Get Paid For Your Pad | Airbnb Hosting | Vacation Rentals | STR Revenue Management

👉 Get a Free Revenue Review → https://www.freewyldfoundry.com/reportFind out how much money your portfolio is leaving on the table. Risk-free.What happens when the biggest revenue opportunities of the year are not Thanksgiving or Christmas, but the quieter holidays most operators barely plan for?In this episode of Get Paid For Your Pad, Jasper Ribbers breaks down how “hidden holidays” create outsized revenue opportunities and why minimum stay settings, not nightly rates, are often the deciding factor between fully monetized calendars and unfillable gaps. Drawing from real-world revenue management across dozens of markets, Jasper explains how demand shifts around federal holidays, long weekends, and observed days off, and why applying the same rules year-round quietly limits upside.Whether you operate in a drive-to market or a fly-to destination, manage a handful of listings or an entire portfolio, this episode helps you rethink how minimum stay rules interact with holiday demand, guest behavior, and booking patterns. Jasper walks through the strategic tradeoffs behind flexibility versus restriction and explains why there is no universal answer, only better decision-making grounded in data and market context.You will discover:• Why minimum stay rules matter more than pricing on holidays• How hidden holidays create demand patterns most operators overlook• When three-night minimums increase revenue and when they backfire• How drive-to and fly-to markets require different holiday strategies• Why flexibility can outperform restrictions in high-demand weekends• How shorter stays often support higher ADR during holidays• Which days should carry minimum stay requirements and which should not• How to loosen restrictions without risking empty high-value nights• Why operational constraints like cleaning schedules change strategy• How owner expectations should shape holiday risk toleranceJasper also explores how to implement holiday strategies inside pricing tools like PriceLabs and Wheelhouse, the pros and cons of manual overrides versus seasonal profiles, and why clean, simple setups outperform complex rolling minimum stay rules. He explains how messy pricing configurations reduce visibility, slow learning, and increase the chance of costly mistakes, especially around peak demand periods.💡 Topics Covered:• Holiday demand patterns in short-term rentals• Minimum stay strategy and revenue optimization• Drive-to vs fly-to market behavior• Booking windows and length-of-stay data• Seasonal profiles vs manual overrides• Operational constraints and cleaning logistics• Owner communication and risk management• Pricing tool setup and strategy clarity🔗 Relevant Links:Learn more about Freewyld Foundry → https://www.freewyldfoundry.comFollow Jasper Ribbers → https://www.linkedin.com/in/jasperribbersFollow Freewyld Foundry → https://www.linkedin.com/company/freewyldfoundryKeywords:short-term rentals, airbnb, revenue management, minimum stay strategy, holiday pricing, hidden holidays, STR demand patterns, booking windows, length of stay, pricing tools, PriceLabs, Wheelhouse, seasonal profiles, vacation rentals, ADR optimization, calendar management, STR operations, Freewyld, Freewyld Foundry, Jasper Ribbers, portfolio performance, revenue strategy, holiday demand

👉 Get a Free Revenue Review → https://www.freewyldfoundry.com/reportFind out how much money your portfolio is leaving on the table. Risk-free.What happens when a hurricane wipes out one-third of your short-term rental portfolio in just two weeks, and forces you to rethink everything about how you operate, scale, and survive?In this episode of Get Paid For Your Pad, Kaye Putnam (Head of Marketing at Freewyld and Freewyld Foundry) sits down with Joe Prillaman, co-founder of Host Help, to unpack how a natural disaster became the unexpected turning point that pushed him from managing his own properties to building a professional STR management company overseeing nearly 70 homes.Joe shares the raw reality of losing properties to hurricanes and floods, carrying fixed mortgages and team costs, and realizing that managing for owners is a completely different business than managing your own portfolio. This conversation explores the operational stress, leadership decisions, and system-building required to rebuild stronger—without sacrificing guest experience, five-star reviews, or long-term vision.Whether you manage 10 listings or are already scaling a full property management operation, this episode offers a clear look at what actually breaks as portfolios grow, why quality must be built upfront, and how crisis often accelerates the lessons most operators learn too late.You’ll discover:• How losing one-third of a portfolio forced a major STR business pivot• Why managing owner properties is far harder than managing your own• What changes operationally when you move from 30 to 70 rentals• Why “cute, clean, comfortable” still drives five-star reviews at scale• How guest experience systems prevent small issues from becoming disasters• Why quality onboarding saves years of operational pain• How pricing becomes the highest ROI activity once systems stabilize• Why removing ego is essential as teams and portfolios grow• How disasters expose weaknesses most operators overlook• What it really takes to scale STR management sustainablyJoe and Kaye also explore how hurricanes and floods reshaped Host Help’s risk management approach, why disaster preparedness must be built into STR operations, how AI is reducing daily workload without replacing people, and why most operators underestimate the staffing and systems required to scale beyond survival mode.💡 Topics Covered:• STR portfolio loss and crisis-driven growth• Scaling short-term rental management companies• Guest experience systems and five-star reviews• Onboarding processes and operational checklists• Pricing strategy as a leverage point• Leadership roles and team structure• Disaster preparedness for coastal STR markets• AI in guest communication and operations• Seasonal profitability in beach destinations🔗 Relevant Links:Learn more about Freewyld Foundry → https://www.freewyldfoundry.comFollow Kaye Putnam → https://www.linkedin.com/in/kayeputnamFollow Freewyld Foundry → https://www.linkedin.com/company/freewyldfoundryKeywords:airbnb, short-term rentals, STR property management, scaling STRs, hurricane disaster, STR portfolio loss, vacation rentals, property management systems, guest experience, five-star reviews, STR operations, revenue management, pricing strategy, AI in hospitality, coastal rental markets, STR growth, Freewyld, Freewyld Foundry, Get Paid For Your Pad, Kaye Putnam, Joe Prillaman, Host Help, vacation rental management, scaling property management businesses

👉 Get a Free Revenue Review → https://www.freewyldfoundry.com/reportFind out how much money your portfolio is leaving on the table. Risk-free.What happens when revenue management is treated like a side task instead of a core function in your STR business?In this episode of Get Paid For Your Pad, Jasper Ribbers breaks down how short-term rental operators should think about revenue management ownership in today’s tighter, more competitive market. With margins shrinking and performance no longer rising automatically year over year, Jasper explains why who owns revenue management can be the difference between breaking even and building a profitable business.Whether you currently manage pricing yourself, are considering hiring in-house, or are evaluating revenue management service providers, this episode walks through the real-world trade-offs of each option. Jasper shares practical insights from years of hands-on experience working with STR portfolios at scale and explains why revenue management now deserves the same level of attention as operations, marketing, and distribution.You’ll discover:• Why revenue management has become one of the most critical roles in STR businesses• The advantages and risks of managing revenue yourself as an owner• Why education is essential before owning or delegating pricing decisions• What makes hiring an in-house revenue manager especially difficult in STRs• Why analytical skills alone are not enough for STR revenue management• How poor revenue management decisions quietly reduce profitability• Why ramp-up time often hurts performance when hiring in-house• How the impact of revenue management differs for managers vs owner-operators• Why revenue gains often outweigh the cost of the right expertiseJasper also explores the risks of key person dependency, why working with a team can reduce operational exposure, and what operators should expect when working with a revenue management service provider. He explains the importance of transparent reporting, access to pricing tools, aligned incentives, and clear communication, along with what to watch out for when evaluating potential partners.💡 Topics Covered:• Revenue management ownership models• DIY vs in-house vs outsourced revenue management• STR profitability and margin pressure• Hiring and training revenue managers• Revenue reporting and performance transparency• Key person risk in STR operations• Pricing tools and access considerations• Incentive alignment and fee structures• Evaluating revenue management partners🔗 Relevant Links:Learn more about Freewyld Foundry → https://www.freewyldfoundry.comFollow Jasper Ribbers → https://www.linkedin.com/in/jasperribbersFollow Freewyld Foundry → https://www.linkedin.com/company/freewyldfoundryKeywords:short-term rentals, STR revenue management, revenue manager hiring, pricing strategy, STR profitability, revenue ownership, in-house revenue manager, outsourced revenue management, pricing tools, STR operations, Airbnb pricing, vacation rentals, revenue reporting, Freewyld, Freewyld Foundry, Jasper Ribbers, revenue optimization, portfolio performance

👉 Get a Free Revenue Review → https://www.freewyldfoundry.com/reportFind out how much money your portfolio is leaving on the table. Risk-free.What happens when a short-term rental operator scales past 100 units in a highly seasonal market and still refuses to compromise on quality?In this episode of Get Paid For Your Pad, Kaye Putnam (Head of Marketing at Freewyld and Freewyld Foundry) sits down with Troy Daily, CEO of Elevated Stays, to unpack the real operational, leadership, and systems work behind scaling a 100+ unit STR portfolio in Traverse City. Troy shares how his business grew from a small operation into a professional short-term rental company managing over 100 units, while maintaining brand standards, guest experience, and owner alignment.Whether you are managing 20 listings or planning to scale toward 50 or 100+, this episode gives you a grounded look at what actually breaks when STR portfolios grow and what needs to be built to support that growth. Troy explains why systems, people, and quality controls matter more than rapid acquisition, especially in seasonal markets with extreme occupancy swings.You will discover:• How to scale a 100+ unit STR portfolio without losing quality• Why systems become non-negotiable as STR operations grow• How leadership responsibilities change when scaling past 50 units• Why in-house housekeeping and laundry improved operational control• How quality standards directly impact ADR and repeat bookings• Why owner alignment is critical when managing large STR portfolios• How to approach growth in highly seasonal STR markets• What to consider when evaluating new acquisition opportunitiesKaye and Troy also explore the reality of renovating older properties to meet modern guest expectations, including turning a 150-year-old building into a boutique-style STR asset. They discuss investing over $700,000 in renovations, why not every property belongs in a growing portfolio, and how splitting housekeeping and operations roles created clarity and accountability. The conversation also covers planning during low season, managing 90% summer occupancy and 10% winter occupancy, and why experience-driven amenities can elevate both revenue and brand perception.💡 Topics Covered:• Scaling short-term rental portfolios past 100 units• STR operations, systems, and quality control• Leadership and team structure for growing STR businesses• In-house housekeeping and laundry operations• Owner relations and portfolio alignment• Seasonal occupancy planning and off-season strategy• Renovating legacy properties for STR performance• Guest experience, amenities, and ADR growth🔗 Relevant Links:Learn more about Freewyld Foundry → https://www.freewyldfoundry.comFollow Kaye Putnam → https://www.linkedin.com/in/kayeputnamFollow Freewyld Foundry → https://www.linkedin.com/company/freewyldfoundryKeywords:short-term rentals, STR scaling, 100+ STR units, STR operations, property management, seasonal markets, guest experience, quality control, STR systems, boutique short-term rentals, Airbnb portfolio, vacation rentals, STR leadership, owner relations, ADR optimization, portfolio growth, professional hosting, Freewyld, Freewyld Foundry, Get Paid For Your Pad

👉 Get a Free Revenue Review → https://www.freewyldfoundry.com/reportFind out how much money your portfolio is leaving on the table. Risk-free.What should STR operators actually focus on in 2026 when demand is flat and growth is harder to find?In this episode of Get Paid For Your Pad, Jasper Ribbers shares five practical pieces of advice to help short-term rental operators strengthen their revenue management and stay ahead of the market in 2026. Drawing from what he sees across more than 50 active portfolios, Jasper explains why the next wave of revenue gains will come from better control, pacing, and flexibility rather than expecting demand to save the business.This episode is especially relevant for STR operators managing their own pricing and for revenue managers overseeing multiple portfolios. Jasper breaks down where operators are most often leaving money on the table, how small decisions compound over time, and why many portfolios with strong occupancy are still underperforming on revenue.You will discover:• Why investing in revenue management education pays off year after year• How misusing pricing tools limits performance without operators realizing it• Why pacing is the most important concept in STR revenue management• How to use Market Penetration Index (MPI) to manage the full booking window• Why last minute bookings often drag down ADR• How daily and weekly revenue cadences improve consistency• What a pacing adjustment did for a portfolio that increased RevPAR by 35%Jasper also explains why operators need to prepare for World Cup driven demand in summer 2026, how international travelers behave differently when booking US travel, and why distribution on Booking.com will matter more than ever. He dives into availability settings, minimum stay restrictions, and cancellation policies, showing how overly restrictive rules quietly block demand and reduce total revenue.💡 Topics Covered:• STR revenue management strategy for 2026• Pricing tools and education for operators• Pacing, booking windows, and forward occupancy• Market Penetration Index (MPI)• World Cup 2026 travel demand• Booking.com and international distribution• Availability settings and minimum stay rules• Cancellation policies and booking flexibility• Daily and weekly revenue management cadences🔗 Relevant Links:Learn more about Freewyld Foundry → https://www.freewyldfoundry.comFollow Jasper Ribbers → https://www.linkedin.com/in/jasperribbersFollow Freewyld Foundry → https://www.linkedin.com/company/freewyldfoundryKeywords:short-term rentals, STR revenue management, pricing strategy, pacing, Market Penetration Index, MPI, booking window, STR pricing, Airbnb pricing, Booking.com, revenue optimization, STR operators, vacation rentals, World Cup travel demand, availability settings, cancellation policies, Freewyld, Freewyld Foundry, Get Paid For Your Pad, Jasper Ribbers, STR growth, revenue strategy

👉 Get a Free Revenue Review → https://www.freewyldfoundry.com/reportFind out how much money your portfolio is leaving on the table. Risk-free.What if the biggest revenue mistake most STR operators make isn’t their pricing tool… but the lack of a daily and weekly pricing routine?In this episode of Get Paid For Your Pad, Jasper Ribbers breaks down the real-world revenue management cadence professional STR operators follow to stay ahead of their market. Instead of talking theory, Jasper walks through what actually happens inside a daily pricing review, how to read bookings as data, and why consistent routines matter more than any single pricing rule.Whether you manage 10 listings or 100+, this episode gives you a clear, practical framework for structuring your revenue management time. Jasper explains why most hosts underperform not because they lack tools, but because they don’t know what to look at, when to look at it, or how to interpret booking behavior once it shows up.You will discover:• Why revenue management must be scheduled, not reactive• How reviewing every booking reveals pricing and demand signals• Why early bookings can indicate underpricing or upcoming events• How to spot mistakes in minimum stays and pricing settings• What last-minute inventory tells you about demand and visibility• Why small daily price changes can increase exposure on OTAs• How weekends require different attention than weekdays• Why experience matters more than formulas in pricing decisionsJasper also explains how to review pacing on a weekly basis using Market Penetration Index (MPI), why you shouldn’t overcorrect pricing too quickly, and how small adjustments compound into meaningful revenue gains over time. He shares examples of bookings that reveal hidden demand, misconfigured rules, and missed opportunities that most operators never notice.💡 Topics Covered:• STR revenue management routines• Daily and weekly pricing workflows• Booking reviews as pricing signals• Market Penetration Index (MPI) explained• Booking windows and pacing analysis• Last-minute pricing adjustments• Minimum stay rules and calendar settings• Peak demand dates and minimum pricing• Portfolio-level revenue strategy🔗 Relevant Links:Learn more about Freewyld Foundry → https://www.freewyldfoundry.comFollow Jasper Ribbers → https://www.linkedin.com/in/jasperribbersFollow Freewyld Foundry → https://www.linkedin.com/company/freewyldfoundryKeywords:airbnb, revenue management, short-term rentals, STR pricing, booking windows, pacing, MPI, Market Penetration Index, Airbnb pricing strategy, vacation rentals, portfolio management, dynamic pricing, last-minute bookings, minimum stay rules, peak demand dates, STR revenue optimization, pricing routine, Freewyld, Freewyld Foundry, Jasper Ribbers, Get Paid For Your Pad, STR profitability

👉 Get a Free Revenue Review → https://www.freewyldfoundry.com/reportFind out how much money your portfolio is leaving on the table. Risk-free.What happens when STR CEOs stay busy all day but still feel like the business isn’t moving forward?In this episode of Get Paid For Your Pad, Kaye Putnam (Head of Marketing at Freewyld and Freewyld Foundry) sits down with Eric Moeller, CEO of Freewyld and Freewyld Foundry, to break down one of the most important leadership questions in short-term rentals: where should a CEO actually spend their time as the business scales?Citing research showing that CEOs waste 30 to 50 percent of their time on low-value activities, Eric explains why this problem becomes more dangerous as STR businesses grow. They unpack how decision fatigue pushes leaders toward reactive work, why action is often confused with momentum, and how solving the wrong problems stalls growth even when demand is strong.Whether you manage 10 listings or 100+, this episode will help you rethink priorities, recognize patterns inside your business, and identify the true bottlenecks that require CEO-level attention instead of more activity.You will discover:• Why being busy does not mean your STR business is progressing• How decision fatigue pulls CEOs into low-value tasks• Why letting small fires burn can protect strategic focus• How to identify the biggest bottleneck in your STR business• Why bottlenecks shift as marketing, sales, and fulfillment scale• How trying to fix everything at once slows growth• Why ego often blocks CEOs from stepping into the right role• What high-ROI CEO work looks like at different growth stagesKaye and Eric also explore why pattern recognition is becoming one of the most important CEO skills, how success in one department creates pressure in another, and why focus must be sequential rather than simultaneous. They discuss AI adoption, not as a replacement for people, but as a way to remove repeatable work so leaders can spend time on reasoning, decision-making, and leadership.💡 Topics Covered:• CEO focus and time allocation in STR businesses• Decision fatigue and low-value work• Business bottlenecks in marketing, sales, and fulfillment• Pattern recognition as a leadership skill• Ego and role responsibility at scale• Action versus momentum in growth• AI as a tool to enhance teams, not replace them• Strategic focus for scaling STR operators🔗 Relevant Links:Learn more about Freewyld Foundry → https://www.freewyldfoundry.comFollow Eric Moeller → https://www.linkedin.com/in/ericdmoellerFollow Kaye Putnam → https://www.linkedin.com/in/kayeputnamFollow Freewyld Foundry → https://www.linkedin.com/company/freewyldfoundryKeywords:short-term rentals, STR CEO, STR leadership, business bottlenecks, decision fatigue, pattern recognition, CEO focus, scaling STR business, STR operations, AI in business, delegation, strategic leadership, Freewyld, Freewyld Foundry, Get Paid For Your Pad, Eric Moeller, Kaye Putnam, STR growth, business momentum, CEO mindset

👉 Get a Free Revenue Review → https://www.freewyldfoundry.com/reportFind out how much money your portfolio is leaving on the table. Risk-free.What happens when a hotel revenue director who once managed 10,000 rooms steps into the Short-Term Rental world… and discovers that pricing Airbnbs is far harder than pricing massive resorts?In this episode of Get Paid For Your Pad, Jasper Ribbers sits down with Adriaan Sonneveld, former Director of Revenue for Riu Hotels & Resorts across Aruba, Jamaica, Bahamas, and Punta Cana. After years overseeing one of the largest all-inclusive portfolios in the world, Adriaan entered the STR space, and immediately realized how unpredictable, volatile, and operationally constrained STR revenue management really is.Whether you manage 5 listings or 500, this episode gives you a deep understanding of why hotel playbooks don’t translate into the STR category, why every listing behaves like its own micro-hotel, and how booking windows, guest behavior, and operational realities create a completely different pricing landscape.Adriaan breaks down the core differences he never saw coming, from product uniqueness to hyper-fragmented demand curves, and explains why STR managers must think differently if they want to win in today’s market.You will discover:• Why STR pricing is dramatically harder than hotel pricing• How product uniqueness turns every listing into its own “mini hotel”• Why hotels can rely on last-minute demand but STRs cannot• How booking windows shape revenue strategy in ways hotels never deal with• Why STR rate drops must be deeper near arrival• How operational constraints (cleaning, check-ins, minimum stays) influence pricing• Why cancellations are low-risk for hotels but extremely costly for STRs• How hotel brands enjoy loyalty advantages STRs rarely have• Why forecasting breaks down when STR listings lose “momentum”• How distribution channels differ and why Airbnb dominance changes strategyAdriaan and Jasper also explore why STR volatility makes forecasting harder, how competition behaves differently on Airbnb maps than in hotel markets, and why STR operators must stay tightly connected to operations if they want accurate pricing. They discuss rate parity, overbooking, last-minute sell-through, and why hotel data systems create stability that STRs simply don’t have.💡 Topics Covered:• Hotel vs STR revenue management• Product uniqueness and pricing complexity• Booking windows and pacing strategies• Distribution differences: Airbnb vs OTAs vs direct• Cancellation policies and revenue risk• Forecasting volatility and market unpredictability• Operational constraints and pricing decisions• Brand loyalty, guest expectations, and conversion behavior🔗 Relevant Links:Learn more about Freewyld Foundry → https://www.freewyldfoundry.comFollow Jasper Ribbers → https://www.linkedin.com/in/jasperribbersFollow Freewyld Foundry → https://www.linkedin.com/company/freewyldfoundryKeywords:airbnb, revenue management, short term rentals, hotel vs STR, pricing strategy, booking windows, pacing, ADR optimization, vacation rentals, distribution strategy, operational constraints, forecasting, cancellations, STR profitability, Airbnb pricing, hotel revenue director, Freewyld, Freewyld Foundry, Jasper Ribbers, Adriaan Sonneveld, revenue optimization, portfolio performance

👉 Get a Free Revenue Review → https://www.freewyldfoundry.com/reportFind out how much money your portfolio is leaving on the table. Risk-free.What happens when an STR operator keeps trying to fix chaos with more hires, more tools, or more units, only to realize the real problems were never the ones they were solving?In this episode of Get Paid For Your Pad, Kaye Putnam (Head of Marketing at Freewyld and Freewyld Foundry) and Eric Moeller unpack the hectic host stage, the operational limbo where everything feels urgent, priorities constantly shift, and growth never creates the relief operators expect. They break down why so many STR businesses stay stuck in firefighting mode, why operators chase “squirrels” instead of closing the hole in the roof, and how strategic cadence, clearer systems, and better decision making change the trajectory of a company.Whether you manage a small team or a fast-growing portfolio, this episode shows what actually moves a business out of overwhelm and into intentional, sustainable scale. Kaye and Eric share the behind-the-scenes lessons from a recent Freewyld offsite, including how they restructured workflows, redesigned communication rhythms, and tapped into external expertise to accelerate problem solving.You will discover:• Why operators stay stuck in the hectic host stage even as they grow• How to identify whether a problem is worth solving right now• Why fixing symptoms instead of root issues keeps teams overwhelmed• How daily huddles and weekly cadences expose bottlenecks quickly• Why operators should let small fires burn to stay focused• The role of external experts in speeding up problem solving• How to use long-term vision vs urgency to prioritize decisions• Why overloaded roles create hidden friction across the companyKaye and Eric also explore how offsites transform clarity, why KPIs only matter when tied to action, and how the “jobs to be done” exercise reveals exactly where a CEO is overextended. They discuss how marketing and operations teams can create alignment through lean metrics, why remote teams need intentional structure, and how specialization increases output across every department.💡 Topics Covered:• Hectic host stage and operational overwhelm• Team structure, delegation, and role clarity• Systems thinking and root-cause problem solving• Meeting cadences, daily huddles, and offsite strategy• KPI design, metric prioritization, and accountability• Project management workflows and process rebuilding• Decision making for scale and CEO mindset🔗 Relevant Links:Learn more about Freewyld Foundry → https://www.freewyldfoundry.comFollow Kaye Putnam → https://www.linkedin.com/in/kayeputnamFollow Eric Moeller → https://www.linkedin.com/in/ericmoellerFollow Freewyld Foundry → https://www.linkedin.com/company/freewyldfoundryKeywords:airbnb, hectic host, STR operations, business systems, delegation, team leadership, project management, meeting cadence, KPIs, short term rentals, operational overwhelm, CEO mindset, property management, business scale, Freewyld, Freewyld Foundry, process improvement, STR growth, organizational clarity, team communication, remote teams, workflow design