The Cohost Bros

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 Show The Co-Host Bros Podcast Instagram: @cohostbros Facebook: @cohostbros YouTube: @cohostbros TikTok: @cohost.bros ⸻ Follow the Hosts Matt 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/

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 Show The Co-Host Bros Podcast Instagram: @cohostbros Facebook: @cohostbros YouTube: @cohostbros TikTok: @cohost.bros ⸻ Follow the Hosts Matt 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 Show The Co-Host Bros Podcast Instagram: @cohostbros Facebook: @cohostbros YouTube: @cohostbros TikTok: @cohost.bros ⸻ Follow the Hosts Matt 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 Show The Co-Host Bros Podcast Instagram: @cohostbros Facebook: @cohostbros YouTube: @cohostbros TikTok: @cohost.bros ⸻ Follow the Hosts Matt 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 Show The Co-Host Bros Podcast Instagram: @cohostbros Facebook: @cohostbros YouTube: @cohostbros TikTok: @cohost.bros ⸻ Follow the Hosts Matt 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/