Walk ’n Talk: The Business Behind Vacation Rentals

In Episode Sixteen, Paul and Chris discuss the downside of head-down building and the importance of creating space to think. They talk about the value of slowing down, understanding how people actually use your product, and why paying attention to the details and the overall feel of a product can matter more than people often realize. You'll hear about: How creating space to think and meditate can...

In Episode Fifteen, Paul and Chris discuss the growing tension between hospitality and process in the vacation rental industry. They explore how rental agreements, fees, upsells, security measures, and other layers of process can sometimes create friction that works against the guest experience. They also share some key takeaways from their experience at Keys100. You’ll hear about: Key takeaways f...

In Episode Fourteen, Paul and Chris discuss the importance of “feel” in software and the challenge of balancing simplicity, speed, and information density in a product as large as OwnerRez. They talk through how the product has evolved over the years, why you sometimes need to prune and strip things back, and how designing for new users can bring a fresh perspective. You’ll hear about: Why “feel”...

In Episode Thirteen, Paul and Chris break down the undervalued power of saying no and how that clears the way for the right yes. They talk through recent investment decisions, how their thinking has shifted over time, and how to recognize a property with the right “feeling.” You’ll hear about: Why saying no matters just as much as saying yes Time in the market vs timing the market What makes a pro...

In Episode Twelve, Paul and Chris are joined by Dan Waldschmidt, an international business strategist, speaker, author, and extreme athlete. They talk about what it really means to be elite, and why it is not just about talent, luck, or having the best idea. They unpack the mindset behind OwnerRez’s long-standing “Elite” messaging and explore how ordinary people and companies can build toward extr...

In Episode Eleven, Paul and Chris dive into the frequently debated topic of cancellation policies and share what the data is actually showing. They walk through why there isn’t a one-size-fits-all approach, and how property type, price point, and booking volume all play a role in choosing the right policy for a vacation rental. They also discuss how cancellation policies tie into the guest experie...

In Episode Ten, Paul and Chris talk about execution, why sometimes “ugly” is the most effective way to build, and the danger of getting caught up in the design before the underlying functionality is there. They also discuss how AI is changing the way they develop the product, lowering the cost of testing new ideas, and making it easier to maintain a consistent mindset long enough to refine and imp...

In Episode Nine, Paul and Chris talk about deep work, the importance of creating that intentional space, and the balance between staying focused and staying available to the team. They discuss how this balance impacts growth, the need to stay lean, and how learning to delegate and trust the team creates space for higher-impact work. You’ll hear about: The importance of making space for deep work W...

In Episode Eight, Paul and Chris discuss the idea of “hiring for pain” and how they are learning to recognize the difference between real problems and temporary pressure. They explore how pain can show up across teams during periods of growth, why understanding the problem is critical before hiring, and how slowing down can sometimes lead to better long-term results. You’ll hear about: How “hiring...

In Episode Seven, Paul and Chris dig into whether conferences actually provide real value for vacation rental operators and software companies. They talk through OwnerRez’s history with conferences, how they think about marketing spend, and why relationship-building is their top priority. They also share some exciting updates around OwnerRez events in 2026. You’ll hear about: Why Paul questions th...

In Episode Six, Paul and Chris talk about personal endurance challenges and how quickly Q1 ramps up once the year gets underway. They discuss the excitement and frustrations of early-year planning, how their approach to delegation is evolving, and why giving teams more ownership is becoming increasingly important as the company grows. They also explore how AI is changing what they build, what comp...

In Episode Five, Paul and Chris reflect on the 2025 OwnerRez company retreat at Tanque Verde Ranch and the deeper conversations it sparked about growth, culture, and what it means to truly level up. They discuss how a fully remote team builds a shared voice, why maturity requires intentional systems, and how AI is reshaping not just how we work, but the pride we take in our work, creativity, and w...

In Episode Four, Paul and Chris dive into the topic of AI, automation, and why doing meaningful work with AI requires discipline and continuous improvement. They discuss how AI is often a marketing buzzword, but when applied effectively, can become a true force multiplier. The conversation explores the moment AI crossed from novelty to a powerful tool, why OwnerRez is uniquely positioned to build...

In Episode Three, Paul and Chris take a look at some of the biggest myths versus realities in the vacation rental industry. They talk through how the industry has shifted over the years from a hobbyist side gig into a competitive, professionalized market where standing out requires true hospitality, well-run operations, and a long-term mindset. Drawing on Paul’s experience running Shenrent with hi...

In Episode Two, Paul and Chris revisit some of the hardest and best days in OwnerRez history, from a server issue that nearly wiped out thousands of booking records to the day they both began working full-time on OwnerRez. They also talk openly about how they have handled burnout, family life, and share some of the hobbies that have helped them stay grounded over the years. You’ll hear about: The...

In the first episode of Walk ’n Talk: The Business Behind Vacation Rentals, OwnerRez co-founders Paul and Chris share the origin story behind their 20-year partnership and the early days that shaped the company. They talk about how appetite, innovation, and execution became the formula that’s guided every phase of OwnerRez, starting as teenage coders, working with their mentor Ed, building early p...