Madeleine Raiford-Holland [00:01:44] Hey there, I'm Madeleine and welcome to The Luxe and The Short of It podcast. I'm a military wife, mom, and entrepreneur that went from a stressed out nine-to-fiver to now a present-minded seven-figure business owner and investor, all through the power of short-term rentals. Here we believe the Luxe life means having the time and financial freedom to be present for the moments that matter most. And I'm here to teach you the exact mindset shifts, insider expertise, and business strategy to make that a reality for you today. So are you ready to actively create the life you want? I'm Madeleine and this is The Luxe and The Short of It podcast.

Kristen Day [00:02:26] I was just having a conversation with someone else this morning after our conversation. I want them to know that there are a lot of people in this world that believe in them and that I am one of them.

Madeleine Raiford-Holland [00:02:41] Love that. And I think that is definitely part of your brilliance, is seeing people's uniqueness and understanding how they can mold that into something that one adds value to other people. And in turn, by default, adds monetary gain back to them. Like harnessing what people are good at for the greater good because when everything works together, then it just comes right on back. Maybe that's what we chat through today. For those of you new here or even related to my mentorship program, Kristen has been involved in-- well, involved is a minor word; instrumental in the growth and scale of helping me be of service to my community in ways that light me up. But most of the time people don't see Kristen because she doesn't like to be in front of the camera unless you've come on one of our Costa Rica retreats or even our Athens retreat. Kristen is there. But really just monumental in helping me grow and scale my different businesses. And so for that I'm extremely grateful and why I say she's all mine, folks. No, I am not sharing in that capacity, but she adds so much knowledge and wisdom in the space and I wanted to make sure that you guys got to hear some of her brilliance. And I think part of where that starts is being open to new friends and new relationships in the business space because our journey together wasn't necessarily conventional and we have our husbands to thank for that.

Kristen Day [00:04:49] And I just want to say too to echo that-- I've told you this privately, but I'll tell it to you again. One of the joys of my entrepreneurial career has been the journey that I have had with you and with your team. And I love watching you soar. So I'm not a mushy person, but I will cut it there. But I just want to make that known. It has been a privilege and I'm very grateful for the journey as well. How we met, I was working another event.

Madeleine Raiford-Holland [00:05:32] Happened to be in the short-term rentals.

Kristen Day [00:05:36] We shall not name names. Yes. And I had been working with that person for a while. I was part of curating their live event and Madeline and John happened to be at that live event. I was very busy and very tired. And my husband connected with them in a networking exercise.

Madeleine Raiford-Holland [00:06:08] It was an interesting networking exercise and we were all just disillusioned by the networking exercise and we bonded over that.

Kristen Day [00:06:20] Yes. So I was actually not present for the networking exercise. I was behind the scenes and my husband was attending to support me. So he met Madeline and John and then he walks up to me and he says, "We're going to lunch. And we're doing with this other couple." And I looked at him and I said, "I'm not going because I am tired and I'm busy." And I was in a very foul mood that day. We had a lot of behind the scenes items going on. And he said, "No, you're going to want to come to this lunch." I was like fine. So I get up from what I'm doing. I go in and there sat Madeline and John. And I am in a foul mood and I sit down and I said I think it was something along the lines of I'm sorry for whatever comes out of my mouth; it's going to be very unfiltered. I think I said something like even better.

Madeleine Raiford-Holland [00:07:23] Yeah. I was like I'm here for this.

Kristen Day [00:07:26] So we had an absolutely lively conversation at that lunch and you basically looked at me and said, "I want more of this." So we parted ways and I had no idea what was going to happen in the next 12 months after that event and meeting you guys. So we hopped on a call, we chatted through what working together was going be like. And here we are almost two years later.

Madeleine Raiford-Holland [00:08:05] Yes. Two years later.

Kristen Day [00:08:07] And not in my wildest dreams if you'd have pulled me out of that event that day and asked me who's that chick and are you guys going to be hanging out together in two years? I would have said absolutely not. And I'm so glad that that is not true.

Madeleine Raiford-Holland [00:08:30] I'm so glad that Nick and John-- because John did the same thing to me. Because he and Nick had connected first and he was like they're looking for other couple friends, other entrepreneur friends just like we are. And I'm like who are we going to meet? And if I give the name where the event was, it might tip it off a little bit. But I'm like we live in Georgia. This is the middle of the country. They live on the other side. Like, is this even going to work out? And I'm so glad that they did. And it's just even more serendipitous now in our stories. That was two years ago. And a little backstory of where John and I were in our journey to give you guys some context if you've been part of the listening to the show. This was when John was living out in Texas for six months while we were in that phase of rapid growth of our business. And so we were still in that struggle of wanting John to leave the nine to five and we were super, super close. And we had still thought about having John being an integral part of that business. And we have since determined that John's best in an advisory role and not in the day to day of our business. And Kristen has her own business and I mainly run our business and Nicholas at the time was still in his nine to five wanting to leave the W2. And he's since left; John has left the W2.

[00:10:02] And so it's been a beautiful journey seeing that play out in their lives as well as our lives. But it's also messy. I say beautiful, but it's like a really messy part. I don't want to speak for Kristen but it was definitely part of our life. It's been such a godsend to have them be part of our support group. People who are going through similar things of, hey, we're trying to find our lanes in our business and we're struggling. Or I've just been really down about this. I think that's one of the biggest struggles of being an entrepreneur, is that it can be so lonely. And the fact that Kristen and I like at this point in our journey are both pretty independently running our businesses, but it was the two of them who brought us together which I just think is extra sweet. I'm just thankful for that. So business besties are where it's at.

Kristen Day [00:11:21] Yes, 1000%.

Madeleine Raiford-Holland [00:11:24] And Kristen and I were chatting through there are so many different ways that we could take this conversation and we'll definitely have a subsequent episode just because we've been through so much of this journey together and she has so much value. But what we wanted you to take away from this was a few ways to find your network and your business besties. Because I think she and I both said like walking down the street, it's hard to know the people that you will truly connect with at a soul level. But that's what makes the difference in being successful entrepreneurs. What has been your experience in places that you've found those people?

Kristen Day [00:12:15] I love this question because it's tricky. If we go back to how we met and how our friendship grew, it was unexpected, I think is the right word. For me especially, I had been very determined to be very much in head down, I'm doing my thing, I'm growing this business. I am very focused. And honestly I felt like having a deeper relationship with my business friends was a little distracting. So if you're in that space where you think that the grind is the only way forward, I would encourage you to consider that that attitude could be keeping you from your best friend. And we get caught up in this really, really big space of I'm building, I'm growing, I'm head down, I am in the grind, I'm working my butt off. And I think oftentimes we can be closed off. I certainly was. That was one of my biggest mistakes. That has been my biggest mistake in business, is being a little closed off to good things, good potential. And I was lucky enough to have you in my life to be, one, persistent.

Madeleine Raiford-Holland [00:14:08] I'm relentless, folks.

Kristen Day [00:14:09] And be very patient, I think. My three things that I would say are number one, try your best not to assume the outcome of a relationship. Number two, if you find someone that you click with, pay attention to what you enjoy about them. I think one of the reasons why we have been able to stay so close friends is because we genuinely just enjoy business. It's our hobby, people. It's not a job. Business is a hobby for us.

Madeleine Raiford-Holland [00:15:04] We love it.

Kristen Day [00:15:04] We love it. And it's so rare to be able to find someone who also enjoys your hobbies. So people think my hobby is skiing or swimming or running or, I don't know, crocheting, but it can be business. So if you're in business and you love it, be on the lookout for other people who love it just as much as you do and be open to that. The third thing that I would say for me personally was do not be afraid. Try to change your mindset to growing relationships in one area of my business takes away from another. I think when we get a little scared of siloing ourselves, especially as business owners-- I think business owners in general we like a lot of wide open spaces. We like autonomy. We like independence. We like the ability to have our own schedule and our own time and our freedom. And sometimes when you're looking for relationships in business, it can feel like if I lean too much into this one, I will take away opportunities.

[00:16:36] And what you should be thinking is if this relationship and this friendship is really aligned with who I am as a person and my interest and my hobbies and my values, that is going to open up a wealth not only monetarily, but personally a wealth of opportunities for you that are in such alignment for you as a person. Any opportunities that it would take away is just out of alignment for. You don't need those things. We don't the buffet of opportunities. That's not helpful. We want the right opportunities. We want to say yes to the right things. And so looking at your friendships in that way has been helpful to me personally, because I'm able to really understand any project that we work on together, whether it's one business, two businesses, personal stuff, like whatever it is, it's so in alignment with who I want to be as a person. It's always fun. It always leads to joy. It's always good. And the things that I'm saying no to, to spend time with you, 1,000%, no regrets.

Madeleine Raiford-Holland [00:18:00] And I feel the exact same way. And you and I have chatted through the thought of this, both as we've kind of navigated things personally with the topic of work-life balance and that difference between work- life balance and work-life integration. And I think as business owners and entrepreneurs, at the end of the day, the buck stops with us. And we're the ones that are responsible for making sure things happen. And as we grow as business owners and entrepreneurs, the way that we do find "balance" is through that integration piece and enjoying people that you do business with. Kristen and I love to hang out outside of work. I'm doing air quotes if you're not watching the video piece of it. But what happens with that, because we love spending time together, we're friends outside of this, but our hobby is also business and we're in alignment with that. I can't tell you how many literal million dollar ideas have come out of conversations on my back porch over charcuterie or a veggie tray. As you grow in that, surrounding yourself with people who are in alignment, who think similarly to you, who have the same goals. It just exponentially multiplies your wealth building opportunities because you enjoy who you do business with. And I think that's something that Kristen and I have grown with as entrepreneurs, is life is too short to do business with people you don't like.

[00:20:01] And she said the things that she says no to in order to spend time with me and some other folks like in our circle. Life's too short, folks. It's kind of a tricky thing. And when she was talking about being afraid, I get that because a lot of times people were like, I don't want to risk our friendship. I don't want to risk a relationship. And we both had a moment of-- typically when Kristen works with somebody, it's in a six month container. And she tells you that from day one. I come into your business for six months and I start training my replacement on day one and at six months I'm out. Peace out deuces, I'm gone. And part of what she said is I'm a little bit persistent. I was like so we really love having you as part of our team. We went quote month to month from that. But at that point when we were saying, hey, can you stay like indefinitely stay as part of our team? It was a conversation of like my relationship with you is so much more important than anything that goes on in the business. And whether you choose to stay or you choose to leave, that won't affect our friendship because I value you as a human. And if you find somebody who is worth having that conversation with, do not let the fear of ruining the relationship keep you from doing business with them because it just becomes better if you like who you're doing business.

Kristen Day [00:21:39] You said something, we were at another event. We were prepping, we were actually prepping for an event coming in March. And I'll chat a little bit about that. But something that has stuck with me, you said it can be beautiful if you let it.

Madeleine Raiford-Holland [00:21:58] I forgot I said that. Glad you remembered.

Kristen Day [00:22:01] It just really resonated with me. And I think that when we are in business together and we're finding friendships and we are finding the people that we want to do business with, if you're the person that is I don't want to ruin the relationship, let's keep it strictly professional; I was that person in this scenario here because I really, really, really enjoyed my time. And that statement of it can be beautiful if you let it, being open to just allowing yourself to enjoy friends in business is so critical because it is very lonely. And we, as entrepreneurs, I think a lot of the time we think we have to do it on our own. And we do have to do a lot of stuff on our own. And that's okay. Because you are the one that is doing it and you are one that's in the weeds with it, doesn't mean that you have to carry it by yourself. And it can be something that is beautiful and is supportive and is a weight off of your shoulders, even to just know that there is another person out there who is going through the same thing that you are, that is in that season or has been in that season. You and John have been in the season, actually that I'm in currently. And it's so incredibly helpful to just note it's going to be okay. And so having that person, if you're too closed off because you're afraid of "things get a little messy" you're an entrepreneur, it's already messy.

Madeleine Raiford-Holland [00:23:57] Just FYI.

Kristen Day [00:24:00] You might as well enjoy that extra color struck in there, like go for it. Be open to having those deep, deep relationships with people and make sure that you're not closing yourself off to something that can be beautiful.

Madeleine Raiford-Holland [00:24:16] I think there's a certain amount of vulnerability that you have to have with that. And you were chatting a bit about that earlier about when you feel lonely at your lowest and you're like why am I still doing this? Because everything feels so hard and you want to give up. I think just about every entrepreneur has at least one, two, a million of those seasons where you question your life choices. And, honestly, are you really in the game if you haven't been kept up at night or woken up in the middle of the night thinking, what the heck? If you have to have one of those moments yet.

Kristen Day [00:25:02] It's coming.

Madeleine Raiford-Holland [00:25:02] It's coming. But if you've listened to the show, I've shared I had a really dark season when we were in Texas earlier this year, three months. It was so personally hard. Guess what, Kristen and Nick hopped on a plane. She came and that was literally the highlight of my entire trip there. And I was in such a really dark place personally. And it was a really special reminder of when things get really hard, you need those people who remind you why you're doing it. Wow, I didn't expect to cry on this episode. We were trying to keep it light and fluffy and airy. Oh, man. Moral of the story, find your people.

Kristen Day [00:26:06] Find your people!

Madeleine Raiford-Holland [00:26:06] I want you to find your people, which is why I'm hosting a stream on your STR journey workshop. We got to lighten this up a little bit.

Kristen Day [00:26:19] We have to, it has to.

Madeleine Raiford-Holland [00:26:21] We have created the space for you to do that, folks, because it's hard. Not everybody goes to in-person events and has husbands who play business bestie matchmaker. If only you're so lucky. But I want you to find your people. So we have created multiple containers for you to do. Kristen has been monumental in helping me do this because. I did not do live events in person, virtual at all before Kristen came into my life. And she helped me build these out for you guys because it's so important. So I think one of my absolutes, well, it is in person, giving a human a hug, sharing a meal is the epitome of what I love doing. Whether that's in Athens, whether that's in Costa Rica, that's our favorite. We do have Costa Rica coming up, which if you guys want to sum up Kristen's goodness, she helps me facilitate that retreat. That's March 3rd through the 8th. And she alluded to it a minute ago that event it can be beautiful if you let it. We were planning what journey we want to take you on through that event. You want to talk through your favorite parts of where we're taking folks?

Kristen Day [00:27:50] Oh man, it is wow. So we've had an evolution of those events throughout. We've done them a couple of times. And this one is going to be transformative like it has never been before. And I think honestly the reason why is because we have transformed.

Madeleine Raiford-Holland [00:28:20] It's a 1000% why.

Kristen Day [00:28:22] And so we both have mentors of our own that we are absolutely so passionate about working on ourselves and being able to face the tough things. Madeline shared you went through a bad season. I'm currently going through a relatively bad season myself. So I think this is part of it. And this retreat is meant to introduce this beautiful, absolutely for us non-negotiable aspect of our life with you all and the people who attend because it is so critical that you know that someone is on your side. And these things are hard to face and you're going to struggle. And there is hard things to overcome and to grapple with. And we do not want to be the people who sugar coat that and say just grind it out. So, for me, personally, my favorite part of this retreat is that we're holding space for you and for anyone who is going to come with us to look at your dream life.

[00:30:12] Where do you want to go? And it's okay if you don't know. Permission to not know. Carte blanche, permission to not what you're doing, period. But I think to look at it and to open, we call it like taking out a flashlight, like looking at the boxes in the attic. It's like peeking around and you're like what's in there? Like what's on there? And to have someone on your side that says, hey, maybe you haven't looked at that box. Maybe you don't know where you're going. Maybe you genuinely haven't ever been asked or haven't every considered truly what you want. And let's have a conversation and hold some space and help you be able to know, yes, it's hard. But like I said, there's someone who believes in you and we're one of them.

Madeleine Raiford-Holland [00:31:18] Love that. And I think with that, we've alluded multiple times in our relationship of knowing your values, knowing what your non-negotiables are. We've thrown out terms like that pretty nonchalantly. But that is a relatively new concept for people that may not have defined that for themselves. And that's what we love to do, especially in the beginning of this. Is if you have something unique about you that is so special that you can bring to this world, to your relationships, let's define the impact that you want to have, but also help you define for yourself what the ideal looks like for you so that you can approach these relationships with confidence saying, this is worth the risk of having something messy. This is the confidence to say yes when things feel good and not be stuck in analysis paralysis, but also the confidence to say no and understand why and have confidence in your boundaries because it's not aligning with where you're headed. And it's a good look at that. And a lot of times we don't have the space to do that in the day to day or the support. And with this group and going through it together, you get built in business besties because you've been through this transformation together. So I love that. I'm excited for March. I'm really stinking excited.

Kristen Day [00:33:06] I cannot wait. It cannot get here fast enough.

Madeleine Raiford-Holland [00:33:10] I'm really trying to figure out another planning session between now and then maybe it's... We just have fun getting together.

Kristen Day [00:33:19] We don't need an excuse. I'm so excited because we've been on our own transformation and that has been so fun. And so it has had a lot of challenges and a lot ups and downs, but it's so fun and I think seeing the joy in that and taking a minute to appreciate it is the other thing. It's like in this space that really you've created through this like magical journey of your own and the journey that we've been on together, I always you can't get a transformation you haven't had before and you have had it.

Madeleine Raiford-Holland [00:34:20] Even a couple episodes, episode one of season two when I talk about that freaking Irish exit taking a break, this came out of our last retreat. And Kristen has had a front row seat to this transformation, but joy, space, deeper friendships, deeper relationships. I mean, stronger boundaries, better work life integration, deeper purpose, truly of a knowledge of where I want to go and as a by-product, legitimately doubling revenue guys. Like if we're going to be quantitative as well as qualitative, it's a by-product of joy and understanding the root thing and that's what we want for you guys. Kristen has been on her own journey of this. I have been on mine and what I'm saying is don't sleep on it, guys. You can grind and hustle your way kingdom come, but don't sleep on the inner work because the grind can only get you so far. Do you have any parting words? This will be a continuing episode because you're going to come on again very soon, but any parting word for folks?

Kristen Day [00:35:46] Yes, I do. Spicy Kristen is not about to appear. If you are gifted, if the universe gifts you a friend like I have found in this incredible human being, if you are unwilling to take a chance on yourself that you can be happier with them in your life, that is just an absolute tragedy. And a lot of people overlook the small gifts in their life. Those little gifts are what make life worth living.

Madeleine Raiford-Holland [00:36:49] It's so beautiful. And I echo that right on back to you. One final question that I almost forgot because it's been months since I've had a guest on this podcast, is what is a time in your life where change has brought an unexpected opportunity?

Kristen Day [00:37:08] The timeliness of that is going to be... What is the time that change has brought an unexpected opportunity? You guys walked into my lunch. That's pretty unexpected for me. I got one.

Madeleine Raiford-Holland [00:37:32] Good.

Kristen Day [00:37:32] It's not a change for me, it was a change for you, but I love that.

Madeleine Raiford-Holland [00:37:36] Turn it back on me.

Kristen Day [00:37:39] So during our first retreat you were super excited because you had someone lined up for this exercise called a lighthouse exercise.

Madeleine Raiford-Holland [00:37:55] Yes.

Kristen Day [00:37:57] And that person ended up-- I actually don't remember what happened, but we were all good, we were going down this road and we were talking about it. We were planning, we were getting the schedule together. And for whatever reason, that person decided to not do that exercise. And that was an unexpected change because it was changing the schedule, changing the marketing, changing all the things. And I had been talking about wanting to-- or that I had really been passionate about life planning and the dream life topic and the topic of the future self. And it was absolutely out of left field for me where a change in your life brought me an opportunity that I genuinely feel like deepened our relationship in a way that I just could not understand at the time. I was on the fence about going to that retreat. I was on my way out the door, it was like right at that crux where I was like six months I'm out.

Madeleine Raiford-Holland [00:39:20] That was at the year mark.

Kristen Day [00:39:22] I know. We were still having those; I still thought for whatever reason I'm not sure why. Yeah. I was like get to the year mark and leave, but here we are. So it was a change in your life that brought me an unexpected opportunity. And it's one that I think of very often. It changed the trajectory of my life, that one change, in ways that I literally cannot describe to you. And it was a life-changing change. And I said, yes, completely unprepared, not confident, scared out of my mind about what it meant for me to go to that retreat, what it meant for me, to even do that talk. And it was just this idea. And again if you're listening to this and you have this person in your life who believes in you, do not walk away from them. Be open to that. Be open to someone believing in you because it is such a gift. And that did change my life. And I have done many things with that particular item that I would have never done, including building a business off of it.

Madeleine Raiford-Holland [00:40:43] She said yes.

Kristen Day [00:40:45] Yes, I know.

Madeleine Raiford-Holland [00:40:46] I'm so thankful that you did. That was a good one. That was an epic one. And for those of you who don't know all the ins and outs of it, her saying yes, she said yes to that one, she said yes to the next retreat and the next couple retreats, at least. Athens and then the one coming up in March and the world is better for it. I appreciate that she shared your gifts with us.

Kristen Day [00:41:14] Yeah, thank you. I will say too that if you guys are scared to say yes to an opportunity like that or you're on the fence about attending something like this, that one decision can change everything. The success of the people who have been on retreat number one, two, that have already signed up for the third, that keep coming back, but the markers of success from the very first to now, they're in completely different places in their life, which is just beautiful to see as part of their journey.

Madeleine Raiford-Holland [00:41:53] So there we are, folks. One, know your values, know the kind of people, start thinking about the people that you want to attract into your life. Find your business besties, put yourself in places where you can find those people and don't be afraid to say yes to opportunities. Kristen, thank you for being here. Tell people where they can find you.

Kristen Day [00:42:16] You can find me on Instagram. I am at the home grind. And you can find me on LinkedIn. I am Kristen Day/affinity. And you can find me in the Zoom chat of Madeline's upcoming workshop.

Madeleine Raiford-Holland [00:42:42] There we go. If you want to join us for that first streamlined workshop, you can find any type of our workshop stuff. This one upcoming is beginner friendly. MadelineRaefordHolland.com/streamlined. There we are. Thank you guys for joining us. Stay tuned for the next episode.

[00:43:04] Hey y'all, if you're loving the show, be sure to hit the follow button or the plus sign on your podcast app to subscribe. This will ensure you don't miss a single episode and I'll see you next week.