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/

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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.

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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

In this episode of Legacy Builders with Kyle McGee, our host sits down with entrepreneur, author, and wealth advisor Chad Willardson to explore what it truly means to live a fully invested life — not just in business, but in faith, family, fitness, and purpose.

Chad opens up about his personal operating system, the vulnerability of writing his most authentic book yet, and why the traditional concept of “work–life balance” is a lie holding leaders back. He shares how intentional decisions, non-negotiable habits, and a values-driven mindset have helped him build a thriving company while staying anchored at home.

Connect with Chad: linkedin.com/in/chadwillardson

Buy Chad's Newest Book: https://fullyinvested.com/

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In this powerful episode of The Legacy Builders with Kyle McGee, host Kyle McGee sits down with Chad Henderson—Founder, CEO, and Managing Partner of Catalyst Healthcare Real Estate, and co-founder of Andrews Medicine alongside world-renowned surgeon Dr. James Andrews.

Chad shares the full arc of his story—from selling ice cream to tourists as a teenager, to navigating great financial crisis early in his career, to ultimately building a multi-billion-dollar national healthcare real estate platform operating in 20+ states with over $2.5B in assets.

You don't want to miss this episode! 

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In this episode of the Legacy Builders Podcast, Kyle sits down with Ryan Schmitt, Founder & CEO of Petticoat Schmidt, to unpack the extraordinary journey behind one of Florida’s fastest-growing heavy civil construction companies. Ryan shares the origin of the business, the early leap of faith, and the brutal season he calls “The Valley of Darkness,” where stacked job losses, financial collapse, and overwhelming pressure nearly took everything he built. Through transparency, grit, and the support of his wife, mentors, and team, Ryan walked “into the punch” every day—emerging with a renewed vision for leadership, culture, and purpose. His mindset, accountability systems, and commitment to open-book management helped transform a struggling company into one defined by resilience and unity.

Ryan also reveals why he chose to sell 30% of the company to his employees through an ESOP, creating shared ownership and long-term wealth for the people who helped rebuild the business from the ground up. He discusses the spiritual and personal rhythms that anchor him, the importance of faith and family in leadership, and the habits that keep him performing at his highest level. This conversation highlights what it truly means to lead with humility, build a culture where people matter, and create a legacy that outlives you.

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In this episode of Legacy Builders with Kyle McGee, host Kyle McGee sits down with Lauren Brychell, founder of Equity Elevated Consulting and author of Beyond the Lead. Lauren shares how she accidentally stumbled into the world of capital raising and went on to raise over $75M across commercial real estate and alternative investments.

From mastering investor relations and building scalable IR systems to creating balance through structure, faith, and gratitude — Lauren opens up about her entrepreneurial journey, her mindset around growth, and what it really takes to turn conversations into committed capital.

💡 If you’re an entrepreneur, investor, or anyone chasing growth with purpose, this episode is for you.

Connect with Lauren: 

LinkedIn: linkedin.com/in/lauren-brychell-capital-raise-consulting

Website: equity-elevated.com

Buy Lauren's New Book Here: https://www.amazon.com/Beyond-Lead-Stress-Free-Capital-Raising/dp/B0FV96C51V/ref=sr_1_1?crid=2TNITHNVVIFM&dib=eyJ2IjoiMSJ9.1WuA0VZVHVmmhK8xPU3iRw.fyCL7rI-Gjm92WtMXUflvn5eH7mlUqfI4A02h5x-DL4&dib_tag=se&keywords=Lauren+brychell&qid=1760376423&sprefix=lauren+brychell%2Caps%2C126&sr=8-1

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In this episode of Legacy Builders with Kyle McGee, our host Kyle McGee sits down with estate planning attorney Blake Johnson to talk about what it really takes to build wealth that lasts. Blake shares how to create a “family bank,” why parents should manufacture challenges instead of removing them, and how faith and intentionality shape a family’s long-term success.

From teaching kids financial responsibility to redefining what legacy truly means, this conversation is packed with wisdom for anyone who wants to build not just wealth — but purpose, character, and confidence across generations.

Want to connect with Blake?: 

LinkedIn: linkedin.com/in/myfamilybank

Website: https://trustedepa.com/

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In this episode of Legacy Builders with Kyle McGee, host Kyle McGee sits down with Jason Langkammerer — architect, builder, and founder of AT6 Design Build — to explore how he’s reshaped the meaning of craftsmanship and client experience. Jason shares how growing up on job sites with his architect-father shaped his approach to blending modern design with historic character, how the 2008 recession sparked his pivot into design-build, and what he’s learned about balancing business, family, and purpose.

They discuss the power of saying “no,” earning client trust through transparency, leading with generosity, and defining legacy beyond revenue. Whether you’re a creative entrepreneur, builder, or leader striving for balance and excellence, this episode is packed with timeless insights on building not just projects—but a life that matters.

Connect with Jason - 

Email: [email protected]

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

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Blaine Flynn’s journey is anything but ordinary. From dropping out of high school at 16 to building one of the most respected home construction companies in Northwest Florida, his story is rooted in faith, family, and the mantra, “Why not me?”. In this episode, Blaine shares the lessons of resilience, the fine line between confidence and arrogance, the role of habits in success, and why true legacy is about impact—not just numbers. Whether you’re an aspiring entrepreneur or simply looking for inspiration to keep pushing forward, this conversation will challenge you to rethink what’s possible.

Contact Blaine: [email protected] 

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