Walk ’n Talk: The Business Behind Vacation Rentals Podcast
Walk ’n Talk: The Business Behind Vacation Rentals pulls back the curtain on what it really takes to build, scale, and run a successful company in the vacation rental industry.
Hosted by Paul and Chris, co-founders of OwnerRez, the show is inspired by their long-standing ritual: taking weekly walks together to think through problems, debate ideas, and talk candidly about the business. These walking conversations have shaped countless product decisions, strategy shifts, and breakthrough moments. Now, you get to listen in.
Each episode dives into the lessons learned from more than a decade of bootstrapping, product building, customer challenges, industry changes, and the day-to-day realities of running a tech company that serves thousands of property managers.
Whether you’re a host, manager, entrepreneur, or just curious how vacation rental software gets built, this podcast gives you real conversations, real experience, and real insight, one walk at a time.
EP6 - Delegation, Company Culture, and What’s Ahead in 2026
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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 company culture means to them, and share a look ahead at what’s coming in 2026, all through the lens of working "on" the business versus working "in" the business.
You’ll hear about:
- Personal challenges
- The excitement and frustration of Q1
- How delegation must evolve with growth
- How AI is changing how we build and what we build
- How to sustain and build culture
- Working on the business versus working in the business
- A look ahead to what’s coming in 2026
It’s a peek behind the scenes at how Paul and Chris are approaching growth and delegation without losing the unique culture that’s defined the product.
EP5 - Inside the 2025 OwnerRez Retreat: Voice, Growth, and Leveling Up
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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 what it means to be authentically human.
You’ll hear about:
- How the retreat was designed to bring people together
- What “leveling up” really means for a growing company
- Why structured PTO and clearer processes can actually be healthier
- How customer focus and pricing strategies shape the future
- What it means to have a human voice in an AI-driven world
- How pride in your work evolves as tools get more powerful
It’s a candid, behind-the-scenes conversation about growth, culture, and the intentional choices required to build a company that continues to scale without losing its identity.
EP4 - AI, Automation, and Continuous Improvement
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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 industry-leading AI tools like Rezzy, and how deep data access and execution make all the difference. They also speak candidly about the risks of copy-and-paste AI, the importance of preserving the human voice, and how AI is shaping the vacation rental industry as a whole.
You’ll hear about:
- Why AI is easy for simple tasks but hard for truly powerful ones
- How deep data access and tooling make AI agents effective
- Why stapled-on AI features fall short
- How Rezzy is changing the vacation rental space
- Using sentiment analysis to understand guest experience beyond reviews
- How AI changes jobs by amplifying people, not replacing them
It is a wide-ranging, honest discussion about where AI is headed, how it is already reshaping the vacation rental industry, and why the companies willing to rethink systems from the ground up, rather than chase trends, will be the ones that win.
EP3 - Myths vs. Reality: What It Really Takes to Succeed in Vacation Rentals
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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 his wife, along with years of watching thousands of OwnerRez users grow, they share what new owners often misunderstand, why a genuine interest in hospitality matters more than most people expect, and how having the right systems in place plays a major role in long-term success.
You’ll hear about:
- Some of the biggest myths in vacation rentals versus the day-to-day reality
- Which early STR “cheat codes” went away as the industry became more professionalized
- The difference a hospitality mindset makes when running a vacation rental
- Lessons from running Shenrent and how OwnerRez continues to be shaped through personal experience
- Why saying no early, buying the right properties, and understanding the true costs matter
- How having the right systems in place makes all the difference
- The balance between caring deeply for your property and giving guests space
- What mindset makes a vacation rental owner a good long-term partner
It is an honest conversation about expectations versus reality, and the hard-earned lessons that separate operators who build something sustainable from those who burn out or become frustrated along the way.
EP2 - The Hardest Day, the Best Day & Avoiding Burnout as Founders
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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 software update that nearly wiped out thousands of booking records
- The emotional and operational impact of the outage
- The moment they realized OwnerRez was here to stay
- How transparency has guided OwnerRez through the years
- What burnout really looks like for founders and why it is not just about long hours
- How Paul and Chris balance work, family, routines, and hobbies through different seasons
It’s an honest, behind-the-scenes conversation about fragility, resilience, and the genuine investment it takes to build something that thousands of people rely on every day.
EP1 - Appetite, Innovation & Execution: How OwnerRez Was Built
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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 products, and eventually rebooting everything in 2013 to create the modern OwnerRez platform.
From burn-down charts and bootstrapping years to landing major channel integrations, this episode dives into the mindset, history, and relentless focus on speed and user experience that built the company.
A raw, honest look at how OwnerRez began and why its founders still love building it.