Michigan Short Term Rentals

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 group⁠⁠...

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...

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....

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...

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  ⁠⁠⁠...

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 reeva...

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...

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 appreciati...

In this episode, Tony and Jordan dive deep into the mindset challenges that hold so many entrepreneurs back from scaling their businesses. From overcoming fear of failure to recognizing limiting beliefs you didn’t even know you had, they share personal stories, lessons from the Michigan STR Conference, and tactical ways to shift your mindset for growth. If you’ve ever felt stuck in a loop, hesitan...

Most people think of Tony and Jordan when they hear the Michigan STR Podcast—but there’s a third partner behind the scenes. Meet Garry VonMyhr: serial entrepreneur, real estate investor, and the man behind multiple multimillion-dollar businesses. In this episode, we unpack his story, why he joined forces with Tony and Jordan, and the biggest business principles he carries into every venture—includ...

In this episode, Tony and Jordan reflect on what worked, what surprised them, and what they’re changing next year after hosting the Michigan STR Conference—an event that drew hosts from across the country (and even Costa Rica). Real talk, real feedback, and what’s next for 2026. Join the  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Michigan Short Term Rentals Facebook group⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

Don’t let your property get tired. In this episode, Tony and Jordan break down a recent stay at a highly rated Airbnb that totally missed the mark—from crooked lamps to leaky dishwashers to sketchy mechanicals. They explain the real cost of letting things slide and how to prevent your short-term rental from becoming “just another place to stay.”  Join the  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

Should you be nervous when a guest has no reviews? Today, Tony and Jordan unpack why some of your best guests might actually have a blank profile, why setting expectations is more powerful than screening reviews, and how to properly protect your properties with smart tech and policies. Plus, hear what guest groups we actually get  more  nervous about. MichiganSTRConference.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

n this episode, we dive deep into the realities of ground-up development with Gina and Justin Cohen. They talk permits, city council approvals, and financing strategies—including how they raised capital through friends, family, and SBA lending. Whether you’re dreaming of your own development or simply fascinated by what it takes to build a destination from scratch, this one’s packed with real-worl...

In this episode, Tony sits down with credit card reward expert  Colin Stroud , founder of Go Somewhere, to break down how vacation rental owners can  turn big upfront property expenses into free travel or cashback . From choosing the best business card to stack points, to unlocking 250,000-point bonuses, Colin shares tips that can 2–10x the value of your purchases. If you’ve got $30K–$80K in renov...

In this episode, Tony and Jordan sit down with tax strategist  Josh Sherrard , CEO of Strategic Navigators, to break down  how real estate investors and business owners can legally save 40–60% on their taxes . Josh shares actionable insights most CPAs aren't talking about. If you’re a short-term rental owner looking to keep more of what you earn, this one’s a must-listen. Strategic Navigators...

In this episode, Tony and Jordan break down the  5 biggest differences  they’ve experienced managing boutique motels versus traditional short-term rentals. Whether you’re STR-curious or already eyeing your first motel, this one’s full of insights you won’t want to miss. MichiganSTRConference.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Join the  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Michigan Short Term Renta...

From an overworked corporate engineer to boutique motel owner, Kassidy Warren’s story is all about transformation, strategy, and purpose. In this episode, he walks us through how burnout sparked a major lifestyle shift, leading to nine short-term rentals and a boutique hotel project in California. Kassidy shares his philosophy on the  velocity of money , the power of  forced appreciation , and how...

In this episode, Tony talks with Kyle Driskell from PriceLabs about optimizing dynamic pricing for short-term rentals. They cover the latest updates to the PriceLabs algorithm, common mistakes hosts make when setting their base price, and why adjusting minimum stays can be more effective than lowering rates. Kyle shares insights on occupancy-based adjustments, leveraging weekday pricing to extend...

Think your high-end Michigan vacation property sells itself? Think again. In this episode, Tony and Jordan challenge the dangerous assumption many luxury STR owners make about prime locations guaranteeing success. The hosts reveal the invisible factors separating consistently booked properties from those sitting empty—even in the most desirable destinations. Discover the psychology behind guest bo...

Networking isn’t just about shaking hands—it’s the fuel that drives real estate and short-term rental success. In this episode, Tony and Jordan break down the  real  value of attending meetups, conferences, and industry events. From unexpected business opportunities to life-changing partnerships, they share personal experiences of how these gatherings have transformed their vacation rental busines...

Airbnb just had a massive earnings call, and Tony and Jordan are breaking down the biggest takeaways that could impact your vacation rental business. From skyrocketing revenue and increased market share over hotels to their removal of 400,000 listings. If you want to stay ahead in the STR game, don’t miss this episode! MichiganSTRConference.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Join the  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

What do the top 1% of Airbnb listings have in common? In this episode, Tony and Jordan break down a data-driven approach to optimizing short-term rental descriptions and amenities. Using AI to analyze high-performing listings, they uncover the key trends that make properties stand out. If you want to attract more bookings and maximize your rental's potential, this episode is packed with action...

In this episode, Tony and Jordan reflect on their biggest highs and toughest lows from 2024, breaking down what worked, what didn’t, and how they’re positioning for an even bigger 2025. From hiring the right team to navigating legislative hurdles, scaling operations, and lessons learned from flipping houses, they share a raw, behind-the-scenes look at the challenges and wins that shape a thriving...

Today, we sit down with Jonathan Wicks, whose company has completed over 200,000 turnovers, to break down what top operators do differently. We dive into the challenges of STR operations and what boutique hotels can teach us about running a successful rental business. If you want to set your property apart and simplify operations, this episode is for you. Well & Good Professional Services Mich...