21 Properties, One Full-Time Job, and a Remote Team: Real Strategies with Jeremy Rosen

04/04/25 • 44 min

In this episode of The Scaling Made Simple Podcast, Jonathan Farber sits down with Jeremy Rosen — a full-time nurse who also manages 21 short-term rental properties. Jeremy breaks down how he successfully balances a demanding job while scaling a thriving STR business, thanks to the power of virtual assistants, strong systems, and smart time management.

Jeremy dives deep into the day-to-day operations of managing multiple properties, including his approach to guest communication, pricing strategies, and creating a five-star experience that drives repeat bookings. He shares the tools and tactics he uses to stay organized, the importance of hiring early, and why building a reliable team (both virtual and local) is the key to long-term success.

Guest: Jeremy Rosen
Role: Full-time nurse & short-term rental operator
Based in: San Antonio, TX
STR Portfolio: 21+ properties
PMS: Hospitable
CRM Tool: Elite 360
Booking Platforms: Airbnb (primary), VRBO, Booking.com (limited), Direct bookings via personal website

Previous Episode

Episode 10 - How to Build and Scale an Airbnb Business Working Only 20 Hours a Week – with Luke Kolk

In this episode, Luke Kolk shares how he went from being a police officer to building a thriving Airbnb co-hosting business with over 60 units — all while working just 15–20 hours a week. He breaks down the systems, strategies, and mindset shifts that helped him scale fast, including how he finds quality leads, builds a strong team, and uses tools like Asana and Indeed to streamline operations.

Luke also dives into the power of execution over information, why effective communication and team incentives matter, and how he structures his time to stay efficient. Whether you're just getting started or looking to scale your short-term rental business, this episode is packed with practical insights you can apply right away.

🎙️ Episode Credits

Guest: Luke Kolk
Follow him on Instagram and Facebook: @kolkhomes
If you’re facing a challenge in your short-term rental business, Luke probably has a solution — whether it’s a VA, bookkeeper, revenue manager, mentorship, or simply the right connection to help you scale.
➡️ “It’s probably not an information problem. It’s an execution problem.”

Host: Jonathan Farber
Thanks for tuning in to this episode of the Scaling Made Simple Podcast.

Next Episode

The #1 Mistake New Entrepreneurs Make (And How to Fix It) – with Cameron Williams

What’s the secret to building a scalable, profitable consulting business? In this episode, Cameron Williams — founder of Kinley Consulting — shares how choosing the right niche and confidently pricing his services transformed his growth. We dive into how he built a solid team, streamlined operations, and used marketing strategies that actually work.

If you're struggling with underpricing, unclear offers, or wearing too many hats, this episode is your blueprint. Cameron breaks down his journey, lessons learned from paid ads, tips for setting client expectations, and how to build a business that runs without you.

Whether you're just starting or ready to scale, this conversation is packed with insights you can apply today.

🎯 Topics covered:

Niche selection and why it matters
Confident pricing strategies
Building a team and delegating smart
Sales and marketing that convert
Operational systems that scale
Client communication tips
Lessons from growing a consulting business

🎙️ Guest: Cameron Williams, Founder of Kinley Consulting
🌐 Website: www.kinleyconsulting.com (K-Y-N-L-I Consulting)
📩 Email: [email protected]
📱 Follow for free content & insights: Facebook page – Kinley Consulting
🧠 Content includes: case studies, client challenges, real-time insights, and valuable business tips (3–5 posts daily)