The Bigger Stage w/ Matt Stone

What do high-performing CEOs, professional athletes, and founders quietly struggle with behind the scenes?
In this episode of Building Business Relationships, Matt sits down with Jen Boyle, founder of a high-touch lifestyle management company serving high-net-worth families and executives across the U.S.

What begins as a story about fixing a scratch on a hardwood floor becomes a powerful metaphor for leadership, scaling, and the hidden pressures of success.

In this conversation, you’ll hear:
  • Why “hustle” may be the wrong mindset for sustainable growth
  • The invisible stress leaders carry — even at the top
  • How trust becomes the true currency in high-stakes relationships
  • Lessons from toxic leadership environments
  • Why failure is often the fastest path to long-term success
  • How to scale a business without losing your humanity
If you’re building something meaningful and want to grow without burning out — this episode is for you.

This is one of the final episodes under the Building Business Relationships pre-launch banner. The show will soon relaunch as The Bigger Stage with Matt Stone, expanding into deeper conversations about leadership, influence, and the human stories behind business success.
Subscribe so you don’t miss what’s next.

A conversation about trust, hustle culture, leadership, and the hidden emotional cost of success — with founder Jen Boyle.

For more on Jen Boyle, visit: https://morelm.com

What is The Bigger Stage w/ Matt Stone?

The Bigger Stage w/ Matt Stone is a conversation series about leadership, relationships, and the stories that expand influence.

Matt Stone sits down with CEOs, founders, leaders, and creatives to explore the human moments behind growth—how trust is built, how visibility changes responsibility, and how storytelling becomes a leadership skill as stakes rise.

This show is for entrepreneurs and leaders stepping into bigger roles, bigger audiences, and bigger impact—who want to lead with clarity, credibility, and connection, not performance.

Edited_FULL_BBR Pre-launch - Jen Boyle
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Matt Stone: [00:00:00] Welcome to the Building Business Relationships Show. I'm Matt Stone, and before we officially launch, we're exploring what matters most when it comes to relationships in business. These early episodes are about testing ideas, learning from guests, and hearing what you think belongs in the conversation.

Matt Stone: So please listen in, share your thoughts, and help shape what the show becomes. I'm super excited about this episode because the guest we have today, Jen Boyle, who's sitting right here, we're gonna get to her in just a second. She's exactly the kind of person that I had in mind when I started doing this show and, Jen's in Denver,

Matt Stone: right? You're based out of Denver, but you've got offices, and we'll get to that in our conversation. You've got offices in multiple cities in the U.S. Jen's got an incredible story from a South Dakota girl, if memory serves,

Matt Stone: I imagine boots and a horse or something, um, to building a great business for high net worth people, uh,

Matt Stone: it's a lifestyle management company called More. Jen helps manage [00:01:00] the homes and lives of people who have a lot of complexity financially and otherwise to make their lives easier and do it in a discreet way. So trust is the coin of the realm if in this business, if there ever were one.

Matt Stone: So that's, I'm gonna leave it at that and let Jen introduce the rest, but I just think your story of entrepreneurship and finding an opportunity, finding where you could do value and build this great business is. You must have a million stories. We're not even gonna get to a fraction of them today, but let's get into the conversation.

Matt Stone: Jen Boyle, welcome to the show.

Jen Boyle: Thank you. I'm so grateful to be here.

Matt Stone: Now I didn't do a great job of introducing your company. It's called More, uh, it's at morelm.com and we'll put that in the show notes. But tell me a little bit more about, more about More and its founding that I think would be important for someone to know.

Jen Boyle: Yeah, you, you didn't do a bad job.

Matt Stone: Okay. Oh, okay. [00:02:00] Alright.

Jen Boyle: Yeah, I, I started it about 12, 13 years ago. I just saw the need for it. Uh, you know, our lives are so busy and they keep getting busier. Whether you're focusing on stepping up in your career, starting a company, maybe you're an athlete and you have to be in multiple cities.

Jen Boyle: Um, or you, you are a parent and you're running the kids around and then having to, to cook a meal and do the laundry, like we all are overrun on business and in lifestyle. So I saw the need of people, uh, really wanting more time and where should they prioritize it? Where should they, uh, should they go to a soccer game?

Jen Boyle: Or should they be at home doing laundry or running the errands? You know, like where and what do they want out of their life? Because we only have a limited amount of time.

Matt Stone: Right. And, life gets complicated pretty fast. Uh, even if you don't have a ton of money, uh, it can be very [00:03:00] complicated. So then if you add on having multiple homes and you're traveling and you have staff, and I can just, I can only imagine. So, a little bit about the founding 'cause I, when we first talked, you talked about working early on with some sports, some professional athletes, was kind of one of the entrees into realizing, hey, there's a real need in the marketplace.

Matt Stone: Can you talk a little bit about maybe one of those first stories about who you met and what you realized from meeting them?

Jen Boyle: Well even, even the start of it, knowing that there's estate managers and then there's executive assistants, but there was still a gap in there. And I remember sitting down with a ton of CEOs and yeah, being surrounded by athletes and just, uh, picking apart their brain a little bit. And I had one, one, um, CEO that couldn't fix a scratch on his wood floor.

Jen Boyle: And we were at lunch and it was an hour lunch and he had 11 phone calls and no one would help fix this dang scratch 'cause it's not worth [00:04:00] their time to go out and fix that. I'm always like a principle-based person, so that made me upset. So we walked out of that lunch and I was like, first of all, I didn't get any of your time.

Jen Boyle: And then second of all, I'm gonna fix this scratch. So I was like, gimme your credit card and keys. And I went over and then I saw we don't just have a scratch issue that I'm gonna fix. We have a whole house issue. Because if his brain was focused on the growth of his company and like being well with his employees and just growing, growing, growing, of course he's not focused on his household, he's just surviving.

Jen Boyle: He needs to sleep and he needs to eat. But you, you need your house to be somewhat set up like a functioning business for you to be successful in all areas. So that's when I made the vision, made the plan, said, here's the type of vendors we need for this household to run, and here's what we're going to do.

Jen Boyle: Whether it's setting up the pantry organization so he knows what food he [00:05:00] has, having a closet organization so he doesn't keep buying clothes. 'cause he can't find his clothes or they're dirty on the floor. So going in, setting up these systems and then maintaining them on a weekly basis. And then, yeah, it grew right away to like three clients, I think in the first month.

Jen Boyle: And then I really got into the athletes, the agents, the coaches, because they have the same sort of demands. Um, and traveling just as much as CEOs or, or even parents, so.

Matt Stone: I'm really dialed into when you were talking about that lunch, I could feel in my heart how frustrated I would've been for all the same reasons. I can imagine you just kind of grabbing the bull by the horns and being like, yeah, just, and he was probably super relieved. Yeah?

Jen Boyle: Mm-hmm. Oh, very, very, yeah. I

Matt Stone: yeah,

Jen Boyle: why he was just gave me all access right away. Yeah. Here you go. Go fix it.

Matt Stone: Yeah. Do it. I love it.

Jen Boyle: Yeah. And then you just,

Matt Stone: Yeah.

Jen Boyle: see what people [00:06:00] need. You, you, you read people, you see their houses, you see their, their stresses, their pain points, and then you just grow and evolve.

Matt Stone: I love the, the literal and metaphorical significance of a scratch. I mean, we use the term like scratch the surface. And actually what you, when you went in and saw the scratch that he wasn't getting fixed, you're like, this is just scratching the surface of the problems around here. And a symptom of like the, the iceberg underneath to switch metaphors all of a sudden, uh, you know, is a whole other opportunity.

Matt Stone: So, um, fantastic.

Matt Stone: Now.

Jen Boyle: yeah, there's nothing, there's nothing wrong. Like we all are living kind of in that survival mode on the home front and the lifestyle, and it's because we prioritize different things. So there's nothing wrong with it that's just coming in and saying, okay, well if we have

Jen Boyle: a business that's gonna be successful, you need a CEO, you need a COO, you need a director, you need the managers, you need the front office. Like whatever it is. We just don't have that [00:07:00] process ever or have ever been taught that a house can be run like that as well. So it's just recognizing that and figuring out where you wanna spend your time, and then hiring the right people on your house front so you can focus on your priorities.

Matt Stone: Now I have to imagine, there's the relationship with your clients that you build, and that was a great example of how you started off with somebody and very quickly had enough credibility by relating to the issue they needed to solve and solving it. But there are probably many relationships that were significant in your business path.

Matt Stone: Is there one that just today for whatever reason, just stands out as a critical relationship that had a big impact on you getting to where you're at today?

Jen Boyle: Yes, and I kind of wanna do a two part of this, so I think unless in life you're looking at the good and the bad, you're not really growing and learning. [00:08:00] So when you ask that question, I feel like most people's minds go to a positive relationship. So I have two positive ones, but then I have a negative one, and I think both guided me down the path where I'm at right now. And if you don't acknowledge those negative ones and grow from them that you are, you're not growing really. So I, I think almost the negative helps me more, but my positive ones, like, so my dad has a financial advising company. And so when I was growing up my mom was a surgical nurse, but she quit, uh, I think when I was like nine, um, to start running the household because my dad got busier and busier, but his priorities were still to coach me in basketball and softball and golf and whatever. So his priorities were on point with me and my brother, but he grew a successful business where my mom had to really come in and, and run our lives and take [00:09:00] care of the trips and the household and everything.

Jen Boyle: So I think, I think seeing my dad as an entrepreneur and thinking outside of the box, like really gave me a great foundation of, uh, yeah, I can do whatever I want in life. Like it is about the choices that you make, um, that stack up. And then my mom had to make a choice, like, does she want sane kids? Um, yeah, I think so.

Jen Boyle: So she had to make the choice to sacrifice, you know, her career and, and to help evolve like my father's career and, and me and my brother. Um, and I, and my dad is still working today, so he loves what he does and he's a very positive impact. And then when I moved to Colorado, I met one of my favorite people.

Jen Boyle: Um, his name's Bob and he was in oil and gas, won a million awards, started a million different companies, and I actually personally trained him when I moved down here. And, uh, but he was an entrepreneur, thick and [00:10:00] thin even though it was all oil and gas. And he just showed me so much positivity and the same thing as like my dad did, is like, yeah, you can do it.

Jen Boyle: Like you, you have so much determination and, and you can grow and evolve with people. But they both on a, on the foundation side of what they taught me was, it is about relationships. It is a like for sure, coming from your heart, coming from care, coming from love, and then your success happens. It's never about the money, it's never about that.

Jen Boyle: It is about the service that you are providing and the love that you're providing to people. That is your point of life. And so they, they help me immensely, but then I can look at my negatives. And my negatives like are, Ooh, I never, uh, really worked for somebody well. I always had my own point of view. I [00:11:00] always do what I wanted to do.

Matt Stone: Are you a bit rogue? Are you a bit rogue? You can't be tamed.

Jen Boyle: can't. I'm off the, I am in outer space.

Matt Stone: Yeah. You're off the reservation people. Yeah.

Jen Boyle: Um, but like my biggest, like, yeah, I didn't do well in jobs even, even growing up. But then my biggest impact was I moved to Seattle when I graduated. 'cause of course when you graduate from college, like you're like, the biggest score is to get a job right away.

Jen Boyle: So I did, I felt super blessed about that. But I went into this job and it was so negative and like they wanted you to be robots. And again, I can't really be held to that structure. Um, but then they told me like I was like their top producing person and I got in trouble on a monthly basis, even though my numbers were so high, like in trouble

Jen Boyle: like, Hmm. Once in a while I chewed gum. Hmm. I guess they didn't like blondes there. They told me to dye [00:12:00] my hair brunette. Hmm. I guess I have, um, a, a speech accent from South Dakota, so they told me I need to go to speech therapy to fix it. Like whatever. But that was like such a big impact where it was like woo, i'm not meant to be here. I'm not meant to be around this type of energy, but also like I gotta do something great, like I gotta do something where I would never hire somebody and treat them like this. So it taught me that I need to not look at it just as I wanna grow a business. It taught me how I want to treat my employees. And how I want to uplevel them and come from love and come from respect and speak, um, encouragement into them and not just be a bad boss.

Matt Stone: You've almost left me speechless. I mean, I'm a man, like the calculus of dyeing your hair brunette. That's crazy. [00:13:00] Um, I mean, the message basically was, from what I can tell from you is we like the production, we just don't like you.

Jen Boyle: yeah.

Matt Stone: And so.

Jen Boyle: my problem.

Matt Stone: And it's like, and I love that, that you had such a sense of self though,

Matt Stone: because not everybody would've, some people might have internalized that and actually thought, maybe I'm just not good enough as a human.

Matt Stone: And you clearly had enough of a foundation of your sense of self worth. That you're like, this is crazy talk. Um, and this isn't what, and I have value. And if you can't see it, that's your problem like you just said. So that good on you, and boy, I wish, I wish I had been that centered, um, when I was younger.

Matt Stone: You know,

Jen Boyle: Yeah. But we have to grow. We

Matt Stone: you

Jen Boyle: like take those and grow from that and that's what makes you stronger and better

Matt Stone: right.

Jen Boyle: But yeah, I think a lot of that came from my foundation of my parents saying, no, you're you, you are different. Like you can do what you want. So then [00:14:00] you grow up with encouragement and that positivity

Matt Stone: Mm-hmm.

Jen Boyle: But then, you're also like literally born with stuff and

Matt Stone: Yeah.

Jen Boyle: so like I was

Matt Stone: Yeah.

Jen Boyle: to fight, so

Matt Stone: Okay.

Jen Boyle: I'm gonna fight through that situation.

Matt Stone: Yeah. And boy, if you got Jen fighting for you, you're in good shape. Okay? I'm gonna bring in my gun slinger over here. She's gonna just take care of business. When you hear like business and relationship talk now what's missing from the conversation, or what is

Matt Stone: the conversation not getting right?

Jen Boyle: I don't know if there's something missing except for my perspective is unless I spend time, literally time with the relationships that I've built, they're not gonna be where they need to be at. So for me. Like starting off so many years ago, it was like, oh, the next close, the [00:15:00] next close. Like, what, what else?

Jen Boyle: Who, how many more people can I hire? But you know, then you hit that wave where woo, you can't, you can't really grow on that level or you're going too fast where you are missing the piece that you actually loved, which is the relationship with is the time that you spend the connection that you have with that, that human. So for me, I just know that if I don't spend enough time with my clients, if I'm actually not hearing their concerns or feeling their pain, or if I don't spend enough time with my employees, we are missing honestly, the whole point of why we're on this earth. Um, but for sure how I've kept my clients and employees for so long, like we have to take the time.

Matt Stone: How are you approaching scaling with more and more clients and still maintaining that kind of high trust, intimate [00:16:00] connection between you and your clients?

Jen Boyle: Yeah, it's hard because for an owner you are pulled in a lot of different directions. Um, I just have to bring the right people around me. I have to bring more leaders on my team that can act like me or can show that love and comfort inside the house and with my employees. Um, and I have made it a priority to take time to go to lunch or go to a basketball game, or go to whatever, one of the, like my client's kids' sporting events with them

Jen Boyle: like, you have to take that time, but I have to bring other people in that can mimic my heart and, and effort as well, so they can be extensions of me.

Matt Stone: Yeah. They genuinely embody the same values that you bring to the table. Yeah. And you're not gonna force them to dye their hair a different color.

Jen Boyle: Absolutely not. We don't do that.

Matt Stone: Sorry. But everyone here has gotta be blonde. It's an old resentment I have and I'm now, [00:17:00] everyone has to be blonde and you all have to have a South Dakota, slight South Dakota accent.

Matt Stone: Yeah. Otherwise get outta here. Yeah.

Jen Boyle: We don't have time for you then.

Matt Stone: Yeah. Yeah. Uh, it's so funny because accents are such an authenticator. You know, when I hear an accent, it's like, oh, you come from a place and there's a whole richness of where you come from. And I don't know, I just think on the whole, it's a value add. Um, so

Matt Stone: yeah. Okay.

Jen Boyle: That's the individualism.

Matt Stone: Yeah.

Matt Stone: Exactly. Well listen, you know, this is a rapid fire pre-launch episode. So there's so much i'd love to go in with you in more depth at a later date, but we do have kind of a rapid fire ending to this, which are some quick questions to get to know you a little better personally,

Matt Stone: have a little fun and see if we can get some quick insights. Are you up for it?

Jen Boyle: Yes.

Matt Stone: Okay, you ready? It starts with a really frivolous thing. Okay. But it, I, I think it's interesting 'cause it's my favorite meal. Alright. So what's your favorite breakfast food?

Jen Boyle: Okay. It's not my favorite meal. I [00:18:00] don't even eat breakfast, but I have probably four cups coffee or espresso shots every morning. I'm trying to survive over here.

Matt Stone: I got it. I got it. I know what you're saying. I can't be over caffeinated enough. How? Alright, so if so then what would be your least? You don't like breakfast and you're not the only person who's answered it that way, by the way.

Matt Stone: Um, yeah. People, some people don't like breakfast. Um,

Matt Stone: uh, your least favorite breakfast food.

Matt Stone: The, like, the thing that at a buffet, you're like, Ugh. You're like, this is why I don't.

Jen Boyle: in probably any meat, the sausage, the bacon, the whatever. I just don't eat meat, so that grosses me out.

Matt Stone: That that is not, it is not humming, that is not, uh, strumming your, your guitar strings. Okay.

Jen Boyle: Not into it.

Matt Stone: Alright, Jen, something that you absolutely must do in your lifetime, like in your bucket.

Jen Boyle: Um, in my bucket is probably, it's, it's a deeper one. It's to have a family.

Matt Stone: Hmm.

Matt Stone: Great. [00:19:00] Yeah. Good. Good. Alright. Um, what is a word in business that is overused or that drives you crazy?

Jen Boyle: Hustle. Hustle because we can use so many different words. And even if we think that we have to hustle, we have to do it at a pace that works for your body, for your team, for your life, or else you burn out, so.

Matt Stone: That's a great one. Oh, so what would be an underused word?

Jen Boyle: Like honestly, it's not like going with the flow, but that's not a word. But you know, just being complacent or being okay with being okay.

Matt Stone: Being okay with being okay. Yeah, no, I mean, going with the flow. Uh, yeah, that's a, that in and of itself is a whole topic. I think it's really quite wise.

Matt Stone: Alright.

Matt Stone: Uh, what's the best advice for a young entrepreneur who's [00:20:00] experiencing their first failure?

Jen Boyle: Get over it. It's not that big of a deal. Like we put more judgment on ourselves than how the world is gonna judge you about that mistake just. Onto the next one.

Matt Stone: Yeah. Yeah. Someone else said, um, congratulations. You're, you're,

Jen Boyle: Yes.

Matt Stone: you're further along your path of, of succeeding. Like, you ha this, this is the way you get there. Um, so

Matt Stone: yeah.

Jen Boyle: That's how you win. The more failures you, you're stacking up is actually how you win.

Jen Boyle: So.

Matt Stone: A hundred percent. Awesome. Okay. Uh, and what are you most curious about right now in your life, whether it's business or not?

Jen Boyle: Scaling my company. Um, I've already done a good job about that, but there's always more levels that you can go on. Um, and then how AI is going to play a part in my business probably in the next five years at like what level capacity, because [00:21:00] it's going to be huge.

Matt Stone: And then trying to figure out, okay, but what is it for me in my business? 'cause it may not be the same. And it's also changing so fast. It feels like a moving target. So it's like, why would I, I, I had a conversation earlier this morning with someone in Singapore and he made a good point.

Matt Stone: He is like, don't ever do the year long subscriptions. I said, I get what you mean. Like if you pay for a year of an AI tool. Like two weeks from now, there's a competitor that's better or you know, there's, something has changed. So it's, it's,

Matt Stone: there's no stability. Yeah. Okay.

Matt Stone: Uh, now if somebody says, man, Jen is the bee's knees, I need to get in touch with her, where would they go to do that?

Jen Boyle: Yeah, website is is morelm.com. Our Instagram's @morelifestylemanagement. Um, my email's jen@morelm.com. yeah,

Matt Stone: And that's

Jen Boyle: fast ways to get ahold of me.

Matt Stone: Morelm is, More [00:22:00] Lifestyle Management,

Matt Stone: right?

Jen Boyle: Only one O in more the regular.

Matt Stone: It's not MOOR, it's, it's M-O-R-E-L-M and I'll put it on the screen. I usually do. And so it'll make it really easy for people to get ahold of you. Jen, thank you for taking time. I know you're super busy, um, but I really appreciate you taking some time to have a chat. You're just a delight and you have such great insight.

Jen Boyle: Thank you. I'm so grateful.

Matt Stone: Alright.

Matt Stone: Cool. Thanks for listening and watching this conversation and the Building Business Relationships Show. The pre-launch phase is all about discovery, so if something sparked your interest, we'd love to hear from you.

Matt Stone: Share your thoughts, ideas, guest suggestions, and any kind of feedback, and help us shape the conversations that come.

Matt Stone: And of course, subscribe so you'll be the very first to know when we officially launch, and in the meantime when new content drops, and it's pretty much every week. So thanks again for listening. We'll see you next time.

Jen Boyle: Thank you.