Advertise on podcast: The Vacation Rental Show

Scott Klein and Shep Love of Prezent join Lynell Gordon on The Vacation Rental Show to explain why vacation rental businesses often struggle with technology implementation rather than a lack of software. With over nine years of Streamline experience, more than 50 new-market launches, and 100-plus onsite evaluations, Scott shares how disconnected departments, inefficient workflows, and underused software features can create unnecessary operational problems. Shep brings a different perspective, focusing on communication, trust, and team alignment. Together, they discuss why operators should understand their existing systems before investing in new tools, how small daily checks can prevent larger problems, and why strong leadership and employee development are essential to improving business performance.

Dana Lubner, Director of Community Development at Rent Responsibly, joins Lynell Gordon on The Vacation Rental Show to explain why property managers need to build advocacy infrastructure before a regulatory crisis puts their businesses at risk. Drawing on her background in property management, advocacy, and leadership development, Dana shares how her own experience with regulatory uncertainty in Denver pushed her to become more involved in representing the STR community. Dana explains why operators don't need to become policy experts to make a difference, how local and state associations can help monitor regulatory changes, and why every property manager should decide how they can contribute through their time, talent, or financial support.

Scott Leggat, Director of Government Affairs & Advocacy at Inhabit, joins Lynell Gordon on The Vacation Rental Show to explain why advocacy should be treated like insurance, payroll, or marketing: a standard cost of doing business in vacation rentals. With 26 years of experience across property management, technology, ownership, and advocacy, Scott has seen firsthand how quickly regulation can change the future of an STR business. Scott breaks down the regulatory issues unfolding across the country, why local rules are often copied from one jurisdiction to another, and how AI-powered regulatory risk assessments can help operators understand what to look out for before making major business decisions.

Bill Faeth believes the short-term rental industry is heading into one of its biggest shifts yet, and AI is going to accelerate it. In his view, the next wave of technology will give guests far more information, choice, and leverage, forcing operators to compete on consistency, service, and trust rather than simply having inventory in the market. In the final part of Lynell's conversation with Bill, they look ahead at what the next few years could mean for vacation rental operators. Bill explains why AI will raise guest expectations, why inconsistent experiences could push travelers back toward hotels, and why smaller operators may actually gain an advantage through personalization. They also discuss how AI is changing daily operations, how quickly tools are evolving, and why human judgment will still matter even as more of the work becomes automated.

Alex Zemianek, CEO of JZ Vacation Rentals, is back for part two of this practical AI series with Lynell Gordon on The Vacation Rental Show. And this time, they’re tackling the move from building an agent to actually training, connecting, and using one inside a vacation rental business. Alex treats AI agents like digital employees: give them access to the right systems, start with limited permissions, teach them how you work, and let their memory and skills improve over time. In this episode, Lynell and Alex show how agents can support executive briefings, email drafting, financial research, bookkeeping, owner reporting, and technical SEO. They also explain why property managers should start with read-only access, how to train an agent on your writing style and internal systems, and why the biggest return on AI often comes from removing the repetitive work that consumes hours every week.

Alex Zemianek, CEO of JZ Vacation Rentals, returns to The Vacation Rental Show with a practical goal: make AI agents simple enough that any property manager can start using them. Rather than focusing on AI hype, Alex breaks the concept down by comparing an agent to a digital employee. It needs a role, a job description, access to the right tools, and ongoing training, just like a human team member. In part one of this series, Lynell and Alex build an executive assistant agent from scratch and show how property managers can use AI to manage email, calendars, Slack, Asana, priorities, and daily commitments. They also explain why you don't need to become an expert prompt writer, how voice dictation can turn your pain points into detailed agent instructions, and why the best place to start is with one repetitive problem you already know you need help solving.

Sofia Rossato, Executive Vice President of Inhabit’s Short-Term Rental division, and Jennifer Cashier, VP of Product for the Short-Term Rental division, bring two complementary perspectives to the AI conversation: Sofia from the strategic and operational side of technology transformation, and Jennifer from the product side, where customer problems are being translated into practical AI capabilities. In this episode of The Vacation Rental Show, Lynell sits down with Sofia and Jennifer to explore how agentic AI is beginning to reshape property management software. They discuss why the industry needs to move beyond “AI for AI’s sake,” how Inhabit is using customer feedback to guide product development, where agents can reduce repetitive work, how AEO could affect direct bookings, and why the most valuable AI investments will be the ones tied to real business outcomes rather than another layer of technology.

Bill Faeth has spent nearly 30 years investing in real estate, but his approach to short-term rentals isn't built around owning the biggest homes or stuffing properties with the most amenities. As the Founder of Build STR Wealth and an active owner and operator, Bill focuses on creating what he calls "super properties": rentals that outperform their market through smart acquisition, a clearly defined guest, strong marketing, thoughtful details, and personal hospitality. In part two of Lynell's conversation with Bill, they unpack what actually separates an average vacation rental from a market-leading one. Bill explains why marketing and revenue management have to work together, why every property should be designed around one specific guest persona, and how small details can create a competitive advantage without competing on price. They also explore personal guest communication, portfolio optimization, owner transparency, and why Bill believes the goal shouldn't be accumulating the most properties, it should be building a business that supports the life you actually want.

Bill Faeth has spent nearly 30 years investing in real estate, building a multi-million-dollar portfolio by strategically shifting from long-term rentals to short-term rentals in 2015. Today, as the founder of Build STR Wealth, he helps investors and operators grow profitable vacation rental businesses through smarter ownership, self-management, and business strategy. But before talking about revenue or returns, Bill believes the industry's biggest opportunity lies somewhere else: bringing people together. In the first part of this three-part series, Lynell sits down with Bill to discuss the divide between legacy property managers and the growing co-host community, why both sides have more in common than they realize, how co-hosting should work when it's done correctly, and why mentorship and community will shape the future of the vacation rental industry.

Resha Shroff is the CEO and founder of Lynx, a hospitality automation technology company that's grown from a startup into a global platform serving thousands of properties. With over fifteen years investing in and operating short term and midterm rentals, plus boutique hotel co-investments, Resha brings a rare, three-sided view of the industry: operator, guest, and technology vendor. In this episode, Lynell and Resha unpack what property managers are getting wrong about AI adoption, starting with the tendency to buy whatever software is marketed as "agentic AI" without understanding what that actually means for their business. Resha breaks down agentic AI as a team of specialized AI agents, not one generic assistant, and makes the case that every AI deployment needs a job description and clear Key Result Areas (KRAs), just like a human hire. She also walks through how she built her own AI executive assistant in Claude, why she recommends operators start their AI journey internally before facing guests, and why honesty with yourself is the real foundation of any AI strategy. This episode is sponsored by Streamline Summit 2026

Dave Roberts is VP of Operations and Strategy at Outer Banks Blue Realty Services and Principal Owner of VRM Excellence, bringing more than thirty years of operational leadership experience across multiple industries. With over a decade in vacation rentals and a Six Sigma certification behind him, he has built a career around lean, data driven systems that keep large scale property management operations running smoothly. Today, he leads operations for a 300 property portfolio while also advising other companies through consulting and collaborative engagements. In this episode, Lynell sits down with Dave to explore why field staff, not the front office, are the true face of a vacation rental company. They discuss where AI and automation genuinely help operations versus where the human element still has to lead, how a Kaizen blitz took Outer Banks Blue's small appliance resolution rate from 63 percent to a sustained 100 percent, why a balanced scorecard across guest, owner, and employee metrics keeps every department accountable, and why micromanagement simply cannot work in high volume vacation rental operations. This episode is sponsored by Streamline Summit 2026

Annie Holcombe has spent more than three decades helping shape the vacation rental industry. As Founder and Chief STRategist at Annie & Co. Solutions, Brand Ambassador for Booking.com, and co-host of Alex & Annie: The Real Women of Vacation Rentals, she helps property managers, suppliers, and technology companies navigate an industry that has become more competitive and more fragmented than ever before. Few people have the relationships, perspective, and industry credibility that Annie has built since entering vacation rentals in 1992. In this episode, Lynell sits down with Annie to discuss how the vacation rental industry has evolved over the past three decades and what operators need to focus on next. They explore the growing divide between legacy vacation rental companies and newer short-term rental operators, why owner retention deserves more attention than owner acquisition, how Booking.com is working to better serve property managers, and why strong relationships remain the industry's greatest competitive advantage.

Alex Zemianek is the CEO of JZ Vacation Rentals, a real estate investor, developer, and vacation rental entrepreneur who has spent years building businesses by focusing on systems, leadership, and operational efficiency. Although he had no technical background, a chance AI roundtable pushed him down a rabbit hole that transformed the way he runs his company. Today, he advises hospitality technology companies while using custom AI agents throughout his own vacation rental operation. In this episode, Lynell sits down with Alex to explore how AI can be incorporated within a vacation rental business. They discuss the difference between simply using ChatGPT and building AI-powered workflows, how custom AI agents are handling everything from bookkeeping and marketing to meeting notes and reporting, why operators should focus on internal AI before customer-facing automation, and how AI can create more time for the hospitality experiences that guests still value most.

Cassondra Liles has spent 25 years helping buyers, sellers, and investors make strategic real estate decisions. As the broker of The Key Team and the author of Real Life Monopoly, she brings a goals-first, data-driven approach to short-term rental investing that cuts through the noise and gets straight to what actually works. Her own vacation rental income portfolio, built across the mountains and the coast of North Carolina, grew from an accidental first purchase near East Carolina University that became one of her best-performing assets. In this episode, Lynell sits down with Cassondra to unpack what separates profitable short-term rental investors from those who struggle to sustain their portfolios. The conversation covers how to evaluate market saturation before you commit, which investment property numbers matter most before you buy, why the hybrid rental model is becoming an increasingly smart ownership strategy, and why so many investors go wrong by leading with emotion instead of data. Cassondra also shares the story behind Real Life Monopoly and the online course she's building to help first-time investors get it right from the start. This episode is sponsored by Streamline Summit.

Some years in vacation rental management leave you with a notebook full of advice you keep coming back to, and 2025 was one of them. In this special compilation of The Vacation Rental Show, host Lynell Gordon revisits sixteen of the year's most listened-to conversations and pulls out the moments that made operators pull over and take notes. The episode moves through four themes that defined the year: building systems that last, putting the guest experience first, protecting your business from safety and payment risk, and remembering that property management is still a people business. You'll hear from founders, operators, advocates, and technologists across the short-term rental industry, each sharing operator-level advice you can act on. Whether you're new to property management or a decade in, there's something here to challenge you or affirm what you already believed. Listen now on Apple Podcasts and Spotify, and stay in community with the best in the business.