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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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