Host Kyle McGee sits down with guest Evan Holladay, Founder & CEO of Holiday Ventures, to unpack the inflection points that shaped Evan’s path into workforce, affordable, and mixed-income real estate development.

They explore Evan’s unconventional career journey, the power of coaching and accountability, and how Holiday Ventures is redefining affordable housing through thoughtful design, nonprofit partnerships, and complex capital stacks that allow investors to do well while doing good. The conversation also dives into mentorship, abundance mindset, faith, and what it truly means to build a legacy that outlives you.

If you care about impact-driven entrepreneurship, real estate as a force for good, or building something that matters long after you’re gone—this one’s for you.

Connect with Evan:

https://holladayventures.com/

https://www.affordabledevelopmentmastery.com/

Coaching with Trevor McGregor

https://trevormcgregor.com/

Stay connected to the conversation by joining us on your favorite social media platform!

https://linktr.ee/legacybuilderskm

In this milestone 50th episode of Legacy Builders with Kyle McGee, our host steps out from behind the guest chair and into a solo, monologue-style conversation—sharing the lessons, failures, convictions, and faith that have shaped both the podcast and his life.

From losing his father and mother-in-law far too early, to confronting alcohol abuse, imposter syndrome, and the lie of “someday,” Kyle reflects on what it truly means to lead—not from position or ego, but from service, obedience, and daily discipline.

He unpacks:

• Why action matters more than certainty
• How faith reframes leadership
• The habits and traits shared by high performers
• Core values that anchor life, family, and business
• Why legacy isn’t built in moments—but in daily decisions

This episode is for builders who want to become better leaders—and leaders who want to become better humans.

No shortcuts. No hype. Just truth, humility, and the call to lead from where you are.

🎯 Keep building your legacy.

Stay connected to the conversation by joining us on your favorite social media platform!

https://linktr.ee/legacybuilderskm

What if the moments you’re most ashamed of are actually the doorway to your greatest impact?

In this deeply vulnerable conversation, JR Lay shares the raw story behind his entrepreneurial journey — from early hustles and building companies to facing addiction, identity collapse, and the moment that almost cost him his family. Together, JR and Kyle unpack what it truly means to level up: confronting the truth, mastering your mind, redefining success, and choosing discipline, faith, and presence over performance and ego.

This episode is about more than business. It’s about identity, legacy, and the courage to walk through the “thick woods” when life demands transformation. If you’re an entrepreneur, leader, or human wrestling with purpose, pain, or calling — this conversation may be the one you didn’t know you needed.

Want to connect with JR?

Phone: 832-549-5792

Website: www.levelupbusiness.com

Stay connected to the conversation by joining us on your favorite social media platform!

https://linktr.ee/legacybuilderskm