Grow STR Podcast

"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Shippo.After becoming a short-term rental host in the Great Smoky Mountains and Branson, he experienced the limits of outdated PMS websites and high-cost agency builds, which led him to create a scalable alternative.CraftedStays launched in January 2024 as a mobile-first platform that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.coInstagram: https://www.instagram.com/craftedstaysFacebook: https://www.facebook.com/gilbertchanLinkedIn: 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!

"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.comRich 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!

"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 to managing 25 units in the Pacific Northwest—including a 15-unit boutique hotel on the Washington coast.Michael breaks down the exact "Second Brain" system he built using Notion and AI to offload the 24/7 chaos of property management, allowing him to take a family vacation to Hawaii just two weeks after launching his biggest project.In this episode, we cover:The Expedia Escape: How Michael used his corporate background to build high-level customer support systems for his own business.The First Client Hurdle: Why Michael "fell on his face" for six months and the mindset shift that finally landed him two clients in one day.The $25,000 Investment: Why Michael spent a "Master's Degree" worth of money on STR coaching and masterminds.Notion for STRs: How to build a "Second Brain" to document every gate code, bed configuration, and SOP.Buy Back Your Time: Lessons from Dan Martell on hiring VAs for purpose, not just tasks.The Future of Management: A look at "Rental Mind" and how AI agents will change the game in 2026 and 2027.Action Item: Stop being a "cog in the wheel." Build the system that allows you to be the architect, not just the executioner.Michael Dinwiddie is the founder of Togetherevacation Rentals, managing 25 short-term rental units in Washington State including a 15-unit boutique hotel on the coast. He has a background in building customer support systems and product marketing in the travel industry from a career at Expedia Group, where he worked for half a decade before going -all-in on STRS in January 2025. He also built and sells a Notion template designed specifically for STR operators and boutique hotel owners who are tired of juggling too many tools and want their team to run the business smoothly. Outside of work, he's a dad of three (fourth coming next month) and loves exploring the Pacific Northwest with his family.Connect with Michael: togetherevacationrentals.com [email protected] @Michael Dinwiddie.dinwiddie / @cometogethereConnect with Grow STR:If Michael’s journey from Nebraska to a coastal hotel inspired you, please follow the show and leave us a 5-star review!

"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 concepts of Memento Mori (Remember you will die) and Memento Vivere (Remember to live) and how these ancient philosophies apply to your short-term rental co-hosting business today.In this episode, we cover:The Institutionalized Entrepreneur: Why we default to 5 AM cold plunges and suffer-centric routines.Conviction Over Scripts: Why the #1 thing missing from your sales calls is the joy of why you’re doing it.The "C8 Corvette" Lesson: Sam’s story of test-driving a dream and realizing it didn’t fit his "joyful" life.Walmart vs. Whole Foods: Determining which "flavor" of client actually makes you happy to work.The 5 Levels of Business Self-Assessment: Do you hate what you do, how you do it, or who you do it for?The Zone of Genius: Lessons from Gay Hendricks’ The Big Leap and Jesse Cole’s Find Your Yellow Tux.Action Item: Stop being a "bad boss" to yourself. Turn your daily tasks into a game and prioritize your "Zone of Genius."Resources Mentioned in this Episode:My Entrepreneur Design: Take the free personality test to find your zone of joy at myentrepreneurdesign.comGo STR Marketing: Ready to scale your co-hosting game with more high-value leads? Book a demo at gostmarketing.comConnect with Grow STR:If this episode gave you permission to enjoy your life today, please follow the show and leave us a 5-star review!

"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 themselves. The escape hatch? A world-class team.Sam shares a personal horror story of a high-level hire "cheating" on his company, while Donnie breaks down the exact math of when you can afford to stop doing the $15/hour tasks.In this episode, we cover:The 60% Rule: Why you need to hire before you hit your goal—and how to know you’re ready.Vetting for Truth: Sam’s 3-step vetting process (The 1-minute video, personality tests, and detail traps).The "I Do, We Do, You Do" Model: The foolproof training framework for offloading guest communication and operations.The Time Study Audit: How to find the "lowest value tasks" on your plate in just 15 minutes.Philippines vs. Latin America: The pros and cons of offshore talent and where to look first.The Sales Trap: Why outsourcing your sales process to a VA without a playbook is a "slow-moving accident."SOPs in 5 Days: Sam’s challenge to build a repeatable business manual, one process at a time.Action Item: Do the "Dollars-per-Hour" audit. Divide your income by your hours. Are you doing work you could pay someone else $8/hour to do?Go STR Marketing: Ready to scale your co-hosting game with a 100% done-for-you lead solution? Book a demo at www.gostmarketing.comConnect with Grow STR:If you found a "gem" in this pre-talk or the main episode, please follow the show and leave us a 5-star review!

"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 tech to build a thriving portfolio of 18 short-term rentals in Florida’s "Nature Coast."David reveals how he transitioned from a six-figure W2 to managing a business that focuses on quality over quantity, resulting in a staggering 25% re-booking rate.In this episode, we cover:The Stability Trap: Why David compares the corporate world to "jail" and how to find the courage to leave.The Partnership Blueprint: How David structures 50/50 deals with friends by "mapping out the divorce" before the wedding.The "Chubby Mermaid" Strategy: Building a hyper-local brand that resonates with guests.Saying "No" to Grow: Why being selective with homeowners and properties is the secret to long-term profitability.Designing the Guest Journey: Partnering with local vendors (airboats and river tours) to create a hub for local experiences.The Student Mindset: Why listening more than you speak is the fastest way to learn a new industry.Action Item: Stop over-complicating your business. Fulfill the experience, outsource the accounting, and focus on the guest.Resources Mentioned in this Episode:Go STR Marketing: Ready to scale your co-hosting game with a 100% done-for-you solution? Book a demo at www.gostmarketing.comExperience Wiki: Check out David’s guest app and properties at www.ExperienceWeeki.comwww.WeekiLife.comConnect with Grow STR:If this episode helped you find your "North Star," please follow the show and leave us a 5-star review!

"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 powerful "Anatomy of a Win" featuring a student named Lee, who signed high-value deals with zero testimonials and no website by simply having authentic conversations.In this episode, we cover:The "Lee" Case Study: How to close clients when you’re just starting out (The anti-perfectionist approach).The Billion-Dollar Chicken Finger: What we can learn from the founder of Raising Cane's about focusing on a single niche.Authenticity vs. Corporate Gloss: Why "Mom and Pop" branding is actually out-performing big management companies in 2026.The 6 Multipliers: Donnie’s framework for scaling anything (Time, Money, Talent, Belief, Relationships, and Space).Revenue-First Decision Making: Sam’s filter for knowing which tech tools to keep and which to cut.The Crumpled Letter: A simple, repeatable marketing lesson that proves "witty" isn't required for profit.Action Item: Stop "Ready-Aim-Aiming." Identify one simple, revenue-generating action you can take today and execute it.Go STR Marketing: Ready to scale your co-hosting game with a 100% done-for-you solution? Book a demo at www.gostmarketing.comConnect with Grow STR:If you’re enjoying the show, please follow us on Spotify and leave a 5-star review! It helps us grow the community and keep bringing you these deep-dive strategy sessions.

"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 Sam break down the "Be, Do, Have" framework and explain how to move from a life that "happens to you" to a life that is "inevitable."In this episode, we cover:The Flow State: Why "Clear Goals and Immediate Feedback" are the requirements for peak performance.The Bee Metaphor: Why pursuing what is "sweet" to you is actually the best way to serve the world.The Blue Sky Exercise: How to dream without letting "how" or "budget" limit your imagination.Be, Do, Have: The 3 deep questions that determine who you will become in the next 12 months.The "RV & Corvette" Lessons: Why it’s okay to "test drive" a dream and realize you don’t actually want it.The Ideal Schedule: Sam walks through his method for building a week based on freedom and family, not just work tasks. Move your vision from Possible (dreaming) to Probable (strategizing) to Inevitable (putting it on the calendar).Go STR Marketing: Ready to scale? Book a demo at www.gostmarketing.comConnect with Grow STR:If this episode gave you a "spark" for your next year, please follow the show and leave us a 5-star review!

"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 already talking to buyers and sellers.In this episode, we discuss:The Target-Rich Environment: Why realtors are the gatekeepers to your next 10 listings.The 160:10 Math: Donnie breaks down the exact conversion numbers you need to stay sane while networking.Being the "STR Expert": How to provide value to a realtor so they look like a hero to their clients.Personality-Based Outreach: Whether you are a "Companion," a "Sage," or a "Fighter," we show you how to align your personality with your growth strategy.The Power of Appreciation: Why a handwritten note and a $100 gift beat a cash "referral bounty" every single time.Key Takeaway: Real estate agents are looking for you—they just don't know it yet. You are the missing piece of their equation.Resources Mentioned:Go STR Marketing: Scale your outreach with a done-for-you solution. www.gostmarketing.comThe Realtor Questionnaire: Reach out to us for the specific questions to ask your local agents!Connect with Grow STR:If you enjoyed this episode, please follow the show and leave us a 5-star review! It helps us bring more STR experts to your ears.

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 properties and is on track to double that in months. We discuss the exact systems he used to stop trading time for money and how he 4x’d his portfolio in just six weeks.What we cover in this episode:The Identity Shift: Why you must stop calling it a "side hustle" if you want to scale.Arbitrage vs. Co-hosting: Why Michael moved away from the arbitrage model to lower financial risk.The "Cave Moment": How hitting rock bottom provided the conviction needed to sign clients.Automated Outbound Sales: The specific tools Michael uses to 10x his outreach without picking up the phone.Building Trust Fast: Using Google Business and professional web presence to beat the competition.Connect with Michael Morrison:Instagram: @PremierHost.bnbFacebook: Michael MorrisonConnect with Grow STR:Follow us on Spotify and leave a 5-star review if this episode helped you!

GROW-STR Podcast Episode: How To Kill Distractions & Stay Consistent In Your STR BusinessJoin 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 intervention.They break down how to stop building “busyness” and start building a real business, why most operators quit right before momentum shows up, and how to simplify your promise, your sales, and your systems so you can actually scale.Listen & Learn More: https://www.gostrmarketing.com/[0:00] Welcome to the Grow STR Podcast (who it’s for + what you’ll get)[1:00] The emotional side of business: when you’re trying and it feels unseen[2:00] The consistency problem: why STR operators keep scrapping plans[3:30] Bright Shiny Object Syndrome (and why basically everyone has it)[4:40] Delegation fails when you “throw it over the fence” and stop inspecting[5:10] Walking the conference halls: endless tools, tech stacks, and “solutions”[6:50] The real issue: business hits you in the face (and people react differently)[8:10] Owning a business vs owning a job in STR operations[9:50] “Process problem” vs “person problem” (and how to tell the difference)[10:50] The hard question: is the system not working… or am I not working?[14:10] Why “just follow the directions” matters (especially in business)[14:45] Donnie’s origin story: building everything except the one thing that mattered (sales)[18:00] What to do when you’re plateaued and need growth fast[19:00] Sam explains the UI method: underperforming listings → owner outreach[21:00] Donnie’s simple reset: promise → sales → systems (in that order)[26:40] Simplify your promise: stop trying to serve everyone like you’re Walmart[27:45] Simplify sales: one market, one list, one conversation at a time[30:00] The simplest “system” that works: a searchable SOP doc[32:00] GoHighLevel reality check: powerful tool, dangerous time-suck if you’re new[33:00] Multi-market cautionary tale: don’t franchise chaos[37:00] FOCUS: Follow One Course Until Success[38:40] Wrap-up: stay consistent, build momentum, stop restarting your business weekly✅ Complexity is the enemy. Your job is to remove complexity for owners, not create more for yourself.✅ Ask the real question: Is it the system failing… or are you quitting before it works?✅ Momentum beats “perfect.” Stop optimizing things that shouldn’t exist yet.✅ Do it in order: Promise → Sales → Systems. Don’t build the machine before you prove the offer.✅ Keep your promise specific. “We do everything for everyone” is not a strategy.✅ Sales can be simple: one list, one outreach script, one conversation at a time.✅ Systems can be simple: a basic searchable SOP doc can beat a fancy stack you never use.✅ Multi-market scaling requires a team. New markets often mean rebuilding everything.✅ FOCUS: Follow One Course Until Success. Then expand.Ready to grow your STR business the right way?Visit: https://www.gostrmarketing.com/Book a demo to learn about our done-for-you solutions for locking in repeat guests and expanding your co-hosting game.Hosts: Donnie & Sam | Powered by Go STR Marketing📍 CHAPTERS & TIMESTAMPS🎯 KEY TAKEAWAYS

GROW-STR Podcast Episode 2: Getting NEW Connections - The Fastest Path To CashJoin 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 & Learn More: https://www.gostrmarketing.com/[0:00] Introduction & Setting the StageDonnie and Sam kick off with energy, discussing the power of connections over traditional referrals and why this episode is essential for STR business growth.[2:57] The Fastest Path to Cash PhilosophyDonnie shares his background as a sales coach and introduces the concept that changed everything: connections as the quickest way to show value and generate revenue.[6:33] The MLM Problem & Reframing ReferralsWhy most people are turned off by "referrals" due to multi-level marketing experiences, and how to reframe this approach as genuine connections instead.[10:52] Sam's Authentic Success StorySam reveals how passion and authenticity led to his first STR deals - speaking from genuine belief rather than following a script.[14:49] The Internal Game: Belief & AuthenticityDeep dive into why your internal belief system matters more than any script. The importance of loving what you do before sharing it with others.[19:45] Why Most People Fail at Getting ConnectionsThe two main reasons people don't get connections: they don't ask, or they lack confidence in their message.[22:10] The School System TrapHow traditional education trains us to memorize and regurgitate, which completely fails in real human conversations and sales.[27:00] Two Life-Changing Internal PhrasesDonnie shares the two mindset shifts that transformed his approach: "Not everyone's a fit" and "It's no big deal."[30:10] The No-Pressure Connection ScriptTHE MONEY SECTION: Donnie walks through the exact 5-step script that works:"Been thinking of you""Hoping you can help me out""Here's what I'm trying to do""Who do you know that I should be talking to?""That's okay, it's no big deal"[23:40] Live Role-Play DemonstrationDonnie and Sam demonstrate the script in real-time, showing how natural and pressure-free it feels when done correctly.[24:25] The 50-Person ChallengeHow to create your list and why reaching out to just a dozen people can transform your business.[27:49] The Realtor Connection StrategySam's actionable advice: Start with ONE realtor conversation. Why realtors are the secret weapon for bootstrapped STR companies.[28:24] Investor Relationships & Multiple DealsHow one investor connection can lead to multiple properties and why this is easier than managing multiple individual owners.[29:40] Wrap-Up & Call to ActionFinal thoughts on taking action this week and information about the Go UIX coaching program.✅ Stop calling them "referrals" - reframe as genuine connections✅ Your internal belief and authenticity matter more than any script✅ The 5-step connection script that actually works (no pressure!)✅ Start with just ONE person - preferably a realtor✅ "It's no big deal" - lower the pressure and watch connections flow✅ One investor relationship can lead to multiple dealsReady to grow your STR business the right way?Visit: https://www.gostrmarketing.com/Book a demo to learn about our done-for-you solutions for locking in repeat guests and expanding your co-hosting game.*Hosts: Donnie & Sam | Powered by Go STR Marketing*📍 CHAPTERS & TIMESTAMPS🎯 KEY TAKEAWAYS

Using Story To SellTransform 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, property managers, and anyone who wants to grow their business without the awkward cold-calling grind.What You'll Learn:• Why stories bypass logical guardrails (people believe 80% of what they tell themselves, only 20% of what you tell them)• The success story framework: character, problem, solution, outcome• How to land the plane when you're rambling: "The reason I tell you this is..."• Real examples of stories that closed six-figure deals• Why "feel, felt, found" makes people hang up on youFeatured Story: How Sam turned a "$75K is good enough" objection into a signed contract by saying two words: "That's it?"🔗 Learn more: https://www.gostrmarketing.com/app