This week’s episode is less “how-to” and more “real life.” I’m giving you a peek behind the scenes into one of the wildest weeks I’ve had in a while — juggling an AWS outage that shut down half my systems, onboarding my first assistant, and closing on our newest Airbnb property (technically two Airbnbs in one!). From appraisal headaches to cat pee clean-up, this episode is pure behind-the-scenes chaos — but in the best, most relatable way possible.

If you’ve ever wondered what really happens behind the scenes of short-term rental investing — this is it. It’s messy, unpredictable, and full of lessons that make you laugh later. Sometimes success isn’t about strategy — it’s about staying calm (and maybe wearing a mask when using KILZ).

Thinking about partnering on an Airbnb or wondering how to manage your own? DM me on Instagram at @theairbnbroadmap with your questions or share your progress! I’d love to cheer you on and help you out.

Ready to start or scale your own short-term rental?
👉 Check out the Airbnb Roadmap Accelerator — my self-paced course that walks you through everything from finding the right property to launching with confidence.

00:00 – Intro + Chaos of the AWS Outage
02:15 – Hiring My First Assistant
04:30 – Closing on the New Airbnb Property
06:40 – The Appraisal Waiver Drama
09:10 – Finding Comps and Finishing the Deal
11:30 – Post-Closing Wins and Clean-Up Realities
13:45 – The Cat Pee Chronicles
15:30 – Game Room + Sauna Design Plans
17:00 – Sneak Peek of Next Week’s Episode
19:00 – Wrapping Up and What’s Ahead

If you enjoy hearing the real, unfiltered side of building an Airbnb business, make sure to subscribe, leave a review, and share this episode with someone who needs a good laugh (or a reminder that every investor has chaotic days).

Insurance can feel like alphabet soup, until something goes wrong. In this interview, I sit down with Nick Sommer of Country Financial (and one of my buyers!) to break down exactly what short-term rental owners need: how to structure coverage for STRs vs. primary/secondary homes, must-have endorsements, loss-of-income realities, and why an umbrella policy can be the difference between a scare and a disaster. Nick also shares the personal house-fire story that led him into insurance and the simple annual habit that can save you months of headache during a claim.

Because “I have insurance” isn’t a plan. If you’ve ever wondered whether your STR is actually covered for what you do, hot tubs, guest injuries, burst pipes, tornadoes, income loss—this episode turns jargon into plain English and gives you a checklist to bring to your agent.

Thinking about insurance for your short-term rental? DM me on Instagram at @theairbnbroadmap with your questions or share your progress! I’d love to cheer you on and help you out.

In this episode, I’m pulling back the curtain on one of the most overlooked—but most powerful—parts of launching your Airbnb: photo-shoot day. From choosing the right photographer to creating scroll-stopping first images, I’m sharing my wins, mistakes, and all the tips I wish I’d known sooner. You’ll hear how every property teaches me something new, why lifestyle photos are worth the effort, and what small “wow” details make your listing stand out online.

Because you can have the most stunning Airbnb in the world—but if your photos don’t tell the story, you’re leaving money on the table. I’ll help you avoid rookie mistakes, guide your photographer like a pro, and give your listing the kind of images that turn browsers into bookings.

Thinking about upgrading your Airbnb photos or planning your first photoshoot?
DM me on Instagram @theairbnbroadmap with your questions or share your progress! I’d love to cheer you on and help you out.

Ready to launch or relaunch your short-term rental the right way?
Check out my Airbnb Roadmap Accelerator course at theairbnbroadmap.com for step-by-step guidance on finding, furnishing, and listing your property like a pro.

00:00 – Intro & Life Update
01:30 – Why Photo Day Matters
03:10 – Not All Photographers Are Equal
06:30 – Real Estate vs Short-Term Rental Photography
08:00 – Prepping Your Home for Shoot Day
09:50 – Wow Factors That Pop (Flames, TV Images, Logos)
14:00 – Lifestyle Shots & Models
17:00 – Simple Staging Ideas Without People
20:00 – Treat Photo Day Like Your Wedding Day
24:30 – Choosing Your Scroll-Stopping Cover Photo
27:00 – Final Tips & Where to Grab the Checklist

If this episode gave you fresh ideas for your next Airbnb photoshoot, please subscribe, leave a review, and share it with another host who’s ready to elevate their listing. Your support helps the show reach more people who are building beautiful, booked-out Airbnbs.

Episode Summary
In this episode, I break down Wisconsin’s short-term rental rules from the top down—statewide requirements (DATCP Tourist Rooming House license and inspections), the county layer (zoning, room tax, and when conditional use permits come into play), and the township layer (minimum night stays, resident agent requirements, occupancy limits, and other quirky rules). I also share our real-life CUP hearing story in Columbia County, why HOAs are risky, what “annexation” or jurisdiction changes can mean for you, and the #1 mistake that can get you shut down before you ever launch.

Key Takeaways

Why Listen to This Episode?
If you’re eyeing a Wisconsin Airbnb, this is the playbook for staying compliant, avoiding fines, and protecting your investment before you hit “Publish.”

Mentioned in the Episode

Let’s Connect
Thinking about Wisconsin STR rules & permits? 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
Want step-by-step guidance? My self-paced Airbnb Roadmap Accelerator is under $500 and covers everything from setup to scaling. If you close on your first STR with an agent I connect you to, you’ll get a 100% refund at closing.

Chapters
00:00 Life update + property under contract
05:46 State level: DATCP Tourist Rooming House license (what it is, inspections)
12:39 County level: zoning, room tax, and when CUPs are required
15:35 CUP story time: neighbor letters, hearings, and outcomes (Columbia County)
24:46 Township level: night minimums, resident agents, spacing/ownership quirks
31:51 HOAs: why they’re risky for STRs
33:05 Annexation & grandfathering: small town becoming part of a city
35:28 Legal occupancy: how towns/counties calculate guest limits
36:50 Don’t list before permits; protecting your launch
38:10 Course + free-at-closing offer

Subscribe and Share
If this helped, share it with a friend who’s eyeing a Wisconsin Airbnb and hit follow so you don’t miss the next episode!

In today’s episode, I’m taking you behind the scenes of our newest “two-for-one” Airbnb deal — a primary home plus an ADU over the detached garage — and walking you step-by-step through exactly what to do the moment you go under contract on an STR. If you’ve ever thought escrow was a waiting period, think again. I break down inspections, appraisal, insurance, financing, and the overlooked prep that saves weeks and brings in revenue faster: design, ordering essentials, project planning, and lining up contractors. I’m literally doing all of this right now with Clay (hello color-coded spreadsheet!) so you can copy the plan and hit the ground running on day one.

If you want your STR live (and profitable) ASAP, this gives you a proven, copy-and-paste escrow checklist and launch plan. You’ll learn the exact moves I’m making on our new two-for-one ADU property so you can avoid delays, budget hits, and stressful “now what?” moments on closing day.

Thinking about launching during escrow? DM me on Instagram @theairbnbroadmap with your questions or share your progress! I’d love to cheer you on and help you out.

In this personal, behind-the-scenes episode, I share how I went from a Six Flags kid in Gurnee, Illinois, to UW-Platteville grad, to wedding and hotel work, to a miserable janitorial sales job… to finally finding my lane as a real estate agent and short-term rental investor. I walk through the domino moments—meeting a Zillow agent who became my mentor, getting laid off during COVID, almost opening a paint-your-own-pottery studio, discovering Airbnbs, and how we bought our first, second, and third properties (plus a “two-for-one” partnership that’s in motion). If you’re curious how someone actually pivots into STRs without a trust fund or a $200k salary, this one’s for you.

If you’ve ever thought, “I didn’t go to school for this—am I too late?” or “I don’t have a perfect plan or pile of cash,” this is your permission slip. You’ll hear what it really looks like to pivot industries, learn in public, and build an STR portfolio step by step—messy mic moments and all.

Thinking about getting into short-term rentals? DM me on Instagram at @theairbnbroadmap with your questions or share your progress! I’d love to cheer you on and help you out.

If this gave you the nudge to start—or restart—your STR journey, hit Follow/Subscribe, drop a quick 5-star review, and share this episode with a friend who keeps saying “one day.” Your support helps more beginners find transparent, hype-free advice.

Text ROADMAP to 608-492-0260 (tell them you came from The Airbnb Roadmap) to get 1 free month off a 3-month accounting subscription and the STR Accounting & Tax Cheat Sheet.

In this episode, I sit down with my bestie, Kari—owner of BOOKED (Accounting & Tax), to demystify bookkeeping and taxes for first-time short-term rental investors. We get real about what matters on day one (hint: separate bank account!), when you actually need QuickBooks, how to track receipts without losing your mind, and the biggest tax levers for STRs (material participation, real estate professional status, and bonus depreciation). Kari also shares transparent pricing, an exclusive promo code: ROADMAP, and a free cheat sheet that recaps the episode. If you’ve ever wondered, “What should I be tracking, and how do I not overpay at tax time?”, this one’s your playbook.

Because you want clean books, maximum deductions, and fewer headaches. You’ll learn exactly what to track, when to outsource, and how to avoid the “I’ll fix it at tax time” premium. Kari’s firm is built for “baby businesses” and first-time hosts, fast replies, transparent pricing, and real-world guidance.

Thinking about bookkeeping and taxes for your short-term rental? DM me on Instagram at @theairbnbroadmap with your questions or share your progress! I’d love to cheer you on and help you out.

If this episode helped you feel more confident about your numbers, follow/subscribe, drop a 5-star review, and share it with a fellow host who needs an accounting upgrade. Your shares help more first-time investors find this show. 💛

Text ROADMAP to 608-492-0260 (tell them you came from The Airbnb Roadmap) to get 1 free month off a 3-month accounting subscription and the STR Accounting & Tax Cheat Sheet.

Episode Summary
Big changes are coming to Airbnb’s fee structure—and hosts need to be ready. Starting October 27, 2025, Airbnb is scrapping the split-fee model and moving to a single host-only fee of 15.5%. In this episode, I break down exactly what this means for you as a host or future investor, how it impacts your nightly rates, and what adjustments you need to make to protect your bottom line. I also share my personal take on the pros and cons of this shift, how it stacks up against Vrbo and Booking.com, and practical steps you can take inside tools like Hospitable and PriceLabs to stay competitive.

Key Takeaways

Why Listen to This Episode?
If you’re an Airbnb host—or planning to invest in your first short-term rental—this fee change directly impacts your ROI, pricing strategy, and competitiveness in the market. This episode gives you a clear action plan to avoid losing profits and stay ahead while other hosts may be caught off guard.

Mentioned in the Episode

Let’s Connect
Thinking about how Airbnb’s new fees will impact your property? DM me on Instagram at @theairbnbroadmap with your questions or share your pricing strategy! I’d love to cheer you on and help you adjust.

Work With Me
Want step-by-step support in scaling your Airbnb business? Check out the Airbnb Roadmap Accelerator—my course designed to help you confidently launch and manage your STR with the systems, tools, and strategies I use in my own business.

Chapters
00:01 Life update: Back issues + missed episode
04:45 The big Airbnb fee change explained
07:32 Real-world math: $100/night before vs. after fees
09:33 Market chaos: Competing with hosts who don’t update pricing
11:04 Comparing Airbnb to Vrbo & Booking.com
13:25 Direct booking movement and why Airbnb is cracking down
15:40 Why Airbnb might advertise this as “no more guest fees”
18:00 Homework: How to adjust your rates in Hospitable & PriceLabs
20:00 Final thoughts and prep for October 27

Subscribe and Share
Enjoyed this breakdown? Make sure to subscribe to The Airbnb Roadmap on Apple Podcasts or Spotify, and share this episode with a fellow host who needs to hear it before the new fees hit.

Hey, it’s Brittany! Big news—Clay and I are officially searching for another Airbnb, this time with our close friends in Texas as our first capital partners. They’re diving into their first short-term rental, and we’re learning the ropes of partnerships together.

That update ties directly into today’s topic: the current real estate market and how to negotiate smart as an STR investor. From seller credits to creative escrow solutions, I’m sharing the exact strategies that help you keep cash in your pocket without scaring off sellers. If you’re thinking about making a move, this episode will help you play it smart in today’s buyer-friendly market.

🔑 Key Takeaways for STR Investors
● It’s a buyer’s market
○ Inventory is up, homes are sitting longer, and sellers are motivated.
○ Nationally, over half of homes are selling below asking price, with average discounts around $45K.

🎧 Why Listen to This Episode?
Because smart negotiations can save you thousands. From seller credits to strategic pricing, I’ll walk you through tested plays that keep cash in your pocket, protect your time, and set your STR up for success from day one.

🤝 Let’s Connect
Thinking about buying an STR in today’s market? DM me on Instagram at @theairbnbroadmap with your questions or send me a property you’re eyeing. I’d love to cheer you on and help you out.

🛠 Work With Me
Want to start or scale your short-term rental business? Check out the Airbnb Roadmap Accelerator to learn how to find, launch, and manage STRs with confidence.

⏱ Chapters
00:00 – Life Update, New STR Partnership in Texas
04:30 – Market Snapshot, Inventory, Discounts, Interest Rates
09:45 – Seller Credits 101
13:15 – Escrow Strategies for Extra Credits
18:00 – Negotiating Professional Cleaning Into the Contract
20:30 – Have the Seller Cover Year-One Property Taxes
24:50 – Offer Anchoring to Hit Your Target Price
27:40 – My Emotional Offer Story (and What It Cost Us)
30:30 – Smarter Deals in Today’s Market

🔁 Subscribe and Share
If you enjoyed this episode, subscribe to The Airbnb Roadmap on your favorite podcast platform and share it with a fellow investor who wants to nail their next deal!

Hey, it’s Brittany! Today we’re tackling one of the least glamorous—but most critical—parts of running a short-term rental: trash management. I know, it’s not the hot tub or the Instagram-worthy décor, but it’s a behind-the-scenes system that can make or break your guest experience and your reviews.

From knowing how local trash service works before you even buy a property, to setting up systems so guests never wonder where to toss a banana peel, I’m sharing everything I’ve learned (the hard way) about handling garbage like a pro.

You’ll hear real-world stories from my own properties and my clients’—including raccoon break-ins, maggot disasters, and the guest who tried to charge me $5 for taking out the trash. This episode will help you prevent avoidable complaints, keep your neighbors happy, and maintain a 5-star cleanliness rating.

Because trash isn’t glamorous—but it’s essential. Getting it wrong costs you time, money, and 5-star reviews. Getting it right keeps guests happy, neighbors quiet, and your property running smoothly without last-minute scrambles.

Thinking about improving your Airbnb’s trash system? DM me on Instagram at @theairbnbroadmap with your questions or share your setup! I’d love to cheer you on and help you out.

Want to start or scale your own short-term rental business? Check out the Airbnb Roadmap Accelerator to learn how to find, launch, and manage your STRs with confidence.

00:00 – Why Trash Management Matters
01:36 – The Three Pre-Purchase Trash Questions
06:50 – City vs. Rural Trash Realities
11:12 – When Trash Service Isn’t an Option
13:50 – Matching Bin Capacity to Guest Count
15:50 – Labeling & Recycling Rules
17:20 – Who Rolls the Bins Out?
21:25 – Rural Property Trash Solutions
26:20 – What Can & Can’t Go in the Bins
29:20 – Trash Done Right vs. Trash Done Wrong
30:18 – Building Trash Costs Into Your STR Budget

If you enjoyed this episode, subscribe to The Airbnb Roadmap on your favorite podcast platform and share it with a fellow host who needs a trash system upgrade!