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When Steven Rea joined Northpoint Asset Management as Chief Innovation Officer, he asked a simple question on Day 1: "How do we track our leasing pipeline?" The answer wasn't a CRM or a specialized SFR platform. It was a Google Sheet. In this debut episode of Year One, Steven pulls back the curtain on the reality of modernizing a legacy Single Family Rental (SFR) operator. This isn't a story about incompetence; it's a story about how versatile tools like spreadsheets evolve from helpful bridges into permanent crutches that silo knowledge and create friction. Steven introduces the concept of the "20-Year Startup"—a company that has successfully achieved scale over two decades, but whose systems never evolved past the "hero mode" of Day 1. He also shares a candid look at his first major mistake: a "perfect" automation workflow that nearly locked residents out of their payment portals. In this episode, we cover: The "Shadow IT" Reality: How spreadsheets become the de facto operating system in SFR when core platforms don't fully fit. The "20-Year Startup": Defining the unique pain of a company that scales its revenue but not its foundation. The High Cost of Tribal Knowledge: Why "local ways" of doing things make accountability impossible. The Automation Trap: A transparent look at an 11:50 PM launch that threatened to break trust with residents, and the lesson learned about human oversight. The Bias for Action: Why waiting for perfect conditions is just a slower way to fail. Timestamps (00:00) - The "Google Sheet" Reality Check. (01:21) - Defining the "20-Year Startup." (03:17) - The hidden cost of "Tribal Knowledge" vs. Documentation. (05:19) - Why you can't have accountability without defined standards. (06:56) - Failure Story: The 11:50 PM Collections automation mistake. (09:06) - The Real Lesson: Why you have to pilot before you fix. (10:30) - Teaser: The Consolidation Decision. Quote of the Episode "The scary part wasn't the spreadsheet. The scary part was that everyone thought it was normal. That moment told me everything I needed to know." About the Show Year One is a documentary series following the digital transformation of Northpoint Asset Management. Hosted by Steven Ray, CINO, it offers an unvarnished look at the strategies, failures, and breakthroughs involved in rebuilding a national SFR operator from first principles. Links & Resources Connect with Steven on LinkedIn: www.linkedin.com/in/steven-rea-cpm Learn more about Northpoint Asset Management: www.northpointam.com