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

1. 
   

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

   
   


2. 
   

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

   
   


3. 
   

   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

  
  

 Travis Makes Money is made possible by High Level – the All-In-One Sales & Marketing Platform built for agencies, by an agency.

 Capture leads, nurture them, and close more deals—all from one powerful platform.

 Get an extended free trial at gohighlevel.com/travis

Learn more about your ad choices. Visit megaphone.fm/adchoices