POWERS Podcast #396: Jason Illian - Co-Founder @ Highmount Capital - Eternal Thinking

Host: Chris Powers
Guest: Jason Illian
Date: October 21, 2025

Episode Overview

In this compelling episode, Chris Powers sits down with Jason Illian, Co-Founder of Highmount Capital, for a deep, wide-ranging conversation about leadership, faith, intentionality, parenting in a digital age, and what it means to live—and lead—with an eternal perspective. The episode dives into the challenges and opportunities of raising a family, building businesses, and shaping culture in today's society. Jason shares candid insights drawn from his life, faith, and experience investing in companies like Dude Perfect, addressing everything from decision-making frameworks to the shifting landscape of media and the unique pressures on the next generation.

Main Themes and Purpose

• Living and Leading with an Eternal Perspective:
  Jason unpacks the concept of playing the “infinite game” versus the finite games of business and life (00:00, 62:21).
• Faith and Family as Foundational Lenses:
  Intentionality in parenting, marriage, and professional life, all anchored through a biblical worldview (04:29, 18:27).
• Navigating Technology and Culture:
  Guidance on raising kids amid social media, technology addiction, and a rapidly changing media environment (21:37, 30:12).
• Building a Legacy vs. Building an Empire:
  What it means to leave a lasting impact through values and relationships, not just business achievement (50:34).
• Hope, Accountability, and Male Loneliness:
  Addressing cultural loneliness, the importance of male friendship, and the power of hope in uncertain times (57:04, 49:09).
• The Realities of Leadership, Failure, and Growth:
  Candid reflections on imperfection, leadership, and being open about both strengths and weaknesses (78:18).

Key Discussion Points & Insights

1. The Infinite vs. Finite Game

[00:00, 62:21]
Jason opens with a reflection on life’s infinite game—the eternal context that frames how he approaches daily challenges and relationships:

• The finite game: Completing projects, selling companies, raising kids until they leave home.
• The infinite game: Living with the perspective that “we have souls that will live forever… the more you think about playing that game, the more you feel free.”

  “You don’t have to win every battle… You can deal with your son or daughter struggling with something because you see it as a growth opportunity.” – Jason (00:00)

2. Intentionality in Parenting, Marriage & Ministry

[03:07–07:03, 08:08–09:06, 12:41–14:45]
Jason discusses the "crazy season" of parenting three active kids, managing sports, work, and faith ministry at home:

• Ministry is woven into daily life (“Deuteronomy 6 framework”):

  “When you're in the home or along the road… wherever you are, you're ministering to people.” (04:29)

• Using sports as a vehicle for character and faith, not just achievement.
• Importance of resetting weekly, intentional conversations, and recognizing each child’s unique temperament.
• Navigating the pressures of athletic recruitment with humility and spiritual grounding.

  “I'm not looking for NIL...I'm looking for what is the leadership, what's the coaching, and what’s the culture on that team.” (12:47)

3. Biblical Decision-Making, First Principles & Callings

[09:06, 14:58, 18:27, 20:30]

• Leadership as “prophet, priest, king”: Truth-teller, merciful guide, and purposeful builder.
• Framework for life decisions:

  “What is the first lens that you look at your life through? If it’s not biblical, it’s something else… Everybody has a lens.” (18:27)

• Stories of turning down lucrative offers, focusing on legacy, time with family, and building something mission-aligned.

4. The Digital Generation: Challenges and New Frontiers

[21:37–33:37, 35:50–38:33]

• Gen Z is the most “faithful generation” by some measures but faces new distractions—tech, short-form content, social media.
• Phones, social media, and their impact on attention, relationships, and even recruitment in sports.

  “Technology itself is neither good nor bad, but it can be used for bad when it’s that distracting.” (23:29)

• Parenting approaches: Delayed phone/social access, established rules, open conversations, treating issues as teachable moments.
• Example of social media downsides (e.g., exposure to porn, algorithmic pressure) and upsides (opportunities for ministry).

5. Family-Oriented Media and Cultural Revivals

[39:19–44:08]

• The rise of family-friendly creators (Dude Perfect, Mark Rober, Nick DiGiovanni) responding to a cultural hunger for trustworthy, uplifting content.

  “What Dude Perfect’s done…is…built an amazing amount of trust with families…The overwhelming response is, this content brings us together.” (39:19)

• Signs of a cultural shift: People pushing back against divisive, toxic content.

  “People have finally stood up and said, enough. We’ve had enough of this nonsense…” (42:14)

6. Free Speech, Truth, and Cultural Courage

[44:08–46:39]

• Speaking the truth with courage and civility, even when it risks personal cost.
• Value of compassion and understanding in dialogue, not just “winning the argument.”

  “We're not here to win an argument. We're here to win the person.” (45:12)

7. Hope, Legacy, and Community

[49:09–58:25]

• Hope rooted in faith, family growth, and the power of positive tech use.
• Building “legacy, not empire”:

  “If you leave a legacy, everybody benefits, right? Because the values…continue and spread.” (50:34)

• Addressing loneliness in men: The power of finding even one authentic friend, and practical steps toward deeper connection and accountability.

8. Identity, Failure, and the Eternal Perspective

[60:55–64:10, 78:18]

• The danger of tying identity to achievement rather than inherent worth or faith.
• The liberation (and resilience) found in an eternal perspective:

  “If my whole firm falls apart tomorrow…my identity as a believer doesn’t change. Eternity’s still within my grasp.” (61:00)

• Being a Christian isn't about perfection:

  “It’s not righteousness. It’s not, I have it all figured out. It’s, I don’t have it figured out…I need a savior.” (77:37)

Notable Quotes & Memorable Moments

• On the Infinite Game:

  “We are all playing the infinite game, whether we like it or not… The more you think about playing that game, the more you feel free.” – Jason (00:00)

• On Intentional Fatherhood:

  “You have to spend… 1,000 hours with your kids, intentional hours, before they turn 18. And for every hour you don’t spend…you have to spend 10 hours to make up for the one you didn’t spend.” – Jason (25:07)

• On Phones and Social Media:

  “I was in the Bay Area talking to guys who started social media…they don’t give their kids phones…if these tech leaders aren’t giving the phones to their kids, they realize something really powerful.” (31:37)

• On Leaving a Legacy:

  “You can leave a legacy or you can leave an empire, but you can't leave both... If you leave a legacy, everybody benefits.” – Jason (50:34)

• On Hope:

  “Each and every day we’re growing. Each and every day we’re getting a little bit better. Each and every day we’re reminded of the hope we have in Christ…” – Jason (80:41)

• On Truth and Emotional Health:

  “If the truth you think is the truth is making you angrier and angrier…that’s not the truth. There is no eternal truth that makes you a meaner, angrier person.” – Brent (72:58)

• On Christian Life:

  “It’s not righteousness…it’s not, I have it all figured out. It’s, I don’t have it figured out…I’m an eternal sinner, and I need a savior to get me through.” – Brent (77:37) “It’s about that daily growth…am I going to make Christ the forefront of my life?” – Jason (78:18)

Timestamps for Key Segments

• Infinite vs. Finite Game: 00:00, 62:21
• Parenting/Ministry Intentionality: 03:07–05:43, 08:08–09:06
• Decision-Making, Biblical Lens: 09:06, 14:58, 18:27
• Technology, Media, Gen Z: 21:37–33:37, 35:50–38:33
• Family-Oriented Media/Dude Perfect: 39:19–44:08
• Truth, Free Speech, Courage: 44:08–46:39
• Hope, Legacy, Male Friendship: 49:09–58:25
• Identity, Failure, Christian Growth: 60:55–64:10, 78:18

Final Reflections

The conversation is a masterclass in integrating purpose, faith, and leadership across all arenas of life. Jason and Chris remind us that success is fleeting, that legacy outlasts empire, and that hope, humility, and intention are the true marks of a life well lived. The episode offers practical wisdom for builders, parents, and leaders alike, without moralizing—full of real, relatable struggles and encouragement for those on the journey.

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