Cash Flow Positive

What does it really take to launch a short-term rental successfully—when things don’t go as planned? In this solo episode of Cash Flow Positive, Kenny Bedwell pulls back the curtain on two recent STR setup experiences that tested his patience, budget, and systems.

Kenneth shares everything he learned while launching properties in Asheville and Kentucky, including working with designers, managing contractors, and navigating delays, disasters, and unexpected design decisions. One project turned into a complete nightmare, with miscommunications, missed deadlines, and a designer who ghosted him in the middle of the process. The other? A more streamlined—but still challenging—process that highlighted the value of clear communication, strong referrals, and aligned teams.

If you’ve ever thought about hiring a designer or project manager to help launch an STR—or wondered what pitfalls to avoid—this episode delivers a firsthand look at what not to do and what you can do instead to protect your investment and timeline.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

In This Episode You'll Learn:

• Why hiring a designer isn’t enough—and what you actually need them to do
• How to avoid costly delays when setting up a short-term rental
• The one mistake that caused a project to go totally off the rails
• Why referrals and vetting are non-negotiable for anyone on your team
• What happens when designers and contractors aren’t in sync
• How small miscommunications lead to big issues (and how to fix them)
• The lessons learned from a 10,000 sq ft STR project in Kentucky
• Why some STR entrepreneurs are choosing in-house design and build teams
• And much more...

Resources:

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What if you could invest in STRs where demand never dries up—without competing in oversaturated vacation markets? In this episode of Cash Flow Positive, Kenny Bedwell sits down with Maria Reith, an experienced STR investor who has built a thriving rental portfolio in military towns, including Dayton, Ohio, and San Antonio, Texas.

Maria didn’t start with a background in real estate—she began investing as a way to prepare for retirement. But what started as a simple strategy quickly scaled into over 30 properties in some of the most stable STR markets available: military towns.

She reveals why military bases create consistent rental demand, how she balances short-term, midterm, and long-term rentals, and why word-of-mouth marketing plays a huge role in her success. Maria also shares her approach to creative financing, how she finds value-add properties, and the one thing investors should always research before buying near a military base.

If you're looking for new STR markets with steady cash flow, this episode will open your eyes to a powerful, under-the-radar investment strategy. Listen now and njoy!

In This Episode You'll Learn:

• How military towns offer consistent demand for STRs, even when vacation spots are saturated
• Why proximity to military bases can be key for STR profitability
• The importance of buying properties with value-add potential for maximum returns
• How to balance between short-term, midterm, and long-term rentals to optimize cash flow
• Why word-of-mouth and community engagement are crucial for military-based STR businesses
• How Maria uses creative financing to scale her STR portfolio
• How to evaluate the future stability of military bases and the surrounding real estate market
• Why Maria’s exit strategy involves preparing for long-term rental cash flow
• And much more...

Resources:

Mariareith.com 

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What if you could invest in short-term rentals without competing in oversaturated vacation markets? In this episode of Cash Flow Positive, host Kenny Bedwell challenges the idea that STR success is only found in traditional vacation destinations. Instead, he explores alternative STR markets that offer consistent demand, fewer competitors, and strong cash flow opportunities.

Drawing from his own experience setting up two STR properties—a 5-bedroom renovation project and a rental on the Bourbon Trail in Kentucky—Kenny shares the realities of launching an STR outside the usual hotspots. He explains why vacation rental markets aren’t the only profitable options and breaks down key STR opportunities in less obvious locations, including college towns, military towns, state parks, and urban areas near hospitals.

Throughout the episode, Kenny highlights how investors can leverage these markets to reduce risks, secure better returns, and manage seasonality more effectively. He also discusses exit strategies and the importance of adaptability when investing in these unique STR locations.

This episode is a must-listen for anyone looking to expand their STR portfolio without getting caught in the vacation rental bubble.

In This Episode You'll Learn:

• Why short-term rental markets go beyond vacation destinations
• How overlooked STR markets can offer better cash flow and stability
• What makes college towns a strong, steady investment choice
• Why military towns are ideal for short- and mid-term rental demand
• How state parks have become an unexpected STR hotspot
• Why STRs near hospitals can provide year-round bookings
• How to evaluate exit strategies in different STR markets
• What investors should consider before entering these less obvious locations
• And much more…

Resources:

Connect with Kenny on LinkedIn

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How do you scale from a single short-term rental to managing over 30 properties and owning a boutique hotel? In this episode, Kenny is joined by Tony Stancato, Founder of Book N' Gather Property Management. He shares how he leveraged partnerships, operational expertise, and a strategic mindset to build a thriving STR business in Southwest Michigan.

Tony walks us through his journey—from buying his first vacation rental in 2021 to managing a diverse portfolio that includes single-family homes, multi-unit properties, and now a boutique motel. He reveals the keys to finding great deals, structuring partnerships, and navigating the challenges of short-term rental investing.

Whether you're just starting out or looking to scale your STR portfolio, this episode is packed with practical insights on building a business that creates wealth, not just cash flow. 

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

In This Episode You'll Learn:

• Why partnerships can accelerate growth and unlock bigger deals
• The mindset shift needed to go from one rental to a full-scale business
• How networking and sharing your journey can lead to unexpected opportunities
• The importance of structuring a property management company for long-term success
• Why successful investors focus on both cash flow and appreciation
• How short-term rental markets like Southwest Michigan offer untapped potential
• And much more…

Resources:

Connect with Kenny on LinkedIn

Follow Kenny on Instagram

Connect with Tony on LinkedIn

Michigan Short Term Rentals Podcast

MichiganSTRConference.com 

Scaling a real estate portfolio isn’t just about buying more properties—it’s about strategic growth, partnerships, and mindset shifts. In this solo episode of Cash Flow Positive, Kenny Bedwell shares his personal journey of scaling his short-term rental business, highlighting the biggest challenges, lessons, and strategies that helped him go from his first investment to a sustainable, cash-flowing portfolio.

Kenny emphasizes the importance of starting small, taking action, and not waiting for the “perfect” opportunity. He also discusses why defining what scaling means to you is crucial before making your next investment decision. 

Additionally, he breaks down why partnerships and collaborations are the key to overcoming capital constraints and how to navigate the quantity vs. quality debate when expanding your portfolio.

If you’re looking to grow your STR investments but feel stuck, this episode provides a clear roadmap for taking the next step—whether that’s buying your first property, securing funding for expansion, or building strategic partnerships to accelerate growth. Enjoy!

In This Episode You'll Learn:

• Why you don’t need a massive budget to start investing in STRs
• The biggest mistake investors make when scaling—and how to avoid it
• Why taking action is more important than waiting for the “perfect” opportunity
• How defining your vision of success will dictate your investment strategy
• The power of partnerships in overcoming capital constraints
• Scaling isn’t just about adding more properties—it’s about smart growth
• How to balance quality vs. quantity when expanding your portfolio
• Why patience and long-term thinking are key to achieving sustainable success
• And much more…

Resources:

Connect with Kenny on LinkedIn

Follow Kenny on Instagram

What if you could increase bookings and nightly rates just by adding the right amenities? In this episode of Cash Flow Positive, Kenny Bedwell is joined by short-term rental expert Jose Cornejo to break down the real impact of STR amenities—and how to choose the ones that actually move the needle.

With 18+ years of experience in the STR industry, Jose has built and managed lakefront homes in the Poconos, beachfront rentals in the Outer Banks, and additional properties in Kentucky. He started before Airbnb and Vrbo even existed, learning firsthand how smart pricing, marketing, and amenities can turn a property into a revenue-generating machine.

Jose shares his insights on why not all amenities increase revenue, how seasonal upgrades can impact demand, and why marketing your amenities properly is just as important as offering them. He also discusses the biggest mistakes investors make when upgrading their properties and how to create an experience that justifies premium pricing.

If you’re looking for data-backed strategies to maximize revenue and optimize guest experience, this episode will help you stand out in the crowded STR market and boost your bottom line. Enjoy!

In This Episode You'll Learn:

• How strategic amenities increase bookings and nightly rates
• Why pictures are just as powerful as physical amenities
• The surprising impact of seasonal amenities on guest demand
• How to create a guest experience that justifies premium pricing
• Why marketing your amenities properly is the real game-changer
• How investing in the right upgrades can pay off quickly
• And much more…

Resources:

Connect with Kenny on LinkedIn

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Connect with Jose on LinkedIn

CornejoRentals.com 

Which amenities actually increase revenue in short-term rentals—and which ones are just a waste of money? In this solo episode of Cash Flow Positive, Kenny Bedwell breaks down the three types of amenities that move the needle: those that increase occupancy, boost ADR (average daily rate), or improve guest experience.

Kenny shares real data and case studies on what amenities truly impact bookings and pricing, revealing the biggest mistakes hosts make when choosing upgrades. He also explains how to market amenities effectively, why seasonal amenities can be a game-changer, and how five-star reviews directly impact revenue.

If you’re thinking about investing in amenities to stand out in a crowded market, this episode will help you make the smartest decisions to maximize profits.

In This Episode You'll Learn:

• The three types of amenities: occupancy boosters, ADR boosters, and guest experience enhancers
• Why not all amenities increase revenue—and how to identify the ones that do
• The impact of seasonal amenities and when they actually generate bookings
• How to market your amenities properly to get the most value out of them
• Why five-star reviews are worth $189 each—and how to get more of them
• How small guest experience improvements can significantly impact long-term revenue
• And much more…

Resources:

Connect with Kenny on LinkedIn

Follow Kenny on Instagram

Episode Mentioned:

Part 2: How to buy deals out-of-state with Jeana Deninger

What’s the key to long-term success in real estate investing? It’s not just about strategy—it’s about the people you surround yourself with. In this episode of Cash Flow Positive, Kenny welcomes Tanya Rooney, a seasoned investor and short-term rental expert, to dive into the power of community, accountability, and networking in building a thriving business.

With 17+ years in real estate, Tanya has built a successful career in commercial real estate, flipping, and STR investing—but she credits her biggest wins to the relationships she’s built along the way. She reveals how masterminds, accountability groups, and surrounding yourself with the right people can accelerate success, plus the hard lessons she learned from a motel deal gone wrong.

Whether you’re just starting out or scaling your investments, this episode will give you actionable insights on leveraging relationships to build wealth faster.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today!

Enjoy!

In This Episode You'll Learn:

• Why accountability groups are a game-changer for real estate investor
• How surrounding yourself with the right people accelerates success
• The importance of celebrating wins instead of always chasing the next goal
• How networking in mastermind groups can save you from costly mistakes
• The key differences between STRs and boutique hotels—and why it matters
• How effective communication can prevent revenue loss in STRs
• And much more…

Resources:

Connect with Kenny on LinkedIn

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Tribe Builders Podcast

Connect with Tanya on LinkedIn

What’s the real secret to long-term success in real estate investing? It’s not just about the numbers—it’s about understanding your progress, defining success, and fueling momentum for the next step. In this solo episode of Cash Flow Positive, Kenny Bedwell shares his personal secret weapon for success, reflecting on how far he’s come and why taking time to acknowledge wins is essential for continued growth.

Kennt discusses how mindset, gratitude, and self-reflection play a huge role in building and scaling a real estate portfolio. He also reveals his latest big investment move—a $1.5M boutique hotel—and how shifting his perspective helped him take on challenges he never imagined a year ago.

If you’re looking for more than just investment strategies and want to build a mindset that drives success, this episode will help you reframe how you measure progress, set goals, and push past your limits.

In This Episode You'll Learn:

• Why success isn’t just about hitting big milestones—it’s about progress
• The power of gratitude and self-reflection in business growth
• How defining your “why” helps guide smart real estate decisions
• Why tracking your achievements fuels momentum for bigger opportunities
• How surrounding yourself with the right people accelerates success
• Kenny’s personal experience with scaling investments and taking on new risks
• And much more…

Resources:

Connect with Kenny on LinkedIn

Follow Kenny on Instagram

Buying out-of-state rental properties can feel like a gamble—so how do you ensure success and avoid costly mistakes? In this episode of Cash Flow Positive, Kenny Bedwell is joined by Jeana Deninger, an experienced short-term rental investor and consultant. With properties in Maine, Florida, and beyond, Jeana has mastered the art of managing STRs from a distance, ensuring they remain profitable while maintaining high guest satisfaction.

Jeana shares the critical steps every investor should take when purchasing and managing out-of-state properties, from choosing the right markets and assembling a reliable local team to marketing effectively and optimizing guest experiences. She also discusses common mistakes investors make and the red flags to watch for when working with property managers, cleaners, and maintenance teams.

If you’re thinking about expanding your real estate portfolio into new markets, this episode is packed with insider strategies to help you buy, manage, and scale STR properties like a pro. Enjoy! 

In This Episode You'll Learn:

• Why hiring the right professionals can make or break your STR business
• The importance of researching local markets and guest expectations
• How to properly vet and manage cleaners, handymen, and house managers
• The top mistakes investors make when buying properties sight unseen
• How to market your STR to stand out and maximize bookings
• Why you should never skip inspections—and how they can save you thousands
• The smart way to budget for amenities that increase guest satisfaction and ROI
• And much more…

Resources:

Connect with Kenny on LinkedIn

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SavvyBreezy.com 

Connect with Jeana on LinkedIn