STR Investing, The Podcast

Fail forward, buy smarter. In this solo deep-dive, Taylor breaks down real-world STR underwriting—no hype, just numbers. If you’ve ever “made a spreadsheet sing” to justify a deal, this one’s for you. Learn the exact framework he’s used to evaluate hundreds of thousands of properties over the past four years and how to stay disciplined when emotion wants the win.What you’ll learnThe anatomy of a winning pro forma: purchase price, debt structure, closing costs, and true Total OOP (down payment, reno, amenities, furniture, vendors).Building an optimization list that actually moves RevPAR (from paint to pickleball).Revenue the right way: comping like-for-like, using data tools (AirDNA/Rabbu), and modeling Low / Mid / High scenarios.Expense reality check: utilities, supplies, PM software, cleaning fees in vs. invoices out, HOA, taxes, insurance, CapEx & reserves.NOI vs. Free Cash Flow: what lives “above the fold,” why debt service ≠ mortgage, and how to compare deals apples-to-apples.Return stack 101: cash-on-cash, principal paydown, long-view appreciation (why you should zoom out 20–25 years), and a primer on the STR tax play.The baseball mindset: why looking at hundreds of deals to land a few great ones is normal—and healthy.__Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 265+ profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com

Monday Market DataBoise, IDAirbnb Performance Data___________________________________3 BedroomAnnual Revenue50th Percentile: $32,34375th Percentile: $40,76290th Percentile: $53,556Average Daily Rate50th Percentile: $13975th Percentile: $17190th Percentile: $220Occupancy50th Percentile: 56%75th Percentile: 66%90th Percentile: 77%________________________________4 BedroomAnnual Revenue50th Percentile: $42,91575th Percentile: $53,98890th Percentile: $67,302Average Daily Rate50th Percentile: $19175th Percentile: $24290th Percentile: $308Occupancy50th Percentile: 54%75th Percentile: 63%90th Percentile: 72%___________________________________5 BedroomAnnual Revenue50th Percentile: $48,95475th Percentile: $58,96690th Percentile: $65,074Average Daily Rate50th Percentile: $23575th Percentile: $26890th Percentile: $305Occupancy50th Percentile: 48%75th Percentile: 57%90th Percentile: 69%_________________________________6+ BedroomsAnnual Revenue50th Percentile: $79,85375th Percentile: $92,83090th Percentile: $100,616Average Daily Rate50th Percentile: $29675th Percentile: $50890th Percentile: $635Occupancy50th Percentile: 45%75th Percentile: 57%90th Percentile: 64%_________________________________Which market do you want to see next?

Mark Lumpkin sits down with Nick Swanson and Alex from Chetu, a technology firm that has spent 25 years helping hotels, operators, and brands navigate digital transformation. Together, they unpack how AI is changing hospitality and what short term rental operators can do right now to stay ahead.Nick and Alex break down what agentic AI actually is, how it is already being used behind the scenes in hotels and restaurants, and why the next wave of tools will feel more like talking to a real person than fighting a phone tree. They also explain how STR hosts can use AI to refresh listings, improve Airbnb ranking, mine historic guest data, streamline pricing, and elevate guest communication without hiring a huge team.They share the story of Chetu's journey from tiny startup to a global company, and why AI is exposing digital weak spots that were papered over by old “transformation” slides. The conversation also tackles the big question on everyone’s mind: AI versus virtual assistants. Will AI replace VAs, or work alongside themIn this episode, you will learn:What agentic AI is and how it fits into hospitalityPractical ways AI can increase bookings and guest satisfaction in STRsHow to use AI to automate repetitive workflows and free your team to do higher value workWhy historic guest data is a goldmine that humans will never fully unlock on their ownHow to think about cost, data security, and using off the shelf tools versus custom buildsIf you are serious about using AI to grow your short term rental business, this episode will give you a clear, grounded starting point.__Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 265+ profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com

Monday Market DataTelluride, COAirbnb Performance Data___________________________________3 BedroomAnnual Revenue50th Percentile: $75,28375th Percentile: $109,62690th Percentile: $141,127Average Daily Rate50th Percentile: $72075th Percentile: $88990th Percentile: $1,040Occupancy50th Percentile: 29%75th Percentile: 41%90th Percentile: 53%________________________________4 BedroomAnnual Revenue50th Percentile: $114,90575th Percentile: $169,34390th Percentile: $201,856Average Daily Rate50th Percentile: $1,09075th Percentile: $1,34090th Percentile: $1,642Occupancy50th Percentile: 27%75th Percentile: 42%90th Percentile: 50%___________________________________5 BedroomAnnual Revenue50th Percentile: $211,63575th Percentile: $283,94690th Percentile: $329,846Average Daily Rate50th Percentile: $1,54875th Percentile: $1,84890th Percentile: $2,816Occupancy50th Percentile: 33%75th Percentile: 50%90th Percentile: 72%_________________________________6+ BedroomsAnnual Revenue50th Percentile: $279,31675th Percentile: $386,92590th Percentile: $416,455Average Daily Rate50th Percentile: $2,33275th Percentile: $2,62490th Percentile: $2,729Occupancy50th Percentile: 37%75th Percentile: 57%90th Percentile: 61%

Mark sits down with Siddhi Mittal, the founder of yhangry—a fast-growing platform that connects guests with private chefs at shockingly affordable prices. Think three-course meals starting around $60 per person… cooked in your vacation rental, cleaned up afterward, and delivered by vetted professional chefs.What started as a simple idea in London has now become a global movement—one that’s reshaping guest experience inside short-term rentals. And here’s the wild part: Siddhi didn’t even realize STRs were half their market until the data smacked her in the face. Since then, yhangry has partnered with over 130,000+ vacation rental units, doubled the number of chefs Airbnb has in the U.S., and is rapidly expanding across the U.S., Europe, and Dubai.In this episode, you’ll learn: • Why private chefs are becoming one of the most requested STR add-ons • How property managers are using yhangry to increase conversions and boost guest reviews • The surprising ways travel habits differ between U.S. and UK guests • What a partnership looks like—affiliate links, dashboards, payouts, and ease of setup • How user-generated content (UGC) from chef experiences drives direct bookings • The story behind yhangrys first-ever booking… featuring eight influencers and an explosion of overnight viralitySiddhi also breaks down the myths around private chefs (spoiler: it’s NOT bougie), the psychology of “vacation mode” spending, and why curated in-home dining is becoming the next major amenity in hospitality.If you're looking for new revenue streams, higher guest satisfaction, and a true differentiator in your market—this episode is a must-listen.___Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 265+ profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com

Monday Market DataBend, ORAirbnb Performance Data___________________________________3 BedroomAnnual Revenue50th Percentile: $41,64275th Percentile: $55,34690th Percentile: $70,594Average Daily Rate50th Percentile: $23375th Percentile: $28190th Percentile: $329Occupancy50th Percentile: 41%75th Percentile: 56%90th Percentile: 69%________________________________4 BedroomAnnual Revenue50th Percentile: $46,17275th Percentile: $68,35090th Percentile: $86,397Average Daily Rate50th Percentile: $31975th Percentile: $37990th Percentile: $475Occupancy50th Percentile: 35%75th Percentile: 49%90th Percentile: 59%___________________________________5 BedroomAnnual Revenue50th Percentile: $70,77175th Percentile: $94,77590th Percentile: $109,959Average Daily Rate50th Percentile: $45675th Percentile: $54290th Percentile: $647Occupancy50th Percentile: 38%75th Percentile: 50%90th Percentile: 58%_________________________________6+ BedroomsAnnual Revenue50th Percentile: $102,52575th Percentile: $112,21490th Percentile: $162,525Average Daily Rate50th Percentile: $60075th Percentile: $78790th Percentile: $1,158Occupancy50th Percentile: 38%75th Percentile: 45%90th Percentile: 54%_________________________________

From pharmaceutical sales to $150 million in short-term rental transactions—this week’s episode dives deep with Chantal, a Colorado-based STR investor and brokerage owner redefining what it means to scale smart.Chantal shares how knocking on doors in pre-foreclosures led her to her first “honeymoon basement” Airbnb, how she built a thriving portfolio in one of the most regulated states, and what she’s learned helping hundreds of clients buy and sell STRs across Colorado.You’ll learn: • How she turned one underdog listing into a multi-million-dollar brokerage • Why most “turnkey” STRs for sale are actually underperforming assets—and how to spot opportunity fast • The insider playbook for selling an STR at a premium (clean books, strong revenue, and transparency) • How to navigate Colorado’s metro, resort, and mountain STR markets for long-term growthWhether you’re an agent eyeing the STR niche, an investor chasing appreciation, or just curious how to make a short-term rental business scale, this episode delivers a masterclass in combining passion with precision.___Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 265+ profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com

Monday Market DataDallas, TXAirbnb Performance Data___________________________________3 BedroomAnnual Revenue50th Percentile: $39,14975th Percentile: $54,68990th Percentile: $75,451Average Daily Rate50th Percentile: $20875th Percentile: $26690th Percentile: $349Occupancy50th Percentile: 46%75th Percentile: 58%90th Percentile: 68%________________________________4 BedroomAnnual Revenue50th Percentile: $50,06375th Percentile: $75,32890th Percentile: $109,206Average Daily Rate50th Percentile: $26975th Percentile: $36990th Percentile: $498Occupancy50th Percentile: 46%75th Percentile: 58%90th Percentile: 68%___________________________________5 BedroomAnnual Revenue50th Percentile: $81,88075th Percentile: $115,92890th Percentile: $154,959Average Daily Rate50th Percentile: $42075th Percentile: $55290th Percentile: $718Occupancy50th Percentile: 48%75th Percentile: 62%90th Percentile: 69%_________________________________6+ BedroomsAnnual Revenue50th Percentile: $100,56575th Percentile: $158,89690th Percentile: $201,354Average Daily Rate50th Percentile: $56475th Percentile: $75590th Percentile: $845Occupancy50th Percentile: 51%75th Percentile: 59%90th Percentile: 67%_________________________________

Monday Market DataYosemite, CAAirbnb Performance Data___________________________________3 BedroomAnnual Revenue50th Percentile: $33,50375th Percentile: $50,71290th Percentile: $78,121Average Daily Rate50th Percentile: $24075th Percentile: $30290th Percentile: $409Occupancy50th Percentile: 32%75th Percentile: 46%90th Percentile: 60%________________________________4 BedroomAnnual Revenue50th Percentile: $40,29875th Percentile: $59,05890th Percentile: $81,795Average Daily Rate50th Percentile: $29675th Percentile: $38590th Percentile: $489Occupancy50th Percentile: 29%75th Percentile: 41%90th Percentile: 53%___________________________________5 BedroomAnnual Revenue50th Percentile: $56,71475th Percentile: $93,68590th Percentile: $121,317Average Daily Rate50th Percentile: $45675th Percentile: $60990th Percentile: $744Occupancy50th Percentile: 30%75th Percentile: 43%90th Percentile: 53%_________________________________6+ BedroomsAnnual Revenue50th Percentile: $92,15675th Percentile: $131,30890th Percentile: $187,263Average Daily Rate50th Percentile: $65875th Percentile: $87890th Percentile: $1,058Occupancy50th Percentile: 33%75th Percentile: 48%90th Percentile: 57%

It’s late—around 10:30 p.m.—when Mark gets a calm call no host ever wants: “We have a little problem…the cabinets just fell off the wall.” In Part 2 of our Halloween Special, operations pro Misty Schmidt walks us through a surreal scene: upper kitchen cabinets ripping off the wall, 24 place settings shattering, and a heroic guest scooping glass with a snow shovel…in flip-flops. Misty shares:How she triaged a true “oh-no” moment with safety-first steps and on-site cleanupWhy installation quality (anchors, weight, wall type) matters more than you thinkWhat thoughtful recovery looks like: immediate response, refund, and personalized gifts (yes, tequila and local cigars)—leading to a 5-star reviewPlus, Mark wraps with real Reddit horror stories (from no-show hosts to “watched on camera” creepiness) and the big takeaway after dozens of convos at VRMA: genuine STR nightmares are rarer than the internet suggests—great systems and fast empathy go a long way.You’ll learn: crisis playbooks for hosts, guest comms that defuse drama, and how to turn a disaster into loyalty.___Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 265+ profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com