you shouldn’t be focused every day on setting an appointment. That’s why so many people don’t in the first place. Instead when you pull back and you relax and you allow naturally for the time to be right, the person to have interest in your proposition to be valuable enough, both intrinsically and extrinsically for that human being. And when we lean into those things harder, instead of just saying. I’m gonna use this pitch and see if it works right. Then, proactively by the end of the day, even if you got hung up on three or four times, you’re gonna have a smile on your face. You’re gonna have a different attitude because you know, tomorrow was brand new and you know, that last week on a Monday, you set six appointments and you’re gonna replicate that.


Great. So what I understand it’s really to be a rebel is to have fun. Is that it?


That’s a great way to put it. 


Thanks a lot. This episode of the virtual selling podcast is over. Thanks for sticking around. Join us twice a week for a new episode, with new stories and challenges of giants in the field. If you enjoy today’s episode, we are always listening for your feedback. Share the show and subscribe on your favorite podcast platform so you don’t miss any episode. This episode was brought to you by, the virtual selling platform that increases your sales team efficiency and sales readiness, enables remote management and vemp sales operational excellence. Book your demo today to discover how you can close more deals with engaging and better prep customer meetings. Thanks a lot Dale. It was really a pleasure. 


Thank you.



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