PODCAST · business
Michigan Short Term Rentals
by Michigan Short Term Rentals
Learn to navigate the nuances of short term rentals in the state of Michigan. On the podcast we talk about: - Vacation rental regulations - Tools for optimizing your rental - Systems and processes for operating your short term rental - How to find a profitable vacation rental area - Amenities for vacation rentalsWe also interview owners of some of the best vacation rentals in the state of Michigan and beyond.
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189: Three Days of Burnout Was Worth It and Our Biggest Conference Takeaways
Tony and Jordan are still recovering from three days of being around some of the sharpest minds in real estate. Coach Bert looked people in the soul with every handshake. Sarah Glidewell reinvented herself multiple times before 35. And Michael Elefante showed why tax strategy is the difference between millions and pocket change. Plus, the story of how consistency and non-negotiables built 189 episodes and a conference people actually want to come back to.https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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188: On the Ground - Real Conversations Around New Projects
We touched down in Georgia and honestly the first thing we did was drive around and take it all in. In this episode it's just us in the car talking. What this town feels like, what's going on in the market out here, and whether this is the kind of place we actually want to be invested in. We get into the deal itself, what we liked enough to get it under contract, and what's been nagging at us since. No agenda, no slideshow, just a real conversation about whether this thing makes sense.https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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187: The Make or Break Skill in Hospitality
Most operators in this business are building themselves a job and calling it a company. Tony and Jordan have spent five years learning the difference and a big part of that lesson came through hiring. In this episode they break down the five biggest hiring pitfalls that cost them time and money, the moves they made that finally worked, and why the operators who figure this part out first are the ones who end up playing the game at a completely different level. If you want a business that runs without you, this one is worth your full attention.https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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186: 7 Tips for Raising Capital for Your Next Project
Most people building their first pitch deck are trying to make everything look perfect. Tony and Jordan have learned that the best investors aren't looking for a perfect pitch, they're looking for the right people to go on an adventure with. In this episode they break down seven things that actually move the needle when you're trying to raise capital, from how much skin you need in the game, to why telling the risks might be your best sales move, to the one slide that does more heavy lifting than everything else combined.https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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185: The AI Tools Running in the Background of Our Business
Tony and Jordan pull back the curtain on the five AI tools quietly running inside their business right now, and they don't start with "Chat." If you're still using the same tools you started with, this one is worth a listen.https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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184: Lawsuits, One Stars, and the Best Quarter We Almost Ignored
Most people only talk about the wins. Tony and Jordan pull back the curtain on the full Q1 picture, the frustrating lows, the unexpected highs, and the personal stuff that almost didn't make the list. Turns out it was a pretty good quarter, they just had to stop long enough to notice.https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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183: One Horse Pulls 8,000 Pounds. Two Horses Pull 24,000.
Most operators are doing the math wrong. Tony and Jordan break down five principles that turn ordinary investments into something that compounds in ways most people never see coming and why in this business, one plus one almost never has to equal two.https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedInKatie Johnson https://www.katiejohnsonplc.com
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182: Kenny Bedwell on the Widening Wealth Divide in Short Term Rentals
Kenny Bedwell is back. This time he breaks down what the data is actually showing in the STR market right now, why the top 10% of hosts keep pulling further ahead, and how his nearly year-long New Orleans hotel renovation has been a crash course in patience and permitting. We dig into which markets are flying under the radar, how to think about boutique hotel and micro resort opportunities, and why regulations might be the best thing that ever happened to serious operators.https://www.strinsights.comFollow Kenny on InstagramFollow Kenny on Facebook https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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181: What Happens When You Actually Use the Right Tools w/ IV Beaton
IV Beaton spent years helping grow Life House, one of the fastest-growing hotel management companies in North America, before carving out its software unit to launch DIAMO. In this episode, he breaks down why small independent hotel owners are finally in a position to compete with the big brands and why switching from short-term rental pricing logic to hotel pricing logic is harder than most people expect. Tony also shares his own early results using DIAMO at The Windmoor Lodge, including nightly rates jumping 30 to 40% after making the switch.https://www.diamo.aiIV Beaton's email: [email protected]https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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180: Creating an Unfair Advantage with this Simple Principle
Most investors are competing for the same deals on the same platforms. Tony and Jordan share the simple principle that's been opening doors nobody else even knew to knock on and why it might be the most overlooked edge in the entire game.staythewarren.comhttps://www.facebook.com/StayTheWarrenhttps://www.instagram.com/staythewarren/https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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179: The Wealth-Building Flywheel and Why Your Equity Might Be Sitting Lazy
Tony and Jordan break down their first cash-out refinance on a 5-unit property they took from $60K in gross income to $220K+. That property just appraised at $1.2M. They share exactly what they're doing with the equity, why a pool could add $75K in annual revenue, and when leveraging equity is a smart move versus a dangerous one.https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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178: Zero Down Seller Financing Could Kill Your Tax Strategy
Tony and Jordan unpack how cost segregation can dramatically reduce taxes for short term rental owners.A cost seg study breaks out components like driveways, pools, cabinets, appliances, landscaping, and sheds into shorter timelines. That allows you to front load depreciation into year one.In one example, about $130,000 was accelerated. For a high income earner in a 25% bracket, that could mean $30,000 to $40,000 in tax savings immediately.Key points:• You must materially participate to use losses against active income. Track your hours.• Portable structures not permanently affixed may qualify for 100% write off in year one. Some may not even require a formal cost seg study.• Seller financing with little or no money at risk can cap or eliminate your deduction. The takeaway. Cost seg is powerful, but only if your deal structure supports it.https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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177: How To Choose a Hospitality Name That Feels Premium and Ranks Online
This episode is a naming playbook for boutique hospitality. Tony and Jordan walk through five naming considerations that directly impact bookings and brand momentum. They share real examples from The Windmoor Lodge and their current Bridgman project, including why some “good” names fail when you search them, map them, or try to match them to the guest avatar you actually want. They close by reinforcing the bigger point.........you are selling an experience, and the right name helps the design team, the community, and future guests feel that experience before they ever arrive.https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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176: Mindset Is The Real Scale Lever w/ Emanuele Pani
This episode breaks down why most people stall even when they know what to do. Emanuele explains mindset as the beliefs shaping how you see yourself and life. They cover imposter syndrome, language traps like “I’ll try,” and why clean decisions plus long term commitment create real change. Growth starts internally, then shows up externally.Follow Emanuele Pani on Instagramhttps://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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175: An $11 Million Dollar STR Legal Mistake w/ Katie Johnson PLC
Katie Johnson is back with a real update from the front lines of Michigan STR law. We talk Park Township’s ongoing battle, why “we’ve always allowed it” is not the same as “you’re protected,” and what happens when a township flips the switch after investors have already poured six figures into a property. Katie also breaks down the legal reality behind deed restrictions, permit caps, and why more Michigan municipalities are using old ordinances to shut down STRs today.STR Law Podcast https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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174: Year One w/ Our First Motel: Real Numbers, Real Lessons
This episode is a behind the curtain look at what it actually takes to make a small motel feel like a high performing group retreat. They talk big group bookings pushing ADR way up, the operational reality of rural markets, and why bigger assets can actually be easier when they support dedicated staff. They also hit the “do it right the first time” principle, including examples like plumbing, aging heating units, and finding efficiency rebates that can materially offset upgrades.https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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173
173: One Hire Away From Breaking Through
Hiring is the bottleneck most STR operators refuse to admit. In this episode, Tony and Jordan break down why growth stalls when the owner is still doing “busy work” and taking every guest problem personally. They unpack the hire that doubled their business, the mindset shift from job to real business, and a simple way to think about ROI on employees. The punchline: stop asking “how do I do this better” and start asking “who can own this so I can grow.”https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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172: The Financing Options Most STR Investors Don’t Know Exist
Most investors focus on price and projections. Experienced operators focus on financing structure. In this episode, Tony and Jordan unpack two lending products that are changing how they and their clients approach vacation rentals and boutique hospitality.https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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171: Michigan STR Conference 2026: How One Event Can Reset Your Trajectory
The 2026 Michigan STR Conference is officially live, and this episode explains why this year is different.Tony and Jordan unpack what happens when you get in the right room, around the right people, at the right moment. They share how proximity to high-level operators, investors, and thinkers has directly led to deals, partnerships, clarity, and faster execution in their own journey.This episode is an invitation. Not just to attend a conference, but to step into a bigger table, sharper conversations, and a higher standard heading into 2026.https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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170: The Mechanical Mind Trap and How to Break It
Tony and Jordan unpack a mindset shift that changes everything: you are not the same person you were when you failed last time. They use an Indiana football clip as a punchy example and apply it to business, fitness, and investing. The core idea is simple. Most people make decisions using a “mechanical mind” that treats past outcomes like permanent limits. But your skills, network, confidence, and experience have evolved, which means your current version deserves a fresh attempt. They also hit a real limiter that shows up when you start using other people’s money: stewardship. You hesitate because you care, but that same care is what eventually builds trust, track record, and the right to play bigger.Join the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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169: How To Be the Most Interesting Person in the Room
Tony and Jordan break down a counterintuitive idea: the most interesting person in the room usually is not the loudest or the funniest. It’s the one who listens, asks elite questions, and makes other people feel seen. They talk about how to avoid shallow conversation starters, how to build real connection even when you don’t share interests, and why stories beat facts every time. They also hit the power of becoming a connector and how relationships compound when you consistently add value without being transactional.Join the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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168: Real Growth Happens Outside the Numbers
This is a candid year-in-review episode focused less on wins and more on evolution. Tony and Jordan unpack the moments that forced them to grow: larger projects, higher stakes, constant problems, and the realization that the next level requires different people, systems, and discipline. They talk openly about calm under pressure, thinking bigger, investing in health, and why the right team matters more than perfect timing.Join the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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167: The 3 Biggest Lessons We Pulled From Our Annual Retreat
Inside this episode, Tony and Jordan unpack their annual strategy retreat and reveal the three levers that are shaping their next five years of growth. They share why hiring earlier creates the breakthrough, how long-term thinking beats short-term perfection, and how stewardship builds the relational capital needed to scale. It’s a candid look at the decisions, discipline, and mindset shifts driving consistent growth. Grass Lake Lodge Join the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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166: How We Attracted Our First Investors and Got Deals Funded
Tony and Jordan break down how their investor journey evolved from doing a first flip with a close friend to bringing new investors into every deals. They talk through what actually attracts capital in real estate deals proof of action, reputation, conferences, and showing your work in public so money starts coming to you instead of you chasing it.Join the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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165
165: Our Newest Motel Deal and How to Start Your Own Boutique Journey
Tony and Jordan walk through their newest deal under contract a twenty four unit motel in Southwest Michigan that they have been tracking for years. They break down why they kept coming back to this specific property, how they underwrote it using real comps instead of the seller’s weak performance, and why they are convinced the market can support boutique level rates once they add design and amenities. Along the way they share candid lessons from earlier multi family and motel projects and what finally gave them conviction to pull the trigger on a larger asset.Join the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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164: Removing Negative Airbnb Reviews w/ the New AI System
This episode breaks down the real-world shift Airbnb made to an AI-driven review removal system and how hosts can get negative review removed within the new system. Tony shares the exact framework he used to get two unfair reviews removed in under 90 minutes after weeks of failed attempts. Jordan adds insight on why strong systems, clear guest expectations, and consistent communication make these appeals stick. If you’ve ever felt powerless dealing with retaliatory or irrelevant reviews, this one gives you a roadmap to take control again.Sean Rakidzich YouTube VideoJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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163: Momentum Beats Perfection
Tony and Jordan make a strong case for a bias toward action. They show how tiny first steps lead to deals, skills, and momentum. From analyzing numbers to touring homes to placing offers, each move compounds. They share how one Stevensville buy opened the door to more properties, a management company, and even a conference. The takeaway is simple. Write the next three steps. Do one today. Repeat tomorrow.Join the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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162
162: The Conference Tip That Saved Us ~$150K
This episode is a tactics deck for closing when “the numbers don’t pencil.” Fresh from a conference insight that effectively saved ~$150K on a deal, Tony and Jordan break down offer architecture (price vs. terms), including 0% seller financing, long amortizations with balloons, and master lease/lease-option approaches that let you invest into operations first and finance later. They walk through a 5-unit partnership that jumped from $60K → ~$235K in annual revenue using zero-interest furnishings and smart ops, explain how to pitch seller tax advantages, and cover lender realities (hospitality caps, new partners). If you need a path when traditional loans kill returns, this is your blueprint.Join the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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161
161: Cracking the Code to Michigan’s Top 1% Airbnbs
Tony and Jordan break down what separates Michigan’s top 1% of short-term rentals from the rest. From hot tubs and privacy to 50-photo listings, perfect reviews, and pet-friendly policies, this data-driven episode reveals what elite operators are doing and how you can apply it to your own property.Join the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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160: Is 4th Quarter a Good Time to Buy a Short Term Rental in Michigan?
Is Q4 secretly the best time to buy a short-term rental? Tony and Jordan break down fall deals, stale listings, cost-seg deadlines, and why onboarding during certain seasons can impact your year one revenue. Join the Michigan Vacation Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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159
159: Turn Browsers into Bookings with Roberto Sidoti from Rentamira
Vacation rental SEO veteran Roberto Sidoti breaks down how to win direct bookings today. From local SEO and Google Business Profile to LLM-ready content, smart backlinks, and conversion funnels that actually turn traffic into stays.RentamiraJoin the Michigan Vacation Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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158: Branding First, Building Second Is the Secret to Iconic Stays w/ Steph Weber
This episode is a mini-masterclass on hospitality marketing. Steph Weber explains how she financed and launched a 12-cabin riverfront development, marketed it mid-construction, and grew direct bookings. Steph talks all things Instagram/FB, influencers, email capture, retargeting, and paid ads. She details naming, mood boards, guest experience design, and the metrics that matter (engagement → list growth → bookings). Expect honest lessons on bank expectations, cash calls, team roles, and the one non-negotiable: brand clarity that drives every decision.Follow Steph on InstagramCheckout The Weber CoJoin the Michigan Vacation Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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157: 3 Lessons From Boutique Hotel Con You Can’t Afford to Miss
Three lessons. That’s what Tony and Jordan pulled from their trip to Boutique Hotel Con in Tennessee, and they’ll change the way you think about building wealth in hospitality. In this recap, they cover why the people you surround yourself with matter more than tactics, how to spot if you’re only “trying” instead of moving mountains, and why grinding through setbacks is the price of entry for big wins. If you’re ready to level up, this episode is your blueprint.Join the Michigan Vacation Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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156: 5 Important Lessons from the 2025 Peak Season
In this episode, Tony and Jordan break down the five biggest lessons they learned from Michigan’s 2025 peak season. From vetting properties more carefully to avoiding unreliable service providers, they reveal the costly mistakes that can drag your business down. Why not all markets are truly “saturated,” and why building a strong team is the ultimate growth multiplier.Join the Michigan Vacation Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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155: Reinvention Season: Why Comfort Could Be Your Biggest Risk
Tony and Jordan open up about reinventing themselves again. From barber to broker, factory floor to founder, they break down the mental barriers (fear, comfort, “golden handcuffs”) that keep entrepreneurs stuck. You’ll hear how masterminds, better circles, and defining your “perfect day” create clarity; why moving from player → coach → owner changes everything; and how to build confidence through action, not theory. If you’re living business Groundhog Day, this is your roadmap out.Join the Michigan Vacation Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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154: 5 Proven Ways to Boost Your STR Revenue Next Year
Is your STR underperforming? Tony and Jordan reveal the five revenue multipliers that separate winning properties from average ones. You’ll hear how a few small design tweaks flipped a property from zero bookings to fully booked, why investing in amenities like pools and pickleball courts can deliver huge ROI, and why networking, photos, marketing, and dynamic pricing aren’t optional anymore. If your revenue has slipped or if you want to crush 2026, this episode is your playbook.Join the Michigan Vacation Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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153
153: No Comps, No Limits and Dreaming Bigger Than the Market
This episode gets real about development math. They discuss site work, vertical builds, and amenities, so they’re planning multiple paths: operate as a high-end resort or pre-entitle as PUD/site condos to give banks a clear exit if needed. They discuss financing realities, raising capital, community alignment, and why scarcity (no true resort-focused stays in the area) creates pricing power.Join the Michigan Vacation Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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152
152: How We Bought a 5-Unit for $0 Down
What happens when you take a tired five-unit building and flip it into a powerhouse STR property? Tony and Jordan share the full story of their Southwest Michigan five-unit acquisition from botched arbitrage beginnings to closing on the property with creative financing and no money out of pocket. They reveal the wins and the challenges. Along the way, they share practical lessons on cutting costs, boosting revenue, and why versatility (breaking a large property down into midterm rentals in the offseason) can be a game-changer.Join the Michigan Vacation Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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151: The Surprises (and Warnings) From Airbnb’s Q2 Earnings Call
In this episode, Tony and Jordan break down Airbnb’s Q2 earnings call and unpack the key insights for short-term rental owners and investors. From revenue surprises to subtle warnings hidden in the details, we explore what Wall Street’s numbers actually mean for Main Street hosts. If you want to understand where the market is heading and how it could impact your business, this episode delivers the must-know takeaways.Join the Michigan Vacation Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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150: Saying “No” is the Ultimate STR Growth Strategy
In this episode, Tony Stancato and Jordan Painter share how they’ve narrowed their motel acquisition focus to one powerful corridor: St. Joseph to New Buffalo, Michigan. They reveal why chasing every “good deal” nearly slowed their growth, the hidden costs of operating outside your core market, and the systems they’ve built to dominate locally. If you’ve ever struggled to turn down opportunities, this conversation will help you protect your time, team, and bottom line.Join the Michigan Vacation Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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149: Consistently Good > Occasionally Great: The Real STR Advantage
Tony and Jordan unpack one of the biggest mindset shifts for STR operators: chasing consistency instead of perfection. Whether it's installing a new AC before it fails in peak season or responding to guests in 10 minutes instead of 40, they explain how consistent execution builds trust, saves money, and reduces stress. They also highlight the importance of culture, team training, and proactive communication with owners. If you're tired of swinging between burnout and hero moments, this episode will help you build a more stable, scalable vacation rental business.Join the Michigan Vacation Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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148: How to Get Direct Bookings by Going All In on Great Content w/ Dustin Baker
In this episode, we sit down with Dustin Baker from Hidden Gem Media to talk about what most STR owners get wrong about their photos and videos. Better storytelling leads to more bookings. Dustin shares how he blends cinematic visuals with direct response marketing frameworks (like hook, story, and offer) to help vacation rental listings stand out in a crowded marketplace. If you want guests to fall in love with your property before they even click “Book Now,” this one's for you.HiddenGem MediaFollow Dustin Baker on InstagramJoin the Michigan Vacation Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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147: Not Every Client Is a Great Fit and That's Ok
Not every client has to be the right fit, just like not every employee has to be the right fit. This episode is about protecting your time, your team, and your peace of mind. Hear how the team identifies poor-fit clients early, handles tough conversations, and ultimately makes space for the kind of clients who help grow the business.Join the Michigan Vacation Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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146
146: One-Night Stays, Price Wars, and the Truth About Launching New Listings w/ Federico Zimerman
From Mount Rushmore to New York, Federico Zimerman has scaled a nationwide STR business—and learned a lot about what works (and what doesn’t). In this conversation, he shares the behind-the-scenes strategies for entering new markets, building local vendor networks, and optimizing pricing in real-time. It’s a deep dive into data, execution, and long-term success in the vacation rental space.Follow Federico on Instagram Revfactor.ioJoin the Michigan Vacation Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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145: Hidden Deal-Killers in Michigan’s Vacation Rental Market
Buying a short-term rental in Michigan? In this episode, Tony Stancato and Jordan Painter break down five common but easily overlooked pitfalls that could derail your investment—before you even hand over the down payment. From sneaky three-day minimums to unpredictable HOAs, deed restrictions, and over-saturated markets, they share what every buyer should consider to avoid painful surprises later.Join the Michigan Vacation Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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144
144: 7 Mindset Shifts That Will Unlock a Bigger, Better Future
In this episode, Tony Stancato and Jordan Painter explore seven foundational mindset shifts from Tony Robbins’ Unlimited Power that are critical for anyone looking to build a bigger, better future. These beliefs aren’t just motivational fluff; they’re tools for navigating the challenges of business, leadership, and life with resilience and clarity. From reframing failure as feedback to embracing responsibility and seeing people as your greatest asset, this conversation unpacks how adopting these mindsets can create momentum and long-term growth. Whether you're building a short-term rental business or simply trying to show up better in your daily life, these shifts are worth reflecting on and implementing.Join the Michigan Vacation Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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143
143: How to Avoid Headaches by Setting STR Owner Expectations Early
How do you prevent scope creep, unrealistic demands, or frustrating conversations with STR owners? Tony and Jordan share their hard earned insights on the importance of setting clear expectations upfront. From service boundaries to revenue conversations, they unpack the key elements of their onboarding process and client agreements so you can build smoother partnerships from day one.Join the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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142
142: 5 Takeaways from the Boston Boardroom Event
Tony Stancato and Jordan Painter break down the powerful takeaways from Tony’s recent trip to the Boardroom mastermind in Boston. From shifting your role in business to sharpening your vision and building stronger teams, this episode explores what happens when you step into a room full of high performers and let it change your trajectory. Whether you're refining systems, exploring AI, or reevaluating how you lead, this one’s packed with reflection and momentum.Join the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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141
141: Time Freedom, Vision, and 90+ Doors with Michael Sjogren
What drives someone to leave a secure corporate life and bet everything on short-term rentals—and later boutique hotels? In this episode, Michael Sjogren joins Tony and Jordan to share his powerful journey, sparked by a family crisis and sustained by a deep commitment to time freedom. You’ll hear how a strong "why" can fuel massive growth, how to transition from side hustler to visionary leader, and how Michael’s story went from a single condo to multiple boutique hotels and one of the industry’s biggest conferences.strsecrets.comFollow Mike on InstagramSTR Wealth ConferenceJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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140: From Airbnb to a 130 Unit Motel: Blake Dailey’s Playbook to Scaling
Tony and Jordan sit down with Blake Dailey to unpack his journey from short-term rental host to boutique hotel operator. From his early days of house hacking to acquiring a 130-unit property near the Smoky Mountains, Blake shares what it took to scale his real estate business. If you've ever wondered what comes after STRs—or how to build a team, create operational systems, and force appreciation—this episode offers a behind-the-scenes look into a growing hospitality portfolio.Follow Blake Dailey on Instagram Grab a ticket to Boutique Hotel ConJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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ABOUT THIS SHOW
Learn to navigate the nuances of short term rentals in the state of Michigan. On the podcast we talk about: - Vacation rental regulations - Tools for optimizing your rental - Systems and processes for operating your short term rental - How to find a profitable vacation rental area - Amenities for vacation rentalsWe also interview owners of some of the best vacation rentals in the state of Michigan and beyond.
HOSTED BY
Michigan Short Term Rentals
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