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Redefining Sales Through Servant Leadership

Dale Dupree is the co-founder of Sales Rebellion, which provides sales training and personal development. He is audacious with his outreach, intentional in his sales walk, and driven to create a community of sales professionals that cause undeniable curiosity and true impact. The rebellion believes in people over products, community over commission sales, fellowship over negotiations, and experiences over performing a pitch. Dale’s sales background dates back to his childhood when he wandered the halls of his father’s business.

“Sales is influence, sales is connection, and sales is impact.” - Dale

Dale DupreeCo-Founder of Sales Rebellion


Welcome to Building While Flying, a Sasha Group podcast where we interview business leaders about how they tackle challenges, stay resilient and navigate ever-changing skies. Hi, I’m Maribel Lara, your sometimes host of Building While Flying. And our guest today is Dale Dupree, co-founder and c s of the Sales Rebellion, which provides sales training and personal development.

He is audacious with his outreach, intentional in his sales walk. And driven to create a community of sales professionals that cause undeniable curiosity and true impact. The rebellion believes in people over products, community over commission checks, fellowship over negotiations and experiences over performing a pitch.

Dale’s sales background dates back to his childhood when he wandered the halls of his father’s. Business. All right, that now we’re done with the formalities, Dale, cuz you and I are buddies. Um, we met I think about four years ago now because it was shortly after we had launched The, Sasha Group in January of 2019.

And we met at a LinkedIn global event, right, like a connect event. And you. Connected with me first. Um, so I’m super happy to, to be here today. I’ve had the pleasure of being on your podcast. Um, and we’ll talk about the sales rebellion, but I wanna start with like, what should our listeners know about you, um, and your journey through sales?

And it was. November of 2019 because the pandemic happened literally four months later. That’s how I remember our meetup the best because, because also we were just starting as a business as well too. We launched in March. Officially of 2019. And, and that was like one of the first conversations that we had had was like, we’re basically both brand new to the businesses that we’ve started and or are running.

And so it was a, it was a fantastic meetup for everybody listening. Uh, Maribel is the exact person that you hear in these episodes that you, you see on social media. She’s an incredible human being and I was, Austra when I got to meet her because it’s not often that you find people that you can connect with, and I think that that would be what I would want people to understand about me and my sales walk is that.

For the most part, I never really lived it in the traditional way. There were definitely some mistakes that I made and some failure that I had in the early stages, but for the most part, the thing that I felt was the most important inside of the role itself was people and, and making connection. Being genuinely authentic with folks, which has a lot tied to it.

Things like perseverance, things like vulnerability. And, and it, it goes deeper than just the words as well too. So, so in my sales career, I’ve experienced all the highs and all the lows. You know, they say to entrepreneurs as an example, they say, Hey, you’re about to have, literally, when you start this business, you’re about to have know and understand better what it means to be like at the highest high and what it means to be at the lowest low.

And I’ll tell you, That, while I do agree with that to an extent, I’ve been way lower in my life than my business not having enough revenue one week to be quite frank with you. And so, so for me, I also have a much bigger picture perspective of the way I look at sales. And I look at my career in that. I don’t subscribe to the way that what I see as mediocrity tells us to run our businesses or to operate as employees or employers inside of an organization.

And I, and because of that, I look at sales as life. And life as sales. I love that. Um, it was actually one of our big points of connection was we actually connected very deeply on the loss that we’ve experienced in our personal lives, both connected to our parents. Um, and I think we share that perspective of like what’s actually important in life.

Um, and when you can. Take a step back and realize like the work you do right needs to be part of a more important bigger picture. Um, you approach work very differently, so, um, let’s, let’s talk about that, right? I think you. Opened my eyes. I think before I met you, I was very hesitant to ever refer to myself as a salesperson.

Um, and then I met you and I was like, no. I like how you talk about sales, like the way that you describe it. Yeah. I would say that my role is predominantly a sales role, right? And really we, we’ve talked about how any like senior role in any company has to have some aspect of sales in it. So, You could take the sales skills you’ve built over your career and be a fabulous, like CSO within any company you wanted to, that’s not what you’ve built.

So talk to us about what you’ve built. Um, what is the sales rebellion? Yeah, so wait, so the 

original conversation of the sales rebellion is very interesting when I reflect back on it in that the idea was ultimately creating a place for others to find freedom and, and, and I think that word alone carries a lot of weight.

People look at it differently to an extent, but we all believe it to be the same thing, which is that it, it unshackled or un tethers us from other things. So, so the original conversation was where, what does freedom look like to people in the sales world? And also how do we help people to not see this stereotypical label like you just talked, discussed of sales, but to help people to realize and recognize that everyone’s in sales all the time, whether it’s when you’re 17 years old and trying to convince your mom that.

Curfew doesn’t really matter anymore cause you’re almost 18. You know, like it, you can literally apply sales to most things, if not everything in your life. Because sales is influence, sales is connection, and sales is impact. Those three things are very important. So in my mind, when we started this organization, the, the number one goal in it was not to build some type of empire or.

Multimillion dollar organization for me to exit and become a unicorn and all the fun stuff, and some people do. I’m like, I don’t, no shade, like it’s all good. Whatever your perspective is. If I wanted to build something that would outlast me, number one, then ultimately that would, even though I would be at the foundation of the buildout, that it would be built by people.

That didn’t even have employment inside of our organization. And the, the, the big picture perspective of that and the more granular thought is how can we get people to believe in the movement of a rebellion inside of sales and then how do we define that? A rebellion built on hope and not fear, a rebellion built on earning.

What it is that you’re building and not buying, you know, or, or getting paid out, you know, in regards to what it is that you’re building, but with your own two hands, doing things that bring joy and happiness and pleasure to your life, and also fulfillment. And, and if we do those couple of things as an example, then the movement turns into something much different because we’re teaching people how to live better lives, ultimately, how to be happier, how to be more fulfilled.

But what happens is, is they see. Financial returns, and this happens all the time inside of the org. We’re four years old now, right? Based on the math we talked about earlier. And we’ve, we’ve got people that have made more money than they’ve ever made in their life. And we’re not talking about a hundred thousand dollars.

Right? We’re talking about big money. And, and it’s because if, if you talk to these people and take a testimonial, this is the craziest part and really where I feel that we’ve done. The best job. So when people come into a testimonial, you have to like scratch and no at getting them to talk about the financial outcome, quote unquote.

What they talk about is how their personal lives have been affected, how their outlooks have changed, how they feel more connected with their work, and ultimately that the, the basically the, the result of those things being better and, and the byproduct of them is, is that they’ve made more money. So, so for us it’s this.

It’s really getting people tied into this idea that sales can be so much bigger than the way that we’ve defined it at this stage, and that we can get past, as I like to call it, the sins of the father. All the things that have created the stereotypes that we are in control of. There is no one that controls those but us.

So if a person says to you, Oh, I don’t really like salespeople or, oh, I, I’m not into cold calls or whatever the case that has nothing to do with you. But the problem is, is that most people see that as, ooh, this is an attack on me. When really it’s a, it’s an attack on the experiences that they’ve had up until this point, and that they, they’re not preferable, and that’s why we need a rebellion.

I love it. Um, we’ve talked about those stereotypical things, right? Like, um, most of us have been on the re receiving end of it, cold calls, cold emails, um, people saying they know us or know something about us, but it really being like a canned approach. Um, talk to us about like what your service offerings are and who your customers are.

Yeah, the canned approach is interesting, right? Because people will say all the time, they’ll say, well, why do people still do it? Well, it’s cuz it works. So we don’t deny that. This idea of like what sales is now doesn’t work. It’s. It’s worked for decades and generations. The thing is, is that in those same organizations where it’s always worked, it doesn’t work the same in the year 2023 especially, there might be some outcomes that are being experienced and, and really from the perspective of understanding why people still dive into this, it’s cuz they’re insecure about change.

They don’t want, they say, well, it doesn’t matter if it’s not working as well. We’ll make it work. We’ll hire more people, we’ll do more volume, whatever the case from a metric standpoint because, Changing isn’t in the cards, right? There are so many people out there that are so tied into this identity of like what they’ve done so far and how they’ve done it.

I don’t sell the same as I sold back in 2007. I don’t sell the same as I sold back in 2013. I don’t sell the same as I sold back in 2020. In 2023, right? And, and sales every year at sales changes. The only thing that I will say that we have stayed very tried and true to, which no sales organization does, is the experience we give.

And that’s the difference between the rebellion and everybody else, is that people will say things like, if you run a better discovery call, you’ll close more deals. And I agree with that. But what is the experience like in the discovery call? And, and the thought is, is that in most organizations, A discovery call has plenty of great questions that they ask people, but why are we asking those questions?

And the difference between our org and others is, is that other orgs will tell you, will you ask these questions to qualify? You ask these questions to make it less about you and more about them. But ultimately what’s really happening is that you’re just being selfish. The questions are selfish. The questions that were asked are things that.

That ultimately create, they make us feel like we’re part of this whole presentation, the dog and funny show, but really it’s just to get us to the end so that we can be sold and right, and, and, and that’s what we do different. We don’t, we don’t advocate for, well, discovery call is a way to sell somebody.

We advocate that the discovery call is a great way to disqualify people. Move on to the next because it’s better for the person that you’re speaking to. To not put them through the, force them through this funnel or this process or these things that they don’t even need to go through in the first place because mm-hmm.

They’re not, they’re, they’re just not the right fit for our businesses. And when we, when you literally just take this one little instance that we’re talking about, this is just one little blip of, of teaching that we give to sellers. Everything changes where you start showing up to, to, to something like a discovery call.

Then you stop thinking about the questions as much as you think about the purpose for these questions and. Ultimately the delivery, the experience that you get to people, they don’t become these canned things. We do stuff like, Hey, I’m gonna share this quick video real quick with you and then ask you a few questions.

Is that okay? And nobody does that in discovery calls. Like, share a video, what are you talking? So we interrupt the typical patterns of people, right? We give them experiences that speak deeply and emotionally to them because that’s how we are as humans. We’re emotional creatures, which then defines.

Defies logic, it start. So if I’m saying like, gosh, I really wanna buy a consultant from Sasha Group, but it’s so much money. What happens is, is my, my heart says, but I, I really want it. And then it tells my brain, well, we’ll figure it out. Like we might not have the money right now, but we’ll figure it out and we’ll tell them exactly what we would need in order to do business.

And this is where. Mutual ground is created, and that’s what sales is all about. So, so from the experience we give, the creativity that backs at the heart of the salesperson and ultimately the act of service selflessly. So we believe in this identity of servant leadership. We don’t just preach it, we teach it.

We show people how to become a servant leader instead of their sales rep. We think that that’s, personally, we think that those things are the defining, uh, Pillars, if you will, and characteristics of the rebellion that make us different from anybody else. I love it. Um, so you work with people who are in sales and you get a lot of folks who are in their first years of their career in sales, um, because there’s a void, right?

They’re not necessarily getting formalized training at their offices. It’s like a sink and swim, um, reality in many places. Um, Or they’re being taught based on what’s worked for their manager or what, or what their manager has been taught over the years. And as we are talking about like authenticity really matters and sort of finding your way and what is authentic to you is probably gonna be more successful.

Than taking on somebody else’s approach. Um, and you’re also doing group work, right? Like you’re being hired by companies to come in and train their staff, and you’re doing consulting and all and all, um, the full gamut. You’re also giving a lot of content away. So talk to us about how that fits into your overall strategy.

We think that, personally, I think that if people can subscribe to what it is that our, our particular viewpoint and belief of sales is founded on inside of tsr. If we think that they can read content. We believe, I should say that if they read content and they are attached to it, this sounds like me, or this challenges me and makes me think different.

Any type of likability, basically, whether it’s it’s, they like it cuz they don’t, so on the emotional spectrum they think, well this, this is intense and I don’t know that I’m like this. Or they just, they feel that. They have found a kindred spirit in this moment In regards to our company and our message, we believe that those people will, they’ll begin to follow, they’ll, they will implement change around some of the ideas that we give to them, and ultimately that will lead to them coming to us and saying, I, I think it’s time that we team up, whether they’re a solopreneur, whether they’re a salesperson at a big organization, whether they’re VP of sales and they have.

50 reps they wanna put through a program. It like the size and scope of the, the ideal client profile for us isn’t as important as the heart of that person. So whether when we look at the demographics and we look at, we know exactly who typically buys from us, but what we really know is that it’s the person that desires change more than.

Anything else inside of their walk. And, and if we, if we align on those things, when those people come in, especially we know those are the people that get the best results. That there’s no denying that the outcomes from those people are ridiculous. Just to put it bluntly, like ridiculous what these people are able to accomplish and not just in their business, walk with their spouses, with their kids, with their grandparents.

I mean, the stuff that happens inside of our system ultimately is, is good for people. Because when we, when we sit down and we say, Hey, let’s make, let’s talk about what a cold call sounds like. We don’t sit down and define all these things that the traditional sales world has done. Instead, we challenge the narrative and say, well, what do you need to unlearn?

And what, what does your personal life look like when you talk to a strange person? You go to a grocery store, you, you, you feel your own call from someone else that you don’t know. What is that interaction like? How do you approach these things? We, we focus more on the identity of the person in that moment.

Their authenticity, like you just discussed and, and laid out for, for all the listeners in a way that. That then we can meet them where they are and say, cool, these are the things we have to ultimately work on. Like you can give a 32nd commercial, but then anybody that I ever met, but it will fail because of the semantics around it and because of the small things that we can identify that are emotionally charged in regards to who you are as a person that show up, selfishness, uh, vulner or uh, lack of vulnerability.

Even the identity even of just like a, a little bit of, of. Being too emotionally attached to the sale itself than helping the person. We can find all these things out by just talking a little bit about what’s going on in your life in most cases, which helps the person to then not just see sales in this tunnel vision.

They see it from every lens possible, which creates a better awareness, which leads to more selling Love it. So, um, I wanna get a little personal, uh, you, you nodded to something earlier. Um, actually you’ve spoken to it throughout, right? Like you’ve spoken about, um, sort of the importance of family and personal life, um, and how your work has had an impact on.

Your clients in their personal lives as well as the professional. But you also noted earlier the type of entrepreneur you wanted to be and how clear you are on that. Um, and and for the context of our listeners, right, like you walk that walk like you’re sitting at a restaurant or cafe right now and your family is with you, right?

Um, and and that’s very common. Like you and I met up and our families actually met cuz I was traveling. With my family. Um, and I was going to York City and you met me with yours. Right? But there’s, there’s really no distinction for you. Like the, it’s all part of your life. You’ve, you’ve been very intentional about how you’ve carved that out.

And so I think there’s a real, um, powerful story there for you to share with our listeners who are. Predominantly entrepreneurs or thinking, or people thinking about setting out onto their entrepreneurial path. So do you mind talking about that and sort of what entrepreneurship looks like for you?

Absolutely. I appreciate the opportunity to, Oh, am I still? You’re back. Cool. I appreciate the opportunity to share this part of my walk because the question’s very important to me as you know, and that it stems from a teaching and an influence on my own life and that I had a dad that was an entrepreneur, but that.

He was so good at involving us in his entrepreneurial walk, and not in a toxic way by any means, but in a fun, exciting, almost a journey is what we were on with our dad. And watching the evolution of his organization, his mindset, his success, his relationships, it was, it was an incredible thing. It’s an incredible thing, I should say, to look back on as an example of what it means to be an entrepreneur that cares deeply and his success, uh, it really like his success.

Speaks for itself and that most of the people that were impacted by my father outside of us, such as his clientele or friends or other family members, they, in his passing, we lost him in 2016 to cancer. One of the things that I found, you know, six hours literally after the, the, the procession, the funeral, we had people just.

Like every shape and size of human being that you could possibly imagine, come up to us and tell us, your dad was my copier guy. Like, this is how most of ’em started. And then they would tell stories about sleeping at our house because of DUIs or the crazy stuff where my dad was, he wasn’t, uh, necessarily the hero in the story cuz my dad always made it about other people, which I thought.

Ultimately was the best example that he gave to me, but he showed that it, that life integrates anywhere. And I remember vividly being 16 ish years old, 15 ish years old. It was around the time that I started touring with my band and, and having a lot of fun on the road and being on a major record label and doing the entertainment thing for quite some time.

And, and I, I’ll never forget it, that we were at an account where this guy, we were picking up a machine and this guy told my dad that it’s nothing personal, it’s just business. And my dad just eloquently looked at this man and said, it’s, it is personal. I pay my bills with the money that’s provided to me.

I, I give my children a better life. I, I, I look at business much differently than that statement. And, and he said, but I, I’m not offended. I I, but I do want you to know that it is very personal to me that I, I’m building my legacy for my existence and my family’s existence based on what I’m doing every day at work.

In a nutshell, that’s what he said to the guy. He said it way. More eloquently than I just did even. But I, I remember that influence vividly because I remember my dad being home af the end of the day from work. He wasn’t home at 10 o’clock at night. He put us to sleep every night. He set our prayers, read a story, did all these things.

Very traditional things that, that created a better relationship. He had kind of hard conversations with us. He was present for me in my adolescent years when I was acting a fool. He wasn’t just like, let’s put him in boarding school or, I don’t have time for this. He was, he was very intentional and very present.

And from my perspective, that’s what created the success of the family unit and not just my father’s success. And I want that for my life so badly. I want that for other people’s life as well too, because I recognize too that as a man that struggles deeply with depression and, and have even attempted suicide in my life, that I, I think about like, well, what, when my son learns these things, he’s sitting right next to me right now.

When, when he learns these things, how will he learn them? Will he learn them as things that count come from shame, right? Will he learn them as things that, uh, I, not necessarily I’m proud of, but I’m open to discussing and being vulnerable about cuz I don’t believe in the whole skeletons in my closet. Try to find them thing like, how will he learn these things?

How will they affect his life? And ultimately how will he use them to supercharge his walk? Because without my dad, I wouldn’t be here today. I would have been successful. In taking my own life and I wouldn’t be stay, I wouldn’t have a son and one on the way any day. Now I wouldn’t have an amazing marriage.

Uh, almost, uh, 20 years together this year. 17 married, um, I wouldn’t have these things if it wasn’t for this, this man that, that didn’t say I have to be an entrepreneur and make all this money. But that did say, I wanna build a legacy that’s worth leaving. And to me like that, that goes beyond the moment that thing’s so much more long term, which is hard for most of us to do.

But I’m bought into that concept entirely because I’ve seen the success of it. I love it. Um, such a powerful note. So, um, I’ll end on one question, which is a nod to our podcast name, Building While. Flying. In what ways would you say you are still building and, and where are you Flying. Yeah, we’re, I, I feel like it’s hard to say that we’re Flying, right?

But I, and I think my co-founder, Jeff Vigas, if anybody that’s listening to this wants to follow, uh, good content on LinkedIn, I post daily and Jeff is starting to post pretty consistently as well too. His story’s incredible. Jeff is one of the co-founders, uh, is my co-founder. Him and I started the organization and, and, and ultimately, You know, you could sit with the two of us and ask us this question.

I think there’d be like a, a big list of, of, well, there’s this, there’s that, there’s this. But, but we’ve got, we’ve done a really good job, especially with the things that we’ve learned from people such as The, Sasha, Group. A little shameless plug for you there. Thank you. That. It’s really important to understand that the failure is the best part about what you’re doing and that that action, you can’t have it without action ultimately.

So you can sit around, you can try to perfect things all you want. And look, everybody talks about this, but what they don’t talk about is that it’s really, it’s not that it’s really hard to take action. It’s that it’s, it’s almost. Embarrassing and or it’s, it’s personal to take action. Because if someone reaches out and says something like, well, you suck, or, I didn’t like this, or had a terrible experience, that can hurt more so than it does look bad on the business.

It can hurt personally. Yeah. And that stuff’s just gonna, the thing that you have to understand is that that’s gonna happen, like we just sent out a survey from a big group that we just did, uh, a pretty massive team training for six, seven total days, virtual and in person. And there was two people out of all of the employees, 60 ish total participants that gave us negative feedback.

And, and you can, you can look at that as like the deal breaker. You can realize that there’s 58 other people that had a really good experience. And you have to say to yourself, cool. So are we now leaned in far enough to the things that we’re good at, that we get a majority of responses that are positive, right?

And are we, and are we letting the negative affect us in a bad way? Or are we learning from the negative and saying, cool, there’s still 2%. Better that we can be at the end of the day. So let’s work on that and if, and if you just change your outlook and perspective on all the things that you’re still building, you never stop building because of it ultimately.

But, but I would say that, that the places that we’re Flying, I’d say the places specifically that we’re Flying is that we have had year over year, we’ve had growth. We are, we’re building something that’s much more of a mu movement in a community than it is this successful business. And we like that. We, we really do like that even though we’ve definitely, we have the criteria of being fastest growing, whatever, or, you know, some of the things that a lot of people go out and, and.

Earn for themselves, which I highly respect. We’re just not interested in that. If that stuff comes naturally great, fantastic. That’s cool. But what we’re more interested in is word of mouth reputation, what people are saying. And I, I believe that that’s the one thing that where we are Flying, we get a lot of, we have a great community, we have a fantastic community of people that nobody can deny that statement like that is the truth.

And I, I take a lot of of. Personal pride in that to say, yeah, this is, this is what it’s about. That, that, this is great. This is something that we’re doing very well. And if you, if you can manage that pride successfully in a way that doesn’t create further arrogance or deeper arrogance, right? Because there’s a, there’s a healthy amount of arrogance that we need to have, right?

But if we can level that and manage that, that pride in a way that says, well, it’s, it’s good and it’s important because it’s other people. And that’s what we do as organizations we serve. Whether you’re Walmart, it doesn’t matter who you are, you serve people. Yep. And as soon as you stop for that perspective, like you become commoditized.

You become just this thing that nobody like Congress, worst freaking, you know, you do a survey, it’s like everybody hates ’em, yet they continue to keep showing up. Right? Like this goes back to that idea of earlier where you said, why? What’s different about you guys and other people? Well, people keep going to the old stuff.

Like that’s how people are. Yeah. But if you can ignite just enough, right? The 10% of the people that do like Congress, right, are the, you like the, the small group of ’em, right? Like, if you can ignite just enough, they’ll keep you going. They’ll keep things in play ultimately. So think about the power of that inside of the, the small quote unquote community you’re building and just how big that actually is.

You might get credit for the best anecdote we’ve had thus far on, uh, building waffle. Um, so listeners like go check Dale out on LinkedIn. Um, uh, we, we didn’t even talk about like your LinkedIn strategy and how really phenomenal the community you’ve built and the, the personal brand that you’ve built.

There has been, but. It is what we try to teach our clients at Sasha about like the importance of content creation and content to provide your community with value as opposed to trying to sell them on something all the time. So please go follow Dale, um, because he is a wonderful example of that brought to life.

Um, my friend. Thank you so much for your time today. I’m looking forward to, uh, celebrating the growth of your family and hopefully, uh, having the ability to see you again sometime soon.

Thanks for joining us for Building While Flying today. I hope you learned as much as we did. We’ll meet you right back here next time for another flight.

Welcome to Building While Flying!

This weekly podcast is brought to you by Sasha Group. We’re the consultancy meets agency arm of the VaynerX family of companies. We help ambitious companies build strong brands that flex with the times through strategy, branding media and marketing.

In ever-changing times, businesses and brands have to shift and adapt. And across all sectors, there is an air of experimentation. Business owners are trying new things out in the wild;  building the plane while flying.

Our pilots, Katie Hankinson, Mickey Cloud, Maribel Lara, and Joe Quattrone will be talking to a diverse range of business leaders and founders. They’ll explore how these guests tackle various challenges while staying resilient and committed to growth. Through these real-life examples of strategies put into practice, we hope to inspire you to experiment and develop your own strategies as we all navigate these uncertain times together.

Redefining Sales Through Servant Leadership

Dale Dupree is the co-founder of Sales Rebellion, which provides sales training and personal development. He is audacious with his outreach, intentional in his sales walk, and driven to create a community of sales professionals that cause undeniable curiosity and true impact. The rebellion believes in people over products, community over commission sales, fellowship over negotiations, and experiences over performing a pitch. Dale’s sales background dates back to his childhood when he wandered the halls of his father’s business.

In this episode of the Building While Flying podcast, Dale joins Maribel Lara to explain why he is rebelling against the typical canned approach to sales and creating a place that offers freedom from it. He gives insight into his sales journey, why sales should be more personal, and why he focuses on connection and community, not numbers.

In-flight topics:

  • Dale’s Sales Journey
  • Building the rebellion
  • Evolving the way you sell
  • Finding mutual ground with your customer
  • What his father taught him about entrepreneurship
  • …and more!
Connect with Jared:

Dale’s LinkedIn:

Sales Rebellion Website:

Sales Rebellion Linkedin:

New York, NY
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Los Angeles, CA