$100K in One Month: Lakefront STR Secrets with Sheboygan Vacation Rentals

👉 Apply for a Free Revenue Review: If you’re running $1M+ in annual STR bookings, you could be leaving serious money on the table. Apply here → https://www.freewyldfoundry.com/get-startedWhat happens when traditional STR deals no longer pencil out, Airbnb’s review system becomes harsher, and local governments push restrictive ordinances?In this episode of Get Paid For Your Pad, Jasper Ribbers sits down with Garrett Ham, founder and CEO of Weekender Management, to reveal how he’s navigating one of the toughest markets for short-term rentals in years.Garrett shares how he has acquired 10+ properties in the past year using creative financing strategies while fighting a legal battle before the Arkansas Supreme Court over restrictive Fayetteville ordinances. He also opens up about the risks of Airbnb’s stricter review system, where even a single four-star review can slash visibility and cost hosts thousands in lost bookings.💡 Takeaways:Why traditional STR acquisitions rarely work in 2025How to use seller financing and other creative deal structuresWhy knowing your bottom line is key to negotiationsHow regulations could reshape property rights in Arkansas and beyondWhat stricter Airbnb reviews mean for revenue and visibilityWhether you manage 5 units or 50, this episode gives you actionable strategies to acquire properties, protect your listings, and grow smarter in a challenging market.🔗 Relevant Links:Weekender Management → weekendermanagement.comFreewyld Foundry → freewyldfoundry.com📌 Keywords: short-term rentals, Airbnb investing, creative financing, property management, STR regulations, 5-star reviews, Freewyld, Weekender Management Hosted on Acast. See acast.com/privacy for more information.

👉 Apply for a Free Revenue Review: If you’re running $1M+ in annual STR bookings, you could be leaving serious money on the table. Apply here → https://www.freewyldfoundry.com/get-startedIn this episode of Get Paid for Your Pad, Kaye Putnam (Head of Marketing at Freewyld) interviews Madi Rifkin, founder of Mount, about how she created the Content Army, a community of creators that is reshaping how hospitality brands, property managers, and tourism destinations collaborate with influencers.Madi shares how she went from being frustrated with traditional influencer partnerships (expensive, inauthentic, hard to track) to building a system that now has 10,000+ applicants and dozens of active creators producing organic, aligned, and highly effective content for travel “hidden gems.”In this episode you’ll learn:What the Content Army is and how it actually worksWhy “wannabe influencers” may be your strongest marketing alliesHow to organize creator retreats that multiply content and generate FOMOThe most important lessons in matching brands with creatorsStrategies for measuring real impact on direct bookings and trafficCommon mistakes when working with influencers (and how to avoid them)We also talk about:How a viral TikTok with 1M+ views launched the projectPartnerships with property managers and tourism boards in Jackson Hole and ArubaWhy the future of hospitality marketing blends content, experiences, and community🎯 Keywords:short-term rental, influencer marketing, content strategy, direct bookings, hidden gems, tourism marketing, Content Army, property managers, hospitality growth, organic social media Hosted on Acast. See acast.com/privacy for more information.

👉 Apply for a Free Revenue Review: If you’re running $1M+ in annual STR bookings, you could be leaving serious money on the table. Apply here → https://www.freewyldfoundry.com/get-startedIn this episode of Get Paid For Your Pad, Jasper Ribbers (Head of Revenue Management at Freewyld Foundry) dives deep into one of the most misunderstood yet powerful concepts in STR revenue management: pacing.Hosts constantly ask:Why do short-term rentals slash prices last minute while hotels and airlines often raise theirs?What KPIs actually matter when tracking pacing?When should you pace behind, with, or ahead of the market?Using real-world examples, from Ibiza flights to Taylor Swift concerts, Jasper explains why STR operators can’t afford to blindly follow hotel or airline pricing models. He breaks down the Market Penetration Index (MPI) as the go-to KPI for forward occupancy, reveals how pickup trends should guide your pricing decisions, and shares exactly when it pays to undercut the market versus hold firm.You’ll learn:The key differences between airline/hotel inventory and STR inventoryWhy most operators panic and drop rates too quicklyHow MPI uncovers whether you’re pacing behind, in line, or aheadScenarios where “last man standing” pricing can win bigWhy seasonality and booking windows must shape your pricing targetsIf you’ve ever struggled with last-minute discounts, inconsistent occupancy, or uncertainty about whether you’re pacing correctly, this episode gives you a practical roadmap to approach revenue management with confidence.Takeaways:Treat pacing as a leading indicator of revenue performance, not an afterthoughtUse MPI + pickup together for smarter pricing decisionsSometimes pacing behind the market is the winning moveAvailability settings and timing can make or break your portfolio’s revenueKeywords:short-term rental, Airbnb pricing, pacing strategy, revenue management, occupancy rate, dynamic pricing, MPI, Freewyld, STR success, booking optimization Hosted on Acast. See acast.com/privacy for more information.

👉 Get Your Free Revenue Review → https://www.freewyldfoundry.com/reportWhat if you could take your short-term rental business from 17% to nearly 50% direct bookings in just six weeks? In this episode of Get Paid For Your Pad, Eric Moeller and Kaye Putnam break down the exact influencer collaboration strategy that turned a $900 investment into over $12,000 in direct revenue.You’ll discover:How to choose local influencers that actually drive bookingsThe giveaway format that generated 233,000+ views and thousands of new prospectsWhy global or personality-driven creators fail to convert for STRsThe must-have contracts and content rights that protect your brandHow single-property landing pages transform attention into bookingsThis isn’t theory. It’s a real case study STR operators can use to reduce OTA reliance, build brand awareness, and grow direct bookings with intentional influencer partnerships.🎧 Listen now and learn how to stop decorating, start branding, and design collaborations that deliver real ROI.KeywordsDirect bookings, influencer collaborations, short-term rentals, STR growth, Instagram giveaways, hospitality marketing, property management, Freewyld case study, Airbnb revenue, OTA alternativesTimestamps00:00 – Tripling direct bookings in six weeks 02:14 – Why some influencer campaigns fail to convert 07:05 – The profile of creators who actually drive bookings 09:08 – How to find and qualify the right accounts 10:16 – Outreach strategies: DM vs. email 11:10 – Timelines, weekday hosting, and trades 13:29 – Setting expectations and giving direction 15:24 – Contracts, content rights, and model releases 17:28 – Giveaway mechanics that create virality 21:43 – Results: 233k views and $12k in direct bookings 24:36 – ROI breakdown and ad-value comparison 27:50 – Improving the direct booking experience 32:05 – Landing pages vs. full websites for campaigns 34:31 – How STR hosts can apply this playbook Hosted on Acast. See acast.com/privacy for more information.

Get Your Free Revenue Report: If you’re running $1M+ in annual STR bookings, you could be leaving serious money on the table. Apply here → https://www.freewyldfoundry.com/reportIn this episode of Get Paid For Your Pad, Jasper Ribbers kicks off our new RefUp Series on revenue management with one of the most overlooked levers in STR revenue: minimum night stay (MNS) settings.Most hosts see MNS as a simple calendar setting, but it directly impacts your availability, visibility, and overall revenue. Hotels handle short stays differently for a reason, and STR operators can learn a lot from that approach.We break down:The 3 key reasons to restrict minimum nights: operations, risk, and revenue optimizationWhy one-night bookings often bring more benefits than problemsHow Airbnb’s algorithm rewards flexibility with more visibilityThe indirect revenue value of reviews, repeat guests, and exposureReal-world examples of operators who unlocked growth by testing shorter staysWhether you manage a few units or a large portfolio, this episode will show you how to think about MNS settings strategically and stop leaving money on the table.Keywords: short-term rental, Airbnb, minimum night stay, revenue management, STR optimization, Airbnb algorithm, pricing strategy, Freewyld, property management, bookings Hosted on Acast. See acast.com/privacy for more information.

👉 Get Your Free Revenue Review → https://www.freewyldfoundry.com/reportWhat if the real ROI in your short-term rental business isn’t just pricing or operations, but design?In this episode of Get Paid For Your Pad, Kaye Putnam sits down with Jordan McDonough, co-founder of Summerled Designs, to reveal how intentional design and branding transform STR properties into high-performing, unforgettable guest experiences.Jordan shares how she and her co-founder combined design expertise with marketing strategy to help investors consistently stand out in competitive markets, command premium nightly rates, and turn ordinary spaces into five-star guest favorites.You’ll learn:🎨 Why design is not an expense but an investment with 30–50% ROI🏡 How to align interiors with your target guest instead of personal preference📸 Why great photography and lifestyle visuals multiply the impact of design📈 How design, branding, and amenities drive direct bookings and repeat guests⚡ The Summerled process for creating standout STR properties, even 100% remotelyWe also cover:The biggest mistakes hosts make when DIY-ing designWhy brand identity is now essential for STR successHow to design “Instagrammable” moments that fuel marketingWhy strategic amenities outperform generic check-the-box featuresReal examples from markets like Nashville where design directly boosted revenue🎯 Favorite Takeaway:“Design isn’t just décor. It’s strategy. It’s what allows you to charge more, book faster, and create experiences guests can’t wait to share.”📍 Ready to see how design can unlock your property’s potential?Apply for your free Revenue Review at https://www.freewyldfoundry.com/reportKeywords: short-term rental design, Airbnb interiors, STR branding, guest experience, property management, hospitality, STR success, design ROI, direct bookings, Summerled Designs⏱️ Chapter Timestamps00:00 – Intro and Summerled origin story03:25 – Why design delivers ROI in STRs06:15 – Current trends in branding and amenities10:30 – How to define a property’s brand identity14:05 – Summerled’s remote design process and deliverables16:20 – The role of AI in design workflows18:00 – Common design mistakes STR investors make20:15 – Why photography is critical to marketing success21:45 – Favorite projects and lessons from Nashville24:55 – Final thoughts and how to work with Summerled Hosted on Acast. See acast.com/privacy for more information.

Want to turn your STR portfolio into a revenue machine? Apply for a free Revenue Review → https://www.freewyldfoundry.com/get-startedIn this episode, Kaye Putnam joins Freewyld co-founder Eric Moeller to reveal the real strategies behind maintaining a top-rated Airbnb portfolio. Spoiler: it’s not just about having a beautiful property.They break down the essentials every STR operator must master to win guest loyalty and outperform the competition:Accurate Marketing & Listing OptimizationMeeting and Surpassing Guest ExpectationsPersonalized Hospitality & Human ConnectionCreating Magic Moments That Drive ReviewsUsing Freewyld’s cabins and client portfolios as examples, Kaye and Eric share how to turn guest feedback into a growth engine, protect your visibility on Airbnb, and build systems that ensure consistent 5-star experiences.Whether you manage 15+ units or are scaling your first few, this episode will give you practical steps to improve reviews, boost rankings, and grow a hospitality-first STR business.Keywords:short-term rental, Airbnb reviews, 5-star rating, guest experience, listing optimization, hospitality, Freewyld, property management, STR success, review strategy⏱️ Episode Chapters00:00 – Intro: Why Airbnb reviews matter more than ever01:32 – Accurate listings and managing expectations04:25 – When great marketing falls short in execution06:36 – Why accuracy beats luxury every time09:41 – Overcommunication and guest connection14:34 – Creating emotional “magic moments” for guests18:23 – Turning friction into positive experiences21:32 – The coffee debacle: learning from reviews26:36 – Reading feedback and fixing small details28:18 – Internal systems and team training for reviews29:51 – Guest journey mapping with Nathan Woods32:05 – Final takeaways: reviews as growth opportunities Hosted on Acast. See acast.com/privacy for more information.

👉 Get Your Free Revenue Report: If you’re running $1M+ in annual STR bookings, you could be leaving serious money on the table. Apply for a complimentary Revenue Report and uncover hidden profits in your portfolio.In this episode of Get Paid for Your Pad, Eric Moeller interviews Jasper Ribbers, co-founder of Freewyld and Freewyld Foundry, about the fast-growing world of revenue management.Jasper shares how their team scaled from managing a handful of Freewyld cabins to overseeing 66 clients, 1,600 listings, and more than $61M in revenue, and why most STR operators are unknowingly missing out on 20 to 40 percent of their potential income.We also dive into:Why revenue management is not just a pricing toolThe number one mistake operators make when setting pricesHow pacing (forward occupancy) reveals untapped demandReal case studies where portfolios jumped 25 to 40 percent in booked revenueWhy strict availability and cancellation policies often backfireIf you want to scale your portfolio, capture hidden revenue, and finally give pricing the same attention as marketing and operations, this episode is for you.TakeawaysTreat revenue management as a core business function, not an afterthoughtMost operators are leaving 10 to 40 percent on the table by misusing pricing toolsPacing is the most powerful and overlooked concept in STR pricingAvailability and cancellation policies impact revenue just as much as ratesA dedicated revenue manager can consistently outperform DIY strategiesRelevant LinksApply for a Free Revenue Report: freewyldfoundry.comFollow Jasper: LinkedInFollow Eric: LinkedIn Hosted on Acast. See acast.com/privacy for more information.

👉 Get Your Free Revenue Report: If you’re running $1M+ in annual STR bookings, you could be leaving serious money on the table. Apply for a complimentary Revenue Report and uncover hidden profits in your portfolio.In this episode of Get Paid for Your Pad, Jasper sits down with Jeremy Udovich, co-founder of Sheboygan Vacation Rentals, to talk about building and scaling a thriving STR business on the shores of Lake Michigan.Jeremy shares the story of how one lakefront property hit $100,000 in a single month, why charging premium rates doesn’t automatically mean unhappy guests, and how mindset + market-driven pricing beats gut instinct every time.We also dive into:Why hospitality experience is the ultimate STR advantageHow to balance growth with a lean teamThe new quality-first direction at Airbnb and how to stay visibleWhy “fair share” isn’t enough, and how to claim your “unfair share” of the marketIf you’re looking to scale your portfolio or fine-tune your pricing strategy, this is an episode you won’t want to miss.TakeawaysLuxury STRs thrive when the experience matches the rate.Market demand, not your gut, should set your pricing.Airbnb is rewarding fully optimized, high-quality listings.A lean team plus automation can drive big results, but hospitality fundamentals are non-negotiable.Mindset matters: challenges are inevitable, but your response determines your success.Relevant LinksApply for a Free Revenue ReportSheboygan Vacation Rentals: sheboyganvacationrentals.comConnect with Jeremy: [email protected] Jasper: LinkedIn Hosted on Acast. See acast.com/privacy for more information.

👉 Get a Free Revenue Review → https://www.freewyldfoundry.com/report Find out how much revenue you’re leaving on the table, risk-free.What’s the real difference between a hectic host and a high-performing CEO in the short-term rental space?In this episode, Kaye Putnam and Eric Moeller break down how successful STR leaders escape the daily grind and create real business freedom. You’ll learn why systems, energy management, and delegation aren't just buzzwords, they're essential tools for scaling without burning out.Eric shares the behind-the-scenes of helping Troy (a client in Northern Michigan) go from 30 to over 100 listings, culminating in his first $1M revenue month. The secret? Getting out of the weeds, hiring elite operators, and focusing on high-leverage activities only the CEO can do.Whether you're still handling pricing yourself or buried in customer service messages, this episode is a wake-up call. You’ll walk away with the mindset shifts and practical systems you need to step fully into your role as a strategic CEO.💡 Topics covered:Signs you’re stuck in “reactive” modeHow to run an “energy audit” on your weekly tasksSystems = freedom: why delegation is non-negotiableWhy pricing your own listings is probably costing you six figuresReal-world example: how Troy scaled from chaos to clarity (and 3x'd his revenue)How to use tools like ChatGPT to scale your SOPs 🔗 Episode LinksEric Moeller (Co-founder, Freewyld) → https://www.linkedin.com/in/ericdmoeller/ Kaye Putnam → https://www.linkedin.com/in/kayeputnam/Freewyld Foundry (RPM Service) → https://www.freewyldfoundry.com/⏱️ Chapter Timestamps00:00 – The Hectic Host vs. The Strategic CEO 02:48 – Understanding Reactivity in Business 05:35 – The Cost of Being in the Weeds 08:40 – Energy Management vs. Time Management 11:32 – The Importance of Delegation and Systems 14:11 – Troy's Success Story: A Case Study 19:52 – Key Strategies for Scaling Your Business 22:57 – The Role of Systems in Business Freedom 26:33 – Effective Delegation and Ownership 32:07 – Final Thoughts and Action Steps Hosted on Acast. See acast.com/privacy for more information.