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How do real estate development deals actually work for passive investors? And what makes them riskier than buying existing properties? Dustin and Adam sit down with Eugene Gershman, a second-generation developer with 20+ years of experience who now partners with landowners across the country to bring projects from raw land to stabilized assets. Eugene explains the two-tier capital structure many developers use: early-stage “GP funds” (comparable to startup seed capital) where investors take more risk but participate in the sponsor’s profit sharing, followed by traditional LP investments once permits are secured and construction is priced. He also shares his “kill list,” the specific deal-breakers that prompt him to walk away, and why stale construction plans and unexplained project delays are immediate red flags. Learn how timelines, market cycles, and capital structures in development deals differ from investing in existing and stabilized assets. Episode Release Notes & Resources: • GIS Companies: https://giscompanies.co • Eugene's podcast – Real Estate Development: Land to Legacy: https://giscompanies.co/podcast • Eugene’s LinkedIn: / eugenegershman Key Timestamps: 00:04:26 Eugene - from finance to the family construction biz 00:07:22 Why he partners with landowners instead of buying properties 00:09:19 How cash flow works (or doesn’t) in development deals 00:12:47 What to look for when evaluating a development operator 00:14:34 The two-tier capital structure for development risk 00:17:48 Red flags that signal a deal should be avoided 00:20:14 Market cycles & why now may be a good time to start projects 00:25:20 The “kill list”: when to walk away from a deal 00:29:24 What “freedom” and “independence” mean to a developer See all Wealth Independence episodes at https://wealthindependencepod.com Connect with Dustin: Big Spring Capital: https://bigspringcap.com LinkedIn: / thedustinbailey Twitter/X: https://x.com/TheDustinBailey Connect with Adam: Bidwell Capital: https://bidwellcapitalfund.com