Patrick McKenzie (patio11) is joined by his father, Jim McKenzie, for an intimate and in depth exploration of commercial real estate development. They unravel the complex web of relationships, regulations, and often absurd situations that shape our built environment. From the intricacies of curb cuts and driveway permits to the art of navigating local politics and lobbyists, the conversation offers a rare glimpse into the hidden mechanisms of urban development. Jim shares the highlights from his career like transforming day-old bread stores into bank branches, dealing with Chicago's infamous aldermen, and spelunking in archives to find century-old telegrams with enforceable contractual implications.– Full transcript available here: https://www.complexsystemspodcast.com/episodes/the-hundred-year-old-telegram-worth-5-million-with-jim-mckenzie-2/ – Sponsor: Check Check is the leading payroll infrastructure provider and pioneer of embedded payroll. Check makes it easy for any SaaS platform to build a payroll business, and already powers 60+ popular platforms. Head to checkhq.com/complex and tell them patio11 sent you. – Links: Bits About Money: https://www.bitsaboutmoney.com/archive/why-is-that-bank-branch-there/ – Timestamps: (00:00) Intro (00:27) Understanding real estate development with Jim (03:13) The great rail lease story (20:02) How real estate ownership is conducted (25:58) Real estate acquisition strategies (28:39) Sponsor: Check (29:41) Banks and location (34:25) Day-old bread: an opportunity (38:45) The Walgreens development dilemma (40:22) Strategic offers and unusual numbers (42:25) The power of personal relationships (46:37) Navigating real estate offers and execution quality (52:51) The LaSalle Bank acquisition and its impact (54:39) The 2008 quadruple whammy (58:39) The West Town shopping center opportunity (01:01:44) The complexities of real estate deals (01:14:24) The 2008 financial crisis and its ripple effects (01:15:36) The energy industry resurgence post-Ukraine incursion (01:16:07) Navigating utility easements and real estate (01:21:43) The complexities of curb cuts and driveway permits (01:23:46) Chicago's political landscape and real estate development (01:32:37) Lobbying and political influence in development (01:51:58) Wrap – Complex Systems is part of the Turpentine podcast network. Turpentine also has a social network for top founders and execs: https://www.turpentinenetwork.com/