

Episode 58. Steven Rea - Founder at Chasing Tomorrow A.I.
Apr 16, 2025
Steven Rea, the founder of Chasing Tomorrow A.I., is a multifamily innovator with over a decade at the nexus of property management and technology. He discusses the significant challenges in the multifamily real estate sector and how technology can drive innovative solutions. Rea emphasizes the need for a mindset shift in operational practices and highlights the critical role of training and leadership. He also unveils his new AI platform aimed at revolutionizing onboarding, advocating for a workforce that values empathy and adaptability alongside technological advancement.
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Steven Rea's Multifamily Start
- Steven Rea started in multifamily by chance, working in sales and with a private real estate investor.
- He quickly fell in love with multifamily after joining RPM Living and engaging deeply with process and technology.
Intentional Scaling Lessons
- Be intentional and selective when scaling multifamily businesses to sustain performance.
- Investing in training early builds a strong talent base enabling long-term growth without losing properties.
Technology Is a Tool, Not Solution
- Technology should be treated as a tool, not a solution, requiring skilled people to use it effectively.
- Overemphasis on software training overshadows essential property management training, causing inefficiencies.