The Cohost Bros

What if your property management company could run on AI agents that message guests, dispatch cleaners, follow up on tasks, and close the loop without juggling five different tools?Matt and Austin sit down with Jan Sahagun, co-founder of Trellis, a Y Combinator-backed company building AI agents for short-term rental operations.Jan spent years in the STR industry, leading early sales at AI tools for property managers, building the STR Tech Report directory, and attending 20+ industry events. He teamed up with co-founder Lodovico Benvenuti, a former founding AI engineer at Conduit who also operates a 150-listing property management company in Milan. After applying to YC without telling Jan, Lodo got accepted, Jan quit his job, and the two went all in. Today, Trellis has eight engineers, with Jan still leading sales.Here's what you'll learn:– Why STR tech fragmentation creates operational headaches across PMSs, messaging tools, task management, pricing software, CRMs, Slack, and phone calls. – How AI agents can troubleshoot guest issues, dispatch the right team member, reassign tasks when someone declines, and follow up with guests until problems are resolved. – Why most chatbots simply apologize while AI agents actually solve problems. – How one operator with 30 listings onboarded in a week and achieved 60% automation in guest communications and task creation. – What Trellis onboarding looks like, from connecting tools in 30 minutes to running messaging and tasks autonomously within one to two weeks. – Why change management is the real SaaS onboarding challenge and how Trellis operates more like a forward deployed engineer. – How Trellis builds a learning knowledge base that identifies gaps and asks operators to confirm answers, including policies like whether guinea pigs are allowed. – Why Jan believes legacy PMS architecture will struggle to become AI-native and expects major consolidation in STR technology. – The story behind Jan's VRMA trading cards featuring industry personalities, complete with rarity tiers and an unexpected number of demos. – Matt and Jan's experience building with Claude Code and Codex, including Matt's homemade price comparison tool and why the best AI projects cut costs or leverage your weaknesses.Check out what Trellis is building at https://trellistech.com🛠️ Want to build instead of buy?Matt is hosting a 3-day, in-person AI Build-a-Thon for STR hosts in Galveston, Texas, April 13–15, 2027. Limited to 10 spots. Bring an idea and leave with a working tool plus some of Matt's own creations.Early bird pricing ends January 31.Grab your spot: https://hooray-stays.kit.com/026f2a4dbfIf you got value from this episode, be a bro and share the show!👥 Follow The ShowThe Co-Host Bros Podcast Instagram: @cohostbros Facebook: @cohostbros YouTube: @cohostbros TikTok: @cohost.brosFollow the HostsMatt Codd Instagram: @creativecodds TikTok: @creativecodds Facebook: @matt.codd.3 LinkedIn: https://www.linkedin.com/in/matthew-codd-9a3761375/Austin Spitzenberger Instagram: @austin_spitzz TikTok: @austin_spitzz Facebook: @austin.spitzenberger LinkedIn: https://www.linkedin.com/in/austin-spitzenberger-70481111b/

No guest. No agenda. Just Matt and Austin sitting down and saying what is actually on their minds about the state of the short-term rental industry right now.Episode 121 is one of those rare solo episodes where the Co-Host Bros skip the interview format and just have a real conversation. And with everything happening in the STR space right now, there is a lot to unpack. From the Airbnb chores controversy blowing up everywhere to VRBO quietly raising their fees, from AI tools being oversold to the growing pile of software subscriptions that may be costing you more than they are worth, Matt and Austin hold nothing back.Here is what they get into:– Why the Airbnb no-chores policy is more complicated than the media is making it sound and what the real liability concern is that nobody is talking about– Why Matt thinks Airbnb is going to keep pushing host restrictions regardless of the backlash and what that means for your business long term– Why VRBO has not updated their platform in what feels like 47 years and why that matters for operators who rely on it– The Amex Platinum and Airbnb partnership coming in 2026 and what it signals about where Airbnb is trying to position itself– Why Matt is pumping the brakes on adding any new tech right now and only interested in cutting costs and removing subscriptions– How Matt reverse-engineered a software solution using AI for a fraction of what he was paying in subscription fees and why that mindset is the right one for most operators– Why leveraging AI where you are weak instead of solving problems that do not matter is the key distinction between operators who win with AI and those who just stay busy– Why the STR tech space is too crowded, too noisy, and too consolidation-heavy right now to be making big new software commitments.Matt also announces a Houston STR meetup on November 14th 2026 at Carbox. If you are in the Houston area reach out to Matt on Facebook or DM the podcast to get the details. Austin is not going but will absolutely have FOMO.Be a bro and share the show. And if you want to be a sis, that is cool too!👥 Follow The ShowThe Co-Host Bros Podcast Instagram: @CoHostBros Facebook: @CoHostBros YouTube: @CoHostBros TikTok: @cohost.bros⸻Follow the HostsMatt Codd Instagram: @creativecodds TikTok: @creativecodds Facebook: @Matt Codd.codd.3 LinkedIn: https://www.linkedin.com/in/matthew-codd-9a3761375/Austin Spitzenberger Instagram: @austin_spitzz TikTok: @austin_spitzz Facebook: @austin.spitzenberger LinkedIn: https://www.linkedin.com/in/austin-spitzenberger-70481111b/

What if you could flip the majority of your bookings away from Airbnb and VRBO and own that relationship directly? Chris Walker did not just talk about it. He built the tools to make it happen and took his own portfolio from 23% direct to 72% direct this year. Matt and Austin sit down with Chris Walker, CEO and co-founder of Direct Booking Tools, owner of Luxury Rentals of Hilton Head, and one of the most battle-tested operators in the vacation rental industry, for a conversation packed with strategies you can start using immediately.Chris came up the hard way. Johnson and Wales culinary school, 15 years in hospitality serving presidents of the United States, pivoting to real estate in 2003, launching a vacation rental company on Hilton Head Island in 2007, and building from the ground up over nearly two decades. After getting tired of being at the mercy of OTA rule changes and fee structures, he and his CTO partner Josh built a real-time price comparison tool that lives directly on your website, showing guests exactly how much they save by booking direct. The result has helped over 220 vacation rental companies increase direct bookings, with a 97% client retention rate and an average 4-month ROI.Here is what you will learn:– Why most operators think direct bookings require a massive expensive lift and why Chris says that is completely wrong– How a real-time price comparison widget on your website changes the entire guest decision-making process and why showing the savings is the missing piece most operators never address– How Chris went from 23% to 72% direct bookings and what specific steps drove that shift, why travel insurance is one of the most overlooked revenue streams in the STR industry and how Chris is converting 18 to 20% of his guests compared to the industry average of 8 to 10%– How to structure a resort fee bundle that includes damage protection, car passes, and ancillary services in a way that guests actually appreciate– What Vacay Gear is and how offering a $250 beach gear credit per booking moves the conversion lever at the point of decision, why the VRMA conference is evolving and what Chris thinks needs to change to bring more cohesion back to the industry– Why building your direct brand now is the only long term play that actually protects your business from OTA dependency.Chris also shares his take on the current state of the STR industry, what operators at every size can do to take back control of their bookings, and why he is passionate about helping the whole industry win, not just his own company.Find Chris at directbookingtools.com and follow him on all social media at Chris Walker. Do not miss this one; be a bro and share the show!👥 Follow The ShowThe Co-Host Bros Podcast Instagram: @cohostbros Facebook: @cohostbros YouTube: @cohostbros TikTok: @cohost.bros⸻Follow the HostsMatt Codd Instagram: @creativecodds TikTok: @creativecodds Facebook: @matt.codd.3 LinkedIn: https://www.linkedin.com/in/matthew-codd-9a3761375/Austin Spitzenberger Instagram: @austin_spitzz TikTok: @austin_spitzz Facebook: @austin.spitzenberger LinkedIn: https://www.linkedin.com/in/austin-spitzenberger-70481111b/

Michael Dinwiddie is back and a lot has changed in the year since his first appearance on the show. A new baby, a burned software company, and a brand new product that might be the most practical operations tool built specifically for vacation rental managers. Matt and Austin welcome back the founder and CEO of RentalMind for a deep dive into the operating system he built to give STR operators their lives back.Michael manages 27 properties in Washington State through his company Togethere Vacation Rentals, and built RentalMind out of his own pain of trying to run a growing portfolio without a centralized system. The result is an AI-powered operations platform that combines your knowledge base, SOPs, tasks, projects, and property data into one place, and even imports your messy Google Drive and Notion exports and organizes them automatically in under a day.Here is what you will learn:Why getting your operations out of your head and into a system is the single highest leverage move you can make in your STR business, how RentalMind’s AI import feature can take your disorganized Google Drive and get 80% of your system built in less than one day, why Michael set a hard rule to never work after 5 PM or on weekends and how RentalMind made that possible, what Macaw is and how it functions as an AI that your team asks questions to instead of texting you at 11 PM, why pricing per property instead of per user is a game changer for growing property management teams, at what stage Michael recommends operators get started (hint: property three is the tipping point), and how to go from zero to a fully functional operations system in 60 to 90 days.Matt also gives a behind-the-scenes update on how Claude Code is now editing the podcast, creating reels, and writing descriptions automatically, which is kind of meta given the guest.Watch the 15-minute demo and start your free trial at rentalmind.ai/demo. Find Michael on LinkedIn and follow along on Instagram at @rentalmind.ai.👥 Follow The ShowThe Co-Host Bros Podcast Instagram: @cohostbros Facebook: @cohostbros YouTube: @cohostbros TikTok: @cohost.bros⸻Follow the HostsMatt Codd Instagram: @creativecodds TikTok: @creativecodds Facebook: @matt.codd.3 LinkedIn: https://www.linkedin.com/in/matthew-codd-9a3761375/Austin Spitzenberger Instagram: @austin_spitzz TikTok: @austin_spitzz Facebook: @austin.spitzenberger LinkedIn: https://www.linkedin.com/in/austin-spitzenberger-70481111b/

What if the biggest revenue lever in your STR business was not your pricing tool, your channel manager, or your listing photos, but your design? Courtney Petrovich has the receipts to prove it. Matt and Austin sit down with Courtney, founder and principal of Denori Designs, a hospitality design firm specializing in short-term rentals, boutique hotels, and resorts, for one of the most ROI-focused design conversations the show has ever had.Courtney came into the STR world as an investor, not a designer. She sold off long-term rentals in 2023 to fund her first short-term rental in North Myrtle Beach, an eight-bedroom duplex in a complex where no comparable property had ever broken $185,000 in revenue. Through intentional market research, guest avatar targeting, and a design strategy built around golfers in shoulder season and multi-generational families in peak season, she generated $254,000 in her very first year. That result launched Denori Designs, and she has been helping STR operators, co-hosts, and property managers replicate that formula ever since.Here is what you will learn:Why design strategy always comes before furniture and why starting with market research and your guest avatar is the difference between a pretty property and a profitable one, how Courtney doubled the revenue of an eight-bedroom property in a market where every comp said the ceiling was $185,000, what amenitizing actually means in practice and how to decide which amenities have the highest ROI versus which ones are money pits, why she never recommends restaining floors on an investment property and how she thinks about spend decisions as an investor-designer hybrid, how Denori Designs works with property managers as a trusted full-service partner so the manager gets the keys and a beautiful listing without ever managing a contractor, why getting design-ready renderings before construction is finished lets property managers launch listings and capture holiday bookings early, and how Courtney is currently completing Cornell’s Hotel Planning and Design certification to bring hotel-level design thinking to short-term rental properties.If you have been thinking about redesigning an underperforming property or setting up a new one for maximum revenue, this episode gives you the framework to think about it the right way.Slide into Courtney’s DMs on Instagram at @denoridesigns or visit denoridesigns.com to learn more and book a consultation.👥 Follow The ShowThe Co-Host Bros Podcast Instagram: @cohostbros Facebook: @cohostbros YouTube: @cohostbros TikTok: @cohost.bros⸻Follow the HostsMatt Codd Instagram: @creativecodds TikTok: @creativecodds Facebook: @matt.codd.3 LinkedIn: https://www.linkedin.com/in/matthew-codd-9a3761375/Austin Spitzenberger Instagram: @austin_spitzz TikTok: @austin_spitzz Facebook: @austin.spitzenberger LinkedIn: https://www.linkedin.com/in/austin-spitzenberger-70481111b/

What does it look like to build a luxury STR management company from scratch, keep your W2, win a Home Innovation Award before your second birthday as a business, and position yourself for acquisition all at the same time? Carey Antoon is doing exactly that, and this conversation is one of the most grounded and relatable episodes the show has had.Matt and Austin sit down with Carey Antoon, founder of Overnight Digs, the premier luxury vacation rental and property management company serving Hot Springs and Lake Hamilton in Arkansas. Hot Springs is a unique and thriving STR market, home to the nation's first national park, healing thermal waters, a legendary historic downtown, and the only horse racetrack in Arkansas, all of which draw millions of visitors a year looking for an experience that goes beyond a standard hotel room. Carey saw the opportunity and built a boutique, concierge-level brand to serve it.Founded in 2022 by three families and fellow investors, Overnight Digs grew from a single investment property to nearly 50 doors in under three years and was recognized with a Home Innovation Award before most companies even find their footing. The brand has become synonymous with luxury in the Hot Springs market and Carey is already thinking several moves ahead.Here is what you will learn:How Carey got into STRs after selling out of a franchise business and why he chose short-term rentals over other asset classes for the tax benefits and cash flow, how he structured his management company partnership from day one with a licensed broker on record and why that decision paid off, what it is like to build and grow an STR business while still working a W2 and managing time between two worlds, why Carey calls STRs lifestyle assets and how that framing shapes the way he thinks about his portfolio and his future, how Overnight Digs built a reputation as the luxury operator in Hot Springs and what concierge-level service actually looks like in practice, how he thinks about acquisitions and the possibility of acquiring other boutique STR brands to expand his portfolio, and why he is seriously considering attending VRMA for the first time and what he hopes to get out of it.Carey also shares his honest take on what it means to set up a business the right way from the start, even when you do not know yet how big it will become.Find Carey and Overnight Digs on all social media channels at @overnightdigs or visit overnightdigs.com to learn more and book direct. You can also email at Care@overnightdigs👥 Follow The ShowThe Co-Host Bros Podcast Instagram: @cohostbros Facebook: @cohostbros YouTube: @cohostbros TikTok: @cohost.bros⸻Follow the HostsMatt CoddInstagram: @creativecoddsTikTok: @creativecoddsFacebook: @matt.codd.3LinkedIn: https://www.linkedin.com/in/matthew-codd-9a3761375/Austin SpitzenbergerInstagram: @austin_spitzzTikTok: @austin_spitzzFacebook: @austin.spitzenbergerLinkedIn: https://www.linkedin.com/in/austin-spitzenberger-70481111b/

If you have ever wondered why direct bookings feel so hard to crack, Matt Sharp has the answer and it starts with a lesson from the newspaper industry. Matt and Austin sit down with Matt Sharp, co-founder of Bookings Cloud, a performance marketing platform built specifically for short-term rental and vacation rental managers who are tired of paying Airbnb and VRBO to rent access to their own guests.Matt spent nearly 20 years as a senior executive at Advance, one of the largest media companies in the country, overseeing the Alabama Media Group and Michigan markets while also co-founding automotive tech businesses Zero Sum and Cloud Theory. He watched first-hand what happens when a platform like Google or Facebook gets between a business and its customers and strips away the direct relationship. He saw the same pattern forming in the STR industry and built Bookings Cloud to help operators fight back.Here is what you will learn:Why the OTA model is identical to what destroyed local media and why history is about to repeat itself for STR operators who are not building a direct business right now, how Facebook and Instagram retargeting works in the STR space and why it is one of the most underutilized and cost-effective tools available to property managers today, what the average vacation rental traveler journey actually looks like (71 days of research before booking) and how to use that window to capture demand before Airbnb does, why most STR operators are wasting their Facebook ad budget because they are targeting the wrong audiences in the wrong way, how Bookings Cloud uses behavioral data, pixel tracking, and paid media to drive direct bookings for property managers at a fraction of what OTA fees cost, what AI search and LLMs mean for the future of vacation rental discovery and why building your direct presence NOW is the smartest thing you can do before AI agents start booking travel on behalf of consumers, and why Matt believes operators who own their guest relationships will have a massive competitive advantage over those who remain 100% OTA-dependent.This is one of the most forward-thinking marketing conversations the show has ever had. If you manage more than 10 properties and you are not thinking about direct bookings yet, this episode is your wake-up call.Schedule a demo and learn more at bookingscloud.com and find Matt Sharp on LinkedIn.👥 Follow The ShowThe Co-Host Bros Podcast Instagram: @cohostbros Facebook: @cohostbros YouTube: @cohostbros TikTok: @cohost.bros⸻Follow the HostsMatt Codd Instagram: @creativecodds TikTok: @creativecodds Facebook: @matt.codd.3 LinkedIn: https://www.linkedin.com/in/matthew-codd-9a3761375/Austin Spitzenberger Instagram: @austin_spitzz TikTok: @austin_spitzz Facebook: @austin.spitzenberger LinkedIn: https://www.linkedin.com/in/austin-spitzenberger-50481111b/

What does true hospitality actually look like in the short-term rental industry, and why are so many operators getting it wrong? Matt and Austin sit down with Jodie Odlin, Australian-born, UK-based STR host, five-time bestselling author, founder of the Hospitable Hosts book series, winner of the International Shortyz Rentpreneur Award, and founder of The Global Hospitality Collective, for one of the most refreshing and globally-minded conversations the show has ever had.Jodie's journey started with a 450-year-old stone cottage in the Cotswolds, managing properties in one of the most picturesque and sought-after destinations in the UK. With a background in hotel management and a career in five-star hotels around the world, she brought a level of hospitality thinking to short-term rentals that most operators simply never develop. During lockdown, she discovered a community of hosts just like her through the Clubhouse app and had a lightbulb moment: what if she brought their stories together in a book? That book became a number one bestseller, and she has not stopped since.The Hospitable Hosts series now spans five volumes, with contributors from all around the world, including a couples edition celebrating the unique dynamics of running an STR business together, and the STR Sisterhood edition launched on International Women's Day to celebrate the women who make up the majority of Airbnb hosts globally.Here is what you will learn:Why you do not need a luxury property with all the bells and whistles to earn five star reviews and what actually matters more than amenities, how setting guest expectations properly from the start is one of the most underrated skills in the industry, why Jodie believes the STR industry desperately needs a formal hospitality accreditation standard and what she is doing about it, how she manages properties in the Cotswolds remotely from Australia using AI tools to maintain a personal and genuine guest experience, why partnering with local businesses is one of the most effective and overlooked ways to elevate the guest experience, and how the Hospitable Hosts movement has evolved from a single book into a global community of educators, hosts, and property managers committed to raising the bar.Jodie also shares her vision for The Global Hospitality Collective, the STR Hospitality Summit, and how you can submit your own story or diary entry to be featured in an upcoming book.Find everything Jodie is doing at theglobalhospitalitycollective.com and connect with her on Instagram and Facebook as Jodie Odlin.👥 Follow The ShowThe Co-Host Bros Podcast Instagram: @cohostbros Facebook: @cohostbros YouTube: @cohostbros TikTok: @cohost.bros⸻Follow the HostsMatt Codd Instagram: @creativecodds TikTok: @creativecodds Facebook: @matt.codd.3 LinkedIn: https://www.linkedin.com/in/matthew-codd-9a3761375/Austin Spitzenberger Instagram: @austin_spitzz TikTok: @austin_spitzz Facebook: @austin.spitzenberger LinkedIn: https://www.linkedin.com/in/austin-spitzenberger-70481111b/

What does it look like to go from defense engineer to 140 doors under management in just two years? Cameron Masters is living proof that the right mindset, the right mastermind, and a willingness to bet on yourself can compress an entire decade of growth into a fraction of the time. Matt and Austin sit down with Cameron for one of the most tactical and inspiring episodes the show has produced on the topic of scaling fast through acquisitions.Cameron started in real estate in 2020, bought his first STR in 2021, left his W2 engineering job in July of 2023 with a single management client, and by the time this episode was recorded had grown to over 140 doors across two companies: Remote Retreats, focused on the Yosemite, Oak Creek, and Bass Lake area, and Lake Tahoe Accommodations, a 46-year-old legacy company he and his business partner Jeremy acquired all around Lake Tahoe.Here is what you will learn:How Cameron went from zero to 140 doors in under two years and what actually drove that growth, why the VRMA conference completely changed his vision for what this business could become, how he found, evaluated, and structured the acquisition of Lake Tahoe Accommodations including the exact deal structure with a deferred payment instead of a holdback, why he chose to take on owner retention risk himself rather than negotiate a holdback and how he priced that risk into the deal, what the first 90 days of an acquisition actually look like and how to keep owners from walking out the door, how to think about raising capital from investors for an STR company acquisition when traditional financing is not an option, and why joining an acquisitions mastermind early is one of the highest leverage moves a growth-minded STR operator can make.Cameron also gets into the operational realities of integrating a legacy company with 46 years of history and how to modernize systems without losing what made the original business great.Find Cameron on Facebook at Cameron Masters and on Instagram at @cameron.masters_ and feel free to DM him directly.👥 Follow The ShowThe Co-Host Bros Podcast Instagram: @cohostbros Facebook: @cohostbros YouTube: @cohostbros TikTok: @cohost.bros⸻Follow the HostsMatt Codd Instagram: @creativecodds TikTok: @creativecodds Facebook: @matt.codd.3 LinkedIn: https://www.linkedin.com/in/matthew-codd-9a3761375/Austin Spitzenberger Instagram: @austin_spitzz TikTok: @austin_spitzz Facebook: @austin.spitzenberger LinkedIn: https://www.linkedin.com/in/austin-spitzenberger-70481111b/

Some people find their way into the short-term rental industry. Jodi Cleer built her entire career inside it and has seen every angle of the business from the vendor side, the property management side, and now private equity and M&A. Matt and Austin sit down with Jodi Cleer, equity partner of Deal Sourcing at AwayDay and former CMO of I Love Vacations, for one of the most wide-ranging and candid conversations the show has produced.Jodi started in hotels in 2010, transitioned to the vacation rental space as a vendor at RealVoice in 2014, and eventually made the rare leap from vendor to property manager by joining the team at Park City Rental Properties. She helped grow that operation from 235 properties to over 800 across Park City, Sedona, Scottsdale, Whitefish, Montana, and right here in the Texas Hill Country before the company was acquired by AwayDay in 2024. She also personally owns 18 vacation rentals across several of those markets and serves on the board of the VRMA, where she is currently running for election to the board of directors.Here is what you will learn:Why the leap from vendor to property manager almost never happens and how Jodi pulled it off, the genius strategy of buying a home in every new market you expand into and why it creates instant credibility with homeowners and communities, how social media went from pretty pictures to a serious demand generation engine and what viral content actually means for your bottom line, what the M&A process looks like from the inside when you are on the buy side at a private equity backed company, why being an owner but not an operator with 18 properties is actually a smart positioning move even for someone with Jodi's experience, what it takes to get a vacation rental company acquisition-ready and what buyers like AwayDay are actually looking for, and why the VRMA conference is a must attend for any serious STR operator or property manager.Jodi also shares her unfiltered take on the "coopetition" culture in the STR industry and why she counts her competitors as some of her closest allies.Find Jodi on LinkedIn by searching Jodi Cleer, the only one in the world, and reach out directly. She responds to every message.👥 Follow The ShowThe Co-Host Bros Podcast Instagram: @cohostbros Facebook: @cohostbros YouTube: @cohostbros TikTok: @cohost.bros⸻Follow the HostsMatt Codd Instagram: @creativecodds TikTok: @creativecodds Facebook: @matt.codd.3 LinkedIn: https://www.linkedin.com/in/matthew-codd-9a3761375/Austin Spitzenberger Instagram: @austin_spitzz TikTok: @austin_spitzz Facebook: @austin.spitzenberger LinkedIn: https://www.linkedin.com/in/austin-spitzenberger-70481111b/