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.

Timestamped Highlights

[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

About the Guest

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.

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Important Links

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• 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.