Author:
Blendi Muriqi
“At the end of the day, the people on the ground, that’s the lifeline of your business.”
That line from Steve Cummings, founder of Misfit Homes, perfectly captures the reality of running a successful short-term rental (STR) business. If you’re managing multiple properties—or thinking about scaling—this episode of Sip & Scale is essential listening. Steve walked me through his journey from graphic designer to STR operator, sharing the lessons he learned about delegation, automation, and streamlining operations to deliver exceptional guest experiences.
Whether you’re an aspiring property manager or a current host looking to scale efficiently, there’s a lot to unpack here.
Steve’s journey is unconventional. He transitioned from the creative world of graphic design into managing multiple STR properties in Nashville, Tennessee. But what really stood out was his focus on systems and processes.
Starting in an industry without prior experience, Steve realized that relying solely on yourself quickly becomes unsustainable. Without processes, tools, and people, your business will plateau, or worse, burn you out. His early days involved late-night check-ins, juggling multiple apps, and handling every little operational detail personally. Sound familiar?
One of the biggest takeaways from our conversation was how Steve leveraged automation and AI to streamline operations. From guest communications to marketing, these tools allowed him to reduce manual tasks and focus on growth.
Automation doesn’t replace the human element—it enhances it. Guests still want personalized interactions, but repetitive tasks like booking confirmations, check-in instructions, and routine messaging can be automated, freeing up time for higher-value work.
For STR owners, the right automation tools are directly linked to profitability. They reduce errors, improve consistency, and allow teams to focus on what really matters: the guest experience.
We also touched on the critical role of social media marketing. Steve shared how leveraging platforms to build brand awareness has significantly boosted direct bookings. Instead of relying solely on listing sites, maintaining a strong social presence allows property managers to engage with guests, showcase properties, and create repeat customers.
Social media is more than a marketing channel—it’s a brand-building tool. For operators scaling multiple properties, it helps maintain visibility, reinforces credibility, and drives long-term business growth.
Perhaps the most important lesson Steve shared is about delegation. Growth is impossible if you try to do everything yourself.
Delegation isn’t just assigning tasks, it’s about trusting your team, establishing clear processes, and giving people the responsibility to make decisions. Steve’s approach shows that empowering your team directly impacts guest satisfaction. A strong team can handle routine operations while management focuses on strategy and scaling.
He also highlighted the role of third-party vendors, weighing their pros and cons. While outsourcing can solve operational gaps, careful management and clear expectations are crucial to maintain consistency and quality.
Another challenge discussed was the evolving landscape of Nashville’s STR market. Regulations and compliance requirements can significantly affect operations, but Steve emphasized that there’s still room for growth with the right systems and team in place.
Markets evolve, guest expectations change, and regulations shift, STR operators need to adapt quickly, leaning on both technology and a reliable team to stay competitive.
One of the most relatable insights Steve shared: maintaining work-life balance requires delegation.
Without a team or automated systems, operators are constantly “on call,” checking messages at midnight or jumping between properties. Delegation allows founders and property managers to focus on strategic growth while still having time for life outside the business.
Steve’s story reinforces a critical truth: success in STRs depends on people and processes, not just properties. Automation, AI, strong branding, delegation, and outsourcing are not optional, they’re essential for scaling efficiently and sustainably.
For anyone running short-term rentals, Misfit Homes is a case study in how to grow without burning out, improve guest experience, and expand strategically.
If you’re a host, property manager, or aspiring entrepreneur in the STR space, Sip & Scale dives deep into real stories, real challenges, and actionable strategies to help you scale smarter.
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