Why Your Multi-6 Figure Business is Burning You Out (And How to Fix It)
8 Aug 2026 · 50 min
Kelsey Kenry, a former inmate turned entrepreneur coach, talks about why high-earning women burn out running their businesses alone. She spent 15 years helping them fix the identity-level issues that trap them in exhaustion, and explains why equating money with freedom keeps them stuck.
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I am in no way ever going to vilify money. We need money. Money is really important, especially as women. We need to make money. We need to make a lot of it, and we need to do that in a way that does not suffocate us.
Hello and welcome back. I'm Bunny Young, serial entrepreneur, mom of 4 beautiful kids, and the host of the Yes And Podcast. This show exists for anyone who is done waiting for permission to build their life the way they actually want it. And today's guest is proof that it is never too late or too early to start over, and that the rebuild is often what builds the best thing. My guest today spent her early 20s in and out of jail, drinking every night, watching her life come apart in real time. She saw the writing on the wall and she did something about it. Instead of giving up, she got up and found her way back. And then she spent the next 15 years going inside the businesses of high-achieving multi-six and seven-figure women to dive diagnose what is broken in the business, not the person, and rebuild what is missing and stay beside them through it all. The operational work and the identity work, which we know I am a full F yes for, and stay and support until the business runs without that woman having to be in the room. She is a multi-industry entrepreneur, a bestselling author, a wife, a mom, and she says something in her work that I have been thinking about ever since I read it, which is a business that only works when you are exhausted and available around the clock is not actually freedom no matter how much money the business is making. So I'm really looking forward to sharing this conversation with you. I've got a juicy bit for the second question, and then I've got a juicy ending as well. So stick with us. And Kelsey Kenry, welcome to the Yes And Podcast. Did I nail the last name?
Having me, Bunny Young, it's always— you did, you did. It's, it's so— it's like the question of the century for people of like, how do I say this? And then I tell them, and it's like the look on people's faces is always great because they're like, how did those letters make those sounds. That doesn't make sense.
I, I mean, but, and yes, and that's like a really great analogy for your life though, because if you guys are watching this on YouTube and you guys are watching the video, like, go check out the video because Kelsey is— she's ripped, she's tattooed, she's tanned, and she also is brilliant. And so I feel like your last name is just like a really good representation of how people underestimate you.
Hmm. It's so true. It's so true. And I think what's interesting about that is I think that so much of it is, and we do this as women all the time, is like, it's our perception of people underestimating us when in reality it's like us underestimating ourselves. And I think like, obviously rebuilding from where I came from, there was so much shame around my story that it was like, do people actually think that? Or am I assuming that they think that because that's what I think about myself?
Oh, okay. Moment of silence for the mic drop that just happened. And let's— the, the thing that I really love about what you just shared is that you've gone and taken full ownership of your story and used it to build something incredible. So I wanna start with that story that you're referring to, which is your early 20s in and out of jail, drinking every night. What did 20-year-old Kelsey think that her life was going to look like?
You know what's so interesting about that is 20-year-old Kelsey didn't have a vision for her life. I think that's why I continued. It was like every single day was just that day in front of me. There was no future, there was no plan, there was no desire for growth or betterment. Um, but a lot of my behaviors and habits were coming from a place of pain and wanting to numb that pain. And so that became essentially my singular goal in each day was like, how do I numb this pain? And that's why I spent 10 years in those self-destructive patterns. So there was no pain, there was no future, there was no desire for anything beyond like, let me make it through another day.
What does 20-year-old Kelsey think of your life now?
That's a great question. I think she would be in disbelief and also be like, yes. And the reason why I think that is one of the stories that I tell often is about the glimmer of hope. And the glimmer of hope was the glimmer that showed up when I was arrested for the third time. And that was my rock bottom. And when I met my eyes in the mirror for the first time, So something that you said was like ownership, right? So radical responsibility is one of my highest values. And that was the moment that I took ownership for recognition that I actually had a choice to live, to not live, to make something with myself. And the glimmer of hope was what showed up in that moment of like, okay, actually this reminder of choice has showed up for me in this moment as hope is what it was disguised in that moment. And so that glimmer of hope, I think, was my internal internal knowing of like, there's more for you that you have not touched yet. And so I think that glimmer of hope, 20-year-old Kelsey knew that was there, but she was too numb in her life, uh, to actually do anything with it.
Oh my gosh. Yes. There's so much here that we could spend the entire episode on. However, are you ready to take 20-year-old Kelsey on this journey to this really juicy question that I've been saving for you?
I have chills, but I feel like if there's anybody that could do it, let's do it. Let's, it's gotta be you, Bunny.
Ah, here we go. Here we go. Like, here's me stepping on the landmine and we're all gonna be okay. We're gonna take a deep breath. And you are fully aware that in the land of female entrepreneurship, actually in the land of dudes and entrepreneurship, there is so many less games that I feel like women in entrepreneurship have to play. And the unspoken rules that I feel like I'm constantly behind on because I grew up with dudes and I grew up with a lot of like male friends and we could get pissed at each other and like, then 2 seconds later, we're just going to get lunch. And there, there really wasn't a whole lot of the behind the scenes drama that I've found in a lot of like sister wounds that I honestly own. We talk about radical responsibility. I own that I walk into rooms sometimes inheriting other people's sister wounds, as well as kind of holding myself back because I'm like, I don't, I don't know what is gonna happen if I let my guard down and I really go into this relationship. So in 22 years of business, for me, I've found that when I don't play by the rules, I don't fit other people's labels of what a woman in business with young kids should look like. It's not okay with some people. And you and I have a few things in common. We're not everyone's cup of tea, which we are fully okay with. We don't do BS and we're not here to perform. We're here to make a difference. And what I, I just, ah, I wanna get into this question of what do you say to the people who question your ability to charge what you charge? Serve who you serve, live your life the way that you just shared you live your life, and run businesses the way that you do?
I think it comes down to you have to face yourself, right? Like, it really does come down to that radical responsibility again, because I believe that everything is a choice. Suffering is a choice, uh, jealousy is a choice, comparison is a choice, everything is a choice. So in each minute and every moment and every day and every week, every month, every year, we have a choice, right? And so for women that are struggling with like, I have to be this in order to be that, you have to go into acceptance of you are breaking the mold of what we have previously seen. Like even in my own career, I remember as I started to even coach women that were, that made more money than me, Right? Like, this was a huge mindfuck for me. It's like when people started hiring me that made more money than me. And what I realized is I had pedestalized revenue over character or over like my skill set or any of those things. And so I'm like, okay, so then I started to go into that performance, right? Which always like pulls us away from our alignment whenever we start doing things for other people. And so I'm like, okay, I'll just wear blazers. Like, that's what I need to do. I have to wear blazers because I'm a professional and then people will think I'm professional. But going back to what I said at the beginning, if I ask myself the question of who am I actually and what is the purpose, what is the reason why I need to impress these people— because what's on the other side of any sort of relationships that we're creating from performance is we're going to be let down. Yeah. So that's where people are like, okay, if I do this, I will get this result. But you know you won't. You actually won't, because you're gonna go into that, you will have let yourself down because you haven't been true to who you are, and you will have let the other person down because it won't be congruent, right? So if you go into every situation, whether it's a sales call, a piece of marketing, any of it with like, okay, is this fully me or is this me trying to mold myself to get somebody to like me? Because it's, we're inherently people pleasers. We want people to like us. So it's like, it's like getting comfortable with people not liking you is really what it comes down to.
How did you flex that muscle? How did you get to the point that you're at where— and, and I know in our, you know, friend conversations and our private conversations that you and I have still discussed the times when it doesn't feel good that people don't like you or like us. And how did you get to the point where you're practicing loving yourself more than caring about the approval of other individuals?
What's interesting is that when you ask me that question, I think if I'm being fully honest, I don't know that we ever stop caring what people think. And I think that's a— that's the lie that we will tell ourselves, is like, oh, if I could stop caring, then I can. But the reality is, is it goes back to the freedom of choice, right? Of like, people are going to— you want be liked. We want to be liked. It is our core desire as human. Research, science shows our core desire as humans is to be seen, heard, understood, right? So we know that. And so to expect that we could ever get to a point where we could be okay with someone not liking us is actually false. What's different is acceptance of knowing people are not going to like me that's going to feel hurtful for me. And yes, and right to your podcast, right? It's like, yes, people are not going to like me. Yes, that is going to hurt me. And I can still be myself and I can move forward from that and I can learn something from that. So if I'm being honest, I don't think that I've gotten to a point where I'm like, I don't care what people think about me. I think that people say that they're lying, because everybody cares. It's what you do with it. It's how you respond to it. It's, it's, it's, it's like, do you let that dysregulate you and then you go into a thought spiral of self-criticism? Or do you recognize that and say, okay, that person doesn't like me, we have different value system, that's hurtful, or whatever it is, and then move forward from it? Those are the— that's how I deal with it, is I care a lot. What people think and if people like me. And I know that everybody doesn't. It's both. Oof.
I think moving from that place, because I do have a genuine care for people, and I also understand that their thoughts and their reaction to me is the projection of themselves. And I think as a retired therapist, that has helped a lot. I'm wondering if you can take us through either like an actual scenario or what you do to slow it down in the moment? Because you gave us some really powerful concepts of the aftermath of it, and yet reacting in that moment when it gets uncomfortable and when you're having those thoughts, like, how do you coach yourself? How do you coach your clients through that? And you're welcome to share a real-life experience as well.
Yeah, so to me, like, I envision anytime that I've come up against this crossroads— I think it happens most for me, um, one of the things that's triggering for me is when somebody says something that's not true about me. And so I think this happens a lot, is like when we feel like there's not justice, or when we feel like somebody's spreading lies, or when we've been accused of something. And so that is, that is a trigger point for me because congruency and integrity, again, high values for me. And so in those moments, or in any moment where I feel that trigger, right, we all have to know what our triggers are. That's awareness, is always the first step. But like when you are triggered, I always this picture in my mind to like a two-way street. So you're at this crossroad, you have to— first there has to be a stop sign, right? Because I think instantly we're going to have the, the reactivity is going to want to speak up. So I think there has to be whatever your stop sign is. So practicality around that is, you know, whether that's breathing, grounding, disrupting your environment. Say it just happened at your computer, an email came in. I'm big on like a physical change So go outside, leave your office, stand up, turn around, sit on the ground, something to disrupt the physical, to kind of break that barrier. And then put yourself at the stop sign. The stop sign, what you do at the stop sign can be breathing, grounding, continuation of whatever physical environment change. Mm-hmm. Um, sometimes it's verbal processing. So everybody's gonna be a little bit different. You have to experiment. And then you have two choices, right? So your one choice is, spiral self-criticism. Your other choice is data, facts, and truth, right? So this is the— this is the point that I come to. So after I've regulated, because regulation always has to come first, and it's like, okay, what I'm realizing here is I'm really hurt. I realize this is triggering because of a value, or whatever that— that naming the thing, right? So as a therapist, you know, like, name the feeling, name the trigger, like, name it, right? And so once you name it and once you regulate, then it's like, what do do with it? And then it goes to like what you said, right? To where like the truth of this is, I know this about myself, or I know this is actually what happens. And I know that their perception of that is different than my perception. So that's the more helpful, because truth, data, and compassion is that one pathway. And then self-criticism and spiraling is your other pathway. And so it's just bringing yourself to that crossroads, and you can even close your eyes in that point and be like, okay, I literally have two choices here. My My natural, like, reaction previously has been like, why did you fuck that up? Why did you say that? What did you do? Pick yourself apart, right? Which is so unhelpful, but like, we all do it. And then there's the other side of that about like, what is true here? What are the facts? Write them down, say them out loud, whatever they are, and going down that path. So that's how I personally walk through it, and that allows me to kind of— that's how I process. And so that way, when I get to the end of it, it's like I can still be hurt or upset or feel the feeling, but at least I have, like, I don't have to be mean to myself about it because I think that's what perpetuates the suffering. I—
yes, yes. And we still have companies to run, we still have businesses, we still have magic to put into this world. And so, you know, I also, like, there's sometimes where my— one of my very best friends in business is a dude, like, and I, I call him and I'm like, this is going on, and he's like, why do you care? Like, it doesn't make you money. Like, that's literally his thing is like, why do you care? It doesn't make you money. And so I think about you working inside the businesses of your clients, of these women who from the outside have made 6, have made 7 figures, teams, clients who love them. And everything that you've walked us through is kind of the inner work. And I think that that is so important to talk about is that But success on the outside doesn't necessarily mean— and, and I've personally experienced this where it's like you have it quote unquote all on the outside, but inside you're just kind of like burning yourself down. And you've shared with me before that across a lot of your clients, you keep saying the same, or keep seeing the same thing at a certain level of success in business. What is it? What would you say that is?
Yeah. So the, the thing that is most common is it's not necessarily at a certain revenue level, but there is a shift in behavior that has to happen, right? So if you think about natural progression, general natural progression of business growth, when you start something and you're building from the ground up, it requires grit, hustle. Like there's a lot of output, if you will. Right. And so that output is generally initiated constantly by you as the owner. So you carry a little bit, even if you have a team right from the start, you carry a little bit of that solopreneur mentality of like, everything is dependent on me. I have to do everything. And then you hit the point, and this is like where all of my clients, they're at this intersection of like, okay, I did it that way. And what it got me was money. You know, I have financial freedom and flexibility. I have cars, houses, purses, shoes, things, um, and I'm empty. So they realize in that moment— and this is what a lot of people, they mask with performative things— if I have the Chanel, I will be happy. If I vacation more and post it on Instagram, I will be happy. And it's all performative, right? Because my belief is that our life should be better offline than it is online. Like, what's happening behind the scenes is actually the most important thing. So this shift, the shift that has to happen, it just— I'm like, I don't give a fuck if you're in Tahiti every other week if like you and your husband hate each other. I'm sorry, that's just how I feel, you know?
I just like— so here's, here's the thing that I want to like— I just really want you guys to listen in on this because the underlying tone of this is success and suffocation can exist in the same space, and they can exist in the same business, and they can exist in the same life. And like what Kelsey is saying is you can fix the operations, you can get the systems in, you can give the founder her life back, but if there's no life to actually live, if there, there is so many walls and so guarded and so burnt out that there's nothing left on the other side of that. It doesn't matter. That's not actual success. That is a really expensive, fancy, Chanel-lined cage that you have built for yourself.
Yeah, to impress other people, to generate more money. For what purpose, right? So I think the— what I was getting to is essentially the behavior has to shift to where Now you have perspective and you realize, okay, well, I don't want to sacrifice the financial flexibility because I am in no way ever going to vilify money. We need money. Money is really important, especially as women. We need to make money. We need to make a lot of it. And, and we need to do that in a way that does not suffocate us, that does not take us out of our values, that does not put us in a position to years from now be so wrought with stress and guilt and regret? Like, that's what I think about is like, am I going to regret this? Because I think a lot of people, the problem that I see across the board, if I could narrow it down to one thing, is it's a very short-sighted approach. It's a very short-sighted decision-making. It's very going in and saying, I get this opportunity. If I don't take it now, I'm going to miss and it's like, is that true, right? And so really the shift is in that longer-term decision-making. It's giving yourself space to make decisions that are in alignment with values. It's, it's recognition of what is actually important for me. Am I building somebody else's version of success? Because I think social media has just done this like fucking mindfuck people of like, oh, this is what success looks like. And I'm like, you guys, the reason why we want to make a lot of money is so we can do cool shit in our lives. But if your calendar is so full that you can't even do any of the cool shit, what is that for? Like, I don't want a laptop lifestyle on the beach. I want to not have my laptop on the beach. That's the point.
Yes. Yes, absolutely. And there's a softer side of this that's been reflected back to me, which is through my kids. And I want to go there with you as a mom in the aspect that we— I'm taking you guys behind, behind the scenes in a conversation that Kelsey and I had actually at the top of the International on like what we really bonded over, this conversation of, for me, birth, bringing my daughter into this world. People talk about like the identity shift of, you know, what it means to look at this other being that you've grown in your belly and now mother on their earth side. I— that was powerful for me. However, one of the most powerful things for me with a heart condition and all of the limitations that I have grown up with being told what my body could and could not handle, having a home birth with my first daughter and going through that, I met this version of myself that was so powerful. And that, you know, I, I— my daughters and I say we can do hard things. Like, we talk about that. However, the, the pain, the, the pressure, the contraction around labor that resulted in, at the end of this thing, like, the total and complete relief. I met this version of myself that was so powerful and so unstoppable and so un-eff-withable and you've shared how you were so clear, your intuition came through so clear through those processes for you in advocating for yourself. And I, like, I want to explore this because I, I didn't just leave that at the home birth. I, A, I had 3 more kids, but I also brought that into my business, I brought that into my marriage, I brought that into my life. And I'm like, if this is— I had that moment from, what is it, Encanto, where it's like, what else can I do? Like, I don't need to search out things that are as hard on my body physically and mentally as labor. However, I just— I— there's no going back once you unlock how, just how powerful you are.
Yeah, I think, you know, and that's exactly what it is, is I think that what it comes down to is I think that unfortunately most women, the hard that they choose is hard that the society has told us makes us worthy., not the hard that actually shows our potential, because these are two different things. And I know for me, I had a hospital birth with my oldest, and then because I had such a terrible experience there, I had home birth and then a free birth, accidental free birth. But just like you said, it changes you at a cellular level to go through an experience and mirror back. Like when I had my daughter, my first home birth, my first words, I think I shared this with you, were like, I fucking did it. It was about me. And it was like, wow, like I did that because we don't know what we're actually capable of until we give ourselves the opportunity to try. But we have all this like whole list of reasons why we can't, why we're not good enough, why we're not smart enough. Like I told myself all the same things in life and business across the board. So I think it really is just recognizing that like you may be choosing a hard, hard, but your hard is probably just busyness. That's a distraction that is causing like central nervous system, like your cognitive load that you're carrying. The actual hard is picking something that rewires your, your brain, is behavioral change, is habit change, is recognition of patterns, is setting boundaries, like a number of things. Like that's the stuff that's the actual hard that changes you, not the hard that just drains you.
Yes.
Because those are separate.
Absolutely. And like, there's 40 weeks of growing a baby to get to that moment. This happens in business where, you know, unless it's your fourth kid, you don't look pregnant right away. I feel like I looked pregnant immediately with my fourth kid. And, but I, I like, we celebrate the, the birth, we celebrate the success, we celebrate the overnight sensation. What we don't see, what we don't celebrate, what we oftentimes give up on is week 20, week 10, week 15, week 35, before we get to that moment. Every time right after I have delivered one of our children, my husband immediately comes to me and he's like, I'm so proud of you, you did it. Like, there's just this— it, it's an amazing sensation and an amazing feeling. And I've also told him, like, how do I have that? How can we hold energy outside of me growing a human for 40 weeks. Because like, let's celebrate along the way. Let's bring that energy to it where, like you said, I'm not necessarily saying celebrate the busy. I'm saying celebrate the needle moving. Celebrate yourself on your journey to that dream life because you deserve it. And how do you celebrate yourself on maybe a daily or a weekly basis and make sure it. It's not just the big milestones that you're seeing, Halcyon, that you're recognizing, and also the support aspect of it. Because, you know, you talked about your last baby was a free birth, and like, if you had started there, it would have been equally as great. However, you've shared with me like the confidence that built up over time to get to where you could literally catch your own child. And bring them into this world and be like, yes. And you were still supported.
It's really interesting because the— one of my biggest struggles is definitely— has always been celebrating myself. So I think this goes back to, if we trace it back to our childhood trauma, if you will, being adultified from a young age. Um, and so it was just like, I— it was always about doing. It was always about like, I just have to— I was in survival mode, right? And so knowing that like we all carry our shit into entrepreneurship, unfortunately, you know, you cannot separate it. Um, I carried that with me. So it was really just like everything was about like hitting the goal. And then if I didn't hit the goal exactly, then it was self-criticism, then it was spiraling. And so one of the things that has been tremendously helpful in learning to celebrate, actually two things. Number one, and across the board every single person should do this, is you need to rewrite your version of success. Because what we know, that our belief system determines everything that we do, right? And so if we believe that success is material or certain milestones or things like that, if that's how we are filing it in our brains and that's what we believe, then that's what we're seeking, right? And so when we don't hit that, it's like we're not successful. So one of the like really pivotal things that I did is I rewrote success from what I saw as a child, right? And what I had grown up to believe was success was based in materials and money, right? I think that's most people. And so when I rewrote my version of success and I was like, okay, I wanna redefine this in a way that like I can quantify, it was about a feeling. It was like, when I close my eyes and sit in my life, am I satisfied? Am I fulfilled? Right? Success to me is about a pizza, right? To where it's like, do I have good friendships? Is my marriage good? Am I treating Am I eating nutritious food? How do I feel in my relationship with my kids? So it's a combination of these things, but it comes back to a feeling. Because if I think about those things, then it's more about an ongoing basis, not a milestone, right? Like, I'm only successful if I reach this thing versus like, oh, I am this. So that's the first thing. And then the second thing that I had to do is I had to really learn— this was so hard for for me, I had to learn to focus on output over outcome. So for me it was like, okay, we're gonna launch this thing or we're gonna do this thing. And it was like, here's the goal. And the goals are generally outcome-based, right? Like this is the thing that we want. And so I found myself, it was like, you know how when things get quiet and when things feel uncertain, we start to shake and then our belief starts to shake and then we're like, am I doing it wrong? Am I fucking it up? Do I need to change everything? Da da da. Like whole spiral there, right? Right? And so for me, it was like, that doesn't feel safe in my body to look at, okay, I have to have that outcome because my body wants certainty. So I want that outcome right now. And that's not realistic, especially like launching business, et cetera. So I had to learn to shift to output. And so output for me was going back to the controllables of, let's say that we're, um, in a launch, right? So what that looks like is daily, it's like, what does success today look like? Um, you know, starting one new conversation, sending an email, posting something on social media, right? To where it's like quantifiable. You could check boxes, if you will. But it brings me back to like, I succeeded today. I hit my goals today because the output is— and, and output over time is what's going to generate the outcome. So that was a shift for me to where I'm like, oh man, I actually I don't have control over the outcome, but I do have control over the output. And so that, that was like, shook me to my core because I was like, for so long spent a lot of time spinning, um, so outcome-focused.
Yeah. We talk about that with like lead metrics and lag metrics and, you know, what people focus on the money in the bank, but they're not willing to focus on the output. They're not willing to focus on those lead metrics that put the money in the think. So I absolutely love that. Okay, we have a wrap-up question that is a juicy one, and then we have our final yes and definition question here. So, uh, last time I got to flirt with you in person, we met in Newport News. We went on a beach walk, and there was this moment where there's a group of us— it was like, I don't know, 20 of us standing on the beach and it's a photographer that I work with. There's all of these women that are just local, and a combination had flown in for this retreat that you were on. And I'm having this chat with you, and we were talking about support, we were talking about relationships. A lot of what we had talked about in this podcast online has been about ourselves, and really from like a what we do. I want to bring in the support aspect of it because because you are so well connected and you have been in some of these most incredible rooms. And we left that beach walk and I think the next day, the next photo I saw was you hanging out with Amanda Francis. And I kind of giggled to myself being like, of course you are. And I think I even text you. I was like, of course you are. Because in your world, something that I love about you is there's no hierarchy. Like you understand that there's no difference between somebody who has a million followers and somebody who has a hundred followers. And so it's a two-part question. One is the support aspect. How do you choose the rooms that you are in and how important is that to everything that you've already shared about the identity and the individual work in being successful in life and in business? And then the second part of the question is. Is when women per— in particular in business, other themselves and see somebody like Amanda Francis, see some of the other names that we could drop that, you know, are in both of our lives and that you put on social media and people are like, oh, that's a known name. When they other themselves, is there a difference between an Amanda Francis and a Kelsey and a Bunny Young and, you know, somebody that is starting a cookie shop from their garage? Judge. So that's my two-parter for you.
Okay, so last question first: the only difference is the one that you create in your mind. Like, I just spent so much of my life pedestaling people and being pedestaled by other people. And some of the feedback that I would get from people— like, people were even— because my old Instagram that's now my podcast Instagram, at one point I had like 27,000 followers, which is nothing now, compared to like people that have millions and stuff. But I remember I started that account like 2012, and people were like surprised it was me answering my messages. And so I'm like, no, like I'm just a regular human. Like I am very sarcastic, I cuss a lot, I make funny jokes. Like that's who you know, you've been around me, right?
Yes.
And so I'm like, I'm not like— don't like put me in this box of like just because I built something that's incredibly successful, like I don't want to be like so far away. Like, I'm still a human, you know, don't dehumanize me by putting me on a pedestal. And so, yeah, I think it's just like, even with Amanda Francis, sitting at the table with her, obviously I knew of her, I had read her book years ago, and I'm not a person who pedestals people based on income. To me, I think it's like, that's— I can separate, like, that is very cool what somebody has done and achieved, And also, this kind of connects with the room question. I care so much about who people are over what they have done.
Yes.
I really do. And that's, I think, obviously being an entrepreneur for 15 years, being with people who are well known, it's like, you guys, I've been behind the scenes of so many businesses and so many conversations. We're all the same. We're actually all the same. And I think that it put— it took me putting myself in those uncomfortable rooms where I felt like I wasn't qualified qualified to be there to actually fully understand that. Because I did pedestal people for so long that until I like shot myself up and like, let me stand next to them on the pedestal for a second and see what this is about, I'm like, oh, there actually is no pedestal. This is me making it up. And so the rooms that I choose to be in, I actually choose— like, the word that's coming to me is like wholeness. I admire the people that I admire are the people who lead with integrity and congruence and honesty and vulnerability, and the people who I meet offline who are the same that they are online, those are the kinds of rooms that I choose. I have chosen rooms previously based on outcomes that those people have created for themselves, and it's always been disappointing me. And so I have found that when I choose a room based on the character of the person, that is when I feel most connected.
That is so good. Like, I literally wrote that down of, "I care more about who you are than what you've done," because of everything— like, that's the perfect way to tie up this episode in a bow is none of it matters unless you're in love with who you are, you're whole with who you are. And that is actually the best space to create success in business, success in life, success in love from, is that wholeness. And so my final question before I just love on you with the deepest gratitude for you being here Kelsey, what is your definition of "yes, and"? Mm.
God, I feel like it's everything that we talked about today. It's, "Yes, I am this, and I am this." To me, I go directly to the whole person, right? It's about an acceptance of the whole person of just like, "Yes, I am smart and a professional and incredible at, you know, business strategy, and—" and very sarcastic, love hip hop, will twerk on a dance floor. That's like, it's like to me it's just like all of the above. It's all of the above. It's like, yes, I love business and I'm so ambitious and I love to also rot on my couch at night. I love it.
I absolutely love it. Oh my gosh. Kelsey, thank you so much for being here. This conversation is everything that I hoped it would be and so much more. I knew it was gonna be golden, and I'm just so grateful that you said yes, that we could record some of our private conversations in real time and share them with the world. So thank you so much.
Yeah, thank you for having me. I mean, it's always, I feel like talking to you is so easy, and thank you for just being so loving and, and reflecting things back to me. It's like my love language is words of affirmation, so I really appreciate just like how loving and how warm you are. And I'm, I just, even though we live on opposite sides of the country, it's like every time I see you or talk to you, it's like just instant connection. So you are just, you are such an incredible human.
Ah, I receive all of that. And I'm so grateful that you're moving 1,500 miles to be closer to me. I just, I take that so personally, moving your entire family halfway across the country. Just to be a little bit closer so we can work out together and we can spend some more time together. So we didn't even get into— we, we have to do a part 2 of this because we didn't even get into our international, uh, manager argument story that is definitely for another time. That's right, I almost bought a manager. Oh man, we are definitely gonna have to follow this.
And that's yes and I can sit and we can have these really intelligent, beautiful conversations at dinner and I will make you hold my So I can fight somebody and Bunny will just hand over her credit card and we'll get the resolution that we need. We, we eat each other out. That's what we're supposed to do. It's like, let just Bunny, Bunny brought me down when, you know, there's, it's like street Kelsey comes out sometimes. It's just, it just happens.
You know what? We'll, we'll give you guys the 2-minute version of this. So we went to. To like a really bougie dinner at the top of the Intercontinental, um, in downtown LA. And it's— it was the first time— no, it wasn't the first time we were in person together, but it was the first time that we were at like an intimate table like that together. And what— there was maybe a dozen women at this table, and you were coming in for a conference, and you had like coordinated— because if there's one thing you guys need to know about Kelsey is if she's in a group chat and things are not getting done, run. Like, she's taking charge of it and it's gonna happen. And so she's not from LA, I am. I drove down to, to meet them, and she just picks this restaurant. It's on like the 70-somethingth floor of this Intercontinental. We're literally even with the airplanes leaving from LAX. It was beautiful. She's got a private dining room. The end of the night, after like 3 and a half hours of us being up there, we go to get the check, and they bring the check and just set it on the table. There had been no discussion about splitting the checks. There had been no discussion about having one check. Like, no one checked— no pun intended— about this. And the server— Kelsey says, you know, we need separate checks. And the server goes, oh no, we don't, we don't do that. And so then, very efficiently, she's like— without emotion— she's like, I need a manager, right? And she shares with us that she has an extensive background in hospitality and knows for a fact that they they can split the checks. So since this is a 2-minute version, I'm gonna save you a lot of the cussing and conversations that happened back and forth as different individuals left the room, came back in the room, gave us different outcomes. Are like, they, they contradicted each other, which was also super frustrating. And we're all entrepreneurs and you're watching this team or this, this table of 12 individuals see how they manage conflict. Kelsey's like, not backing down, you know. I, I'm like here for the ride. And these other women are having discussions, and some people are getting uncomfortable and getting up and leaving the room, right? So moral of the story is Kelsey did not back down, and she got exactly what she wanted, which was splitting the check. And so then the server comes back to collect the payment. And in the meantime, because we're entrepreneurs, everybody had Venmo'd me because we were, we were having— you remember that? They solved it. Yeah. Yeah. In, in between. So the server comes back and says, okay, we split the check. So I've got 12 checks for you. We just split it. And I hand him— you, you finish this because this was the epic.
This was the crème de la crème where you handed him your card and he was like flabbergasted that he didn't have, and you were like, you hand him the card and you're like, just put it all on here after we went through the whole thing.
Well, it got even better than that because he split the check. So we had to scan one card 12 times.
Oh, that's what it was. Yes. I forgot about that part. Yeah. The thing is, is that like, I just, I don't, I, I pretty much don't take no for an answer anywhere in my life. And so like, I'm gonna find a solution no matter what I'm finding, I'm finding a way. Through hell or high water. So it was an experience, but it was also the way because the manager was a man and he started talking down to me, and that I will not stand for because one of the things that I teach every single day in effective communication is you have to advocate for your needs and you have to set boundaries. It's not like I was cussing at him or going to fight him. It luckily didn't escalate to that point, but I wasn't going to back down from— and especially if you're going to talk down to me because it's a room full of women and you think we're idiots when literally we had some of the most brilliant women in that room. Like, absolutely not. We're not standing for that. And I think there's a part of me that feels— I feel like a protector of people. Like, if I— for me to put a group of women together, it's like I just naturally almost like assume assume, like, leadership, if you will, or, or protection over. And I'm like, this doesn't— like, I'm going to put myself in the fire to protect these women. So that's just more my personality.
I loved it. And, and the conversation that Kelsey and I were able to have afterwards is we both achieved success. Like, we arrived at the definition that we had for success. I got my credit card points, I got my rewards points, and, you know, got Venmo'd, so it's not like I had to cover everybody's bill. And we allowed, like, people to total up their own totals, and it would have also been okay to get the split checks. Like, we— neither Kelsey nor I had a really controlling relationship with what success was going to look like, and we both got back in the elevator, like, completely content with everything that went down down with that situation. Not the way that, that she was treated, not the way that it was handled. The outcome though, we focused on the output, which was, okay, how do we solve for this? Yes, if no one else is going to solve it for us. And then Kelsey's working on having somebody else actually provide the solution as well. So it was just so beautiful, and we laugh about it to this day because it was just this moment where, you know, she looks across the table at me and she's like, somebody's gonna need to hold my hoops because this is, this is about go down. And I was like, all right, take those earrings off, here we go, I got your back. We're about to have a Toby Keith bar moment here, and I don't, I don't know what's going down, but I got your back.
It's fine, we got it, we got it handled. One of my clients once said to me, uh, she was like, the thing about Kelsey is that if you ever are in a situation where you're gonna go to jail Kelsey's probably coming with you. I mean, yes, I will fight for you. Oh my gosh.
Okay, so if you want that kind of person, woman energy in your corner, please go deeper with Kelsey. Please follow her on Instagram. Please tag her in your takeaways. It's @kelseykenrych, which is K-O-E-N-R-E-I-C-H. It's going to be in the show notes, all of her links, including her incredible mastermind. I have not personally been a part of it, but you guys know after this entire episode the caliber of the women and the support that's being held in there. All of that is right below this episode in the show notes. You can also DM her, you can DM me, and we will get you hooked up. And her book is Below the Surface, and go, go read it because it's, it's a real one. You guys are gonna love it. I am so grateful again, Kelsey, for you being here. I'm grateful for everybody else for being here until the very end. I know this episode hit, so do me a favor right now, go ahead and share it with one other person, that person who would also be in, in that jail cell next to you. You know who they would be. I like how we opened the episode with jail, we ended it with jail. This is just a full, full relationship here. Download this episode, leave a review, tag Kelsey and I on Instagram with your takeaways. We want to hear it. And every share of this episode, every share on social is so meaningful. It's so— it just means the world to me. And I just— my desire is that you put this conversation in front of someone who needs it today, because that's why we're here. That's the point of this podcast. And until the next episode, as always, I'm leaving you with these two words: yes, and.
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