The STR Sisterhood

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 forwardGolden 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/4bPybnWEnjoyed the show? Subscribe, Rate, Review, Like, and Share!

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 termsBut 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/staceySign Up for the Clean Connection: https://cleanconnection.futurestay.com/Enjoyed the show? Subscribe, Rate, Review, Like, and Share!

What if the secret to a high-performing short-term rental isn’t adding more amenities or dropping your prices, but simply designing with more intention? In this episode, I’m joined by designer and investor Sarah Glidewell. Sarah shares her fascinating transition from architecture to Airbnb arbitrage and ownership, eventually building a business so successful she was able to bring her husband out of the insurance world and into real estate full-time.We talk about:Why a "pretty" space can still fail if it lacks functionality (and how to fix the disconnect)How small details, like towel hooks by the hot tub or adequate dining seating, communicate to guests that they are seen and valuedInspired by luxury travel, Sarah shares her favorite touches, from spa slippers to take-home linen spraysWhy "loud," over-the-top interiors often fail to convert and how to use refinement to win in a saturated marketHow Sarah’s team uses 3D renders and a strict "Do’s and Don’ts" list to design 100% remotely without losing qualityBut this isn't just about decor. It’s about operational excellence. Sarah pulls back the curtain on the "unsexy" side of design, choosing fabrics with high rub counts, avoiding light-colored rugs, and checking dining chair weight limits. You’ll hear why your off-season design strategy is just as important as your peak-season look, and how smart material choices reduce management headaches rather than creating them.If you’re ready to move past "surface-level" hosting and build a property that is truly guest-obsessed and high-performing, this conversation is your playbook. Get ready to stop decorating and start designing for the five-star experience.HIGHLIGHTS AND KEY POINTS:[01:08] A short introduction about our guests Sarah Glidewell, and shares how her design and architecture background led her into Airbnb investing[03:32] Sarah Glidewell explains the difference between designing a beautiful space and designing a profitable short-term rental [06:54] Sarah shares how she spoils guests with thoughtful luxury-inspired details [10:59] Why overly flashy designs may look good online but underperform on Airbnb[15:30] Sarah outlines how she would allocate a $5,000 upgrade budget for a short-term rental to increase their nightly rate [18:22] What are the the top design mistakes Sarah sees in short-term rental properties and how they impact guest experience and ROI[22:11] Sarah addresses the challenge of standing out in markets where multiple properties share the same layout, amenities, and building, like high-rise condos in Myrtle Beach[26:47] How understanding the emotional concerns and fears of guests is critical for designing short-term rentals that truly delight[31:02] Sarah shares her approach to selecting materials and furniture that withstand the high traffic and unpredictability of short-term rental guests[36:26] Sarah Glidewell recommends using realistic room renders to guide online furniture and material purchases[38:57] Sarah’s words of wisdom for nervous first-time investors worried about the cost of hiring a designer[44:03] The lightning round Golden Nuggets:“When I'm guiding anyone through where to spend their money on their BnB, I'm always prioritizing the things that I think are going to get the most traffic for their guest avatar.”“One thing that a lot of people do wrong when it comes to design is they don't necessarily think through splurge like where they need to splurge and where they need to reel back.”“When you put higher quality items in your property, and you attract higher quality guests, they absolutely take better care of your property.”Let’s Connect:Instagram : https://www.instagram.com/studiohost.co/Website : https://www.studiohost.co/TikTok : https://www.tiktok.com/@studiohost.coEnjoyed the show? Subscribe, Rate, Review, Like, and Share!

Have you ever considered that one misunderstood clause in your insurance policy could cost you tens of thousands of dollars? Most hosts view insurance as a "set it and forget it" expense, but in the world of short-term rentals, what you don't know can absolutely bankrupt your business.In this episode, I’m joined by Darren Nix, the founder of Steadily Insurance. Darren is a real estate investor and former software developer for the world’s largest carriers who realized the industry was broken—so he built a better way for landlords to protect their assets.We talk about:Why treating insurance as a tool for major disasters, not minor claims, is the secret to lowering your premiumsWhy your standard homeowners policy is a ticking time bomb and how a true STR policy differs in the eyes of an adjusterThe dangerous mistake of insuring for "purchase price" instead of "rebuild cost," and how to estimate your true riskDarren’s personal story from a Chicago rental and the one simple email every host should send their agent to avoid a denied claimWhy $300,000 in coverage might only cover your legal fees, and how to match your limits to your actual wealthThis isn't just about fine print and premiums, it’s about strategic risk management. Darren pulls back the curtain on the "unsexy" side of scaling, from how past claims influence your future growth to the difference between homeowner- and landlord-focused carriers.You’ll hear practical tips on content coverage for furnished rentals and why a higher deductible paired with a solid reserve fund is the ultimate wealth-protection move.If you’ve ever felt uneasy about whether you’re actually covered, this conversation is your reality check. Get ready to stop crossing your fingers and start protecting your rental business with total confidence.HIGHLIGHTS AND KEY POINTS:[00:59] A short introduction about our guest Darren Nix, and shares how personal frustration with rental property insurance led to founding Steadily[04:53] Darren outlines the biggest misconceptions investors have about insurance before filing a claim, and explains why insurance should protect against catastrophe, not cover every minor issue[08:49] Darren talks about Steadily’s national coverage and the rare exceptions to insurability[10:11] Darren outlines the key differences between short-term rental policies and standard homeowner or landlord insurance[13:47] Darren highlights common insurance gaps, especially underinsuring property replacement costs and emphasizes when insurance policies should be reviewed[19:20] Darren explains insurance considerations when shifting from short-term to midterm rentals, including vacancy risks[22:30] How to maintain insurance coverage during property renovations and extended vacancies[24:35] Darren confirms it’s possible to insure his own properties and shares that Steadily’s very first policy was written on his own rental property in Indianapolis[25:19] Darren emphasizes that the single most effective way to lower insurance costs is simply to avoid filing claims for minor incidents[28:12] The importance of sufficient liability coverage for short-term rental hosts[31:18] Darren advises key areas to review in an insurance policy and emphasizes that being proactive and informed can prevent surprises when a claim arises[32:36] Darren explains insurance and safety considerations for house-hacking and STRs[35:42] Darren advises new property investors to start locally and build the right support system[48:11] The lightning roundGolden Nuggets:“What you paid for the house doesn't typically have that much of a relationship with what it costs to rebuild the house.”“The single best thing you can do to reduce your cost of insurance is to not file a claim.”“I like to carry roughly the amount of my net worth in liability coverage, because the juicier target someone is the more aggressively a plaintiff's attorney is going to go after them to get a payday.”“Buy a property in a city that you know very well, that you can keep close eyes on until you've built the reps of knowing the ins and outs, because there are so many surprises of things that will happen.”“It's so important to surround yourself with people who push you and also are smarter than you.”Connect with our guest:Website: https://strsisterhood.steadilypartner.com/Enjoyed the show? Subscribe, Rate, Review, Like, and Share!

What if your “ideal guest avatar” is the very thing keeping your best guests from ever booking with you? Most hosts treat an avatar like a worksheet to fill out, giving them a name, an age, and a salary, but they never actually reach the person behind the booking button.In this episode, I’m pulling back the curtain on my "Iceberg Method" to combat this very problem. We’re moving beyond demographics and diving into the silent pressures, anxieties, and hopes that drive your guests to hit "Book Now."Inside the episode, I dive into:A framework to stop marketing to surface-level actions and start speaking to the deep emotional layers underneath.Understanding the silent fear your guests carryWhy a calm, confident, and predictable listing will beat a "salesy" one every single time.How to use your reviews and description to prove you are the solution to their stress, not another problem to manage.Shifting your focus from who your guest is to what they are feeling when they find your listing.This isn't just a marketing lesson. It’s about strategic empathy. I’m challenging you to look at your guest journey, from your first photo to your checkout instructions, through a new lens. You’ll learn why your guest isn't really choosing between three bedrooms and four; they are choosing between regret and confidence.If you’re ready to stop talking at your guests and start speaking to their real needs, this episode will show you exactly how to find the "hidden" copy that's already waiting in your guests' fears. It’s time to evolve from a property owner into a strategic filter for the guest experience.HIGHLIGHTS AND KEY POINTS:[00:00] Introducing a more powerful, results-driven way to define your ideal guest avatar so it truly impacts your business[01:48] Why bookings are driven by emotion, not demographics, and how most hosts are marketing to the wrong layer[03:41] Why real ideal guest avatars live below the surface, and why most hosts are stuck marketing above it[05:08] The Iceberg Method – how actions, thoughts, and emotions shape every booking decision[06:58] How understanding hidden fears like letting family down, wasting money, or creating stress, is key to attracting the ideal guest[12:57] The difference between shallow and deep avatar thinking when defining your ideal guest[14:13] What are the five strategic questions to uncover the emotional drivers of your ideal guest[15:24] How truly understanding your guest transforms your listing copy, photos, communication, and even pricing confidenceGolden Nuggets:“When you understand the psychographics of your ideal guest avatar, that's where you start to create a booking engine with your listing.”“You are not selling excitement. You are not selling an amazing stay. What you are selling is confidence.”“Predictability beats promises. So your listing must be written so that it feels predictable.”“Your best listing copy is already hiding in your guests’ fears not your amenities.”Let’s Connect:Website : https://staceystjohn.com/Enjoyed the show? Subscribe, Rate, Review, Like, and Share!

What happens when success looks good on paper—but feels heavy behind the scenes?In this episode, Stacey sits down with longtime friend and seasoned short-term rental operator Beata Lorinc for a deeply honest conversation about leadership, loneliness, and the power of the right community. With over a decade in the STR industry, Beata shares what it was like building before there were playbooks, Facebook groups, or proven paths—and how connection became the missing ingredient that changed everything.This episode goes beyond tactics and into the emotional and identity shifts required to sustain success without burnout.We talk about:What it was really like building an STR business before community and resources existedWhy isolation is one of the biggest (and quietest) threats to successful entrepreneursThe concept of “borrowed courage” and why even confident leaders need itHow to recognize when you’ve outgrown a room—and what to do nextLetting go of properties, paths, or identities that no longer alignWhy alignment, nervous-system safety, and support matter more than scale aloneIf you’ve ever felt successful but unsupported, confident but quietly overwhelmed, or strong while still wishing someone could walk you off the ledge—this conversation is your reminder that community isn’t a luxury. It’s a requirement.⏱️ Highlights & Key Moments[02:52] Beata shares what it felt like building in the early days with no roadmap[07:14] The emotional cost of “figuring it out alone”[10:54] Borrowed courage: leaning on others when your confidence wavers[15:18] Knowing when a property—or a season—is no longer aligned[19:17] Outgrowing communities and why staying too long can stall growth[24:47] Why success without support is not sustainable[30:04] Redefining what “enough” looks like in business and lifeGolden Nuggets“You don’t need more information—you need the right people.”“Borrowed courage can carry you until yours catches up.”“Just because something is profitable doesn’t mean it’s sustainable for you.”“Outgrowing a room isn’t betrayal—it’s evolution.”“You were never meant to do hard things alone.”

What would your life look like if you actually designed it on purpose—down to how you spend your mornings, who you work with, and where you pour your creative energy? In this episode, I sit down with certified Airbnb stylist and designer Erica Egner, whose journey from a burnt-out graphic designer to a thriving short-term rental entrepreneur is a masterclass in intentional living.We talk about:How Erica and her husband worked backward from a vision of freedom to escape the 9-to-5 commute and daycare cycleThe story of a scruffy 1970s A-frame in Washington that transformed Erica from a DIY novice into a soulful hospitality expertWhy Erica is choosing to keep her boutique co-hosting portfolio small to protect her boundaries and her "people-pleaser" tendenciesHow graphic design principles translate into physical spaces to guide a guest’s eye, and their experience, through a homeThe power of plugging into mentors and communities to build systems and avoid the chaos of figuring it out alone.But this isn't just about beautiful interiors. It’s about alignment. Erica pulls back the curtain on the grit and creativity required to turn a tired space into a high-performing rental that guests describe as "healing." You’ll hear how she navigated the transition from remote design work to full-time hospitality, and why she views her business not as a machine, but as an engine for the life she actually wants to lead.If you’ve ever felt like your business is dictating your life instead of the other way around, this conversation will give you the permission—and the plan—to start designing your exit. Get ready to align your daily actions with your biggest vision.HIGHLIGHTS AND KEY POINTS:[01:01] A short introduction about our guest Erica Egner, how she got started into the world of short term rental, and how it has changed her life[03:35] Erica explains how shared values around time, freedom, and family guided major life and career decisions with her partner[07:05] Erica describes how patience, research, and shared values guided conversations around starting in short-term rentals[12:09] How reframing the short-term rental as an easy family escape helped Erica’s husband embrace the idea[13:28] Erica reflects on how applying design fundamentals in a real-world renovation revealed a natural shift toward interior design[17:23] How foundational design training shaped the way Erica approaches interior design in short term rentals[18:28] Erica describes how methodical pacing and hands-on involvement defined her co-hosting growth and journey [22:56] Erica explains how proximity, standards, and fit now guide her co-hosting client decisions[24:28] Erica shares how learning to set boundaries became essential to protecting her time and energy, and [27:20] How designing Erica’s own short-term rental revealed a clear and natural entry point into the interior design world[31:40] How learning from others helped Erica avoid overwhelm and keep moving forward instead of giving up[34:19] Erica outlines how timing, self-awareness, and life stage have shaped how she integrates work she loves with family life [36:05] Erica reflects on how intentional daily actions, not luck, are what ultimately shaped the life she and her partner built[39:43] The lightning round Golden Nuggets:“I am learning about how to have boundaries for myself, and also just that having those boundaries really makes you better at doing your job, and so you have to have them.”“Each of us can accelerate our growth, whether it is growing our businesses or just growing our knowledge and expanding opportunities by knowledge hacking.”“If you have a goal, and that's what you're working for, and every single decision you make is wondering if that's in alignment with this goal, then it's not luck. You're doing the right thing.”“When we have our daily actions in alignment with our goals, the things that are important to us, when those are aligned, that is exactly how we reverse engineer what it is that we want.”Let’s Connect:Website : https://perennial.style/about https://perennialstays.rentals/Instagram : https://www.instagram.com/perennialstyle_wahttps://www.instagram.com/perennialstays.rentals/ Enjoyed the show? Subscribe, Rate, Review, Like, and Share!

What does it really take to build a multi-billion-dollar real estate enterprise, raise a family on your own terms, and still have the energy to show up as the face of your brand every single day? Most people think it requires sacrificing your personal life; Avery Carl is proof that it requires a better system.In this episode, we’re skipping the basic tactics and going deep on the woman behind the empire—the one who went from a $37,000 salary to leading the country’s largest STR-focused real estate team.We talk about:How Avery and her husband structured a massive business so that, to their kids, it feels like they have two stay-at-home parentsAvery’s intentional prioritization filter—how she decides what stays on her plate and what gets delegated to her teamWhy telling a client not to buy a property is the secret to building a decade of trust (and a billion-dollar legacy)How Avery dominates Instagram, YouTube, and TikTok when she’d actually rather not be on camera at all.The relentless focus on what actually moves the needle versus what just feels like "busy work."Avery pulls back the curtain on the hard conversations, the fear of letting go, and why she insists on writing every word of her books herself. You’ll hear how she transitioned from "doing it all" to becoming a leader who empowers a team, all while maintaining the boundaries that protect her family time. If you’ve ever felt torn between your ambition and your afternoon with the kids, this conversation is your blueprint.Get ready to rethink your role and learn how to build a business that supports your life instead of consuming it.HIGHLIGHTS AND KEY POINTS:[01:05] A short introduction about our guest Avery Carl, a seasoned real estate investor and short-term rental expert[03:23] Avery explains how consistency, lived experience, and transparency shaped her cohesive personal brand[06:43] Avery shares her experience on encountering shiny object syndrome without abandoning her strategy[08:17] Avery reflects on losing focus, learning fast, and recommitting to her core business[09:46] How Avery Carl decides what deserves her attention inside a growing business and shares how delegation, focus, and integrity guide her leadership style[18:19] Avery explains how fluid boundaries help her balance business demands and family life[19:45] Avery shares how virtual assistants and AI reduce the constant demands of short-term rental hospitality[23:57] How Avery develops content ideas, refines the message, and publishes with consistency[26:23] Avery looks back on when she realized content creation mattered and why she started later than most[28:06] Avery explains how she evaluates content performance beyond likes, views, followers and how her platform strategy evolved from a few core channels to everywhere[30:47] What are the biggest lessons Avery learned about focus, credibility, and follow-through from writing multiple books[33:38] Avery’s advice to anyone dreaming of writing a book and emphasizes blocking time daily and putting words on the page, rather than getting stuck in planning or self-doubt[35:07] What are the habits of people who can build teams and scale different businesses versus the people who kind of stay stuck in day to day operations[37:00] Avery highlights how fear of making the wrong decision prevents people from taking necessary action[42:32] The lightning roundGolden Nuggets:“The less income producing it is, the more delegated it is.”“It's important to always stick with what you believe in.”“​​You have to be somebody who's willing to take control of your own destiny.”“If one of my kids says something like, Oh, I never get to or like that never works for me; I'm like, No, we don't talk like that. You make things happen for yourself.”Let’s Connect:Instagram : https://www.instagram.com/theaverycarl/YouTube : https://www.youtube.com/@TheShortTermShopTikTok : https://www.tiktok.com/@theshorttermshopFacebook : https://www.facebook.com/groups/shorttermshop/ Enjoyed the show? Subscribe, Rate, Review, Like, and Share!

Ever felt like you’re building an empire on an island, carrying the entire mental load of your business while wondering why there isn’t a roadmap for women like you? Scaling to the top of this industry requires more than just strategy; it requires the grit to go first and the heart to bring others with you.In this episode, I’m joined by the legendary Lisa Roads, a trailblazer who grew a UK property portfolio into a powerhouse managing over 175 luxury villas in Cyprus, all while pioneering a movement for women in hospitality.We talk about:How Lisa spotted a gap in the Cyprus market and scaled to 175+ luxury units before the industry had a manual.The raw reality of the loneliness and lack of support that often comes with rapid growth.Why Lisa is dedicated to solving the representation crisis and lifting the "unique burdens" women face in property management.The essential boundaries you must set to ensure your business doesn’t consume your life.But this isn't just about property counts or profit margins. It’s about reclaiming the narrative of the female entrepreneur. You’ll hear why true success isn’t just about the daring leaps you take for yourself, but about the space you carve out for others to be heard, supported, and celebrated.If you’ve ever felt the weight of being the "only one" in the room or are ready to scale a business that aligns with your deepest values, this conversation is your blueprint. Get ready to move beyond the grind and start leading with legacy.HIGHLIGHTS AND KEY POINTS:[01:01] A short introduction about our guests Lisa Roads, and shares her journey from long-term investor to industry leader while explaining her mission to elevate and support women in the short-term rental space[05:31] Lisa Rhodes and I reflect on the power of women-centered communities to build confidence, visibility, and leadership in short-term rental businesses [11:38] Lisa shares the realities of scaling a property management business to 175 high-performing properties by prioritizing alignment, systems, and long-term profitability [14:22] Lisa emphasizes the importance of intentional, systems-driven growth over chasing door count and scaling chaos in large property management portfolios[16:29] How intentionally defining the ideal guest, designing for that audience, and building strategic partnerships allowed Lisa to create demand in an undeveloped short-term rental market [18:11] Lisa on creating high-trust travel agent partnerships and the operational systems that made them scalable [20:51] Lisa explains how she built custom systems to manage bookings, property operations, and service delivery in a market without established short-term rental technology[22:31] How building a support network was essential to managing the invisible mental load of running a business and caring for family[25:50] Lisa emphasizes the importance of setting boundaries, protecting mental and physical health, and intentionally scheduling downtime to prevent burnout as an entrepreneur[29:19] Lisa reflects on growing up in an entrepreneurial, nomadic family, and emphasizes the importance of self-belief and having a solid business plan when facing naysayers[33:28] Lisa reflects on starting over in short-term rentals, emphasizing foundational strategy, guest experience, and building a direct booking brand[35:57] The lightning round Golden Nuggets:"It's incredibly powerful to have a community around you where you can hack into that knowledge.”“It's better to have 175 really good properties and really good aligned relationship landlords than to have 220 just not doing very well.”“To try and scale on something that's not solid is going to be painful. You're just going to have big holes.”“Without a support network, it can be virtually impossible to pull through certain situations.”“Don't let those naysayers derail you from something you're incredibly passionate and committed to doing.”“When you focus on the right things, the money will follow.”“Keep on top of your finances. Know your numbers, don't operate a business and be naive about your numbers.”Let’s Connect:LinkedIn: https://www.linkedin.com/in/lisaroads/Website: https://theholidaypropertycoach.wordpress.com/Facebook: https://www.facebook.com/profile.php?id=100082839816462Enjoyed the show? Subscribe, Rate, Review, Like, and Share!

Have you ever fantasized about quitting your corporate job to buy a run-down motel and turn it into a boutique empire—even if you have zero experience in hospitality or design? Most people keep that dream in their head; April and Sarah actually did it.In this episode, I’m joined by the visionary co-founders of The June Motel, April Brown and Sarah Sklash, two friends who traded their steady city lives for power drills, YouTube tutorials, and a lot of pink paint.We talk about:The "Wine-Fueled" Leap: How a casual brainstorm in Toronto turned into the bold acquisition of an aging roadside motel.The Reality of "DIY" Hospitality: From learning to use power tools on the fly to handling mountains of laundry and mid-reno panic.Building an Instagram Icon: Why "Instagrammable" was just the hook, and how they built a deep, meaningful brand culture to back it up.The Netflix Pivot: The behind-the-scenes chaos and courage required to scale a business while the cameras are rolling.But this isn't just a story about pretty renovations. It’s about the grit behind the glamour. April and Sarah pull back the curtain on the financial hurdles, the steep learning curves, and the power of a partnership built on radical trust.If you’ve ever felt like you’re waiting for "enough experience" to start your dream project, this conversation will be your wake-up call. Get ready to stop playing it safe and start building your own version of "The June Way."HIGHLIGHTS AND KEY POINTS:[01:05] A short introduction about our guests April Brown and Sarah Sklash, how they met, and what got them thinking about the world of hospitality[04:20] April and Sarah’s mindset shift from cautious transition to shared conviction while building a new hospitality vision[07:14] April and Sarah’s transformation of a no-frills fishermen’s motel into a visually driven, experience-led boutique destination [10:06] April and Sarah’s perspective on how “Instagrammable” has evolved from bold backdrops to cohesive, authentic storytelling[12:38] April and Sarah talk about their ability to see potential and design guest experiences beyond technical renovation skills [16:14] April and Sarah’s reckoning with the reality of hospitality and the doubts that come with it[18:53] The expansion journey of April and Sarah, and the behind-the-scenes challenges of opening new properties while launching a Netflix show [26:37] April and Sarah discuss the necessity of creating repeatable systems to maintain the quality and character of their properties when they couldn’t be on-site every day [29:19] The importance of hiring for cultural alignment and understanding the “why” to foster team buy-in and preserve the vision of their properties[31:14] April and Sarah share their hands-on, values-driven approach to hiring and staff retention to ensure cultural alignment and long-term team growth[33:02] April and Sarah reflect on managing perfectionism and making collaborative decisions while keeping the big picture in focus[36:45] April and Sarah discuss collaborative decision-making and how differing perspectives strengthen their business outcomes [38:33] Sarah shares key advice for first-time motel buyers, emphasizing passion, partnership, and a hands-on approach to hospitality[40:14] The lightning round Golden Nuggets:“Helping people understand the why behind what you're doing, allows them to buy in to the vision at a much deeper level.”“You don't have to do it all yourself. I think for us, initially, just due to budgets, we did feel like we had to wear all of the hats. But as we've grown the business and realized you can find really great partners, and what you can create with other people is sometimes just way more impactful than what Sarah and I do just ourselves.”“If it's not a Hell yeah, it's a hell no. Because anything, everything we say yes to, takes us away from something else.”Let’s Connect:Website: https://thejunemotel.com/Instagram: https://www.instagram.com/thejunemotel/Enjoyed the show? Subscribe, Rate, Review, Like, and Share!

What truly sets apart a vacation rental that’s always booked from one that simply gets browsed? In this episode, I’m sitting down with industry veteran Kiera McGrath, a real estate investor and marketing expert who was filling calendars long before Airbnb even existed.We talk about:Kiera’s signature framework for diving into the mindsets and motivations of your ideal traveler.Why trading generic descriptions for emotional, sensory language is the key to resonating on a deeper level.How to analyze your feedback (and your competitors') to uncover the unique value gaps in your market.Why the "vibe" between your photos and your words is the silent deal-breaker for most guests.But this isn’t just about marketing tricks. It’s about becoming a master of the guest experience. Kiera pulls back the curtain on how to bridge the gap between a generic house and a sought-after brand. You’ll hear why managing expectations and crafting personal touches before a guest arrives is the secret to scaling a rental business that guests actually rave about.If you’ve ever felt like your property is just a commodity in a crowded sea of listings, this conversation will give you the blueprint to stand out. Get ready to stop hoping for bookings and start engineering them, evolving from a passive host into a strategic market leader.HIGHLIGHTS AND KEY POINTS:[00:51] A short introduction about our guest Kiera McGrath, and how she got started in the short-term rental industry[05:29] Kiera shares her methodology for turning lookers into bookers by applying guest psychology, neuroscience, and deep guest–listing alignment [09:18] Kiera’s perspective on attracting broad audiences through shared emotional triggers rather than marketing to everyone [11:13] Kiera’s framework for turning guest emotions into bookings through data, reviews, and booking psychology[15:20] Kiera’s perspective on using sensory language, mental imagery, and guest fears to strengthen booking psychology [17:52] Kiera dives into the nuts and bolts of booking psychology, emphasizing that understanding a guest’s mindset involves both logic and emotion[22:55] Kiera’s approach to listing precision through careful language, proofreading, and attention to detail [25:14] Kiera’s approach to crafting exceptional guest experiences across the entire journey from booking to post-stay[28:54] The importance of setting realistic expectations to prevent negative experiences and reviews [32:43] Kiera stresses the importance of ensuring that the guest experience aligns with expectations set by the listing, even when elements outside the property[34:45] Kiera’s strategy for leveraging competitor reviews to identify market gaps while staying true to guest demographics [41:23] Kiera’s perspective on resisting one-size-fits-all strategies and focusing on unique listing value [43:44] The lightning round Golden Nuggets:“Guests make booking decisions using both sides of their brain, so both logic and emotion.”“Your reviews leave clues, and it's such an untapped resource. Your previous guest will actually tell you everything you need to know about who your property fits, why it fits, and what those emotional experiences are.”“I always share with folks pretending like you're taking someone on a visual tour of a property through the listing description.”“If you have a direct booking website, go through the entire booking funnel, and experience it as a guest.”“To thine own self, be true.”Let’s Connect:Facebook: https://www.facebook.com/kiera.turn.lookers.into.bookers Email: [email protected]: www.turnlookersintobookers.comEnjoyed the show? Subscribe, Rate, Review, Like, and Share!

Have you ever felt trapped in the whirlwind of your own business, wishing it could run itself so you could finally breathe, and maybe even enjoy a family dinner? That’s not just a dream. That’s a system at work.In this episode, I’m joined by the powerhouse Marisa Grover—a mom of two toddlers who manages over 50 properties and has mastered the art of the "enough is enough" pivot.We talk about:How Marisa went from "accidental" host to a systems-driven entrepreneur managing 50+ unitsThe raw reality of handling guest requests while literally in labor (the spark that changed everything)The "Progress over Perfection" method—why a Loom video or a notebook is better than a perfect manualBut this isn't just about automation. It’s about reclaiming your humanity.Marisa pulls back the curtain on the grit required to scale, from navigating licensing hurdles to building a team aligned with your values rather than just their resume. You’ll hear why letting go isn't a loss of control—it’s the key to leading, creating, and enjoying the life you’ve worked so hard to build.If you’ve ever wondered if you’re "doing it right" or felt buried by the daily grind, this conversation will give you the blueprint to step out. Get ready to rethink your role in your business, and evolve from an overwhelmed operator into a confident CEO.HIGHLIGHTS AND KEY POINTS:[00:51] A short introduction about our guest Marisa Grover, and how she got started in the short-term rental industry[03:36] Marisa’s early trial-and-error journey and the wake-up call that systems are what make a short-term rental business sustainable[07:48] Marisa’s approach to building systems by starting small, documenting in real time, and valuing her time as a business owner[12:31] Marisa’s perspective on team-building rooted in self-belief, leadership mindset, and intentional delegation[15:22] Marisa shares her mindset evolution through support, delegation, and gradual practice[21:14] Marisa’s strategic approach to building a team around culture, outcomes, and intentional hiring[25:34] How Marisa’s local team member who started as a cleaner naturally advanced to lead cleaner and eventually Operations Manager[26:17] Marisa shares the first task she delegated, driven by a desire to reclaim personal time and be fully present with her family during meals[29:29] Marisa’s approach to next-level business growth by aligning with personal values, focusing on what she enjoys, and improving existing services[35:13] The lightning round Golden Nuggets:“I think a common misconception about building systems is that it is gonna suck your soul for a full year of your life, like there's no alternative, right? And so I just started, yes. I just started.”“Having belief in yourself and believing that you have value is the start of a domino effect that's much bigger.”“You have to believe that you are the valuable and the most important part of your team.”“If you want to change your mindset, first of all, commit to changing that mindset.”“Do the things that you love with the people that you love and build a business that integrates with that life.”“All feedback is good feedback.”Let’s Connect:Instagram: https://www.instagram.com/marisa.grover Enjoyed the show? Subscribe, Rate, Review, Like, and Share!

Ever scroll past a vacation rental photo and feel like you had to stay there—like, yesterday? That’s not an accident. That’s story-driven strategy at work.In this episode, I’m joined by the incredible Nicole Alexander—a woman who’s mastered the art of making STRs look so inviting, guests can’t help but click “Book Now.”We talk about:How Nicole went from wedding photography to capturing the soul of spacesHer three-month adventure across Europe, camera in hand, documenting dreamy cabinsWhy cozy corners, golden light, and personal touches matter more than you thinkBut this isn’t just about pretty pictures. It’s about creating an emotional connection.Nicole walks us through her process—how she uncovers what makes a property special and translates it into visuals that spark curiosity, desire, and trust. You’ll hear why professional photography isn’t just a “nice to have.” It’s a brand builder. A booking booster. A guest experience enhancer.If you’ve ever wondered whether great photos really move the needle in your STR business... this conversation will open your eyes.Get ready to rethink how you show up online—and how guests see your property through the lens of story.HIGHLIGHTS AND KEY POINTS:[01:03] A short introduction about our guest Nicole Alexander, and how she got started in the short-term rental industry[03:01] Nicole’s shift from wedding photography to cabin photography, and her approach to translating storytelling and vision into impactful property photography[07:46] Why it's so important for hosts to invest in high quality story driven images, instead of just hiring a real estate photographer, or snapping their own pictures with their iPhone[12:22] Nicole’s emphasis on atmospheric moments as the emotional bridge that turns a property into an experience guests can already feel themselves living[14:51] Nicole’s commitment to honest, accurate photography as a trust-building tool rather than a marketing illusion[18:15] What are some of the biggest mistakes that Nicole sees when hosts rely on subpar or non-experiential photography[20:34] Nicole emphasizes that while professional photography is essential for listings, candid and non-professional shots play a crucial role in storytelling, particularly on social media[22:42] Nicole talks about the common styling mistakes and preparing a property for photography[25:32] Nicole’s advice on finding a creative photographer beyond traditional real estate specialists[28:06] Nicole’s insights on vetting photographers to ensure they can deliver on your vision [29:56] Nicole breaks down realistic photography investment ranges and what hosts should expect in return[35:18] How investing in professional, story-driven photography directly drives stronger cash flow, higher nightly rates, and better guest alignment[37:39] Nicole’s guidance on prioritizing hero images that quickly communicate space, amenities, and setting to drive booking decisions[39:18] The lightning round Golden Nuggets:“Photos truly are the only thing that are consistently working for you, 24/7.”“Your photos sell the charm of the space. It's history, it's personality, the feeling of the location.”“There's nothing worse than walking into a space and being like this doesn't look like what I was sold.”“Ask to see galleries, ask to see their work, because social media can be fake.”Let’s Connect:Website: www.cabinhunter.comEnjoyed the show? Subscribe, Rate, Review, Like, and Share!

Building a successful vacation rental portfolio isn’t just about numbers—it’s about strategy, intuition, and having the confidence to trust both. In this episode, we explore what it really looks like to invest with intention, think long-term, and build a business rooted in education rather than hype.In today’s episode, I sit down with the incredible Parker Borofsky, whose passion for lending and vacation rental investing shines through every story she shares. From her early days as Avery Carl’s lender to becoming a seasoned investor herself, Parker offers a behind-the-scenes look at a journey shaped by curiosity, courage, and thoughtful decision-making.In this conversation, Parker shares:How her early career in lending gave her an “under the hood” view of what truly makes a short-term rental successful—and how she used that insight to build a portfolio spanning the Smokies and Florida’s PanhandleThe remarkable story behind acquiring a bona fide Frank Lloyd Wright home in Kentucky, including the family connections and moments of serendipity that led her thereWhat it’s really like to invest during uncertain and unpredictable times, and why balancing solid research with gut instinct allowed her to seize opportunities others overlookedThe unique challenges and rewards of restoring and short-term renting a historic home, from navigating appraisals to thoughtfully weaving the property’s history into the guest experienceWhy putting heart and education above hype—and surrounding yourself with the right community—is essential to building a more meaningful, sustainable businessParker’s insights and grounded enthusiasm make this episode a must-listen for anyone looking to build a smarter, more intentional vacation rental portfolio. It’s filled with practical takeaways, mindset shifts, and real-world lessons for scaling with clarity and purpose.HIGHLIGHTS AND KEY POINTS:[01:00] A short introduction about our guest Parker Borofsky, and how she got into investing in short-term rentals[03:00] Parker walks through her growing short-term rental portfolio across Tennessee, Florida, and Kentucky, highlighting a pivotal purchase in Townsend, Tennessee[08:43] Parker explains how intuition, timing, and storytelling led her to an unexpected Kentucky purchase[13:01] Parker shares how stewardship and storytelling shape the experience of owning a Frank Lloyd Wright home[18:56] Parker reflects on the emotional full-circle of stewarding a historic Frank Lloyd Wright home[21:24] Parker dives into the complexities of securing a mortgage for a one-of-a-kind Frank Lloyd Wright home, emphasizing that unique properties often create appraisal challenges[26:51] How to handle appraisal challenges for unusual properties, emphasizing preparation, collaboration, and clear communication[31:24] Parker talks about the mortgage options that are trending for real estate investors, particularly for self-employed borrowers or those with complex income streams[34:57] The importance of connecting with experienced loan officers as a critical first step for anyone looking to grow their property portfolio in 2026[37:13] Genuine appreciation for Parker’s commitment to giving back to the short-term rental industry, and Parker’s role as a speaker at the upcoming Short-Term Rental Virtual Summit for Women[38:30] The lightning round Golden Nuggets:"It's not always perfect when you're finding properties in the market. So, go and see and feel and trust your gut feeling.”“It's so important that we balance the numbers with our intuition.”“Look ahead of what's coming.”Let’s Connect:Website: wealthbuildersmortgage.comEnjoyed the show? Subscribe, Rate, Review, Like, and Share!