You don’t have to stop at single-family short-term rentals. You can build the systems and businesses that help others scale, too.

In this episode of Cash Flow Positive, host Kenny Bedwell sits down with Tyler Gruskiewicz, a full-time real estate investor and entrepreneur from Louisville, Kentucky. Tyler shares his journey from leaving a W2 job to building a growing portfolio of STRs, boutique hotels, and vertically integrated businesses, including a cleaning company, renovation arm, and property management service, all designed to solve the pain points he faced as a host.

They dive into the mindset shifts needed to scale sustainably, the lessons learned from operational chaos, and the power of turning real problems into real opportunities. Tyler also reveals his latest project: transforming one of Kentucky’s oldest bed-and-breakfasts into a mission-driven property supporting veterans and children with speech challenges.

If you’ve ever felt “stuck” at the single-family level, this conversation will show you how to think and build bigger.

[00:00] Meet Tyler: From Ohio roots to full-time investor in Louisville

[01:00] Growing a 7-property STR portfolio + hotels in Florida and Missouri

[02:00] What vertical integration really looks like for real estate investors

[05:00] Faith Renovations and Signature Stays: turning problems into services

[07:00] How Tyler built cleaning, install, and property management teams

[08:30] The cleaning nightmare that pushed him to start his own company

[13:00] Why checks and balances matter in STR operations

[17:00] How one bad turnover led to a total systems overhaul

[21:00] Building culture, communication, and shared vision inside your team

[25:00] The importance of purpose-driven leadership

[29:00] Turning early check-ins into new revenue and guest satisfaction

[32:00] The story behind Kentucky’s oldest B&B—and how it became a mission

[36:00] Giving back to veterans and kids through real estate

[40:00] The takeaway: No one’s coming to save you—build the solution yourself

Tyler Gruskiewicz is a real estate investor known for owning several short-term rental properties in Kentucky with a proven track record in the short-term rental (STR) market. He has gained recognition through interviews and podcasts for his unique approach to growing wealth through STR investments, highlighting both the challenges and strategies for success in this niche real estate segment.​ In addition to his property investments, Gruskiewicz also owns and operates a renovation and cleaning company, leveraging his experience to support and scale his rental business. Recently, he expanded his real estate portfolio by purchasing a 29-door hotel in Branson, Missouri, indicating significant growth and diversification in his hospitality ventures.

🔗 LinkedIn | Website

• Want us to find the deals for you? https://strinsights.com
• Get Top Markers for STRs (2025) https://www.strinsights.com/top-investable-short-term-rental-markets-2025-report
• Instagram – @kenny_bedwell
• YouTube – Cash Flow Positive

What does “scaling” really mean for you?

In this episode of Cash Flow Positive, host Kenny Bedwell breaks down what it truly takes to grow beyond single-family short-term rentals and why the definition of “scaling” should be unique to every investor.

Kenny walks through his personal evolution from duplex house hacking to managing multi-unit portfolios, building a co-hosting business, and partnering with investors to acquire large-scale STRs and boutique hotels.

Along the way, he shares the mindset, strategies, and lessons that help hosts move from buying one property at a time to building a sustainable, scalable business model that fits their goals, not social media’s definition of success.

[00:00] Why “scaling” looks different for every STR owner

[00:01:00] Kenny’s early investing story, from house hacking to Airbnb

[00:04:45] How Buffalo, NY shaped his mindset on scaling and diversification

[00:06:30] Breaking through capital limitations with rental arbitrage

[00:09:00] The rise (and fall) of arbitrage and what works better now

[00:10:30] Scaling into co-hosting and property management

[00:11:45] The power of sharing your wins to attract partnerships

[00:13:40] How to start small but think like a business owner

[00:15:20] Diversifying across markets for long-term stability

[00:18:00] Leveraging other people’s money (OPM) to scale faster

[00:20:20] Building partnerships and equity deals with no capital invested

[00:22:00] Why hotels aren’t the only way to scale and how big STRs can outperform

[00:24:00] Choosing properties that match your goals, not trends

[00:25:15] The truth about hotel deals vs. high-performing STRs

[00:26:40] Redefining success and scaling on your own terms

[00:27:50] A look ahead: scaling through new business opportunities

• Launch Hosts by Kim Fitzpatrick - Example of scaling through services

• Want us to find the deals for you? https://strinsights.com
• Get Top Markers for STRs (2025) https://www.strinsights.com/top-investable-short-term-rental-markets-2025-report
• Instagram – @kenny_bedwell
• YouTube – Cash Flow Positive
• LinkedIn – Kenneth Bedwell

Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights and Podcast Your Brand. Production and editing by Podcast Your Brand.

What if your next short-term rental deal isn’t failing because of the numbers… but because of your reviews?

In this episode of Cash Flow Positive, Kenny Bedwell digs into the “curse” of review-driven real estate—how guest expectations, property condition, and first impressions can quietly make or break your returns. He breaks down the two sides of STR investing (real estate + hospitality), shares real-world examples from his own portfolio, and explains why operations and guest experience are just as critical as deal analysis.

You’ll learn what details guests really notice, how to find properties that support great reviews from day one, and the simple fixes that turn complaints into five-star ratings.

If you want your short-term rental to outperform the market, hit play and start thinking like a guest, not just an investor.

[00:00] Why Kenny “hates” reviews 4and how they shape investor behavior

[01:00] The two-headed monster of STR investing: real estate + hospitality

[02:30] Why being a great host directly impacts revenue

[04:00] How property age and updates influence guest satisfaction

[06:00] Lessons from a historic 1860s home that became a five-star stay

[09:00] The hidden cost of ignoring capital expenditures

[10:40] When old systems (like HVAC) destroy the guest experience

[12:00] How unfinished basements and outdated designs kill reviews

[15:20] External factors: neighbors, privacy, roads, and power lines

[20:00] Designing for privacy, accessibility, and comfort

[23:00] How to impress guests from the moment they arrive

[25:00] The power of small touches, like Kenny’s ice cream bar idea

[27:00] Why first impressions make or break your ratings

[30:20] The link between five-star reviews and long-term revenue

• Want us to find the deals for you? https://strinsights.com
• Get Top Markers for STRs (2025) https://www.strinsights.com/top-investable-short-term-rental-markets-2025-report
• Instagram – @kenny_bedwell
• YouTube – Cash Flow Positive
• LinkedIn – Kenneth Bedwell

Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights and Podcast Your Brand. Production and editing by Podcast Your Brand

If you’ve been chasing the next “get rich quick” shortcut in real estate… this episode is your reality check.

In this episode of Cash Flow Positive, Kenny Bedwell flips the script on fast money and exposes the truth about building real wealth through real estate. He shares insights from conversations with high-level investors: Those who buy $100M hotels and still play the long game and reveals why the biggest wins come from appreciation, tax strategy, and equity paydown, not just monthly cash flow.

You’ll learn the four true pillars of wealth in real estate, how to think like an investor instead of a speculator, and why repositioning your assets the right way can transform your portfolio faster than chasing short-term returns ever will.

Stop looking for overnight success. Press play now to learn how the smartest investors actually get rich with patience, data, and a long-term plan.

[00:00] Back from the flu and fired up about “get rich quick” myths

[01:30] The problem with chasing only cash flow

[03:35] Lessons from top-tier investors who buy $100M properties

[05:00] The four wealth pillars: cash flow, appreciation, tax savings, and equity paydown

[07:00] What “repositioning” really means and why it’s where wealth is built

[09:25] When cash flow should be your priority and when it shouldn’t

[10:30] Why high-income professionals invest differently (and what that means for you)

[12:30] How to calculate true ROI using total return, not just cash flow

[15:20] The mindset shift: stop chasing income, start building net worth

[18:30] Defining your investment goals before you buy your next STR

[21:15] How Kenny evaluates deals now and why forced appreciation beats “good enough”

• Want us to find the deals for you? https://strinsights.com
• Get Top Markers for STRs (2025) https://www.strinsights.com/top-investable-short-term-rental-markets-2025-report
• Instagram – @kenny_bedwell
• YouTube – Cash Flow Positive
• LinkedIn – Kenneth Bedwell

Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights and Podcast Your Brand. Production and editing by Podcast Your Brand

Most investors look at bedroom counts at face value. Kenny Bedwell doesn’t.

In this episode of Cash Flow Positive, Kenny reveals a deal-finding strategy he’s seen quietly pay off in competitive short-term rental markets: targeting properties with extra square footage and converting them into higher bedroom counts. From Sedona to the Poconos, Kenny explains why “heads in beds” is the #1 revenue driver, how to legally add bedrooms to force appreciation, and why average-performing STRs will always lose out to top properties.

You’ll hear how to spot these overlooked opportunities, the math that makes them work, and why moving quickly under contract is often the difference between landing a deal and watching it slip away.

Don’t settle for average returns. Press play now to learn how Kenny turns overlooked listings into high-cash-flow, high-appreciation wins.

• Want us to find the deals for you? https://strinsights.com
• Get Top Markers for STRs (2025) https://www.strinsights.com/top-investable-short-term-rental-markets-2025-report
• Instagram – @kenny_bedwell
• YouTube – Cash Flow Positive
• LinkedIn – Kenneth Bedwell

Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights and Podcast Your Brand. Production and editing by Podcast Your Brand.

Is refinancing your short-term rental a smart move—or a trap that eats away your cash flow?

In this episode of Cash Flow Positive, Kenny Bedwell sits down with veteran mortgage broker and STR financing expert Matt Stout. With over 32 years of lending experience and thousands of deals funded, Matt pulls back the curtain on when refinancing actually makes sense. From dropping interest rates and shifting housing trends to creative ways to redeploy “dead equity” into higher cash-flowing properties, this episode delivers the unvarnished truth about refinancing in today’s market.

You’ll learn the right (and wrong) reasons to refinance, how to weigh costs versus cash flow, and why keeping versus selling a property can make or break your long-term wealth.

Don’t guess your way through one of the biggest financial decisions you’ll face as an investor. Press play now to get Kenny and Matt’s proven framework for knowing when to refinance and how to use it to build real generational wealth.

Matt Stout is “The STR Loan Guy” and founder of Consumers Financial, a mortgage brokerage licensed in 48 states. With over three decades in lending and a personal background in real estate investing, Matt specializes in STR and DSCR loans that help investors unlock equity and scale their portfolios. He’s known for creative lending strategies, hybrid loan solutions, and his straight-shooting approach to helping investors win deals.

🔗 STR Loan Guy Website | YouTube – STR Loan Guy | Facebook | TikTok @thestrloanguy

• Want us to find the deals for you? https://strinsights.com
• Get Top Markers for STRs (2025) https://www.strinsights.com/top-investable-short-term-rental-markets-2025-report
• Instagram – @kenny_bedwell
• YouTube – Cash Flow Positive
• LinkedIn – Kenneth Bedwell

Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights and Podcast Your Brand. Production and editing by Podcast Your Brand.

If someone handed you $250,000 in cash to invest in a short-term rental, where would you buy and what strategy would you use to make that money work?

In this episode of the Cash Flow Positive Podcast, host Kenny Bedwell is joined by Erin Wegrzyn, a real estate consultant with STR Insights, to explore exactly that scenario. Together, they break down how to choose the right markets, set realistic expectations, and avoid the “amenities arms race” that eats into cash flow.

Erin shares her journey from long-term rental investor to short-term rental specialist and why her strategy has shifted toward properties that both cash flow and create memories for her family. Kenny and Erin discuss how to research markets, stay ahead of competitors, and build a property that can grow with the market over time, without burning out or over-renovating.

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!

Key takeaways:

• How to choose markets without spreading yourself too thin
• Why being “one of one” in a market is a huge advantage
• How to avoid competing in an endless amenities war
• What to look for in properties that allow for future upgrades
• Why following where large investors are putting money can reveal emerging markets
• The best way to build a reliable local team of contractors and cleaners
• Why you should visit and experience a market before you invest there
• And much more...

Guest Bio:

Erin Wegrzyn is a real estate consultant with STR Insights, where she helps investors analyze markets and identify profitable short-term rental opportunities. Based in Kentucky, she brings firsthand experience as an investor and a deep understanding of market trends, property selection, and building reliable local teams. Erin is passionate about helping clients choose properties that cash flow, grow in value, and fit their lifestyle goals.

Resources:

Connect with Kenny on LinkedIn

Follow Kenny on Instagram

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

If $250,000 dropped into your lap today, would you actually know what to do with it?

In this episode of Cash Flow Positive, Kenny Bedwell pulls back the curtain on exactly how he’d put that money to work in short-term rentals. He breaks down why your financing strategy can make or break a deal, the five cost buckets most investors forget about, and why setting your ROI goal up front is non-negotiable.

You’ll hear Kenny think through real markets, from Florida beaches to Shenandoah cabins, and explain how to spot which ones fit your budget and which ones will bleed you dry.

Don’t guess your way into a $250K mistake. Hit play now to hear Kenny’s no-fluff, data-backed roadmap and get clarity on where your money will actually cash flow.

[00:00] How a $250K windfall changes your investing strategy overnight

[02:14] The financing trap that torpedoes deals before they close

[04:18] The five hidden costs every STR investor must budget for

[07:36] Kenny’s minimum ROI goals—and why cash flow beats percentages

[10:53] The “process of elimination” method for picking your markets

[14:25] Why Bradenton, FL, might work—and the brutal barrier to entry

[21:00] Shenandoah’s low-barrier charm vs. beach market competition

[24:38] How lakefronts in Michigan and urban rentals in Cincinnati stack up

• STR Insights software
• Top Markets Report (via STR Insights website)
• Dave Ramsey podcast (benchmark reference)
• Zillow & Redfin (for market comps)

Evergreen Links

• Want us to find the deals for you? https://strinsights.com
• Get Top Markers for STRs (2025) https://www.strinsights.com/top-investable-short-term-rental-markets-2025-report
• 📲 Instagram – @kenny_bedwell
• ▶️ YouTube – Cash Flow Positive
• 💼 LinkedIn – Kenneth Bedwell

Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights and Podcast Your Brand. Production and editing by Podcast Your Brand.