Grow STR Podcast

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!

From 20 Years in IT to 33 Units: The Glenn Russo W2 Exit Story

"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" for "wealth architecture" through real estate. Glenn shares the raw truth about the "operational weight" that almost broke his business and his marriage, and the exact mindset shift that allowed him to move from a stressed-out side-hustler to a world-class CEO. In this episode, we cover: * The Breaking Point: Why Glenn almost walked away from STRs and how a single visualization exercise changed everything. * The EOS Framework: How hiring an "Integrator" saved Glenn's wife from operational burnout. * The Identity Shift: The difficulty of letting go of the "W2 Identity" to embrace being a full-time entrepreneur. * Closing on the Move: How Glenn signed 5 new co-hosting deals during a 6-week family road trip through Canada and Maine. * The "Paid Internship": Why dealing with difficult property owners early on prepared Glenn for his current luxury portfolio. * Multiplication vs. Growth: Moving from one property a year to one deal a week. Action Item: Stop being "motivated by laziness" and start being motivated by intentionality. Set your standards for the clients you want, and the growth will follow. Resources Mentioned in this Episode: * EOS (Entrepreneurial Operating System): The framework Glenn used to scale. * Go STR Marketing: The system Glenn used to automate his lead generation. www.gostmarketing.com [https://www.google.com/url?sa=E&q=http%3A%2F%2Fwww.gostmarketing.com] * Books: The Pumpkin Plan by Mike Michalowicz & Rich Dad Poor Dad by Robert Kiyosaki. Connect with Glenn Russo: * Instagram: @GlennMRusso [https://www.google.com/url?sa=E&q=https%3A%2F%2Fwww.instagram.com%2Fglennmrusso] * Website: www.russopg.com [https://www.google.com/url?sa=E&q=http%3A%2F%2Fwww.russopg.com] Connect with Grow STR: If Glenn’s journey from IT to 33 units inspired you, please follow the show and leave us a 5-star review!

Why I Smiled During a Mass Layoff: The Ironman Mindset with Matthew Pearce

"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 resilience: from being the #1 health insurance producer in Louisiana to navigating a sudden corporate layoff that became the greatest gift of his career. Matthew and Sam dive deep into the synergy between short-term rental operators and real estate agents. If you are an STR operator, Matthew reveals exactly what realtors are looking for and how you can make yourself an indispensable part of their team. In this episode, we cover: * The "Ironman" Breakdown: Completing a 140-mile race with a separated shoulder and what it taught Matthew about business adversity. * The Writing on the Wall: Identifying the signs of corporate micromanagement and preparing your "exit letter." * Asset Protection: Why short-term rentals actually protect physical property better than long-term tenants. * The Realtor Pitch: How to provide value to real estate agents so they want to refer their best investors to you. * Ninja Selling: Adopting the "Go-Giver" mindset to provide more value than you ask for in return. * The Success Hierarchy: Why Matthew puts Faith and Family before Business—and how it drives his production. Action Item: Stop operating from a place of fear. If the W2 is capping your potential, it’s time to start betting on yourself. Resources Mentioned in this Episode: * Books: Who Not How by Dan Sullivan & The Go-Giver by Bob Burg. * Go STR Marketing: Ready to scale your co-hosting game? Book a demo at www.gostmarketing.com [https://www.google.com/url?sa=E&q=http%3A%2F%2Fwww.gostmarketing.com] Connect with Matthew Pearce: * Instagram: @mtcop91 [https://www.google.com/url?sa=E&q=https%3A%2F%2Fwww.instagram.com%2Fmtcop91] * Facebook: Matthew Pearce [https://www.google.com/url?sa=E&q=https%3A%2F%2Fwww.facebook.com%2Fmatthew.pearce.52] * Website: MatthewPearce.revrealtors.com [https://www.google.com/url?sa=E&q=http%3A%2F%2FMatthewPearce.revrealtors.com] Connect with Grow STR: If Matthew’s "Ironman Mindset" inspired you, please follow the show and leave us a 5-star review!

Quitting My 6-Figure Career with Only 20% Income Replaced: Gil Chan’s Story

"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-term rental industry: the over-reliance on Airbnb. Gil shares the radical story of leaving a healthy six-figure tech salary when his STR business had only replaced 20% of his income. He breaks down the "perfect storm" that led to the creation of the "Shopify for Short-Term Rentals" and how he used e-commerce principles to 4x his company’s revenue in just one year. In this episode, we cover: * The "Kick Myself" Test: How to know when it is finally time to leave your W2. * The PowerPoint Strategy: How Gil treated his marriage like a board meeting to build trust and get his wife on board with remote investing. * The Shopify Moment: Why property managers need a high-converting direct booking site that works as well as an e-commerce store. * Bootstrapping vs. VC: Why Gil turned down outside funding to keep his customers at the forefront of his product design. * The Future of Search (AEO): How LLMs like ChatGPT and Perplexity are changing how guests find your properties in 2026. * The Best Growth Move: Why Gil still onboards every single customer personally. Action Item: Stop being a "viral influencer" and start being an expert. Use AI to learn what you don't know, but keep your authenticity in what you do. Connect with Gil Chan: * Gil Chan is the founder and CEO of CraftedStays, a direct booking website platform for short-term rental operators, recently named Website Builder of the Year by Travel and Hospitality Tech Outlook. He has spent 15 years in tech and worked at six startups across eCommerce, IoT, and logistics, including leading API integrations with Shopify, Wix, and Squarespace at Shippo. After becoming a short-term rental host in the Great Smoky Mountains and Branson, he experienced the limits of outdated PMS websites and high-cost agency builds, which led him to create a scalable alternative. CraftedStays launched in January 2024 as a mobile-first platform that integrates with systems such as Guesty, Hostaway, Hostfully, Hospitable, and OwnerRez, enabling operators to launch SEO-ready sites in minutes. Gil also hosts the Booked Solid Show podcast, speaks at industry events, and focuses on helping operators gain more control over their direct bookings. * Website: https://craftedstays.co [https://craftedstays.co/] * Instagram: https://www.instagram.com/craftedstays [https://www.instagram.com/craftedstays] * Facebook: https://www.facebook.com/gilbertchan [https://www.facebook.com/gilbertchan] * LinkedIn: https://www.linkedin.com/in/thegilbertchan/ [https://www.linkedin.com/in/thegilbertchan/] Connect with Grow STR: If Gil’s risk-taking spirit inspired you today, please follow the show and leave us a 5-star review!

Why I "Retired" from My 6-Figure Career at 39: Sam Mistretta’s STR Journey

"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. Sam reveals the irony of his corporate exit: how he was recognized with national awards one month and put on a "Performance Improvement Plan" the next. That moment of corporate betrayal became the catalyst for Sam to finally use the resignation letter that had been sitting on his desk for an entire year. In this episode, we cover: * The "Chili" vs. "Steak" Management Model: Why Sam moved from the low-margin world of long-term rentals to high-cash-flow STRs. * Mowing the Lawn to Wealth: How a single audiobook (Rich Dad Poor Dad) sparked a real estate empire. * The 12-Month Build: How Sam added one property per month for a year while still leading his region in his W2 career. * Deciding vs. Choosing: Why "deciding" means killing off all other options and burning the boats. * The Resignation Secret: Why Sam calls it "retiring" from a job rather than resigning. * Cheat Codes for Growth: Why Sam spends more on his own mindset and coaching every year than the year before. * 3 Minutes of Power: Sam’s direct advice on financial runways and avoiding the "regret of the rocking chair." 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] * Rich Dad Poor Dad: The "Purple Book" that started it all. Connect with Grow STR: If Sam’s story inspired you to bet on yourself, please follow the show and leave us a 5-star review!