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In this episode of Right About Now, Ryan Alford sits down with real estate investor and entrepreneur Jamil Damji to unpack a story that starts with rejection—and turns into full ownership of life, business, and purpose. After being denied entry into medical school despite doing everything “right,” Jamil made a decision that changed everything: no one else would control his future again.
From his first wholesale deal—turning a $50K opportunity into a life-changing moment—to losing everything during the 2008 financial collapse and rebuilding from the ground up, Jamil breaks down what it really takes to create success on your own terms.
The conversation goes deeper than business, touching on addiction, self-discovery, and the internal work required to evolve as a leader, father, and human. Jamil also shares how he’s now using his platform to solve real-world problems—from housing affordability to helping people experiencing homelessness build new opportunities through real estate.
This is more than a business story—it’s a blueprint for taking control, making different choices, and building a life you’re proud of.
🎯 Topics Covered
Why Jamil rejected the traditional path after medical school denial
The first wholesale real estate deal that changed everything
Lessons learned from losing everything in the 2008 financial crisis
Why success is an “inside job” (mindset, habits, and identity)
Addiction, recovery, and rebuilding from within
Building a scalable real estate business through relationships (not cold leads)
The power of personal branding and TV (Triple Digit Flip)
Why real estate investors must take responsibility for housing challenges
Co-living, affordability, and solving real-world housing issues
🤝 Connect with Host & Guest
Ryan Alford (Host)
Instagram: https://www.instagram.com/ryanalford
Website: https://ryanisright.com
Jamil Damji
YouTube: https://www.youtube.com/@JamilDamji
Instagram: https://www.instagram.com/jdamji