Grow STR Podcast

Jeff Smith’s first startup pitch went so badly that the organizers asked him to stop talking. At his next competition, he finished on time—and won first place. In this episode of the Grow STR Podcast, Jeff shares his path from banking and real estate photography into accelerators, pitch competitions, proptech, and the venture-backed startup world. He explains the major difference between building...

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, an...

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 fr...

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 throu...

"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...

"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 rea...

"We were at a breaking point three years ago. We were either going to quit the business or sell our properties. Today, we manage 33 units and have a $10 million goal." In this episode of the Grow STR Podcast, Sam Mistretta sits down with  Glenn Russo , founder of Russo Property Group. Glenn spent two decades as a systems architect in corporate IT before trading "system architecture&...

"I saw grown men and women crying in the corporate office. I looked at the manager and said, 'How do I keep my number and start selling for myself?' That was the day I chose freedom." In this episode of the Grow STR Podcast, Sam Mistretta is joined by  Matthew Pearce —a D1 athlete, Ironman triathlete, and high-level real estate professional. Matthew shares his masterclass in resi...

"I knew that if I didn't take this chance, I would be kicking myself for the rest of my life." In this episode of the Grow STR Podcast, Donnie Dimes and Sam Mistretta sit down with  Gil Chan , the founder and CEO of  CraftedStays . Gil is a veteran of six Silicon Valley startups (including one bought by Samsung), but he risked it all to solve one of the biggest problems in the short-...

"I slid the paper across the table. One of them looked like she saw a ghost; the other looked like they saw somebody die. That was the day I chose freedom." In this special episode of the Grow STR Podcast, Donnie Dimes flips the script and takes co-host  Sam Mistretta  back in the "DeLorean" to trace his journey from corporate IT management to full-time Short-Term Rental mogul....

"I was moonlighting at Expedia, plotting my escape. Two years later, I’m managing a boutique hotel and buying back my time." In this episode of the Grow STR Podcast, Donnie Dimes and Sam Mistretta are joined by  Michael Dinwiddie , founder of Together Vacation Rentals and the creator of Hospitality HQ. Michael reveals how he transitioned from a corporate marketing role at Expedia Group t...

"We leave our W2 and say, 'I'm free!'—but because we don't learn  how  to be free, we bring the same corporate chains with us." In this episode of the Grow STR Podcast, Donnie Dimes and Sam Mistretta tackle the "Hustle Culture" trap. If you find yourself waking up with dread instead of joy, you might have accidentally built a business that you hate showing up to. Donnie and Sam discuss the concept...

"If you do this thing wrong, it can terminate your business. If you do it right, your business starts humming while you sleep." In this episode of the Grow STR Podcast, Donnie Dimes and Sam Mistretta tackle one of the most requested (and feared) topics in the short-term rental world:  Virtual Assistants (VAs).  Most operators escape the W2 only to build another 80-hour-a-week prison for...

"They trade freedom for stability. If you just want a roof, a bed, and a meal, just go to jail. If you want a life, take the leap." In this episode of the Grow STR Podcast, Donnie Dimes and Sam Mistretta are joined by  David Winterling , the force behind "Wiki Life" in Wiki Wachee, Florida. David shares his "no-filter" journey of leaving a 20-year career in corporate...

"Simplicity is an avenue for action. Overcomplication is just adding more streets to the intersection." In this episode of the Grow STR Podcast, Donnie Dimes and Sam Maretta break down why so many entrepreneurs are "stuck in the snow globe"—over-thinking their technology, their websites, and their "professional" image while missing out on actual revenue. They share a...

"People without a vision will perish." In this episode of the Grow STR Podcast, Donnie Dimes and Sam Mistretta dive into the single biggest reason entrepreneurs fail to hit their goals:  A lack of clear vision.  If you find yourself starting projects but never finishing them, or if you feel busy but not "productive," this conversation is the manual you need to reset. Donnie and...

"If you want to grow fast, you have to go to where the investors already are." In this episode of the Grow STR Podcast, Donnie and Sam break down the #1 growth strategy used by operators with 40+ properties:  Realtor Relationships.  While most people are distracted by the "shiny objects" of new tech, the real winners in hospitality are building networks with the people who are...

In this episode, we dive into the "burnout to breakthrough" journey of Michael Morrison. Michael spent 12 years as a high-level financial advisor, grinding through 80-hour work weeks. After a sudden corporate layoff left him stranded in a new country with a new wife, he was forced to turn his "side hustle" into a professional management company. Today, Michael manages 12 proper...

GROW-STR Podcast Episode: How To Kill Distractions & Stay Consistent In Your STR Business Join Donnie and Sam as they talk about the #1 silent business killer in short-term rentals: bright shiny object syndrome . If you’ve ever scrapped a plan, started a new plan, bought a new tool, switched systems, switched markets, and somehow ended up more busy with less progress , this episode is your int...

GROW-STR Podcast Episode 2: Getting NEW Connections - The Fastest Path To Cash Join Donnie and Sam as they reveal the most powerful strategy for growing your short-term rental business: building genuine connections (not cold calling!). Learn why this approach is called "the fastest path to cash" and discover the exact script that generated multiple deals after just 50 attempts. Listen &a...

Using Story To Sell Transform cold calls into warm conversations. Hosts Donnie Dimes and Sam Mistretta reveal how storytelling makes sales feel natural instead of scary. Learn why memorizing success stories beats scripted pitches, how to handle objections without feeling pushy, and the exact framework that turns "no thanks" into signed contracts. Perfect for short-term rental co-hosts, p...