The STR Sisterhood

Hospitality.FM
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Whether you’re brand new to Airbnb or an experienced Superhost, you’re giving yourself the gift of financial freedom and FUN when you enter the short-term rental space. If there’s anyone who knows this, it’s Stacey St. John. She built a 7-figure STR portfolio in less than two years and was able to leave her W2 thanks to the earnings from her properties. Today, she’s living the life she was always meant to live – on her terms. And on her new podcast, The STR Sisterhood, she’s sharing how you can, too! On this show, it’s all about you and your short-term rental journey. You’ll hear actionable advice from industry experts as well as inspiring stories from real women about their experiences, achievements, frustrations, and challenges…and how they’ve managed to turn their short-term rental dreams into reality. If you’re an ambitious woman who’s looking to have a 5-star Airbnb business on your hands without having to sacrifice the things you love, then tune in every week for all the goodness!

  1. 2D AGO

    From Rock Bottom to STR Success: Rebuilding with Mindset and Strategy with Elle Anderson

    What would you do if you lost everything—twice—and had to rebuild your life, your finances, and your identity from the ground up? Most people would let the weight of that loss define them. In this episode, I sit down with acquisitions expert and STR investor Elle Anderson. We’re diving into her extraordinary journey from the depths of financial loss to building a business rooted in mindset, identity work, and high-level strategy. Inside the episode, I dive into: How Elle jumped into buying businesses with no money, raising equity, and learning the high-stakes game of investor relations on the flyWhat happened when Elle’s last $5 became the catalyst for a total identity shift, moving her from chronic worry to conscious creationHow Elle applies deep due diligence to real estate, spotting market gaps and adding high-ROI amenities like year-round pools to outperform the competitionA creative, guest-centric approach to winning over neighbors and building community goodwill around your rentalsExploring the connection between your nervous system, your identity, and the actual results in your bank account But this isn't just a story about a comeback. It’s about the freedom of choice. Elle pulls back the curtain on why she walked away from a company with 120 employees to find the flexibility and creativity of short-term rentals. You’ll hear how she designs for "memorable moments", from slides between floors to interactive design touches, and why she believes bold action is only possible once you’ve done the inner work to support it. If you’ve ever wondered if you can truly recover from a setback and build something even better on the other side, this conversation is your proof. Get ready to stop praying for things to go wrong and start training your mind for what’s possible. HIGHLIGHTS AND KEY POINTS: [00:54] A short introduction about our guest Elle Anderson, and how she began her entrepreneurial journey with no experience or capital, relying on belief, resourcefulness, and investor support [04:12] Elle explains how she navigated entering business acquisitions with no experience or capital, relying on belief, resourcefulness, and investor support [06:05] Elle describes the wide variety of businesses she acquired and shares how her follow-up approach helped build trust and credibility with investors. [08:58] Elle recounts the second time she was left with only $5, no food for her two-year-old son, and describes how a profound shift in mindset transformed her path forward [13:01] How Elle recognized her lifelong tendency to worry and transformed it into intentional focus on positive outcomes. [15:29] Elle shares how she learned to harness awareness and intention to transform her mindset, even after repeated setbacks [18:37] Elle talks about the emotional impact after her first financial loss and how she began the long journey of rebuilding without the knowledge she needed [21:22] Elle describes her recipe for success, emphasizing the power of momentum and decisive action in rebuilding and growing her businesses [23:05] Why taking imperfect action and learning from mistakes is more powerful than waiting for the perfect moment [26:56] Elle’s transition from large-scale business acquisitions to short-term rentals and how she identifies gaps in competitive markets [32:38] Elle shares how she translates lessons from business acquisitions into short-term rentals, using due diligence, creative design, and strategic ROI-driven decisions [37:20] Elle talks about the foundational mindset shift that transforms success, even in moments of uncertainty or doubt [38:47] The lightning round Golden Nuggets: “Where you put your attention is where your energy goes, and that grows.”“I would celebrate my success long before it happened. And it just kept coming and coming and coming.”“Worrying is one of the biggest wastes of energy ever possible, because you end up putting out into the world what ultimately you're going to attract.”“My brain is literally just a data center. It's just a big old, massive computer, right? And what we input into that computer directly affects the output that we're able to get from it.”“Once I understood about mindset and identity, like who you believe you are inside, then it all made sense. You don't have to be smart, you don't even have to be good, you don't even have to have the best tactics. You just have to believe that it's going to be successful.”“You have to have action, even if it's not perfect action. You're going to learn and you're going to adjust, and you're going to get better.”“Perfectionism is one reason why people don't take action because they're waiting to do something until they get that home run, or it's a slam dunk, or they know for sure.”“Failure comes from mistakes only when we don't learn from them.” Let’s Connect: Facebook : https://www.facebook.com/elle.ande.10 Resource Mentioned: Innercise: The New Science to Unlock Your Brain's Hidden Power Proudly sponsored by Futurestay: futurestay.com/stacey Enjoyed the show? Subscribe, Rate, Review, Like, and Share!

    45 min

  2. MAY 5

    Fixing the Messy Middle of Airbnb Hosting: The Story Behind Simpli Host with Beth Turner

    What happens when the “messy middle” of short-term rental hosting gets so chaotic that you decide to build the software you wish already existed? Most hosts just keep duct-taping systems together; my guest today decided to build a better way. In this episode, I sit down with Beth Turner, the non-technical founder of Simpli Host. We’re talking about the unfiltered reality of operating multiple short-term rentals while working a demanding full-time job, and how that operational anxiety pushed her to create an all-in-one platform designed for the hands-on host. We dive into: The "messy middle" of juggling seven different apps and the constant anxiety of wondering if the cleaner showed up or the hot tub is actually hot.Practical tools for reclaiming your peace—from the power of a deep breath to reframing yourself as a true business owner rather than a "side-hustle" host.How repeated requests for help led to a platform with unified messaging, integrated locks, and seasonal maintenance reminders.The hard lessons of hiring and firing dev teams, trusting the experts, and resisting the urge to "just learn to code."Why establishing firm policies and guardrails around things like pets and trash days is the only way to protect both your profit and your sanity. But this isn't just about software. It’s about buying back your time. We pull back the curtain on the importance of quiet time, journaling, and surrounding yourself with a community that understands the unique weight of this industry. You’ll hear about the power of a daily gratitude practice and a vision for building a business that serves your life, rather than one that consumes it. If you’ve ever felt like you’re drowning in notifications and logistics, this conversation will offer you a roadmap to systems, support, and a more aligned way of hosting. Get ready to move out of the chaos and into a more intentional way of leading. HIGHLIGHTS AND KEY POINTS: [00:47] A short introduction about our guest Beth Turner, her accidental journey into short-term rentals, and how she started Simpli Host [02:52] Beth describes the chaotic behind-the-scenes reality that quietly overwhelms hosts before they realize something has to change [05:13] Beth and I challenge the “passive income” myth and highlight the hands-on reality of running short-term rentals [06:51] Beth shares how the “messy middle” actually begins earlier, when juggling a full-time job, constant travel, and nonstop guest demands [09:40] Beth reveals how simple mental shifts, not complex systems, helped her regain control in high-stress hosting moments [12:18] How separating identity from the business helps operators lead more objectively, improve standards, and make stronger operational decisions [16:44] How documenting processes, especially through simple repeatable methods, prevents knowledge from being siloed and ensures business continuity and consistency [20:41] How using policies as a neutral authority helps operators remove emotion from guest decisions and maintain consistency, even when running solo [21:54] Beth explains how fragmented systems and operational overload led her to create Simpli Host as a unified solution for short-term rental management [25:37] Beth describes how the software functions as a centralized system that brings together the core operational layers of short-term rental management [31:58] Beth explains how building Simpli Host forced her to delegate, stop coding herself, and shifting from frustration and control to empowerment and trust in her team [34:36] Beth and I explore how clarity, creativity, and business insight emerge through quiet reflection, self-awareness, and intentional disconnection from noise [43:56] The importance of surrounding yourself with a supportive network of women and operators at different stages of their short-term rental journeys [47:26] The lightning round Golden Nuggets: “One thing that people don't realize is, STRs are not passive.”“You feel that rising and you know that you're no longer in a good mental space to make good choices. And even if you do make good choices, you're rolling the dice on that choice when you're in that state. So one of those is taking, taking that deep breath.”“I think it is so important that we learn as business owners to separate ourselves from the business.”“Having good people in your business is 100% essential. However, I will say, you know, I learned a huge lesson. Yeah, along with those good people, we have to make sure that if they're smarter than you about something, they're helping you build your policies, your processes and procedures. So that if they ever got hit by a bus, you know you would still operate without them.”“Exploit your strengths and hide your weaknesses.”“Having a network of other women around us who have experienced different things that are in all different stages of their businesses, I will tell you, I have mastermind programs. I have mentorships, I learn as much from the folks that I have the opportunity to support in their journeys as they learn from me.”“All of these masterminds, all these beautiful women, all of these smart, ambitious people that I've been around have gotten me where I am today. I carry a little bit of them everywhere I go.” Let’s Connect: Website : https://simplihost.com/ Instagram : https://www.instagram.com/simplihostinc/ Facebook : https://www.facebook.com/simplihostinc Enjoyed the show? Subscribe, Rate, Review, Like, and Share!

    56 min

  3. APR 28

    Building an STR Business Through Faith & Grit with Christina Tracy

    Have you ever felt a deep nudge to change your life, but had no idea what the path ahead would look like, and stepped forward anyway? Most people wait for a perfect plan; Christina Tracy is proof that you only need the courage to take the first imperfect step. In this episode, we’re tracing her journey from a handshake deal on an off-market property in Ohio to building a multi-market portfolio across Florida and Charlotte, all while navigating the messy reality of flipping houses with a toddler in tow. We talk about: How Christina jumped into real estate with zero experience, relying on grit and YouTube tutorials to build her first successful portfolio.How Christina’s background in public health turned her into a "data nerd" who uses tools like PriceLabs to master pricing and performance.A candid conversation on rebuilding trust, reconnecting with God, and finding peace after seasons of grief and "hustle culture."The healing power of quiet time, prayer, and meditation as tools for hearing your own voice, and God’s, again.Shifting from "controlling tasks" to "empowering outcomes" and how inner growth changes the way you hire and lead a team. Christina pulls back the curtain on what it means to lead a values-driven, people-first business while protecting your own energy. You’ll hear why intentionality is the ultimate secret to scaling, and how a deep spiritual foundation provides the peace required to navigate the growing pains of entrepreneurship. If you’ve been sensing that there is a different, more peaceful way to build your empire, this conversation will speak straight to your heart. Get ready to stop surviving the grind and start leading with purpose. HIGHLIGHTS AND KEY POINTS: [00:59] A short introduction about our guest Christina Tracy, the owner of STR Host Company [05:31] Christina shares her background in public health and real estate and describes how she transitioned into short-term rentals by combining data analysis with hospitality [06:15] Christina shares taking action on their first investment property without experience and reflects on the challenges and lessons from learning through doing [10:19] Christina’s shift from a grind mindset to a more intentional approach, explaining how she learned to move through challenges with greater awareness, grace, and alignment over time [12:19] How Christina developed awareness of limiting beliefs through intentional practices like solitude, journaling, and daily routines that build self-trust and mental clarity [15:55] Christina and I share how reconnecting with God profoundly shaped our personal growth and resilience, illustrating the role of faith in navigating life’s challenges [22:20] Christina shares how cultivating inner peace has transformed her daily life, relationships, and business [23:34] Christina shares her daily habits and mindset practices for maintaining inner peace, protecting her energy, and creating a positive, aligned environment both personally and professionally [27:38] How Christina mentally prepares for challenging situations by grounding herself, focusing on service, and detaching from outcomes while trusting the bigger picture [29:48] The challenges of building and leading an aligned team while the host shares leadership strategies for hiring, developing, and empowering team members as a business evolves [37:21] How I integrate mindset and emotional awareness into leadership through coaching, trust-building, and proactive communication rather than formal discussions about mindset [42:41] Christina shares practical advice for those feeling stuck or disconnected by encouraging them to dream freely, identify internal resistance, and grow through small, intentional steps [45:08] The lightning round Golden Nuggets: “You can't sit in the planning forever. You have to take action.”“If I'm sandwiching my day with truth, then it kind of keeps me more aligned as the day goes on.”“In every failure, there's always a seed of benefit being planted.”“It's really important that you're working towards a goal.”“I don't delegate tasks. I empower people to produce business results.”“Give yourself space to dream. That's always where we start.” Let’s Connect: Instagram : https://www.instagram.com/christinatracy/ Proudly Sponsored by PriceLabs: https://pricelabs.co/users/sign_up?referral=STRSISTER Enjoyed the show? Subscribe, Rate, Review, Like, and Share!

    50 min

  4. APR 21

    Designing for Bookings: The Power of Cohesive STR Experiences with Ashlyn & Olivia

    What if the secret to a standout short-term rental isn’t just great design, but a fully cohesive experience that starts the moment a guest clicks on your listing? In this episode, I’m joined by sisters Ashlyn and Olivia, the creative powerhouses behind Abideaway. We’re diving into how a simple idea shared over a Marco Polo video evolved into a full-service studio that helps hosts build standout stays through the perfect marriage of design and strategy. We talk about: How interior design, branding, and web presence work together to create a seamless narrative for your propertyMoving beyond "who" your guest is to what they are worrying about, and how to solve those fears through intentional layout and amenitiesWhy custom art is more than just a "photo op" and how it can be used to stop the scroll and reinforce your property’s storyPractical, high-impact advice on where to spend a limited budget in your kitchen, living room, or outdoor space for maximum ROIHow to mine architecture, local history, and personal passions to guide every design decision you make But this isn’t just about aesthetics. It’s about intentionality. Ashlyn and Olivia pull back the curtain on their creative process, from using Procreate mockups to ensure owner confidence to scoping mural projects that actually last. You’ll hear their "design hotline" wisdom on how to avoid the "I wish they’d thought of that" moments that kill guest reviews, and how to create a space that feels custom, memorable, and deeply resonant. If you’ve been looking for the bridge between "just a rental" and a "cohesive brand," this conversation is your roadmap. Get ready to stop guessing and start designing with a clear, story-driven purpose. HIGHLIGHTS AND KEY POINTS: [00:59] A short introduction about our guests, Ashlyn Feller and Olivia Gerber from Abideaway, and shares how the idea started organically between them as sisters with complementary creative skill sets [04:31] Ashlyn and Olivia emphasize defining the ideal guest and starting with priorities to build a cohesive STR brand [07:45] Olivia explains starting with the ideal guest avatar and using a phased approach to build a cohesive STR brand experience [11:35] Olivia shares her philosophy of designing with intentionality and uncovering the story of a property [13:27] Olivia describes ways for hosts who are bootstrapping their STR design to uncover and build the story of their property [16:04] Ashlyn and Olivia explain when themed properties make sense and the role of data in decision-making [17:44] Olivia shares why engaging a designer early in the acquisition process is beneficial [18:45] Olivia and Ashlyn talk about what to consider in design before closing on a property and explain that designers can also refresh or elevate underperforming properties [20:37] Ashlyn shares why murals are a powerful design tool for short-term rentals and describes how hosts can budget for them based on size, complexity, and customization [24:16] Ashlyn describes her mural creation process from concept to installation, including design mockups, painting techniques, and care, and [27:26] Ashlyn shares creative ideas for placing murals in both large and smaller spaces and introduces the STR Sisterhood Design Hotline as a resource for hosts seeking design guidance [29:21] Ashlyn and Olivia describe the STR Sisterhood Design Hotline and what folks can expect if they've never been to a design hotline [32:39] Ashlyn and Olivia explain how even a modest $1,000 budget can meaningfully improve different areas of a short-term rental when spent strategically [34:01] Ashlyn explains how to approach branding with a limited budget by focusing on defining the overall guest experience and building a cohesive brand beyond just a logo [37:44] The lightning round Golden Nuggets: “We have to go deeper and understand what that person is thinking when they're looking at properties, what that person is thinking when they are making a booking decision, what that person is stressed out about, what they're afraid of, what they're concerned about if they book the wrong property, because those are the things that ideal guest is not actually telling anyone that's a conversation he or she is having with themselves.”“Pull some piece of the puzzle and use that as, like a seed of inspiration.”“I am a huge believer that we are all in business to, not only, you know, improve our own lives. But isn't it great that we can proactively help each other like that just makes us all go to bed at night feeling that much better, right?”“Build your network and build it strong.”“If we're not aware, number one of things we need to tackle in our businesses, or things that may need improvement in our businesses, if we don't dedicate focused thinking time, which is that white space, we can go for months and even years without having those problems solved or those new ideas generated.” Let’s Connect: Website : https://www.abideaway.com/ Facebook : https://www.facebook.com/profile.php?id=100090299230620 Instagram : https://www.instagram.com/abideaway/ Enjoyed the show? Subscribe, Rate, Review, Like, and Share!

    51 min

  5. APR 14

    Scaling STRs Together: The Airbnb Sisters’ Secrets to Success with Jen Stone and Lauren Schmidt

    What happens when two sisters team up to build a powerhouse short-term rental brand in two of the most competitive markets in the country? Most people think working with family is a recipe for disaster; Jen and Lauren prove it’s actually a competitive advantage. In this episode, I sit down with Jen Stone and Lauren Schmidt, better known as The Airbnb Sisters. We’re unpacking how they’ve grown a thriving portfolio across Nashville and 30A while keeping their standards sky-high and their sisterly bond intact. We talk about: How a single CMA Fest booking turned into a professional management career for Nashville’s biggest developersThe strategy behind their iconic pink-themed homes and how they attract high-value group stays like weddings and bachelorette partiesHow Jen transitioned from personal assistant to the engine of the business, managing guest flow and flawless check-insThe story of finding (and fiercely protecting) a standout cleaning crew to maintain five-star standards from hundreds of miles awayA candid look at hosting large groups, and how their branding and screening process attract guests who actually respect the property But this isn't just a story about pretty houses. It’s about the evolution of a brand. Jen and Lauren pull back the curtain on the delicate conversations they have with owners about decor budgets and why they now insist on being involved before a home is even furnished. You’ll hear how they still run a high-volume business with a personal touch, and my honest take on where they can finally let technology take some of the weight off their shoulders. If you’ve ever wondered how to turn a "side hustle" into a recognizable brand or how to successfully partner with family, this conversation is your front-row seat. Get ready to learn what it really takes to dominate the high-energy group stay market. HIGHLIGHTS AND KEY POINTS: [01:15] A short introduction about our guests Jen Stone and Lauren Schmidt, and share how they started and grew their short-term rental business together as sisters [05:42] Jen explains how she and Lauren divided roles while building their short-term rental business [07:16] Lauren shares why she brought her sister Jen into the short-term rental business [08:29] Jen explains how social media helped grow their short-term rental business and attract large group bookings [10:54] Lauren outlines their mixed short-term rental business model of ownership and management, and how a long-term developer partnership shaped their portfolio [13:41] Lauren highlights that running properties far from home, like their 30A beach rentals, is very different from managing Nashville homes [14:35] Jen and Lauren discuss managing long-distance properties and finding the right cleaning team [18:19] Lauren and Jen explain how they maintain quality and consistent design across their properties [20:12] Lauren describes managing guest communications themselves and my advice to them about dynamic pricing tool and property management software [26:57] Jen explains that their approach to adding properties is highly selective, focusing first on the relationship and communication style with the owner rather than just the property itself [29:19] How Jen and Lauren use experience and firm standards to guide budgeting and property fit decisions [33:12] Jen and Lauren debunks bachelorette myths and highlights the reality of high-quality group guests [36:00] Lauren and Jen share how they generally don’t actively screen bachelorette parties or other group bookings and they treat all guests equally and welcome those who want to book [37:47] The lightning round Golden Nuggets: “It's so important that we've got backups and backups for our backups.”“You can have a beautifully designed property, but if it's poorly run, you're not going to get great reviews.”“If somebody is giving you trouble, kill them with kindness.” Let’s Connect: Instagram : https://www.instagram.com/the.airbnb.sisters/ Enjoyed the show? Subscribe, Rate, Review, Like, and Share!

    44 min

  6. APR 7

    Story-Driven Design That Boosts Airbnb Bookings with Andrea Moxham

    What if the secret to an Airbnb or short-term rental that stays fully booked isn’t just a high-end renovation, but a story that dictates every decision you make? Most hosts start with a mood board; Andrea Moxham starts with a narrative. In this episode, I’m joined by virtual STR designer Andrea Moxham, who has mastered the art of turning properties into experience-driven destinations—often without ever stepping foot on-site. We talk about: How Andrea’s background in buyer psychology gives her a competitive edge in creating spaces that don’t just look good, but convert.How to craft a "story" for a property by mining local history, architecture, and even competitor reviews.Why leaning into a specific identity is the only way to win in saturated markets like beach towns or mountain retreats.Practical, high-impact design strategies for rugs, bedding, and curtains that transform a guest’s first impression.Navigating the challenges of remote projects—from color matching online to managing the guest journey from afar. But this isn't just about picking out furniture. It’s about design as a strategic business tool. Andrea pulls back the curtain on how she builds "memorable moments" around everyday features to ensure a property stands out in a crowded feed. You’ll hear why she believes hosts should never operate in a silo and how "knowledge hacking" through mentorship and community is the fastest way to scale a design-forward business. If you’ve been looking at your property as just a collection of rooms, this conversation will challenge you to see it as a story waiting to be told. Get ready to stop decorating and start designing for results. HIGHLIGHTS AND KEY POINTS: [01:00] A short introduction about our guest Andrea Moxham, her journey getting into interior design, and the short term rental space [02:39] Andrea shares how her marketing background led her to short-term rental design and blending creativity with business strategy [06:32] How grounding bold design decisions in a property’s story and guest experience makes them intentional and strategic [09:18] Andrea explains how she creates a compelling property narrative when clients don’t have one [12:43] Andrea shares how hyper-niching and experience-driven amenities help properties stand out in saturated markets [17:41] How Andrea’s marketing background informs thoughtful design for multi-generational short-term rentals [24:27] Andrea discusses practical upgrades and key design elements for impactful short-term rental bedrooms on a $1500 budget [33:40] Andrea addresses a common challenge in virtual design: the discrepancy between how colors appear online versus in real life [36:09] Andrea reflects on the pitfalls of working in isolation and the value of community [38:26] The lightning round Golden Nuggets: “Creating something really specific, it kind of allows you to make the home the destination.”“I would say that the biggest mistake is trying to figure things out on my own. It wastes so much time, waste so much money, leads to mistakes on real projects.”“You get what you pay for. I find that there is always a cost with choosing a cheaper option.”“The value of our time is so so, so important to keep in mind, because we can always earn more money. We cannot always create time while we can't create time at all.” Let’s Connect: Website : https://www.moxieandco.ca/ Instagram : https://www.instagram.com/andreamoxham/ Enjoyed the show? Subscribe, Rate, Review, Like, and Share!

    49 min

  7. MAR 31

    From Strangers to Strategy: How One Week Built a Powerful Women’s Tribe

    What actually happens when you say “yes” to a women’s real estate retreat where you barely know anyone? Most people assume it’s all networking and small talk, but the reality is much deeper. It’s about the moment you stop overthinking and start showing up for yourself. In this episode, I’m joined by my friends from the Outer Banks Girlfriends & Growth Rereat– Sue, Shae, Karey, and Jamie. We’re pulling back the curtain on what it really feels like to trade the daily grind for a house full of strangers and leave with a tribe. We talk about: From five-minute "just booked it" moments to following a gut feeling, how each woman pushed past the "introvert's anxiety" to get into the room.How a simple hallway conversation can spark an entirely new revenue stream or a "true north" business realignment.Why we designed a retreat that prioritizes breathing room over back-to-back PowerPoints.Using the retreat to turn scattered ideas into actionable structures—from team building to smarter automations.How these women are using tools like Notion and AI to document processes and clarify their guest avatars without losing the human touch. But this isn't just a recap of a trip. It’s about the courage to invest in yourself. We dive into the emotional side of growth, navigating the "grumpy" voice of self-doubt and balancing businesses with families and W-2 jobs. You’ll hear why shared values in real estate and hospitality can turn a house of strangers into a powerful support system in less than a weekend. If you’ve ever wondered if a retreat is "for you" or if you’re too new, too seasoned, or just too busy, this conversation is your honest, unfiltered answer. Get ready to discover why stepping into the right room is the fastest way to find the clarity and momentum you’ve been looking for. HIGHLIGHTS AND KEY POINTS: [01:32] A short introduction about our guests Sue, Shay, Carrie, & Jamie, and their experiences at a recent Girlfriends & Growth Retreat in the Outer Banks [04:42] Sue shares deciding quickly to attend the Girlfriends and Growth retreat [06:55] Shay’s experience when she first heard about the Girlfriends & Growth and shares that her decision to attend the retreat came from a place of curiosity mixed with hesitation [09:43] Jamie shares that her decision to attend the Girlfriends & Growth retreat was driven primarily by intuition [10:51] Carrie’s initial reaction to the retreat concept was skeptical, particularly about hosting it at the beach during winter [14:54] Sue talks about her experience when arriving at a house full of women she didn’t know and how she navigated the initial discomfort [17:40] Jamie reflects on walking into the retreat and feeling completely at ease, even though she didn’t know who she would connect with [19:21] Shay’s experience on stepping into the retreat feeling a little shy and uncertain, worried that everyone else might have more in common or be more experienced since she no longer hosts [21:51] How Carrie’s takeaways from the Outer Banks retreat are shaping a more flexible, intentional experience in Pigeon Forge [28:13] Jamie explains that the retreat helped her clarify and organize the next steps for her business, particularly around building foundational systems, automations, and processes [32:00] How Sue used the retreat to refocus on guest experience, processes, and collaborative innovation [36:39] How Shay discovered the value of technology and the power of a supportive industry tribe [38:38] Carrie emphasizes the joy of watching 25 strangers enter a retreat and leave as a connected tribe, having shared experiences and exchanged contact information [41:02] Jamie advises trusting both gut and logic when making retreat decisions, especially for those who may not feel their intuition guiding them [42:39] Shay advises anyone on the fence about attending a retreat to just go, emphasizing that it’s a net gain no matter the outcome [43:52] Sue encourages silencing self-doubt and embracing the investment in oneself [45:05] The importance of mastering mindset, silencing “Grumpy Greg,” and paying it forward Golden Nuggets: “Being surrounded by smart women in real estate, but also just having sound boards you know, to be able to share ideas and get perspective in a non threatening, non judgmental environment, I think is so helpful.”“Just having alone time in my room to think and process the things that I've learned is incredibly helpful for me to be able to walk away from that retreat and walk away with an action plan.”“If anyone is thinking about making decisions, it is a breeding ground for the type of collaboration and brainstorming that you really need to not be stuck in making your own decisions.”“The more skilled that we can become at controlling those voices and controlling our mindset, the stronger we are, as women, as individuals, as entrepreneurs.” Join Our Next Retreat: https://bit.ly/4bPybnW Enjoyed the show? Subscribe, Rate, Review, Like, and Share!

    49 min

  8. MAR 24

    The Rentalpreneur Advantage: Competing with the Giants with Phil Kennard

    Most people think they need a huge portfolio to win; Phil Kennard is here to prove that "rentalpreneurs" with just a few properties can actually outperform the giants. In this episode, I’m joined by Phil Kennard, the founder and CEO of Futurestay. Phil’s journey started with a tiny loft in Greenwich Village and a realization: a handful of strategic bookings could cover an entire mortgage. That sparked a mission to build a platform for hosts who treat short-term rentals as an investment, not a second full-time job. We talk about: How technology and community-driven education have shifted the power from legacy managers to everyday independent hostsWhy income isn’t distributed evenly in any market, and how to get your property into the top tier of performersWhy great photos aren't enough, and how strategic positioning and thoughtful policies drive real RevPARA deep dive into a new tool we developed together that tracks how cleaning standards and fees directly impact your bottom lineFuturestay’s mission to provide smaller operators with the infrastructure, like direct booking and Google Vacation Rentals, to grow on their own terms But this isn't just about software. It’s about taking back control. Phil pulls back the curtain on how solo hosts can leverage systems and the right partners to thrive despite constant platform changes. You’ll hear why operations and guest satisfaction are your non-negotiables, and how focusing on "cleanliness sentiment" can save your reviews and your revenue. If you’ve ever felt intimidated by the "big players" in your area, this conversation will give you the confidence to compete. Get ready to stop worrying about the competition and start building a business that works for you. HIGHLIGHTS AND KEY POINTS: [01:20] A short introduction about our guest, Phil Kennard, the founder and CEO of Future Stay, and how he got into the world of short term rentals [06:31] Phil explains how the early development of his platform was fueled by an obsessive, entrepreneurial mindset [09:33] Phil defines rentalpreneurs as hands-on investors using rentals to build income and control their future [12:06] The importance of community, education, and competition in outperforming the rental market [17:31] Phil explains evolving Futurestay’s service to include listing optimization alongside direct bookings and outlines three key pillars of optimization [23:41] Phil stresses that operations and guest experience outweigh design in short-term rental success [26:05] The importance of hosts giving feedback to Airbnb to protect supply interests [27:59] Phil advises focusing on one channel at a time while starting direct bookings early [31:45] Phil introduces the Clean Connection, a new tool designed to help hosts understand how cleaning impacts their short-term rental performance. [33:25] How Clean Connection bridges the resource gap for smaller hosts who don’t have access to Airbnb market managers [43:47] The lightning round Golden Nuggets: “I think people think of Airbnb optimization as like, here is your Airbnb listing. Let us change content on your Airbnb listing, and that will make you successful. Unfortunately, that's like one of the three pillars of optimization. If you just change the listing content, and you do nothing to your competitive set analysis and to also the consistency of how your listing is performing, you will never be super successful in your market.”“It is imperative that you deliver a quality experience for your guests, because in the absence of a good operation that allows you to deliver that consistent experience, you could have the boat, the most beautiful property and the best photos, but your listing will tank if you can't deliver.”“I think it's important for us as hosts, if Airbnb does come out with policies that we feel like may benefit the guests more or feel short sighted as a host, it's really important to share that feedback with Airbnb.”“One of the most important aspects of our guest experience is the cleanliness, and I also think it is one of the most important, most scary yet controllable pieces to the puzzle as a host.”“Doing one thing better than anyone else really matters.” Let’s Connect: Website : https://futurestay.com/stacey Sign Up for the Clean Connection: https://cleanconnection.futurestay.com/ Enjoyed the show? Subscribe, Rate, Review, Like, and Share!

    54 min
See All (180)

5
out of 5
28 Ratings

About

Whether you’re brand new to Airbnb or an experienced Superhost, you’re giving yourself the gift of financial freedom and FUN when you enter the short-term rental space. If there’s anyone who knows this, it’s Stacey St. John. She built a 7-figure STR portfolio in less than two years and was able to leave her W2 thanks to the earnings from her properties. Today, she’s living the life she was always meant to live – on her terms. And on her new podcast, The STR Sisterhood, she’s sharing how you can, too! On this show, it’s all about you and your short-term rental journey. You’ll hear actionable advice from industry experts as well as inspiring stories from real women about their experiences, achievements, frustrations, and challenges…and how they’ve managed to turn their short-term rental dreams into reality. If you’re an ambitious woman who’s looking to have a 5-star Airbnb business on your hands without having to sacrifice the things you love, then tune in every week for all the goodness!

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