The STR Sisterhood

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...

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...

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...

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...

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:li...

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 2026p...

From corporate hustle to hospitality powerhouse, Janel’s story is the kind every host needs to hear.In this episode, I sit down with the inspiring Janel Gallucci, who walked away from a high-pressure San Francisco career to build a short-term rental business on her own terms. What began with a single Lake Tahoe cabin quickly evolved into a thoughtfully scaled portfolio — each property designed with intention, creativity, and an unwavering commitment to delivering a true 5-star guest experience.You’ll hear how Janel shifted from “one-property owner” to savvy portfolio builder, the systems and mindset she used to scale sustainably, and the decisions that helped her create guest-loved stays while protecting her time and energy. This conversation is a powerful reminder that a purpose-driven business can grow without sacrificing the life you’re building it for.Janel shares:The pivot point: How a moment of burnout prompted her and her husband to leave the corporate grind and dive head-first into STRs.Taking control: Why early missteps with property managers forced her to self-manage—and how applying her corporate skills dramatically boosted her returns and created unforgettable stays.Guest-Magnet Strategies: The exact systems she uses to turn listings into best-in-class properties, from leveraging market data and building local partnerships to offering dog-friendly welcome baskets and locally sourced amenities.The Blueprint for Growth: Why defining your ideal guest and implementing robust systems is essential for managing properties confidently, whether they're nearby or across the country.Janel’s story is a powerful blueprint for building a richer, more flexible life through short-term rentals. It's packed with actionable tips, mindset shifts, and the courage required to build an intentionally successful business. Tune in now to unlock the strategies for your own STR success!HIGHLIGHTS AND KEY POINTS:[01:15] A short introduction about our guest Janel Gallucci, and how she got into the short-term rental industry[04:24] Janel reveals how miscommunication and poor property care pushed her to replace her property manager with direct self-management[08:04] Janel’s approach to shifting into self-management to enhance confidence and control in her short-term rental[11:02] How Janel handles tough guest situations to enhance satisfaction and protect reviews[14:23] I share my experience at Airbnb headquarters and unpack why hosts have seen a dramatic shift in Airbnb’s willingness, and ability to remove unfair reviews [17:12] Janel’s thoughts about the challenges of subjective guest ratings to highlight the flaws in Airbnb’s value and accuracy metrics[20:12] Janel outlines her strategy for breaking past her revenue ceiling by elevating her property into the luxury tier[22:06] How small luxury touches elevate the guest experience and reinforce premium positioning[23:27] Janel outlines the intentional upgrades and guest-avatar strategy that fueled her jump from average earnings to six-figure revenue[27:20] How low-cost, locally sourced, and thoughtfully branded welcome baskets enhance the guest experience while

Are you ready to stop relying on a single platform and take true control of your bookings, brand, and profits?In this episode, I sit down with Jennifer Spencer— who left her corporate career to master the world of direct bookings. Jennifer’s journey from a single property in the Canadian Rockies to a diversified portfolio in Maui taught her one powerful lesson: you need to own the guest relationship.We dive deep into her proven, anchor strategies for success:Crafting property brands that guests instantly recognize and remember.Leveraging email marketing to drive loyalty and repeat, direct bookings.Implementing smart automations that scale income without sacrificing the personal, top-notch guest experience.If you feel overwhelmed by the thought of shifting from one platform to multiple channels, Jennifer offers a practical, step-by-step roadmap for taking manageable action, discovering your unique hosting style, and building a supportive network.Tune in to learn how to brand boldly, optimize smarter, and turn casual stays into lifelong fans.HIGHLIGHTS AND KEY POINTS:[01:03] A short introduction about our guest Jennifer Spencer, and how she got into the short-term rental industry in the Canadian Rockies to expanding to Maui[03:53] Jennifer shares how her transition from corporate sales and marketing into the vacation rental space happened almost unexpectedly[06:08] Jennifer highlights the mindset shift required to move from an Airbnb-only approach to a diversified, business-driven booking strategy[10:16] Jennifer shares her go-to tools and guest-experience strategies that reliably drive repeat direct bookings[12:19] Jennifer outlines a balanced, human-first approach to using AI in guest messaging without sacrificing authenticity[16:05] Jennifer shares her compliant, subtle strategy for priming guests for direct bookings without violating platform rules[18:28] Jennifer’s top strategies for helping a property go from staying afloat in the market to truly outperforming its competitive set[21:31] Why dynamic pricing tools only work when paired with proactive revenue management[25:20] Jennifer explains why a defined, memorable brand is critical for driving direct bookings and standing out in a saturated market[29:13] The critical role of guest communication and proactive problem-solving in creating memorable experiences and earning five-star reviews[34:54] Jennifer highlights that the biggest challenge in shifting to a diversified direct booking strategy[39:15] The lightning round Golden Nuggets:“If you're really wanting to grow, whether it's one or two or an empire, you need to have a diversified strategy.”“I'm also super passionate about making sure that we are doing the work– number one that is within our genius zone. But it's also work we enjoy. If you don't enjoy that, don't just not do it. Delegate it to someone else.”“If there's nothing unique about you, it can be very difficult to stand out.”“You can turn any negative situation into a positive if you handle it properly.”“Find the support that matches what you need and what you're looking for.”Let’s...

Are you accidentally making one of the five deadly mistakes that could be sabotaging your short-term rental co-hosting dreams?In this candid episode, I pull back the curtain on the real pitfalls that derail even the most ambitious hosts. These errors are far more common than people admit, and they quietly chip away at your confidence, your profits, and your ability to grow.We’re breaking down the 5 critical errors that hold co-hosts back:Lacking the non-negotiable systems that keep your business running smoothly and efficientlyUndercharging for your services just to land your first clientBelieving every client is the right client for your co-hosting businessTying your professional worth and boundaries to your constant availabilityNot knowing exactly what to say to owners when it matters most This is more than just spotting mistakes—it's about transforming missteps into momentum. I detail the clear professional standards, streamlined systems, and mindset shifts that will elevate you from busy to unstoppable.Plus, discover The Co-Host Code—my step-by-step guide packed with templates, scripts, and proven strategies to build your business the right way from day one.Tune in now to start charging your worth, setting boundaries, and building a sustainable co-hosting empire!HIGHLIGHTS AND KEY POINTS:[00:00] Co-hosting – the smartest way to grow and scale an STR business in 2026, and the quote that inspires me about ambition and believing in yourself[01:34] Introducing my e-book The Co-Host Code – a step-by-step guide for building a profitable co-hosting business, and where to grab it[02:29] Why do I believe co-hosting is one of the best ways to start and scale your short-term rental business[04:42] How co-hosting allows me to support both guests and fellow real estate investors[06:26] The First and the Biggest Mistake in Co-hosting: Lacking systems[10:04] The Second Mistake: Undercharging for your services just to land your first client[11:49] The Third Mistake: Every client is the right client for your co-hosting business[15:22] The Fourth Mistake: Tying your worth to your availability[17:36] The Fifth Mistake: Not knowing what to say to owners[19:50] What are the things that you need to have in place for success in co-hosting [24:49] The importance of building confidence through systems and action to scale a co-hosting businessGolden Nuggets:“Ambition is not a dirty word, it's just believing in yourself and your abilities.”“Co-hosting is a way for you to grow your portfolio without having to invest cash.”“If you are looking to grow a co-hosting business, or launch a co-hosting business, you absolutely need systems that are outside of what you are utilizing in your day to day.”“When you undercharge for your services, it is the fastest way to begin resenting your business.”“Not all owners are created equal.”“Your value is so much greater than the time you have for your business.”“The right words when you're selling your co-hosting services create confidence in your owners, and confidence...

How can you turn your dreams into a profitable real estate strategy that builds both wealth and freedom?In this episode, I sit down with Sandy Lee, who pivoted from a 30-year career in oil and gas engineering to become a savvy short-term rental investor with properties across four different states. Sandy’s story is about reimagining what’s possible when you combine strategic thinking, personal passion, and a relentless drive to learn.What started as a family joke about buying a ski condo her son dreamed of turned into a thriving investment portfolio that now generates meaningful retirement income. Sandy’s approach is rooted in intentional, long-term wealth building—where every property reflects both financial foresight and lifestyle design.We dive into how Sandy leveraged her engineering mindset and financial modeling skills to build a short-term rental business that delivers more than just cash flow. From managing remote teams to identifying the financial metrics that truly matter, she shares the systems and mindset shifts behind her success.This episode is a powerful reminder that it’s never too late to reinvent your career or your financial future. Sandy’s journey proves that with clarity, structure, and purpose, your investments can become more than assets—they can become the foundation for the life you’ve always envisioned.HIGHLIGHTS AND KEY POINTS:[00:50] A short introduction about our guest Sandy Lee, and how she got into the short-term rental industry[05:10] Sandy shares how she went from doubting property ownership to building a multi-state portfolio that fuels her retirement [08:04] How aligning Sandy’s investments with her personal mission brings both joy and purpose to her real estate journey [10:44] Sandy talks about how continuous learning shaped her mindset shift toward early retirement and business reinvention [14:37] How leadership and appreciation elevate Sandy’s short-term rental business[18:12] The importance of building genuine, caring relationships with the cleaning team and how Sandy found them in four different locations[20:35] Sandy shares the challenges and lessons of managing teams across multiple short-term rental locations[24:06] Sandy talks about the realities and rewards of managing short-term rentals from afar [26:40] The key financial metrics that Sandy uses to evaluate short-term rental investments [28:20] Sandy discusses the importance of tracking data-driven performance metrics after purchase to guide strategic decisions [32:08] Sandy discusses the importance of moving away from “ego pricing,” and trusting experts to strengthen business performance [34:42] Sandy shares her enthusiasm for bringing fresh energy into the short-term rental, and emphasizes the importance of thinking beyond the “get rich quick” mentality [35:38] The lightning round Golden Nuggets:“It's really important to figure out who you are, what you want from life, put that together and then make it happen.”“Don't wait for an opportunity, create it.”“You've got to keep learning, or you're paced out.”“People are your business, no matter how tiny your business is.”“It's okay

Ever feel like scaling your STR biz means sacrificing your sanity?Jessica Hill is living proof it doesn’t have to be that way.In this episode, we chat with the inspiring mama, healthcare pro, and STR entrepreneur behind Jet Setter Property Management — where intentional design meets boutique profitability. With just 12 hand-picked properties, Jessica has built a wildly successful short-term rental business that’s rich in personality and profit… without managing dozens of doors or burning the candle at both ends.She gets real about:Designing properties that connect emotionally (hello, custom murals and curated guest experiences)Balancing a demanding W-2, motherhood, and business ownershipThe systems, boundaries, and support that make her model sustainableThis convo is a masterclass in doing STRs differently — and doing them on your terms.If you’re craving a business that feels good and does good, this episode will remind you that “more” isn’t the goal — meaning is.HIGHLIGHTS AND KEY POINTS:[00:56] A short introduction about our guest Jessica Hill and how she got into the world of short-term rentals[03:32] Jessica talks about her company and explains why she intentionally operates a boutique, hands-on property management model instead of scaling into a large, volume-driven portfolio[05:19] Jessica emphasizes the importance of intimate, hands-on management that boutique operators provide compared to large-scale property managers[09:55] Jessica’s active involvement in the guest experience and daily operations despite having a team[11:03] Jessica shares about her W-2 job and what she has pulled over from her W-2 into her short term rental business[12:35] Jessica explains explains why strategic design is a performance lever, not just aesthetics, in driving bookings and brand demand[16:11] Jessica talks about how she monetizes design and listing optimization as value-add services within her boutique hosting model[17:31] Jessica shares the key foundations smaller hosts should prioritize to deliver a high-touch guest experience through a boutique-style approach[20:11] How Jessica balances a full-time W2 career, motherhood to a special needs child, and her co-hosting business through intentional time management[22:32] Jessica shares how motherhood shaped her communication philosophy in short-term rentals[25:15] Jessica emphasizes the power of over-communicating with her team to build ownership and brand-aligned service[27:27] Jessica shares her piece of advice for all women who are chasing big dreams while also navigating life, being a mom, working a full time job[29:51] The lightning round Golden Nuggets:“Start and make sure that you have the proper systems in place.”“I have brought those people on my team to help with those things, so that way I can be a more effective property manager and do the things that I love to do.”“When you love what you do, you never work a day in your life.”“Don't lose yourself in the day to day of motherhood. Carve out a little time for yourself, because

Ever wondered how to successfully manage a short-term rental hundreds of miles away—without losing your sanity or your weekends?In this episode, I sit down with Lydia Patel, a pharmacist who’s mastered the art of remote property management while balancing a full-time career and family life. Lydia’s story proves that you don’t need to live near your investment to make it thrive—you just need the right systems, people, and mindset to make it work.From setting up her Florida rental property while caring for a newborn to building a trustworthy team of local professionals, Lydia walks us through the practical steps that turned her long-distance investment into a sustainable success. Her journey is a blueprint for anyone looking to create a business that fits seamlessly into real life, not the other way around.We explore the exact tech tools and strategies that make remote management possible—from noise monitoring and digital locks to streamlined property management software. But at its heart, this conversation is about more than tools—it’s about resilience, resourcefulness, and redefining what freedom looks like in real estate.Lydia’s insights will inspire you to think differently about investing, scaling, and balancing it all. Her story is proof that with strategy, systems, and heart, you can manage your business from anywhere and still have a life you love.HIGHLIGHTS AND KEY POINTS:[00:52] A short introduction about our guest Lydia Patel, how her hosting journey began, and walks us through the long-distance managing her Florida short-term rental while living full-time in Minnesota[05:59] Lydia opens up about the steep learning curve and operational surprises of managing her Florida rental remotely right after giving birth[09:45] Lydia details how she built a dependable remote team by combining local expertise, reliable systems, and open communication[14:02] Lydia shares how smart technology and integrated systems make remote property management seamless and secure  [19:23] Lydia opens up about overcoming the emotional challenges of managing from afar and learning to let go of control[24:04] How to turn preventable mistakes into refined systems that strengthen business operations over time [29:12] Lydia shares the real challenges of juggling motherhood, work, hosting, and the mindset shift that helped her find balance[32:24] How sharing Lydia’s journey through content creation became an authentic way to give back and connect with others on a similar path [35:22] Lydia shares how she balances creativity and delegation in managing her content creation process [39:43] The lightning round Golden Nuggets:“Never make assumptions; look for those opportunities where slip ups happen, and write a process to fill in a gap so that there's no question.”“There's something very rewarding about feeling like you're helping someone else. And so if I can share something that I've done, a tip, a helpful trick, a strategy that's been beneficial for me, if I'm able to pay it forward and help someone else.”“Slow months are real. Don't panic over it, just budget for it.”“Just stay human. Yes, it's a business, but there's a human aspect to it. Whether it's the relationship with your team members, relationship with your guest and

How do you turn a single-property hustle into a thriving, purpose-driven business that actually gives you freedom?Join me as I sit down with Brindy Bringhurst, a trailblazer who transformed her entrepreneurial journey from managing one property to leading a successful multi-property management operation in Arizona. We dive deep into the art and science of building a strategic short-term rental business that goes far beyond just hosting guests.Brindy shares the pivotal lessons she learned along the way—from defining her ideal owner avatar to building a supportive, high-performing team that became the backbone of her success. Her story is a masterclass in resilience and strategic growth, proving that the key to scaling isn’t just about more properties, but about smarter systems and stronger relationships.We unpack her early challenges of working solo and feeling stretched thin, and how she intentionally built a team that understands both the business and the heart of hospitality. Brindy reveals how protecting your team’s energy and aligning your business with your values can completely redefine success.This isn’t just a conversation about rentals—it’s about designing a business that supports your lifestyle, empowers your people, and creates lasting impact. Get ready for an honest, inspiring dialogue that will challenge how you think about entrepreneurship, leadership, and sustainable growth.HIGHLIGHTS AND KEY POINTS:[00:55] A short introduction about our guest Brindy Bringhurst and how she got started in the world of short-term rentals[04:16] Brindy shares her early experiment in full-home hosting that taught her adaptability, connection, and the trade-offs of earning more while giving up stability[05:24] Brindy’s reflections on the emotional toll of renting out her own home [08:49] Brindy walks us through the long, unpredictable transition from her early hosting hustle to establishing a full-fledged co-hosting business[15:56] Brindy opens up about the defining moment she stopped “trying” and fully committed to making her business work[20:29] Brindy reflects on the stark contrast between her early years of nonstop hustle and how she now approaches fear, self-doubt, and confidence[27:08] How growing Brindy’s team transformed her business from a one-woman juggling act into a well-rounded, collaborative operation powered by trust, learning, and honest feedback [36:11] How leading a team transformed Brindy’s purpose in business from proving herself to creating a company built on collaboration, accountability, and genuine care for her people[40:29] Brindy recalls the pivotal moment when she realized not every property—or owner—was the right fit for her growing business[43:53] The challenges of dealing with difficult owners and how those moments have shaped Brindy’s approach to leadership[48:22] The lightning round Golden Nuggets:“If you have an idea and you think it'll work, just commit to it and it'll work. It will happen.”“What we believe, is what we can achieve.”“As business leaders, it's critical for us to learn skills about how to be a good business leader.”“You don't have freedom unless you have a team.”“Don't give advice unless you're asked. People don't

The right tech stack could give you back your time, your freedom, and the space to focus on what truly lights you up in your business.In this episode, I sit down with Margot Schmorak, CEO and co-founder of Hostfully, to explore how the right property management software can transform your short-term rental business. Margot isn’t just another tech executive—she’s a visionary leader who believes technology should simplify your operations, elevate your guest experience, and help you reclaim your time.We dive into what really matters when choosing tools for your rental business—from selecting a property management system that scales with you, to optimizing your workflows, to building a cohesive tech foundation that supports both growth and balance.Margot also shares her journey from big tech to entrepreneurship, her philosophy on human-centered technology, and how she leads a company rooted in joy, purpose, and personal growth. Beyond business, she opens up about finding harmony as a CEO, mom, and lifelong learner.This episode is a must-listen for hosts and entrepreneurs ready to use technology intentionally. Margot’s insights will inspire you to design a business that runs efficiently, aligns with your values, and gives you the freedom to focus on what matters most.HIGHLIGHTS AND KEY POINTS:[00:58] A short introduction about our guest Margot Schmorak and shares her vision for building Hostfully around human connection, real-world impact, and a culture that uplifts people[04:07] Margot highlights how hiring for passion and fostering authenticity are key to building a thriving, people-centered culture[07:15] Margot breaks down the essentials of building a strong tech stack that drives bookings, streamlines operations, and supports long-term business growth[11:14] Margot emphasizes the importance of starting with the right property management software and choosing tools that can scale with your business through integrations [14:22] How to shop smart for property management software and the importance of spotting red flags in emerging technology[19:39] Margot’s insights on using AI to elevate customer experience, strengthen team efficiency, and personalize communication at Hostfully[22:35] Margot’s perspective on overcoming “Shiny Object Syndrome” to build a focused, intentional tech strategy [24:30] The importance of aligning technology and planning with clear goals to set up a strong start for the new year[28:06] Margot’s perspective on revisiting annual plans and adapting to change while staying confident in the industry’s long-term growth [29:39] Margot’s outlook on the next big shifts shaping the short-term rental industry from AI innovation to a new era of professionalism [32:15] Margot’s reflections on rediscovering joy, grace, and the freedom to be imperfect outside of work[37:55] Margot’s journey toward embracing joy, self-compassion, and the simple art of celebrating life’s small wins[42:51] The lightning round Golden Nuggets:“One of the most important things is to make sure that you're hiring people into jobs that they're really excited about.”“When you're selecting tech, it's really critical to not only know where your business is today, but where you want to be in the...

What if standing out in the short-term rental industry isn’t just about the property—but the experience you create?In this episode, I sit down with Candice Menard, the powerhouse behind Rent It Like a Saint, to explore the transformative philosophy of “Unreasonable Hospitality.” Candice isn’t just managing rentals—she’s redefining modern hosting by crafting heart-centered guest experiences that turn first-time visitors into lifelong fans.Candice shares her inspiring journey from long-term property management to becoming a visionary in short-term rental hospitality. She breaks down how understanding her ideal guests—hardworking professionals who crave comfort, connection, and care—helped her anticipate needs before they were spoken, setting a new gold standard for guest experience.We also dive into Travel Like a Saint, her complementary travel service that elevates the guest journey from start to finish. Candice reveals how she blends technology with personal touch through AI-assisted communication, community partnerships, and holistic brand storytelling that keeps guests coming back.This episode is a must-listen for hosts and entrepreneurs ready to elevate their hospitality game. Candice’s story is a masterclass in business growth, intentional service, and brand differentiation—proving that true success comes from serving with heart, purpose, and a touch of the extraordinary.HIGHLIGHTS AND KEY POINTS:[01:00] A short introduction about our guest Candice Menard and how did she get into short-term rental business[02:57] Candice’s approach to embracing unreasonable hospitality and gaining clarity on her ideal guest to elevate the guest experience[06:24] Candice talks about how an unexpected Airbnb booking helped her discover her ideal guests and shape the future direction of her rental business[08:42] How Candice brings “unreasonable hospitality” to life by anticipating guest needs through fast communication, personalization, and gratitude[12:33] Candice explains how she blends AI with human communication to deliver efficient yet personal guest experiences[15:43] How the idea of “unreasonable hospitality” inspired Candice to expand from Rent It Like a Saint into a full travel service with Travel Like a Saint[18:35] Candice explains how she promotes Travel Like a Saint across multiple channels and the enthusiastic feedback she’s received from guests[20:33] Candice details the foundational systems she built within Rent It Like a Saint to free up her time and focus for launching Travel Like a Saint[23:23] How Candice’ involvement in the Louisiana Travel Summit unexpectedly turned into an opportunity to build stronger ties within her local community[28:06] Candice offers thoughtful, grounded advice for anyone who wants to infuse the spirit of “unreasonable hospitality” into their business[32:00] The lightning round Golden Nuggets:“Providing excellent world class customer service is the best way to get those five star reviews.”“The most valuable asset you can have in your hosting arsenal is your speed of communications.”“Relationships are where referrals come from.”“What's important to you, what's important to your guests, find your who's that can make that connection to get your puzzle piece...

How do you rebuild your life and create extraordinary success after everything falls apart?In this episode, I sit down with Ashley Freeman, a former tennis pro who turned the pain of divorce into the fuel for a thriving 115-property short-term rental business—all in just three years. Her journey is a testament to resilience, reinvention, and the power of daring to believe in something bigger for yourself.Ashley opens up about the pivotal moment she discovered Airbnb, transforming her four-acre property into a surprising income stream. What started as a survival strategy quickly became a passion-driven business that redefined her career and her sense of purpose.We dive into the entrepreneurial strategies that fueled her rapid growth—from scaling one unit into 115, to building a powerhouse team of predominantly women, to designing systems that keep her business thriving. Alongside the practical insights, Ashley shares the mindset shifts, faith, and intuition that became the foundation of her success.This is more than a business story—it’s a masterclass in courage, vision, and personal growth. Ashley’s journey will inspire you to see challenges as stepping stones, trust your intuition, and embrace the kind of bold thinking that can transform both life and business.HIGHLIGHTS AND KEY POINTS:[00:56] A short introduction about our guest Ashley Freeman and her unexpected journey from tennis pro to scaling a 115-property management company in under three years[06:37] Ashley shares her mission-driven approach to short-term rentals and her passion for helping others after finding purpose again[11:28] Ashley’s journey from her first client to managing 135 properties, and how she learned to grow with humility, faith, and adaptability[15:38] How surrendering control to God after Ashley’s divorce transformed her life and taught her to recognize His guidance[18:48] Ashley shares how a trip to Africa ignited her mission to reach “broken women” and how she learned to trust whispers from God[25:10] Ashley’s approach to starting simple and building her property management growth one step at a time[26:49] Ashley’s team growth and systems that transformed her property management business[30:18] Ashley’s share her intentional decision to keep cleaning in-house as part of building a trusted team and aligning hospitality with her deeper mission to serve guests with excellence[35:10] How building systems and processes early allowed Ashley’s business to scale smoothly and avoid breakdowns during rapid growth[38:44] Ashley’s biggest challenges as she has grown her property management company to now well over 100 units and how she navigated them[43:12] How I sustain my team by focusing on open communication, removing roadblocks, and empowering them to contribute solutions that strengthen the company[49:39] The lightning round Golden Nuggets:“I do think there's a sense of faith that you have to have in business, regardless if you believe in the Lord or not. You know you have to have faith. It's that leap of faith that you're taking to even get started.”"God is talking to each of us; we have to be willing to open our ears to listen.”“Cleaning, to me, is like the most important part of the experience, and so we've never even considered trying to go...

Could a tiny glamping dome really be the first step toward a thriving real estate empire?In this episode, I sit down with Zoey Berghoff, a young entrepreneur who’s redefining what’s possible in the short-term rental industry. Six years ago, she launched her journey with a 300-square-foot dome and a bold vision. Today, she’s mastered land development, ground-up builds, and extensive renovations—all while staying focused on equity, cash flow, and lifestyle investments that work for her family.Zoey opens up about the strategies that set her apart, from leveraging forced appreciation to uncovering hidden potential in overlooked properties. She shares how she’s built a reliable team, the importance of outsourcing effectively, and the lessons she’s learned while scaling her portfolio—all while raising a toddler and building a business that supports her life.What makes Zoey’s story so powerful is her ability to challenge the traditional path of real estate investing. Instead of chasing trends, she’s built a portfolio rooted in long-term value, strategic growth, and resilience. Her approach is a blueprint for anyone who wants to build wealth on their own terms.This conversation will inspire you to see opportunities where others see obstacles. Zoey’s insights prove that with the right mindset, systems, and strategy, ordinary properties can become extraordinary investments.HIGHLIGHTS AND KEY POINTS:[01:03] A short introduction about our guest Zoey Berghoff, and her journey in short-term rentals[04:18] How Zoey’s first short-term rental was a 300-square-foot glamping dome that she and her husband partly lived in before deciding to rent it out while traveling[07:34] Zoey explains how freelancing income, self-education, and trial-and-error opened the door to real estate investing[12:34] Zoey shares her approach to telling her story on social media and encourages others to start small, stay consistent, and focus on impact over perfection[15:49] Zoey highlights the dangers of comparison on social media and shares how focusing on slow, intentional growth in real estate helped her define success on her own terms[19:13] How Zoey’s first ground-up construction project taught her the value of delayed gratification, forced appreciation, and learning the hard way through trial and error[24:00] Zoey’s advice for vetting contractors and builders to protect your investment and avoid costly mistakes [29:38] Zoey’s philosophy on pay structure to protect yourself and maximize value in contractor agreements [33:07] The concept of forced appreciation in real estate and how buying undervalued properties can create massive equity gains in a short time[36:50] How forced appreciation doesn’t always require major renovations—sometimes strategic cosmetic updates are enough to build equity and long-term wealth[40:45] Zoey explains how equity and forced appreciation play a central role in scaling short-term rental portfolios[44:38] Zoey reflects on her biggest mistake of trying to do everything herself instead of outsourcing sooner[49:14] The lightning round Golden Nuggets:"Just share what you're doing. It doesn't have to be perfect. People want the behind the scenes. They want to know the challenges.”“You, as the investor, need to be logical about your

What if the biggest obstacle to financial success isn’t strategy or hard work—but the beliefs you hold about yourself?In this episode, I sit down with Esmeralda Alba to explore the inner work of abundance and how simple mindset shifts can create profound changes in your financial life. She shares her personal journey from struggle to transformation, and how a powerful practice called Intensati helped her rewrite her inner dialogue and step into a new reality of possibility.Esmeralda opens up about moving from a scarcity mindset to one of abundance, showing how even small adjustments in thought patterns and daily practices can unlock growth. She also shares practical tools—from gratitude to intentional language—that helped her transform her relationship with money and opportunity.We dive into the wisdom of her spiritual mentor, Patricia Marino, who taught her that abundance isn’t something you chase, but something you cultivate within yourself. Esmeralda’s raw and vulnerable stories reveal how doing the inner work can lead to breakthroughs that ripple into every area of life.Whether you’re building a business, investing in real estate, or simply seeking more alignment in your personal journey, this episode will inspire you to reset your mindset. Esmeralda’s story is proof that financial success starts on the inside—and grows outward from there.HIGHLIGHTS AND KEY POINTS:[01:20] A short introduction about our guest Esmeralda Alba and shares how an exercise class introduced her to the power of affirmations and an abundance mindset[05:19] Esmeralda explains how shifting her money mindset during tough times transformed her family’s business journey[09:21] Esmeralda outlines the daily practices she uses to cultivate an abundance mindset and describes how she actively shifts from fear to gratitude when facing life’s toughest moments[14:15] How solitude and daily discipline support Esmeralda’s shift toward an abundance mindset [16:33] Esmeralda shares how she shifted her money mindset from scarcity to abundance through daily language changes and affirmations[21:26] Esmeralda explains how repeating present-tense affirmations like “I am a money magnet” programs the subconscious to attract financial abundance [25:23] How mindset practices, abundance beliefs, and reframing money stories transformed Esmeralda’s life[33:00] Esmeralda credits her late mentor for reshaping her money beliefs and emphasizes that abundance requires consistent daily practice[36:58] How intuition and leaning on a trusted community helps Esmeralda vet opportunities within an abundance mindset [41:47] Esmeralda credits Alicia for pushing her out of her comfort zone and helping her step into the spotlight [43:17] The lightning round Golden Nuggets:"What you put out, or what you say, or even what you think is what you're attracting, these are the things that you're going to attract.”“We're able to set fuel to our fire and power behind ourselves when we train our brain to work for us.”“The more grateful you are for the things that you have, the more abundance that you attract into your life.”“Having an attitude of gratitude helps you, not only again organically begin to see shifts in your life, but it also makes life

What does it take for a young entrepreneur to turn a family’s real estate legacy into a thriving vacation rental business?In this episode, I sit down with Allison Bayley, the powerhouse behind Bayley Vacation Rentals, for a conversation that blends business strategy with personal transformation. Allison’s story proves that passion and grit—not age—are the true drivers of success.From summers working at her grandparents’ campground to becoming a scuba diving master in California, Allison never followed a straight line. When her mom, a real estate agent, called her home with a bold business proposition, Allison took a leap of faith. While bartending at night and working out of a tiny 600-square-foot office by day, she built the foundation of a company that now dominates her market.Allison’s journey hasn’t been without challenges. As a young, tattooed, non-traditional professional, she often faced judgment in an industry that loves to size people up by appearances. But she turned those doubts into fuel, building not just a successful business but a women-owned, women-operated powerhouse spanning generations With a cutting-edge tech stack and an obsession with guest experience, she’s redefining what a family business looks like in the modern era.This episode is more than a success story—it’s a masterclass in resilience, mindset, and the power of bold risks. Whether you’re a seasoned entrepreneur or just dreaming of your first venture, Allison’s journey will inspire you to rethink what’s possible when family, vision, and courage come together.HIGHLIGHTS AND KEY POINTS:[01:08] A short introduction about our guest Allison Bayley and how she got into short-term rentals[03:14] How Allison’s mom’s phone call felt like the right moment to return home and take on more responsibility[04:47] Allison shares how she and her mom set up the vacation rental business in the early days[07:43] Allison reflects on the early fatigue and mental strain of building her business while juggling long shifts in hospitality [10:52] Allison shares how she faced misjudgments for her tattoos, piercings, and colored hair and the way she navigated those perceptions[15:41] How Allison’s early responsibility and guidance from her sister and therapist shaped her emotional resilience and wisdom[18:26] Allison’s perspective on what makes a good boss and recalls lessons from a former mentor about keeping doors open and not burning bridges [19:47] Allison talks about her all-female, close-knit team and the challenges of balancing friendship with leadership in her seasonal business[28:42] Allison describes her evolving use of systems and technology to streamline operations and manage growth[32:54] Allison shares her evolving perspective on team feedback, communication tools, and embracing growth through discomfort[37:15] Allison’s post-season shift in strategy and vision for guest experience and future concierge services[39:46] The lightning round Golden Nuggets:"They say, mind over matter, and that's where I really just had to often remind myself, is mind over matter. And having a good mindset around it is what is required to continue on.”“The grass is only greener where you water it.”“Training our brains to actually recognize when those...

Ever wondered how to turn your short-term rental into more than just a stay—but a shopping experience?In this episode, I sit down with Nisha Franklin, co-founder of From Where, a platform that turns your STR into a fully shoppable experience. Imagine your guests falling in love with your mattress, coffee table, or artwork—and then being able to purchase those exact items through your personalized digital storefront.Nisha’s path to entrepreneurship is anything but typical. From her days as a marketing maven in Los Angeles to running a cheese education business, she and her husband David stumbled on a brilliant idea while vacationing in Hawaii. Their lightbulb moment? Creating a platform where hosts can effortlessly monetize the items guests constantly ask about, earning commissions on every single sale.We dive into the nuts and bolts of how From Where works, including how to set up your storefront, source forgotten items, and start generating new income streams. Nisha also shares insider tips on promoting your digital store, the types of products guests love most, and how even local furniture finds can be made shoppable.Beyond the tech and strategy, this conversation is a refreshing look at entrepreneurship, time management, and building a community-driven platform. Whether you’re a seasoned host or just getting started, Nisha’s insights will inspire you to see your short-term rental not just as a place to stay—but as a goldmine of untapped opportunity.HIGHLIGHTS AND KEY POINTS:[00:46] A short introduction about our guest Nisha Franklin and including how she first got started in the short-term rental space and what drew her into the industry[05:17] Nisha explains what From Where is — a unique platform designed for hosts to share, recommend, and earn from the products they use in their properties — and why it’s becoming a valuable tool for the STR community[07:25] How hosts without receipts or with locally purchased items can still participate on FromWhere and create storefronts that reflect their property’s style[10:04] Nisha talks about the items that are trending on FromWhere storefronts[10:48] Nisha walks us through the From Where sign-up process, explaining how pricing works, what commissions look like, and how hosts can leverage promotions to boost their earnings[14:08] Nisha describes how timing for sales varies depending on host engagement and promotion [16:09] How Nisha juggles multiple businesses and family life through planning and time blocking [18:00] Nisha shares her vision for From Where’s growth over the next five years and how she relies on her tech-savvy team to power the backend[20:37] The lightning round Golden Nuggets:"Don't be afraid to make mistakes.”“The biggest failure is not the mistake itself. It's failing to learn from that mistake.”“When we have that one thorn in our side, that one pain point, if we ignore it and we just say, Oh, it'll go away; It might, but it might come back to bite you in the future. So take care of that pain point, solve the problem.”Lets Connect:Website: https://fromwhere.com/Facebook: