Michigan Short Term Rentals

Ten years ago Tony was rigid. Someone would invite him to coffee and he'd say "yeah, we should do that" and never follow up. Then he changed one thing: he started saying yes. To podcasts, to events, to lunches with people. That one shift led to speaking invitations, exclusive event tickets, and opportunities he never would have gotten staying in his routine. He's sharing the less...

Tony had one of those weeks where everything compounds at once. A lawsuit, hotel construction delays worse than expected, new issues discovered during renovation, and three client deals hitting problems. He walked through how to keep perspective when everything feels like the valley of despair. The key insight is that these aren't disasters, they're the exact problems he dreamed about havi...

Tony and Jordan just realized they've gotten this far despite not being aware of their most important role: capital allocation. They talk about Fred Boothby doing deals with zero of his own money while they're still setting up property management software themselves. Revenue is just vanity metrics. What matters is cash on cash return and IRR. The real question isn't how do I get more b...

Tony got invited to an exclusive Booking.com vendor event in Washington DC and came back convinced they've been leaving money on the table. Booking.com is actually the world's largest vacation rental platform, not Airbnb. While Airbnb dominates the US, international travelers use Booking.com. Since Tony isn't on it, he's probably missing international guests completely. Now he'...

Tony and Jordan have paid serious money for masterminds over the years and they keep doing it because the returns compound in weird ways. A $500 program turned into half a million. An expensive program they thought was a waste ended up sending them four house referrals years later. The real lesson? You're paying for proximity to people thinking bigger than you, and that changes everything. Joi...

The Warren Hotel is 15 days from ribbon cutting and it's the biggest project Tony and Jordan have ever tackled on the fastest timeline. They bought a beat-up property for $1.2M, committed $750K to renovation, and split the 20% down payment between four investor groups. Now they're watching moles burrow through fresh landscaping, scrambling to find a fence guy on Thursday for a Tuesday open...

Frank Fear has been coming to the Michigan STR Conference three years running and he's ready to pull the trigger on his next deal. He brings his investment thesis to Tony and Jordan including buy box criteria from Kenny Bedwell's wildly profitable properties framework, why acreage beats lakefront in today's market, and the harsh reality of exit strategies when you're stacking ameni...

Someone told Tony not to buy a motel in Grayling, Michigan. They did it anyway. Now The Windmoor Lodge just hit 1,000 nights booked and has more revenue on the books this year than all of last year, with peak season barely starting to fill. Tony shares the real numbers including a 17.5% profit margin at the lowest rate period of the year and an average daily rate climbing to $232 during May throug...

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 epis...

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 naggin...

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 o...

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...

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.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Join the  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Michigan Short Term Rentals Facebook group⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

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.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Join the  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Michigan...

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.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Join the  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Michigan Short Term Rentals Facebook group⁠⁠⁠⁠⁠⁠⁠...

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 wh...

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 peopl...

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.com https://www.facebook.com/StayTheWarren https://www.instagram.com/staythewarren/ ⁠https://michiganstrconference.com⁠⁠⁠⁠⁠⁠⁠⁠⁠ Join the  ⁠⁠⁠⁠⁠...

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.com⁠⁠⁠⁠⁠⁠⁠⁠ Join the  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

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...

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 reinfo...

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 Instagram https://michiganstrconf...

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...

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, agin...

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 be...