Evan Holladay is an experienced real estate developer and investor who has developed over $694 million in projects and more than 2,600 affordable multifamily units. As the Founder and CEO of Holiday Ventures, Evan specializes in intentionally designed, sustainability-focused affordable and mixed-income communities. He also teaches other aspiring developers through his 12-month mentorship program, Affordable Development Mastery. In this episode, Evan shares the scrappy, relationship-driven journey that took him from pre-med student to nationally recognized affordable housing developer.

On this episode we talk about:

Why relationships often create more opportunity than credentials

How Evan leveraged mentorship and persistence to break into real estate development

The mindset shift from “being qualified” to becoming resourceful

Using podcasting as a networking accelerator and personal MBA

Building 1,200+ affordable housing units in seven years — and scaling with impact

Top 3 Takeaways

Opportunity comes from proximity. Getting in the right rooms — even before you feel ready — can change the trajectory of your career.

Professional persistence beats passive applications. Evan didn’t just apply for jobs — he engineered access to decision-makers.

Impact and profit aren’t mutually exclusive. Thoughtful affordable housing can create strong investor returns while transforming communities.

Notable Quotes

“Opportunity comes from people. Value comes from competence.”

“Every major pivot happened when I wasn’t 100% ready — but I took action anyway.”

“You jump off the cliff and build the plane on the way down.”

Connect with Evan Holladay:

Instagram / LinkedIn / YouTube: @evanholladay

Holladay Ventures

Affordable Development Mastery

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