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How to Start an Airbnb: Daily Summaries Delivered
by Brittany Wenninger
Want to learn how to Find, Run, and Manage a Airbnb? This podcast has you covered! Welcome to The Airbnb Roadmap, your ultimate guide to building, scaling, and thriving in the world of short-term rentals (STRs). Hosted by Brittany Wenninger, a real estate expert and highly-rated Airbnb Superhost with over 350 glowing reviews and a 4.95-star rating, this podcast is your go-to resource for all things Airbnb, VRBO, and beyond. Each week, Brittany delivers actionable advice, industry secrets, and practical strategies to help you start and grow your short-term rental business. From setting up your first property and navigating local regulations to mastering marketing strategies and creating unforgettable guest experiences, we cover it all. Whether you’re just curious about hosting on Airbnb, managing multiple VRBO properties, or looking to scale your STR portfolio, this podcast answers questions like: ”How do I get started with Airbnb or VRBO?” ”What are the best ways to market my STR/ Airbnb?” ”Beginner Guide to STRs” ”Beginner Guide to Airbnb” ”Airbnb 101 or STR 101” ”What are the steps needs to start a Airbnb” With solo episodes packed with Brittany’s expertise and interviews with top hosts, real estate pros, and hospitality industry leaders, The Airbnb Roadmap is here to help you design a profitable and sustainable short-term rental business. If you’re ready to create financial freedom, master the art of hosting, and build a thriving STR portfolio, this is the podcast for you. It’s time to unlock the secrets to short-term rental success!
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- May 2, 202641 min
65. STR Cleaner Tells the Truth
Link: Airbnb Roadmap Accelerator Course Link to the Airbnb Roadmap Website Episode Summary In this episode, I sit down with Carlos Saavedra, a cleaning expert who operates a high standard Airbnb cleaning company, and we get into the REAL behind the scenes of what makes or breaks your short term rental. We talk about everything from why your cleaner is actually the backbone of your business, to the small details guests notice that can tank your reviews, to how to properly vet and hire a cleaner who actually understands hospitality, not just “cleaning.” We also go deep into systems, communication, linens, staging expectations, and the biggest mistakes I see investors make when setting up their Airbnb for success. If you have ever struggled with a cleaner, questioned your setup, or want to avoid costly mistakes from day 1, this episode is for you. Key Takeaways Your cleaner is not just a cleaner, they are protecting your income • Hospitality cleaning is VERY different than residential or office cleaning • Small details like hair, linens, and supplies can make or break reviews • You should always interview multiple cleaners before hiring • Ask about pricing structure, experience, and consistency systems • White linens win every time for cleanliness perception and sanitation • 3 full linen sets per bed is the sweet spot for operations • Over staging your Airbnb can create unnecessary workload and inconsistency • Systems and communication between you and your cleaner are everything • Not all cleaners are built for short term rentals, and that is okay Why Listen to This Episode? If you are building or scaling an Airbnb, this episode will save you time, money, and headaches. I am not kidding when I say your cleaner can either elevate your business or completely destroy your guest experience. This conversation will help you hire smarter, set better expectations, and build systems that actually support long term success. Whether you are brand new or already hosting, this is one of those foundational episodes you do not want to skip. Let’s Connect Thinking about hiring a cleaner or setting up your Airbnb the right way? DM me on Instagram at @theairbnbroadmap with your questions or share your progress! I’d love to cheer you on and help you out. Work With Me Ready to launch your Airbnb the RIGHT way without all the trial and error? Inside my Airbnb Roadmap Accelerator, I walk you through everything from finding the right property to setting up systems like cleaning, pricing, and guest experience so you can actually make money and not feel overwhelmed. Use code 5STARPODCAST for a special discount Chapters 00:00 Intro and guest welcome 02:00 How Carlos got into Airbnb cleaning 05:00 What most cleaners are doing wrong 08:00 Going above and beyond as a cleaning company 12:00 3 must ask questions when hiring a cleaner 18:00 Real life cleaner interview hor
- Apr 1, 202638 min
64. FREE Subscription to Hospitable?! Sit down with Hospitables Founder Pierre-Camille (PC) Hamana
Link: Airbnb Roadmap Accelerator Course Link to the Airbnb Roadmap Website This episode is a big one 👀 I sat down with Pierre-Camille Hamana, the CEO of Hospitable, to talk about something that I honestly think is going to change the game for new Airbnb hosts… 👉 They just launched a FREE Essentials plan Yes… free. And if you are someone who has been holding back on getting started because of costs, systems, or just feeling overwhelmed with all the tools out there, this is exactly what you needed. We break down: Why they made this move What is actually included How it helps first-time investors And how you can use it to start building your Airbnb business the right way from day one We also dive into mindset, taking action, and why waiting for “perfect” is what keeps most people stuck. Key Takeaways What the Hospitable Essentials (FREE) plan actually includes Why this is a huge opportunity for first-time Airbnb investors How to start your Airbnb WITHOUT stacking expensive tools Why automation should not stop you from getting started The biggest mistake new hosts make when trying to “prepare everything first” How Hospitable is helping hosts make money, not just manage properties What features you can access for $0, including messaging and multi-platform syncing How this creates long-term systems from the very beginning Why loyalty and simplicity matter when choosing your tech stack The connection between systems, scalability, and time freedom Why Listen to This Episode? If you have ever thought… “I want to start an Airbnb but there is just too much to set up” “I don’t want to spend a ton of money upfront on software” “I feel overwhelmed with all the moving pieces” This episode is going to simplify everything for you. The reality is, you do NOT need a massive tech stack to get started anymore. This free plan gives you the ability to: Automate your messaging Sync calendars across platforms Stay organized from day one And most importantly… actually take action. Let’s Connect Thinking about starting your first Airbnb or trying to simplify your systems? DM me on Instagram at @theairbnbroadmap with your questions or share your progress! I’d love to cheer you on and help you out. Work With Me If you are ready to go from idea to income, my Airbnb Roadmap Accelerator walks you step by step through finding, laun
- Mar 17, 202625 min
63. Top 10 things I would not do/buy for a Airbnb
Link: Airbnb Roadmap Accelerator Course Link to the Airbnb Roadmap Website Get your Amazon Shopping Cart In this episode, I’m sharing a real, honest breakdown of what I no longer buy for my Airbnb properties, and why. After getting hit with a massive 30-inch snowfall at our cabins and managing guest expectations in the middle of chaos, it reminded me just how important it is to have systems and smart decisions in place. I walk through the biggest purchasing mistakes I’ve made over the years, from cheap furniture that doesn’t last, to design choices that actually hurt guest perception. If you’re in the furnishing, upgrading, or scaling phase of your short term rental, this episode is your reality check. Not everything that looks good or feels like an upgrade will actually increase your bookings, your reviews, or your nightly rate. And if it doesn’t do at least one of those things, it’s probably not worth your money. Key Takeaways Cheap furniture will cost you more long term, you are better off investing in quality upfront White bedding builds trust with guests and signals cleanliness, darker colors can raise doubts Strong scents, candles, and plugins can negatively impact guest experience Fragile items, including wine glasses and decor, will break quickly and create safety risks Overly complicated smart home systems lead to confusion and more guest messages Every upgrade should serve a purpose, bookings, ADR, or reviews Some amenities sound great but do not perform based on your market or location Pinterest design does not always translate into a functional or guest friendly space Avoid anything controversial, including religious or political decor Furniture layout matters more than you think, flow impacts guest experience Do not cheap out on towels, guests notice comfort details immediately Why Listen to This Episode? If you are currently setting up your first Airbnb or thinking about upgrading your space, this episode will save you money, time, and frustration. I am sharing real mistakes I have made across multiple properties so you do not have to learn the hard way. This is also a great episode if you feel like you are constantly spending money on your property but not seeing a return. I will help you shift your mindset into making strategic, ROI driven decisions instead of emotional or aesthetic ones. Let’s Connect Thinking about what to buy or skip for your Airbnb? DM me on Instagram at @theairbnbroadmap with your questions or share your progress! I’d love to cheer you on and help you out. Work With Me If you are ready to launch or scale your Airbnb the right way, my Airbnb Roadmap Accelerator walks you through everything from property selection to full setup and systems. You will learn how to make smart investment decisions, avoid costly mistakes, and build a short term rental that actually performs. Chapters 00:00 Life update and upcoming guest interviews 02:00 30-inch snowstorm and managing guest expectations<span style="font-weight:
- Mar 10, 202624 min
62. First Airbnb, Should you Invest Local or Long Distance?
Link: Airbnb Roadmap Accelerator Course Link to the Airbnb Roadmap Website Episode Summary In this episode, I’m diving into one of the biggest questions new short term rental investors ask me all the time. Should you buy your first Airbnb close to home or invest long distance in a stronger market? After a week of Airbnb chaos and dishwasher drama, I also share why I took a short break from the podcast and what that experience reminded me about time, systems, and running your rental like a business. I walk through the real pros and cons of both strategies, including why long distance investing can actually force you to build better systems, how a strong team becomes the backbone of your Airbnb business, and why investing close to home can sometimes create more work than you expect. If you’re trying to decide where to buy your first Airbnb property, this episode will help you think through the decision from a practical, real world perspective. Key Takeaways Close by properties feel convenient, but they can pull you into doing everything yourself. Long distance properties force you to build systems and rely on your small but mighty team. Your cleaner, handyman, lawn care provider, and even neighbors can become critical partners in running your Airbnb. Property management software can automate guest communication and reduce your daily workload. Your time has value, driving hours to fix small issues may cost more than paying someone locally. For first time investors, owning a property nearby can help you learn the operations before scaling further away. Successful Airbnb businesses rely on systems, processes, and trusted people. Why Listen to This Episode? If you are thinking about buying your first short term rental, location is one of the most important decisions you will make. In this episode I share real experiences from managing properties within a few hours of home, including the good, the frustrating, and the lessons learned along the way. You will learn how distance affects your systems, your time, and your mindset as an Airbnb host. Whether you plan to invest locally or across the country, understanding these differences can help you build a more sustainable Airbnb business. Let’s Connect Thinking about where to buy your first Airbnb? DM me on Instagram at @theairbnbroadmap with your questions or share your progress. I’d love to cheer you on and help you out. Work With Me If you want step by step guidance on finding, launching, and managing your own short term rental, check out my Airbnb Roadmap Accelerator course. Inside the course I walk you through: Finding the right Airbnb propertyRunning the numbers and evaluating ROIDesigning and furnishing your rentalBuilding your team and automating systemsLaunching and optimizing your listing Learn more here:https://theairbnbroadmap.com Chapters 0:00 Life update and why I skipped last week3:00 The dishwasher chaos continues
- Feb 24, 202629 min
61. Airbnb Guests Threatened Bad Reviews, This Is What I Did
Link: Airbnb Roadmap Accelerator Course Link to the Airbnb Roadmap Website Episode Summary In this episode, I am sharing a very real behind the scenes look at what the past week has looked like in our short term rental business. Between a dishwasher claim, rude guest messages, and review threats, it has felt like when it rains it pours. Instead of letting it spiral, I used these situations as a reminder of why being proactive instead of reactive is everything in this business. I walk you through two real guest scenarios, exactly what was said, how I handled it, and what I did behind the scenes to protect our listings, reviews, and sanity. If you have ever felt stressed by a guest, worried about a bad review, or unsure how to handle a tricky cancellation situation, this episode will help you think 3 steps ahead instead of constantly putting out fires. Key Takeaways Why proactive communication protects your reviews • How to handle guests who threaten bad reviews • When to call Airbnb and document everything • Why small refunds can protect long term revenue • How automation tools like Hospitable help create consistency • Why keeping communication inside Airbnb matters • How reviews shape your visibility and bookings • Why sometimes you have to spend $50 to protect thousands Why Listen to This Episode? Because hosting is not about avoiding problems. It is about having a plan before problems happen. I break down a situation where a guest refused to cancel and openly admitted he wanted to leave a bad review. Instead of panicking, I called Airbnb immediately, documented everything, and had a note placed on the reservation. If he leaves a retaliatory review, it gets removed. That is proactive hosting. I also share how I handled a dishwasher breaking mid bookings, what I did to soften the inconvenience, and how one guest still pushed back. These are the moments that test you as a host. We also talk about the power of reviews and where the whole review culture actually started, shoutout to Michelin for creating the original rating system that evolved into the Michelin Star system. Wild, right? This episode is equal parts strategy and real life hosting therapy session. Mentioned in the Episode Airbnb Vrbo Booking.com Hospitable Michelin Let’s Connect Thinking about how to protect your Airbnb reviews or handle difficult guests? DM me on Instagram at @theairbnbroadmap with your questions or share your progress! I’d love to cheer you on and help you out. Work With Me If you want systems, scripts, automation, and proactive hosting strategies built out step by step, check out the Airbnb Roadmap Accelerator. I teach you how to protect your time, your revenue, and your sanity while building a 5 star short term rental business. Chapters 00:00 Life update and guest chaos 05:00 Guest threatens bad review over cancellation<span style="font-
- Feb 17, 202631 min
60. The Exact Conversation I Have With Every New STR Client
Link: Airbnb Roadmap Accelerator Course Link to the Airbnb Roadmap Website Episode Summary In this episode, I am sharing exactly what I tell every first time investor who calls me wanting to buy a short term rental in Wisconsin. From understanding state, county, and township regulations to septic capacity, negotiations, inspections, and writing strong offers, I break down the full process step by step. If you have ever thought about buying a $600,000 cabin near Wisconsin Dells, Baraboo, or Castle Rock, this is your behind the scenes look at what actually happens from first phone call to closing day. And yes, there is a little life update in the beginning involving a dishwasher disaster and a flooded kitchen. Because real life still happens while building businesses. Key Takeaways How Wisconsin short term rental regulations work at the state, county, township, and neighborhood level • What a Tourist Rooming House license inspection includes • Why septic capacity can make or break your investment • Why I personally avoid properties in HOA neighborhoods • How I protect my buyers with strategic offer language • Why sellers do not need to know you are an investor • What happens during due diligence and inspections • The risks of negotiating too hard • Why three bedroom properties are my personal sweet spot • What experienced investors look for versus first timers Why Listen to This Episode? Because buying a short term rental is not just about finding a cute cabin in the woods. It is about understanding local regulations, septic ratings, conditional use permits, resident agents, and knowing how to structure your offer correctly so you do not get blindsided later. If you want to invest in Wisconsin and avoid expensive mistakes, this episode is your crash course. Let’s Connect Thinking about buying your first Airbnb in Wisconsin? DM me on Instagram at @theairbnbroadmap with your questions or share your progress. I would love to cheer you on and help you out. Work With Me If you are ready to buy a short term rental in Wisconsin, I cover anywhere in the state. I walk my clients through regulations, numbers, offer strategy, and everything in between. Want the full roadmap before you even start shopping? Check out my Airbnb Roadmap Accelerator course where I break down finding, analyzing, launching, and scaling your STR the right way. Chapters 00:00 Dishwasher disaster and life update 06:45 First call with a new STR buyer 08:30 Wisconsin state level licensing explained 12:00 County and township regulations 16:30 Septic capacity and occupancy limits 18:45 Running the numbers and cash flow expectations 21:00 How I preview properties for out of state buyers<span style="font-wei
- Feb 5, 202635 min
59. Airbnb Cancellation Policies Explained, Short Stays vs Long Stays
Link: Airbnb Roadmap Accelerator Course Link to the Airbnb Roadmap Websitert Episode Summary In this episode of The Airbnb Roadmap Podcast, I am breaking down Airbnb cancellation policies in real life terms, not just the fine print. This episode was inspired by a recent midterm guest who booked for 3 months and left after only 2 weeks, plus ongoing damage claim frustrations with Airbnb support. I walk through what actually happens when guests cancel short stays versus long stays, why rejecting an alteration can sometimes protect you financially, and how different cancellation policies impact both hosts and guests. I also share personal stories from my own properties, including extreme cold weather stress, property damage realities, and how distance from your rentals forces you to become a better manager instead of a reactive host. If you have ever been confused, frustrated, or blindsided by Airbnb cancellations, this episode will give you clarity and confidence moving forward. Key Takeaways Airbnb has different cancellation rules for short stays 27 nights or fewer and long stays 28 nights or more • All Airbnb listings include a 24 hour free cancellation window if the booking is made at least 7 days before check in • Flexible policies are guest friendly but offer the least protection to hosts • Moderate policies provide a balance between bookings and host protection • Limited and firm policies increase host protection but may reduce booking conversion • Long term stays function more like leases and can guarantee up to 30 nights of income • Rejecting an alteration does not penalize your host account • Never cancel on behalf of a guest or you risk losing Superhost status • Distance from your properties can actually help you scale and systemize better Why Listen to This Episode? If you host short term or midterm rentals and want to avoid losing thousands of dollars due to misunderstandings around cancellations, this episode is a must listen. I explain Airbnb policies using real numbers, real scenarios, and real outcomes so you can make smarter decisions for your listings. This episode is especially helpful if you are considering midterm rentals, traveling nurse stays, or longer bookings and want to understand how to protect your income while still staying guest friendly. Let’s Connect Thinking about Airbnb cancellation policies or midterm rentals? DM me on Instagram at @theairbnbroadmap with your questions or share your experience. I would love to cheer you on and help you out. Work With Me If you are looking to buy, sell, or scale a short term rental, or if you want access to my Airbnb Roadmap course and resources, reach out. I also connect investors with STR focused agents across multiple states because there is a huge difference between a regular agent and one who truly understands short term rentals. Chapters 00:01 Life update and recent guest damage 02:18 Temporary fixes and real world hosting decisions 04:40 Managing properties near vs far 07:05 Midterm guest cancellation story 10:
- Jan 27, 202632 min
58. I Went on Vacation and My Airbnb Fell Apart Here’s What Happened
Link: Airbnb Roadmap Accelerator Course Link to the Airbnb Roadmap Website This episode is a full vacation recap turned Airbnb reality check. I’m sharing what happened when I traveled with a baby, lost my voice, and still had to manage multiple Airbnbs from Mexico while dealing with extreme cold, frozen pipes, surprise early check ins, guest damage, and a very expensive plumbing bill. Normally my systems are automated and smooth, but this trip was back to back shenanigans that no amount of prep could have fully prevented. If you think owning Airbnbs means passive income with zero stress, this episode brings you right back to reality. Key Takeaways Owning Airbnbs does not mean nothing will ever go wrong, even with great systems Extreme cold can expose hidden issues in older properties You need backup contacts and solutions when contractors are unavailable Clear check in boundaries matter and early arrivals can create real problems Guest damage can happen fast, even with families and short stays Automations are helpful but can backfire if you forget they exist Vacations are still worth it, even when things go sideways Why Listen to This Episode? If you own or want to own short term rentals, this episode is a real behind the scenes look at what can happen when life, travel, weather, guests, and maintenance all collide at once. I walk through how I handled each issue, what frustrated me the most, and what I learned from it all. This is the honest side of hosting that rarely makes it to Instagram. Let’s Connect Thinking about managing Airbnbs while traveling or dealing with guest damage? DM me on Instagram at @theairbnbroadmap with your questions or share your progress. I’d love to cheer you on and help you out. Work With Me If you want help building systems that actually support your lifestyle and not run it, check out my Airbnb Roadmap Accelerator. I teach you how to set up, automate, and manage your short term rentals with confidence, even when things go wrong. Chapters 00:00 Losing my voice and recording anyway 04:00 Getting sick before vacation and traveling with a baby 06:00 Midterm guest issues and washer dryer expectations 08:45 Extreme cold and frozen toilet pipes 13:30 Plumber chaos and a $450 bill 20:45 Early check ins and cleaner boundaries 23:00 Guest damage and burned countertops 27:30 Unauthorized re entry after checkout 31:00 Airbnb reimbursement and review frustration 33:40 Dishwasher issues and wrapping up the trip Subscribe and Share If this episode felt real, relatable, or helpful, please subscribe, leave a review, and share it with another Airbnb host who needs to hear that even the messy weeks are survivable. I’ll see you next week, hopefully with my voice back.
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About How to Start an Airbnb
Want to learn how to Find, Run, and Manage a Airbnb? This podcast has you covered! Welcome to The Airbnb Roadmap, your ultimate guide to building, scaling, and thriving in the world of short-term rentals (STRs). Hosted by Brittany Wenninger, a real estate expert and highly-rated Airbnb Superhost with over 350 glowing reviews and a 4.95-star rating, this podcast is your go-to resource for all things Airbnb, VRBO, and beyond. Each week, Brittany delivers actionable advice, industry secrets, and practical strategies to help you start and grow your short-term rental business. From setting up your first property and navigating local regulations to mastering marketing strategies and creating unforgettable guest experiences, we cover it all. Whether you’re just curious about hosting on Airbnb, managing multiple VRBO properties, or looking to scale your STR portfolio, this podcast answers questions like: ”How do I get started with Airbnb or VRBO?” ”What are the best ways to market my STR/ Airbnb?” ”Beginner Guide to STRs” ”Beginner Guide to Airbnb” ”Airbnb 101 or STR 101” ”What are the steps needs to start a Airbnb” With solo episodes packed with Brittany’s expertise and interviews with top hosts, real estate pros, and hospitality industry leaders, The Airbnb Roadmap is here to help you design a profitable and sustainable short-term rental business. If you’re ready to create financial freedom, master the art of hosting, and build a thriving STR portfolio, this is the podcast for you. It’s time to unlock the secrets to short-term rental success!
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