Welcome to Hassle-Free RE! Today, Dave Menapace and Will Van Wickler break down what it really takes to scale beyond 10 properties in the short-term rental business. From hidden costs to operational complexity, they reveal the challenges no one talks about and the mindset shifts required to build a sustainable, profitable business.

Dave and Will discuss why scaling isn’t just about acquiring more doors—it’s about building systems, hiring the right team, and stepping into the CEO role. They share stories from managing dozens of properties and a boutique hotel, highlighting the importance of financial organization, operations across different markets, and learning to coach your team instead of trying to do it all yourself.

This episode also explores the personal side of scaling—how to manage the mental load, avoid burnout, and focus on the few things that actually move the needle. Whether you’re just getting started or looking to expand your portfolio, this conversation will help you prepare for the realities of growth and avoid costly mistakes. Tune in now to gain the insights you need to scale with confidence and clarity.

TIMESTAMPS

1:22 – Scaling beyond 10 properties and the myth of “easy scaling”

2:23 – The hidden costs of growth

3:09 – The foundation for scaling

3:59 – Beach vs. mountain STRs and diversifying across markets

4:59 – Managing 40+ properties and shifting into the CEO mindset

6:00 – Building a team before you think you can afford it

7:56 – Lessons in leadership: coaching, mentoring, and emotional intelligence

8:57 – Obsessions that drive business growth: owners, teams, and guests

10:00 – Breaking the “grind first, hire later” mindset

10:38 – The importance of roadmaps, reps, and purposeful scaling

12:00 – Hyperfocus on 1–3 strategies to 10x faster

13:14 – Final takeaways: team, mindset, and staying disciplined with growth

#ShortTermRentals #BusinessGrowth #RealEstateInvesting #ScalingSTRs #PropertyManagement