Top STR Voices Every Scaling Property Manager Should Learn From

The short-term rental industry thrives on people who are building, experimenting, and sharing as they grow. For small and mid-sized property managers, learning from those who are “in the trenches” can be far more actionable than following large-scale operators. This group of creators, operators, and educators brings exactly that—practical, relatable, and highly implementable insights for anyone looking to scale smartly in the STR space.

Jasper Ribbers

Jasper Ribbers is one of the most recognizable voices for independent hosts and small property managers. As the co-founder of Overnight Success and the creator of the “Get Paid For Your Pad” podcast, he has long focused on helping hosts turn their properties into profitable, systemized businesses. More recently, his work has evolved deeper into revenue management, helping operators optimize pricing, demand, and overall performance to drive stronger returns.

What makes his content particularly valuable is the balance between mindset and execution. He breaks down how to build systems, automate intelligently, and make data-backed revenue decisions without burning out. For small PMs, that combination makes growth feel far more structured—and far more achievable.

Alex & Annie

Alex Husner and Annie Holcombe bring a refreshing, narrative-driven approach through their podcast Alex & Annie: The Real Women of Vacation Rentals. In a space often dominated by tactics, their conversations blend storytelling with deep industry expertise, shaped by leadership roles across companies like Vrbo, Vacasa, and NextPax.

Rather than presenting a polished version of success, they dig into the realities of scaling—mistakes, pivots, and everything in between. That honesty makes their insights feel both relatable and credible. For small PMs trying to grow without compromising on quality, their perspective offers a grounded mix of inspiration and real-world learning.

Katie Cline

Katie Cline, through her platform Buy Your Second Home First, brings a sharp, strategic lens to entering the STR space. Rather than pushing aggressive scaling, she focuses on helping hosts make smarter early decisions—whether it’s choosing the right market, structuring financing, or managing risk. Her credibility extends beyond STRs, with her first podcast Suite Success being acquired by Skift—a strong signal of her influence across the wider hospitality space.

Her content consistently leans into long-term wealth creation over quick wins, making it especially relevant for those moving from one property to a growing portfolio. For small PMs, her approach feels measured, intentional, and—most importantly—built to last.

Tyann Marcink Hammond

Tyann Marcink Hammond brings a refreshing shift in focus—from transactions to true hospitality. Her experience as both an operator and educator shows in the way she approaches the business: with equal parts empathy and strategy. Rather than chasing short-term gains, she encourages property managers to build experiences that guests remember and return for.

Her insights often center around sustainability, brand identity, and creating a business that feels both profitable and meaningful. For small PMs looking to stand out in a crowded market, her perspective is a reminder that great hospitality is still the strongest differentiator.

Heather Bayer

A true veteran in the space, Heather Bayer continues to be a guiding voice for operators at all stages. As the co-founder of Vacation Rental Formula and host of the “Vacation Rental Success” podcast, Heather’s content is rooted in decades of experience.

For small PMs, her advice is especially useful in building strong operational foundations and understanding how the industry has evolved over time.

Wil Slickers

Wil Slickers, known for the Slick Talk podcast and as the CEO & Founder of Hospitality.fm, brings a modern, media-savvy approach to hospitality conversations. Through his platforms, he connects with founders, operators, and tech leaders across the STR ecosystem, giving small PMs exposure to a wide range of perspectives.

What sets him apart is his ability to translate industry trends into conversations that feel both accessible and relevant. Instead of surface-level insights, his discussions often unpack the “why” behind shifts in the market—making it easier for small PMs to stay informed without getting overwhelmed.

John Hildebrand

If you’re someone who learns best by seeing real numbers and real properties in action, John Hildebrand offers exactly that through his HildeHomes channel. His content doesn’t just stay at the level of theory—it dives into actual deals, revenue breakdowns, and performance metrics.

By walking viewers through both wins and mistakes, he creates a transparent learning experience that’s easy to follow. There’s a strong emphasis on execution, helping small PMs understand what works (and what doesn’t) in real scenarios. It’s this clarity that makes his content particularly useful for those ready to move from learning to doing.

Crystal DeLoach

Crystal DeLoach brings a level of transparency that’s rare in the STR space. Drawing from her experience at VTrips, she shares the realities of running and scaling a property management business without glossing over the challenges. Her content resonates because it reflects what operators actually face day to day.

By openly breaking down her experiences, she offers a clearer picture of what it really takes to grow. Alongside that honesty, she provides step-by-step guidance that’s practical and easy to implement. For small PMs looking for grounded advice without the fluff, her voice stands out.

Sue Jones

Sue Jones brings a structured, systems-driven lens to the STR space. Through her platform Sue Jones Property Management, she focuses on turning small operations into well-oiled businesses by emphasizing processes, consistency, and operational clarity—areas often overlooked in early growth stages.

Her frameworks help property managers shift from reactive day-to-day management to a more proactive, scalable model. What sets her apart is the focus on building a strong operational backbone before expanding further. For small PMs looking to grow without chaos, her approach is both practical and essential.

Heather Richer

Rounding this out, Heather Richer brings a sharp focus to an area many small PMs overlook—marketing and brand positioning. As a partner at Richer Logic and former Board Member of the Association for Short-Term Rental Homeowners, her perspective is rooted in both strategy and industry leadership. She goes beyond listing optimization, helping property managers build cohesive, recognizable brands that stand out.

Her insights consistently emphasize attracting the right guests rather than just more guests, with a strong focus on differentiation in an increasingly crowded market. For anyone looking to move from being “just another listing” to a memorable brand, her approach is both practical and impactful.

Together, these voices don’t just share advice—they reflect the reality of building and scaling as a small property manager. Their insights are shaped by hands-on experience, constant experimentation, and a deep understanding of what actually moves the needle. For anyone navigating growth, tightening operations, or trying to build a more resilient STR business, these are the perspectives that cut through the noise and deliver real value.

And as you start thinking about what comes next, it’s worth zooming out. In our companion piece on large, professional property managers, we explore how these same principles evolve at scale—highlighting the operators shaping enterprise-level strategy, and the lessons small PMs can borrow as they grow.