Jake & Gino: Real Estate Investing & Multifamily · 2026-03-09 · 49 min
In this episode of the Jake & Gino Podcast, hosts Jake Stenziano and Gino Barbaro sit down with real estate developer and investor Evan Holladay. In this conversation, Evan shares his journey into real estate development, the challenges of breaking into the industry, and the key lessons he learned while scaling large projects. He also explains how aspiring developers can get started, what it really takes to succeed in this space, and how real estate development can become a powerful path to building long-term wealth. 00:00 Intro 01:12 Introducing Evan Holladay 03:05 Evan’s Background and How He Got Into Real Estate 07:18 First Challenges Breaking Into Development 11:42 Understanding Affordable Housing Development 16:05 How Real Estate Developers Actually Make Money 20:34 The Complexity of Development Deals 24:10 Lessons From Leading $694M in Projects 28:20 How Beginners Can Enter Real Estate Development 32:15 Common Mistakes New Developers Make 36:05 Workforce & Affordable Housing Opportunities 40:10 Mentoring the Next Generation of Developers 43:20 Advice for Aspiring Real Estate Developers 46:10 Final Thoughts and Where to
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