In this episode of Uncontested Investing, we sit down with Sean Miller, Chief Revenue Officer at Lessen, to explore how technology is reshaping property management. From single-family rentals to multifamily and commercial portfolios, Sean shares how Lessen streamlines maintenance operations, uses AI and IoT to anticipate repairs, and helps investors scale more efficiently without losing control of their assets.
Whether you’re a landlord managing two homes or a professional operator with hundreds of units, this conversation unpacks how to combine local expertise, operational systems, and smart technology to stay ahead in today’s evolving real estate landscape.
Key Talking Points of the Episode
00:00 Introduction
01:00 How Sean got into real estate investing
02:06 The common characteristics of successful leaders
03:09 Building Lessen and scaling to 3.5M+ work orders
04:37 Property management as a tech-enabled service
06:30 Sean’s Deal Breaker/Deal Maker: the most pivotal moment in his career
08:02 When should a real estate investor hire a property manager?
10:22 Leveraging tech in property management with Lessen
11:36 Core features every scalable property management system needs
13:49 IoT use cases: From smart fridges to HVAC monitoring
16:23 The resident experience & retention strategies
17:40 What is IoT?
19:03 Managing turnover timelines & vendor reliability
20:46 Lessen’s use of AI for task routing & QC optimization
22:19 What’s next for Lessen and how to partner with them
Quotables
“Tech is powerful, but it has to solve a real need. For us, it’s about making operations more efficient and predictable.”
“You miss 100% of the shots you don’t take—and if you’re afraid of mistakes, you’ll never innovate.”
“Cost is what you pay. Value is what you get. And faster turns mean more value, even if the price is higher.”
Links:
Lessen
RCN Capital
https://www.rcncapital.com/podcast
https://www.instagram.com/rcn_capital/
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