『The STR Sisterhood』のカバーアート

The STR Sisterhood

The STR Sisterhood

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

    Multiply Yourself with AI: Building a Smarter Short-Term Rental Business with Ana Shapiro
    2026/10/13
    What if AI could help you grow your short-term rental business without removing the very thing that makes hospitality feel human?In this episode of the STR Sisterhood, I’m joined by Ana Shapiro, a real estate investor with nearly two decades of experience and the founder of Chillin Away, a collection of family-friendly short-term rentals designed around connection, comfort, and creating memorable experiences.After years of managing the moving pieces that come with short-term rentals, Ana realized something important: the biggest limitation in her business wasn’t the properties, the capital, or even demand.It was that everything depended on her brain.That realization changed the way she thought about AI. Instead of using it simply as another tool—or trying to automate herself out of the business—Ana began building specialized AI agents to support different functions like revenue management, operations, guest experience, marketing, and financial intelligence.In this episode, we talk about:Why short-term rentals are anything but passive when you’re the one operating themHow Ana uses AI to multiply herself rather than replace herselfTurning the knowledge in your head into systems that can support different areas of your businessWhy AI still needs guardrails, quality checks, and human judgmentUsing “useful AI” to solve real operational problems and surface issues before they become bigger onesProtecting the human side of hospitality while using AI to remove unnecessary chaosWhy the systems behind your property are what create consistency, scalability, and growth without burnoutBecause the goal isn’t to automate every single thing you do.Hospitality still requires judgment. It requires taste. It requires understanding the people who are trusting you with their vacations, celebrations, families, and time away.Ana’s approach is a reminder that technology should create more room for those things—not replace them.Use AI to remove the chaos. Keep the heart. And create more space to lead the business instead of carrying every part of it inside your head.HIGHLIGHTS AND KEY POINTS:[00:50] A short introduction about our guest Ana Shapiro, and her background in real estate, transition from long-term to short-term rentals, and how she built Chilling Away[04:28] The reality behind the idea of “passive income” in short-term rentals and why operating an STR requires active involvement[06:17] Ana explains the operational differences between long-term and short-term rentals, from guest touchpoints and pricing to the systems required behind the scenes[08:14] Ana shares the turning point that led her to use AI not to replace herself, but to multiply herself and distribute her thinking across different areas of the business[11:00] How Ana trains AI to think more like she does, the tools she uses, and how brainstorming can evolve into actual systems, implementation plans, and workflows[14:31] The realities and risks of building AI agents, including the importance of guardrails, quality checks, human approval, and learning from automation that goes too far[19:00] How Ana is training AI agents to take over repetitive tasks and give her more time to focus on growth[21:24] Ana shares the parts of hospitality she believes should remain human—including judgment, taste, and understanding what guests should feel—and why AI should remove chaos rather than the heart of the business[22:52] Ana explains how AI helps her see where her time is going and focus on what the business actually needs[25:24] Ana explains how she uses weekly strategy time and AI to make smarter pricing and marketing decisions[27:43] Where hosts can begin using AI in their own businesses—from organizing the day and monitoring cleaners to financial intelligence, branding, market insights, and direct bookings[29:37] Ana explains how she wants AI to connect more of her business and guest data to create smarter opportunities[31:11] Ana’s words of wisdom to encourage hosts to start small with AI and train it to work the way they want[32:07] The lightning roundGolden Nuggets:“It is not about just doing more. It's about building smarter with purpose in a way that helps us support the life that we want to live.”“I’m not looking for AI to replace myself. I’m using AI to multiply myself.”“It's so important as a business owner to surround yourself with people that are smarter than you in multiple areas.”“I don’t want AI to remove the heart of the business. I want it to help me remove the chaos.”“Owning a property is not the same as building a business.”“Stop confusing motion with progress.”Let’s Connect:Instagram : https://www.instagram.com/chillinaway/LinkedIn : https://www.linkedin.com/in/ana-shapiro/Website : https://chillinaway.com/Enjoyed the show? Subscribe, Rate, Review, Like, and Share!
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    42 分
  • Start Before You’re Ready: Building a Short-Term Rental Business Around the Life You Want with Laura Sides

    Start Before You’re Ready: Building a Short-Term Rental Business Around the Life You Want with Laura Sides
    2026/10/06
    What if the goal of real estate investing isn’t simply to own more properties—but to create a life you actually enjoy?In this episode of the STR Sisterhood, I’m joined by Laura Sides, a former middle school science teacher turned stay-at-home mom, real estate investor, house flipper, and short-term rental host. Laura’s journey into real estate began in 2021 after realizing there was another way to think about money—one where she could put her money to work instead of working for every dollar.What followed was a journey of saying yes to opportunities, learning as she went, flipping properties, and eventually owning two short-term rentals.And one of Laura’s biggest lessons?You don’t have to know everything before you start.In this episode, we talk about:Shifting from a scarcity mindset to thinking differently about money and investingHow Laura used profits from house flipping to fund her first short-term rentalWhy she eventually walked away from a large property management company and began self-managingHow the right systems, automation, and consistent cleaners made hosting far easier than she expectedLooking beyond financial ROI to consider the return on your time, energy, and enjoymentBuilding a real estate business around the life and experiences you want for your familyLaura’s story is also a reminder that growth doesn’t have to mean constantly acquiring more properties.Sometimes growth looks like knowing what deserves your attention. Staying in the lane you’re good at. Creating systems that give you back your time. And using what you’ve built to create experiences for the people you love.You can build for cash flow. You can build for lifestyle. You can build something that gives your family opportunities you once thought were years away.And you don’t need every answer before taking the first step.As Laura says, surround yourself with people who know more than you, put the right systems in place, and start before you’re ready.HIGHLIGHTS AND KEY POINTS:[00:41] A short introduction about our guest Laura Sides, her journey from middle school science teacher, to real estate investor, house flipper and short-term rental host[04:04] The scarcity mindset around money we grew up with and how learning to think beyond simply saving and living within their means changed the way they approached investing[06:14] How flipping houses led Laura into short-term rentals and how profits from her first flip helped fund the purchase and renovation of her Bethany Beach property[08:49] We compare our experiences hiring large property management companies and the loss of control we experienced around cleanliness, communication, and the guest experience[12:28] Laura shares why she eventually decided to self-manage and how taking control of the property led to significantly better reviews and revenue[13:32] Why self-managing a short-term rental can be much easier than expected when you have the right framework, systems, automations, and focus on guest experience[16:47] Laura breaks down the systems and technology she uses to simplify her hosting business and manage properties from a distance[17:55] Why relying solely on Airbnb can leave a short-term rental business vulnerable and the value of diversifying with direct bookings[19:31] The value of digital guidebooks for creating a more professional, streamlined guest experience[21:26] Laura shares how she protects her bandwidth by focusing on what matters most and creating a life that prioritizes family over constant growth[25:27] Laura redefines ROI by looking beyond money to your return on time, effort, energy, and enjoyment—and choosing opportunities that actually support the life you want[27:29] Laura shares why she loves flipping condos, what makes them efficient and predictable investments, and how strong HOA, neighbor, and property manager relationships can reduce risk and uncover new opportunities[36:30] The lightning round Golden Nuggets:“How do we put this money to work, and how can we also enjoy our life while we're doing it?”““What is your ROI—which is your return on your investment—but also the return on your time?”“Honing in on what you're good at, but also what you enjoy doing, and you can do really well, staying in that lane, then just optimizing those systems to make that opportunity the best that it can be.”“Start before you’re ready.”“The best thing you can do is take that first step and just keep going.”Let’s Connect: Instagram : https://www.instagram.com/lauraflipslife/Enjoyed the show? Subscribe, Rate, Review, Like, and Share!
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    42 分
  • The Power of Emotional Intelligence in Hospitality with Daniella Morganelli

    The Power of Emotional Intelligence in Hospitality with Daniella Morganelli
    2026/09/29
    What if becoming a better host has less to do with knowing every strategy—and more to do with understanding people?In this episode of the STR Sisterhood, I’m joined by Daniella Morganelli, a school counselor, former property manager, and Airbnb host who has been in the short-term rental space since 2018. Daniella brings a unique perspective to hospitality because so much of her professional life has centered around people—understanding their emotions, navigating conflict, solving problems, and learning to meet people where they are.And those skills translate beautifully into hosting.We dive into emotional intelligence—being aware of your own emotions, beliefs, and perspectives while recognizing that the person on the other side of a situation may experience it very differently.In this episode, we talk about:What emotional intelligence looks like in short-term rental hospitalityWhy meeting guests where they are can completely change how you handle difficult situationsPutting yourself in someone else’s shoes before reacting to a conflictThe difference between solving a problem for someone and working through it with themWhy great hospitality means accommodating guests—within reasonRecognizing when being a people pleaser can lead to being too accommodatingHow self-awareness can make you a stronger communicator, host, and business ownerBecause the truth is, guests aren’t always showing up relaxed and carefree. Travel can be stressful. People have different expectations, preferences, and ways of communicating—and sometimes that stress comes out as a complaint.That doesn’t mean you have to say yes to everything.But it does mean there’s tremendous value in slowing down long enough to understand what’s really happening before you respond.Sometimes the better question isn’t, “Who’s right?”It’s, “How can we work through this?”And that small shift can help you handle challenging conversations with more clarity, create a better experience for your guests, and become a more confident host along the way.HIGHLIGHTS AND KEY POINTS:[00:47] A short introduction about our guest Daniella Morganelli, and how her passion for hospitality evolved from property management into a short-term rental and travel-focused business[05:41] Daniella shares the operational realities of hosting strangers in her backyard pool through Swimply, including last-minute bookings, towels, amenities, and setting boundaries [07:36] Daniella explains how her background in property management and school counseling has taught her to meet people where they are and navigate guest emotions [11:00] How emotional intelligence can help short-term rental hosts better understand themselves, their guests, and the conflicts that come with hospitality[14:35] Daniella explains how emotional intelligence can help hosts diffuse guest frustrations by focusing on solutions, accommodation, and giving guests space [17:40] Daniella shares how emotional intelligence, hospitality, and a desire to help others shape the way she approaches her many businesses[23:12] How Daniella learned to prioritize self-care while balancing motherhood, a full-time career, and multiple hospitality businesses [28:03] Daniella shares how travel, Disney, and hospitality have become a meaningful part of her life and the way she creates memories with her family[31:15] Daniela shares how entrepreneurship transformed her confidence and taught her to trust herself[38:06] The lightning round Golden Nuggets:“Understanding your own self helps you understand other people too.”“I'm glad that I have taken all the risks that I have because it's helped build my confidence and my self esteem.”“My light, my confidence, my ability to have a positive outlook can shine through that plexiglass, but the negativity never penetrates me.”“You can have a beautifully designed space when it's not operated well, it is not going to go so well. But design plus the operations, I really feel are super important.”Let’s Connect: Instagram : https://www.instagram.com/crimsoncocoachalet/ https://www.instagram.com/dmtravelvibesFacebook : https://www.facebook.com/VacaVibesinD5/ https://www.facebook.com/DMTravelVibes/ https://www.facebook.com/morganellibabe/ Enjoyed the show? Subscribe, Rate, Review, Like, and Share!
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    48 分
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