The Peak Season

Mike O'Connell built Happy Guest because the slick guest portals big property managers had weren't accessible to everyday hosts. He breaks down the full platform, why calling guests after they book is one of the highest-ROI moves in the business, and what their MCP launching next week unlocks. 🏠   http://www.happyguestofficial.co   Happy Guest is built around three pillars: pre-arrival requiremen...

PC built Hospitable into the only PMS processing $60M+ in direct booking payments, and now he's giving the software away for free. He explains why, and walks through four moves reshaping how STR operators run their business: the industry's first MCP, a live VRBO integration, a free plan, and a marketplace matching owners to property managers.   🔌 HOSPITABLE'S MCP: WHAT IT ACTUALLY DOES - First PM...

Brandon Pottebaum left college athletics after 10 years to go full-time in STRs, running 14 doors with one VA and a freelance revenue manager. No employees, no overhead, just a lean system built on smart tools and clear priorities. This week: how he built it, what he still does manually, and where AI is about to change his whole operation. 🎙️   ---   🧠 FROM W2 TO 14 DOORS - Left football after co...

Your calendar is your inventory. When a guest cancels a premium week, how you respond affects your rebooking odds, your Airbnb ranking, and sometimes your review score. Luke and Tyler break down every cancellation scenario — last-minute, weather-related, peak season, and the one move Luke will never make no matter what the guest says. 🏔️ --- 📅 DYNAMIC CANCELLATION POLICIES Airbnb now lets you set...

Big news for STR hosts — Hospitable just launched a full API integration with VRBO, and it changes everything. Luke and Tyler break down what the old (broken) connection looked like, what the new integration actually delivers, and whether it's finally worth getting back on VRBO. 🏠 🔌 Old vs. New Integration Before: VRBO ran on a public API — tons of manual work, no automated guest messaging, cons...

🎙️ Peak Season Podcast Show Notes DIY Design Mistakes Short-Term Rental Hosts Are Making (with Andrea Moxham) Guest: Andrea Moxham, Founder of Moxie & Co. | Hosts: Luke Miller & Tyler K. Interior designer Andrea Moxham joins Luke and Tyler to break down the most common design mistakes STR hosts make when DIYing their properties — with actionable tips you can implement right away, no renova...

Your guidebook is one of the most powerful tools you have for delivering a 5-star guest experience. In this episode, Luke and Tyler break down what to put in it, how to deliver it, and which platform makes the most sense for where you are in your hosting journey. What's Covered (00:30) — What to Include Directions, local restaurants, attraction info, and specialty amenity instructions are the non-...

Luke and Tyler take listeners behind the scenes as they run the full pro forma on the Kentucky bourbon‑trail property introduced in the previous episode. This is where the deal gets real — revenue assumptions, expense modeling, financing scenarios, and risk analysis all collide to reveal whether this property is a cash‑flowing gem or a pass. If you’ve ever wondered how experienced STR investors tu...

🌄 Episode Overview Luke and Tyler take you inside their underwriting process as they break down a promising short‑term rental opportunity in Lawrenceburg, Kentucky —right in the heart of bourbon country. They dig into market data, analyze comps, and stress‑test the numbers to determine whether this property has real investment potential. This episode is packed with practical insights for both new...

In this episode, Luke and Tyler break down a real-world case study from a luxury short-term rental on 30A in Florida. What started as a casual conversation at cheer practice turned into a full revenue turnaround. The property was generating roughly $63,000 annually before Luke stepped in to manage pricing and provide strategic consulting. With no major renovation and only minor amenity upgrades, t...

Episode Summary In this episode, Luke and Tyler unpack a real-world lesson from two newly launched Northern Michigan properties. When you’re scaling short-term rentals — especially from a distance — your cleaning crew can make or break your business. Luke shares a recent experience hiring and quickly replacing a cleaner after quality and scheduling red flags started stacking up. The takeaway? Five...

Luke and Tyler reunite and hit record while reviewing a real short-term rental listing in Northwest Michigan: a vintage chalet inside a resort community with beach access, five bedrooms, two baths, and a 4.79 rating. They don’t “rip it to shreds” — they walk through practical upgrades that could improve bookings, reviews, and revenue with relatively small changes. ### What We Cover 1) Title Optimi...

Episode Description Renovating a short-term rental is hard. Renovating one  six states away  while working full-time, raising kids, and protecting family life? That’s a different level. In this solo episode, Luke breaks down  six hard-earned lessons  from launching and renovating a short-term rental in Bellaire, Michigan while living in Houston, Texas. From budget overruns and holding costs to lea...

Episode Summary In this episode of  The Peak Season Podcast , Luke and Tyler break down real-world, low-effort strategies that directly increase short-term rental profit. Using recent bookings at White Birch Cabin as a case study, they explain how small system tweaks—like minimum stay adjustments, direct booking visibility, and smart upsells—can add thousands of dollars to the bottom line without...

🎙️ Episode Show Notes Episode Title: Evaluating a New STR Market from 30,000 Feet: The Bourbon Trail (Part 1) --- ### Episode Description In this episode of the Peak Season Podcast , Luke and Tyler step outside their usual Michigan focus and evaluate a brand-new short-term rental market: Kentucky’s Bourbon Trail. Rather than jumping straight into spreadsheets and underwriting, this episode intenti...

Show Notes In this episode of  The Peak Season Podcast , Luke and Tyler return to PriceLabs for a hands-on walkthrough of one of the most underused (and misunderstood) features in the platform:  Neighborhood Data and Market Dashboards . The conversation starts with a familiar host fear— “I was way more booked this time last year… should I be worried?” —and quickly turns into a data-driven framewor...

📝 Episode Summary In this episode of the Peak Season Podcast, Tyler and Lucas unpack one of the most debated levers in vacation‑rental strategy: Should you hold firm to a seven‑night minimum during peak season, or open the calendar to shorter stays to fill gap nights? They explore how each approach affects revenue, workload, guest satisfaction, and operational flow, weaving in real examples from...

The Peak Season Podcast – Part 2 with Brandon Wood In Part Two of our conversation, Brandon Wood goes deep on what actually powers a scalable short-term rental operation—without burning out or over-engineering too early. We cover Brandon’s full tech stack (from PMS to insurance), how he thinks about outsourcing versus control, and why  time  is the real bottleneck most operators ignore. Brandon al...

📄 Episode Summary In this episode of  The Peak Season Podcast , Luke and Tyler sit down with  Brandon Wood , founder of Adventure Nest, for a candid conversation about what it  actually  looks like to scale a short-term rental portfolio without losing your sanity—or your family in the process. Brandon shares his journey from a demanding W2 career into full-time short-term rentals, including how h...

🎙️ Peak Season Podcast The AirDNA 2026 Outlook: Why the Next STR Buying Window Might Be Closer Than You Think In this episode, Luke Miller and Tyler K break down the latest  AirDNA 2026 Outlook  and what it means for short-term rental owners, investors, and operators heading into the next cycle. We unpack a rare convergence of market forces—falling mortgage rates, stabilizing home prices, and reco...

Episode Summary In this solo episode of  The Peak Season Podcast , Luke breaks down a practical, repeatable system for forecasting short-term rental revenue using PriceLabs and a simple spreadsheet. Instead of vague goals like “make more money,” Luke walks through how to set clear monthly revenue targets, track progress in real time, and adjust pricing strategy based on occupancy, seasonality, and...

Episode Description In this episode of  The Peak Season Podcast , Luke shares a behind-the-scenes look at what it  really  takes to launch a short-term rental at warp speed. From the closing table to live in just six days — and from over 1,000 miles away — this was not a smooth, Instagram-worthy rollout. Between delayed closings, Midwest blizzards, scattered Wayfair boxes, canceled deliveries, mar...

🎙️ Episode Summary In this episode of the Peak Season Podcast, Luke and Tyler break down the property management system Hospitable and how hosts can use it to streamline operations and elevate the guest experience. They cover automated messaging rules, review workflows, team communication, and smart home integrations, sharing practical tips from real hosting experience. Whether you manage one prop...

Episode Summary Luke and Tyler sit down for a real-time catch-up as Luke races to bring  two new short-term rentals online before year-end . One is  Alm Haus , Luke’s first major renovation, and the other is a newly acquired  “tree house vibe” property  near Bellaire. They unpack winter booking softness, renovation realities, vendor coordination during the holidays, and why  soft openings  with tr...

Summary In this Real Talk episode of the Peak Season Podcast, Luke opens up about something every short-term rental host eventually hits: end-of-season burnout. Between wrapping renovations, racing toward year-end tax deadlines, juggling slow-season bookings, and navigating holiday stress, it’s a lot. Luke shares the simple mental framework he leans on when the entrepreneurial pressure cooker gets...