From 40 Rentals to 20: Bernie Cesario on STR Profit, Midterm Rentals, and Investor Partnerships

From 40 Rentals to 20: Bernie Cesario on STR Profit, Midterm Rentals, and Investor Partnerships

Bernie Cesario built Eagle Stays by learning that more properties do not always mean a better business. In this episode of the Grow STR Podcast, Bernie shares how he transitioned from a W2 career in mortgage banking and IT into short-term rentals, midterm rentals, and investor-backed property management. He explains why he cut his portfolio from 40 units to around 20, how revenue stayed strong, and why smaller units were taking too much time for too little return. Bernie also breaks down how insurance relocation stays and construction crews became powerful midterm rental opportunities, how large homes perform in urban markets, and why investor partnerships work best when trust, sweat equity, and clear agreements are in place. This episode is for short-term rental hosts, midterm rental operators, Airbnb co-hosts, property managers, and real estate investors who want to grow smarter instead of simply adding more doors. Connect with Bernie: Eagle Stays is an accomplished Airbnb Superhost and VRBO Premier Host, as well as co-host a portfolio of properties under their own platform,  [http://eaglestays.com/]EagleStays.com [http://eaglestays.com/].   In addition to short-term rentals, they also rent the portfolio as mid-term rentals. They work closely with investors to host properties, identify and acquire homes for STR and MTR use, and create opportunities designed to fill sustainable, long-term financial goals and passive income through professionally managed rentals. Socials: https://www.facebook.com/bernie.cesareo [https://www.facebook.com/bernie.cesareo] https://www.instagram.com/the_str_bnb_guy [https://www.instagram.com/the_str_bnb_guy] https://www.linkedin.com/in/bernie-cesareo-6979647/ [https://www.linkedin.com/in/bernie-cesareo-6979647/] https://EagleStays.com/ [https://eaglestays.com/]

From Healthcare to STR Co-Host: Kelsey Johnson on Networking, Design, and Growing a Rental Management Business

Kelsey Johnson traded her healthcare career for short-term rental co-hosting and property management, and built her business through referrals, networking, guest experience, and better owner support. In this episode of the Grow STR Podcast, Kelsey shares how she discovered short-term rentals, learned through mentorship, landed her first co-hosting client through BNI, and eventually stepped away from healthcare to focus on her property management business full-time. She also talks about the real work behind growing a co-hosting business: networking consistently, onboarding owners, setting expectations, improving design, using professional STR photography, avoiding unnecessary tech tools, and knowing when to hire help. This episode is for short-term rental hosts, co-hosts, Airbnb operators, and property managers who want to grow through relationships, referrals, better systems, and unforgettable guest experiences. Connect with Kelsey: Instagram/Facebook: @embarkpropertymanagementllc Email: info@embarkpropertymanagementllc.com

From Firefighter to 30 Rentals: Kyle Myers on Scaling Roadrunner Property Management

Kyle Myers left the fire service and built Roadrunner Property Management from the ground up. In this episode of the Grow STR Podcast, Kyle shares how he went from firefighter and paramedic to short-term rental operator, co-host, and property management founder. He talks about buying a six-tiny-home property, moving his family into a fifth-wheel to make the business work, learning operations through real pressure, and scaling into multiple markets. Kyle also breaks down the practical side of growth: handling guest complaints, hiring VAs, building remote teams, managing cleaners and inspectors, choosing the right markets, and knowing when to say no to the wrong clients. This episode is for short-term rental hosts, co-hosts, Airbnb operators, and real estate entrepreneurs who want to grow with better systems, stronger vendor relationships, and more intentional leadership. Kyal Meyers is the founder of Roadrunner Property Management, committed to building legacies through uncommon care. He specializes in cultivating long-term relationships with intentional investors by delivering excellence in both property operations and guest experience. Guided by the core values of uncommon care, legacy building, and humble integrity, Kyal is focused on growing a healthy, high-performing short-term rental portfolio that truly meets the needs of its market. A former firefighter who left the service after nearly a decade, Kyal embraced risk—moving his family into an RV while launching his business and investing heavily in personal growth—to build something lasting. Above all, he is a leader and helper devoted to his family, community, and living in a way that loves like Jesus. Where to find me: web: roadrunnerstr.com [http://roadrunnerstr.com/], insta: @roadrunner_propertymanagement email: kyal@roadrunnerpm.com [kyal@roadrunnerpm.com]

From 1st Grade Teacher to 19 Airbnb Listings: Colleen Cole’s STR Journey

"I didn't wave a magic wand. It took nine months after starting to get our first 'Yes.' Today, we are managing 8 properties with 11 more launching this season." In this episode of the Grow STR Podcast, Sam Mistretta sits down with Colleen Cole, co-founder of Hereford Place Hospitality. Colleen shares her raw and inspiring journey from being a first-grade teacher to building a thriving short-term rental management company in the Pocono Mountains. Colleen reveals the mindset shift required to move from the "institutionalized" world of the W2 to the 24/7 reality of property management. We discuss how she landed her first client through a larger competitor, why she refuses to pay realtor referral fees, and her massive vision for an "ADA-Compliant Empire" that changes how families with disabilities experience vacations. In this episode, we cover: * The 9-Month Wall: Why most people quit before the "Yes" and how Colleen stayed persistent. * Networking with "Competitors": How a conversation at a conference with Wanderhome led to their first listing. * The Realtor Partnership Blueprint: How to provide resources to agents that help them sell more houses and look like heroes to their clients. * Commission-Free Growth: Why Colleen focuses on long-term relationships over transactional referral fees. * The Teacher to CEO Identity Shift: Overcoming the "Identity Crisis" when leaving a lifelong career. * The ADA Vision: Why Hereford Place is focusing on creating high-end, truly accessible stays for families with extra needs. Action Item: Stop assuming people don't need your help. Start conversations, lead with value, and find your support tribe. Resources Mentioned in this Episode: * Go STR Marketing: Ready to scale your co-hosting game with a 100% done-for-you lead solution? Book a demo at www.gostmarketing.com [https://www.google.com/url?sa=E&q=http%3A%2F%2Fwww.gostmarketing.com] * Short-Term Rental Secrets: The mastermind where Colleen and Sam connected. Connect with Colleen Cole: * Colleen Coale co-owns and operates Hurford Place Hospitality with her husband, Matt, specializing in vacation rental management in the Pocono Mountains of Pennsylvania. As parents to two daughters, they’ve built their business around a shared love for hosting and creating welcoming spaces where families can make lasting memories. Their approach combines deep knowledge of the local market with hands-on, above-and-beyond hospitality. They are passionate about helping homeowners succeed while ensuring every guest experience feels thoughtful, comfortable, and memorable. Together, they focus on serving others through genuine care, attention to detail, and a commitment to excellence. Social Media:Instagram @WelcomeToHurfordPlaceFacebook Colleen Coale or https://www.facebook.com/profile.php?id=61553603442076 [https://www.facebook.com/profile.php?id=61553603442076] Connect with Grow STR: If Colleen’s story of resilience helped you push through a tough week, please follow the show and leave us a 5-star review!

How to Scale from 17 to 200+ Clients: The Power of a Niche with Ben Coons

"We packed our backpacks, got a one-way ticket to Cancun, and spent 16 months traveling. We made it all the way to Japan before I realized I was ready to build something of my own." In this episode of the Grow STR Podcast, Sam Mistretta sits down with his own bookkeeper, Ben Coons, the founder of Keystone Bookkeepers. Ben isn't your average accountant—he’s a world-traveler, a real estate investor, and a systems genius who has built a specialized firm managing the finances of over 150 short-term rental property managers. Ben shares his radical journey from turning down a CFO position to living out of a rooftop tent in Africa, and then returning to the states to scale a global team of 85 people. If you are an STR operator looking for financial clarity or an entrepreneur looking for the blueprint on how to "buy back your time," this conversation is a goldmine. In this episode, we cover: * The CFO "No": Why Ben walked away from a corporate ladder to find freedom in a backpack. * The Buy vs. Build Hack: How Ben used Google Maps and handwritten postcards to buy his first 18 bookkeeping clients. * The "Two Laptop" Grind: Training a team at 5:00 AM while working a full-time corporate job. * Simulated Onboarding: How Ben uses AI (Claude) to create a simulated environment that trains his global team in record time. * Protecting the Marriage: Why Ben and his wife (a former teacher turned property manager) never skip their Thursday date night. * Business on Wheels: Ben’s upcoming plan to run his multi-million dollar business while traveling Europe in a custom Ford Transit van. Action Item: Stop being a "generalist." Find your niche, document one process a day, and build a team that allows you to live the life you actually want. Resources Mentioned in this Episode: * Keystone Bookkeepers: Get financial clarity for your STR business at www.keystonebookkeepers.com [https://www.google.com/url?sa=E&q=http%3A%2F%2Fwww.keystonebookkeepers.com] * Book: Buy Back Your Time by Dan Martell. * Go STR Marketing: Scale your co-hosting game at www.gostmarketing.com [https://www.google.com/url?sa=E&q=http%3A%2F%2Fwww.gostmarketing.com] Connect with Ben Coons: * LinkedIn: Ben Coons * Facebook: Ben Coons Connect with Grow STR: If Ben’s "Van Life" vision inspired you, please follow the show and leave us a 5-star review!