Short Term Rental Riches

By: Tim Hubbard
  • Summary

  • Tim Hubbard, successful investor and CEO of a seven-figure short term rental management company shares it all. The insider tips you need to know to acquiring, operating and scaling a successful short term rental business.
    Tim Hubbard
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Episodes
  • 272. Is Starting an Airbnb in 2025 Still Worth It? Here’s the Truth
    Jan 28 2025

    Is 2025 the right time to jump into the short-term rental (STR) game? It’s a question I get asked a lot, especially as the STR market continues to evolve. With rising competition, new regulations, and changing guest expectations, it’s natural to wonder if Airbnb is still a good investment. The truth is, while the industry has shifted, the opportunity to create a profitable Airbnb business is very much alive—if you know how to adapt. After nearly a decade in the short-term rental space, I’ve learned that success isn’t just about having a great property—it’s about understanding the trends, navigating challenges, and offering an experience that keeps guests coming back.

    Today, I’ll share an honest look at the current state of the Airbnb market in 2025. We’ll talk about key factors like market saturation, guest preferences, and the impact of new tools and technology. Whether you’re considering starting your first Airbnb or scaling an existing short-term rental business, I’ll help you decide if 2025 is still the right time to jump in—and how to do it profitably. Let’s get started!

    In this episode, you’ll learn:

    • Competition Is Rising: With more people entering the STR space, market saturation is a real challenge in some areas. That’s why finding a unique selling point (like a killer design or standout amenities) is more important than ever.

    • Guest Expectations Are Changing: Today’s travelers are looking for more than just a place to sleep—they want unique, Instagram-worthy stays with all the comforts of home. Use tools like my Recommended Resources to help you stand out.

    • New Regulations in Some Markets: From city-specific rules to stricter licensing, it’s important to research regulations in your target market before you invest. These rules can impact profitability, so do your homework.

    • Technology Can Be a Game-Changer: From dynamic pricing tools like PriceLabs to automated guest communication, leveraging the right tools will save you time and help maximize profits.

    • Opportunities Are Still Out There: Even with challenges like competition and regulations, demand for short-term rentals remains strong in the right markets. Focus on high-demand locations and offer something guests can’t find elsewhere.

    So, is starting an Airbnb in 2025 still worth it? The answer really depends on your strategy, market, and willingness to adapt to changes. Short-term rentals are still a great way to generate income, but success comes down to planning and execution.

    Need help managing your short-term rental and you don’t want to go it alone? Shoot us a message here and we’ll see if we can help.

    Are you enjoying the podcast? Please subscribe, leave a rating and a review, and share it! This helps us reach others that may find the info helpful as well.

    You can find all of our links here including our website, recommended resources, upcoming live event, short-term rental playbook, Instagram, and more!

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    14 mins
  • 271. Boutique Hotels vs STRs: Rich Somers Explains Why They're the Future of Real Estate in 2025
    Jan 21 2025

    If you’ve ever wondered how to scale your short-term rental business or pivot into a new real estate niche, boutique hotels might be the perfect opportunity for you. Boutique hotel investing combines the fundamentals of STRs—guest experience, revenue management, and location—but on a much larger scale. And the best part? Unlike single-family STRs, boutique hotels are valued based on income, not comps, giving you more control over asset appreciation.

    In this episode of Short Term Rental Riches, Tim interviews Rich Somers, a seasoned real estate investor with an $80M portfolio of boutique hotels. Rich shares his journey from managing Airbnbs to acquiring and renovating underperforming boutique hotels in some of the most competitive markets. Along the way, he highlights essential strategies, like leveraging seller financing, navigating Airbnb regulations, and mastering SEO and direct bookings. Whether you’re just starting in real estate investing or are a seasoned STR operator, this episode is packed with actionable insights to help you grow your portfolio while maximizing guest experience and revenue.

    In this episode, you'll learn:
    • STRs vs. Boutique Hotels: Boutique hotels offer scale and operational control, and their valuation is based on income instead of comparable properties. This allows investors to force appreciation by increasing revenue.

    • Creative Financing Strategies: Many boutique hotels are owned outright by baby boomers, creating unique opportunities for seller financing. Offering flexible terms can help you close deals faster.

    • Airbnb Regulations Are an Advantage: Tight short-term rental regulations in many cities are driving demand back to boutique hotels. Choosing markets with strict Airbnb rules can create high occupancy and premium rates.

    • Direct Bookings & SEO: Focusing on direct bookings through SEO and social media marketing can reduce reliance on OTAs (Airbnb, Vrbo) and significantly boost your bottom line.

    • Overcoming Challenges: From high-interest bridge loans to unexpected renovations, boutique hotels require proper contingency planning and operational excellence to mitigate risks.

    The boutique hotel space is rapidly growing, and as Rich Somers explained, it’s one of the best ways to scale your portfolio while navigating strict Airbnb regulations and a high-interest rate environment. Whether you’re leveraging seller financing, using bridge loans, or refining your guest experience strategy, the potential for forced appreciation and profitability is massive in boutique hotels.

    Need help managing your short-term rental and you don’t want to go it alone? Shoot us a message here and we’ll see if we can help.

    Are you enjoying the podcast? Please subscribe, leave a rating and a review, and share it! This helps us reach others that may find the info helpful as well.

    You can find all of our links here including our website, recommended resources, upcoming live event, short-term rental playbook, Instagram, and more!

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    46 mins
  • 270. 12 STR Hacks to Maximize Revenue & Enhance Guest Experience
    Jan 14 2025

    I’m excited to have you here because today’s episode is all about improving your short-term rental game with practical, actionable tips. I’ve been in this business for years, and if there’s one habit that’s made a huge difference, it’s taking notes on everything—whether I’m listening to a podcast, attending an event, or watching STR success stories on YouTube. I recently went through my inbox, where I save all my ideas, and pulled out 12 incredible tips to help you boost Airbnb visibility, improve your listing, and enhance your guest experience.

    In today’s fast-paced STR market, standing out is key, and small changes can make a massive impact. From ensuring your property is categorized correctly on Airbnb (yes, you can request a category change!) to investing in high-quality photos with drone shots and twilight lighting—this episode covers it all. I’m also diving into smart tech upgrades like wireless chargers and pet-friendly touches that guests love. And if you’re scaling your business or managing properties remotely, stay tuned for operational tricks, including how to leverage same-day deliveries for emergencies. Let’s dive in!

    Key Takeaways:

    • Optimize Airbnb Categories: Request up to 5 new categories for your listing to improve visibility using the Airbnb category request page (visit elevate.translated.com/categories).

    • Professional Photos Matter: Invest in drone photos, twilight shots, and highlight parking or nearby attractions to attract more guests.

    • Add Convenience with Tech: Install wireless chargers by bedsides and in common areas—guests love having quick access to charging.

    • First Impressions Count: Check your doormat! Ensure it’s clean and welcoming. Bonus points for adding a fun message that makes guests smile.

    • Consistent Lighting: Make sure your lightbulbs match in color temperature (stick with warm 3000K for a cozy feel)—no "hospital lights"!


    Thanks for tuning in! Whether you’re updating your photos, adding smart tech upgrades, or fine-tuning your pricing strategy, remember that every step brings you closer to running a standout short-term rental. These small but impactful changes can lead to higher bookings, glowing reviews, and a smoother operation overall.

    Need help managing your short-term rental and you don’t want to go it alone? Shoot us a message here and we’ll see if we can help.

    Are you enjoying the podcast? Please subscribe, leave a rating and a review, and share it! This helps us reach others that may find the info helpful as well.

    You can find all of our links here including our website, recommended resources, upcoming live event, short-term rental playbook, Instagram, and more!

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    15 mins

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