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 renovation or furnishing costs coming up, this episode could help you turn that spend into thousands in rewards.

Follow Colin Stroud on LinkedIn

Colin's company, Go Somewhere

Choosing the Best Travel Credit Card

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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

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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.

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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 to turn real estate into a scalable business. If you’ve been craving freedom, this one’s for you.

Follow Kassidy on Instagram

Check out Kassidy's Podcast "For Your Own Good"

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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 guest stays, and how to strategically set maximum prices.

Whether you're managing a single Airbnb or scaling a portfolio, this episode has actionable tips to help you maximize your revenue.

Connect with Kyle on LinkedIn

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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 booking decisions, learn which amenity investments deliver the highest ROI, and hear real-world examples of properties that transformed from overlooked to overbooked with strategic enhancements.

Whether you're struggling with seasonal vacancies or simply want to maximize your property's earning potential, this episode delivers actionable insights for crafting a listing that commands attention and premium rates in any market.

The difference between "nice place" and "must-stay experience" is smaller than you think. Listen now and unlock your property's full potential.

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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 business.

Whether you’re looking for referral partners, new deals, or just some encouragement, this episode is packed with insights on why showing up is half the battle.

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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!

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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 actionable insights.

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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 STR business.

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