Season 2: David Oakley - Founder and Chief Executive Officer @ Oakley Group

🎙️ In this episode, I sit down with David, Founder and Chief Executive Officer of Oakley Group, for a thoughtful conversation about entrepreneurship, capital markets, and building something that lasts.David’s career spans more than two decades in multifamily real estate — from acquiring and renovating properties since the early 2000s to closing over $8 billion in multifamily transactions throughout his career. At Oakley Group, he leads the firm’s strategic direction, focusing on identifying investment opportunities, shaping long-term vision for portfolio assets, and cultivating strong, aligned equity partnerships.Before founding Oakley Group, David served as Senior Managing Director at Berkadia, where he led the Alabama office and delivered fully integrated capital markets and sales solutions for multifamily owners. He also built and successfully exited two operating companies —Select My Space and Blue Canoe Properties — experiences that deeply shaped his perspective on operations, scale, and disciplined growth.What made this conversation especially meaningful was David’s openness about his journey — the lessons learned building businesses, navigating market cycles, and balancing ambition with responsibility. We talked about what great investors look for, how conviction is built over time, and why community involvement and purpose matter just as much as performance.In this episode, we dive into:(1) David’s entrepreneurial journey and evolution as a real estate leader(2) How Oakley Group approaches multifamily investment and partnerships(3) Lessons from capital markets, operations, and long-term ownership(4) Why leadership, values, and community engagement matter in this industryBeyond real estate, David is deeply committed to giving back - serving on advisory boards at Samford University and the YMCA of Greater Birmingham, and helping found organizations that support families during critical moments in their lives. That same sense of purpose carries through everything he builds.This episode is a must-listen for anyone interested in multifamily investing, entrepreneurship, or building businesses with both discipline and heart.🟢 Now streaming on Spotify, Apple Podcasts, and wherever you listen.