What does a banking password that reads “retire@40!” have to do with radical generosity? For John Cortines, it was the starting line. At Harvard Business School, a men’s Bible study cracked open a question none of them could answer: what is a Christian stewardship philosophy? The search for that answer became a book, then a framework, then a life, and this conversation captures the heart of it.

John Cortines, co-author of God and Money and True Riches and a generosity leader at the Maclellan Foundation, joins Justin Forman for a wide-ranging conversation recorded live at Kingdom Advisors. They walk through the biblical case for financial finish lines (pre-set guardrails for lifestyle spending and net worth that create genuine freedom) and the four-stage heart transformation every investor must navigate: pride to gratitude, coveting to contentment, anxiety to trust, and indifference to love.

The episode closes with a vision for the future: professionally managed giving funds that bring the same rigor investors already expect from their financial advisors to their Kingdom capital. John believes these will become as standard as index funds, and he’s already building toward that reality through the Maclellan Foundation’s collaborative giving model.

CHAPTERS

00:00 Opening — King Nebuchadnezzar vs. King David on ownership

01:05 Who is John Cortines? Family, farm, and homesteading

03:33 The journey begins: “retire@40!” and encountering generosity

04:05 Harvard Business School and the men’s Bible study that changed everything

05:30 Taking the “God and Money” class at Harvard Divinity School

06:13 The wrong relationship with giving — and the mindset shift

07:00 The right question: not “how much to give” but “how much to keep”

08:09 Research with Harvard MBA alumni: what radically generous investors look like

11:33 Why joy is the difference between effective altruism and Christian generosity

14:04 Financial finish lines: lifestyle and net worth guardrails explained

15:17 The shadow side of entrepreneurial ambition

16:13 Introduction to True Riches and the four heart transformations

16:45 Heart condition #1: Pride — and the antidote of gratitude

20:24 Practical rhythms for cultivating gratitude

21:52 Heart condition #2: Coveting — and the antidote of contentment

23:31 Social media, discontentment, and radical surgery

25:12 Biblical pairing of financial sin and sexual sin in Scripture

27:45 Breaking down the wall: why money is the last taboo in the church

29:08 Heart condition #3: Anxiety — and the antidote of trust

29:45 Heart condition #4: Indifference — and the antidote of love

33:31 Going on offense: collective and collaborative giving

34:08 Personal conviction: giving toward what’s on God’s heart, not just yours

37:27 Professionally managed giving funds — the vision for the future

39:38 The mutual fund parallel: from $100B to $15 trillion

42:31 How to build joy and community into collective giving

44:38 Celebrating generosity as a family and as a community

45:49 First step for investors: offer 100%, not just 10%

47:15 Closing encouragement and call to action

What does America’s greatest competitive advantage look like in the age of AI? Richard Cunningham and Luke Roush bring Donna Harris — founder and CEO of Builders and Backers, veteran venture investor, and co-author of the redemptive investing playbook at Praxis — into this America 250 special edition of Marks on the Market to answer exactly that question.

Donna challenges the assumption that venture capital is the default path for founders, explains why startups are creating a third fewer jobs than 15 years ago despite record startup rates, and makes the case that AI has permanently lowered the barrier to entrepreneurship. For faith-driven investors, her framework for identifying who actually wins in the AI era — not which model, but which people — offers a clear-eyed investing lens for a moment that demands one.

The episode closes with a conversation about “re-risking” from a faith perspective. Luke draws from Luke 7 and John 6, and Donna reflects on Moses, Elijah, and Jeremiah — reminding us that God has always done his greatest work through broken, obedient people willing to step off the sidelines.

CHAPTERS

00:00 Introduction — America 250 & Marks on the Market

02:01 Welcome & Opening Commentary from Luke Roush

02:35 Meet Donna Harris — Builders and Backers

03:30 The Venture Capital Model: What We’ve Gotten Right (and Wrong)

06:50 VC as Jet Fuel: Luke on Power Law Dynamics and Appropriate Use

08:03 Donna’s Counsel to Founders: VC Should Not Be the Default

10:00 Builders and Backers: Getting America’s 62% Off the Sidelines

15:41 The Faith Aligned Institutional Investing Summit & “Get in the Game”

16:31 How Storytelling Gets Entrepreneurs Off the Sidelines

19:21 The Heart of the American Experiment — Henry Kaestner’s $5 T-Shirt

20:24 Re-Risking: The Praxis Concept and What It Demands

21:21 Donna’s Personal Re-Risking Story — Downtown Detroit to Builders and Backers

23:52 The AI Job Loss Narrative: What We’re Getting Right and Wrong

25:48 AI as Entrepreneurial Renaissance: Unbundling and Rebundling Every Industry

29:37 Luke on Barriers to Entry and the Speed of Disruption

31:46 Conscious Storytelling, AI Literacy, and the Skills Society Needs

35:35 Investor Counsel for the AI Era: Bet on People, Not Models

38:25 What Excites Donna Now: ER Nurses, Dog Breeders, and Everyday Builders

41:05 The New MVP: Build, Learn, Rebuild for $20

43:10 Abundance, America’s Birthday, and God’s Economy

44:40 Donna’s Scripture — God’s Book of Broken People

46:01 Luke’s Scripture — The Alabaster Jar and Five Loaves

48:20 Closing & How to Connect with Builders and Backers

What happens when a designer who never took a business class ends up building one of the most distinctive venture studios in America? Kristian Andersen, co-founder and partner at High Alpha, sits down with John Coleman at the Main Street Summit in Columbia, Missouri to unpack that exact journey — and what it reveals about the future of venture capital, enterprise software, and faith-driven work.

High Alpha is a hybrid venture studio and fund that doesn’t just source deals — it builds companies from the ground up. Over 10+ years, Kristian and his partners have learned that the most dangerous thing a founder can say is “I’d never have done this without you.” The founders they want are the ones who are going to run through walls with or without High Alpha. In this conversation, Kristian explains how that conviction shapes everything about the way they invest, the companies they build, and the people they back.

From the collapse of seat-based SaaS licensing to the rise of agentic AI, Kristian offers a clear-eyed framework for understanding where enterprise software is going — and what it means for early-stage investors. He also makes a case that most people are dramatically underestimating how fast the agentic revolution will reshape the workforce, and what that means for builders and capital allocators who want to be on the right side of history. Closing on a more personal note, Kristian shares the two biblical mandates — adventure and creation — that drive his mission as an investor and the theology of taste that gives that mission its shape.

CHAPTERS

00:00 Introduction & Main Street Summit

02:15 Kristian’s background: From designer to venture capitalist

06:30 How High Alpha originated: Two days in the woods

08:32 Studio vs. traditional VC: Early results and hard lessons

11:00 Slowing down company creation and going deeper

13:30 What High Alpha wants in a founder: “Pregnant with the idea”

14:51 Beyond capital: Why VCs must bring more than a check

17:00 The High Alpha origin story and the Indianapolis ethos

20:11 Supporting founders’ families, not just founders

22:27 AI disruption and the death of seat-based SaaS licensing

26:37 Zero to $50M in a year: What AI is unlocking

27:30 The agentic revolution vs. the Industrial Revolution

30:07 Enterprise SaaS recession: The buying barbell

32:20 ServiceNow joins as Fund 4 LP — what that signals

35:07 What makes a good corporate venture capital partner

37:15 Faith, the adventure mandate, and the creation mandate

39:00 The theology of taste: Truth is beauty

40:53 Closing thoughts

Wall Street is sounding the alarm on private credit — but is the panic warranted? Kyle Brown, CEO of Trinity Capital (NASDAQ: TRIN), sits down with Richard Cunningham, John Coleman, and Luke Roush to separate the signal from the noise in private credit markets, offer a frank assessment of AI infrastructure investing, and share why — despite the headlines — this remains a remarkable time to be building and investing in America.

Brown breaks down why software-sector credit concerns, while real, are being conflated with systemic private credit risk — and how the deeper problem is concentrated capital, compressed spreads, and a cost-of-capital environment that has fundamentally shifted since 2020. Trinity’s approach: conservative underwriting, low LTV, and short-duration AI infrastructure bets that focus on getting repaid before the speculative overbuild catches up.

The hosts also cover the US macro landscape — GDP, unemployment, the US-China summit fallout, the new Fed chair, and the Iran-driven energy price spike — before closing with what God has been teaching them in His Word, including Kyle’s unforgettable concept of “oodles” and the Parable of the Rich Fool.

CHAPTERS

00:00 Introduction & May Marks on the Market

01:07 Meet Kyle Brown, CEO of Trinity Capital

02:13 What’s Really Happening in Private Credit Right Now

05:39 Retail Investors, REIT History & Private Credit Gates

09:08 AI-Driven Fears vs. Actual Credit Quality Issues

11:00 Concentration Risk: 90% of Allocations to 50 Funds

15:31 Credit Quality Erosion & Lower Middle Market Dynamics

16:34 Banking Volatility, SVB & the Shift to Private Credit

18:49 Software Moats in the Age of AI — Where’s the Risk?

20:55 Trinity’s Portfolio: Only 10% Software Exposure

23:00 Incumbency Power & Switching Costs in Enterprise Software

26:59 Valuations, NAV Risk & Attachment Rates

29:16 Trinity’s 20% LTV Strategy & Software at 1x ARR

29:36 Manager Quality Is the Defining Factor

30:40 Macro Overview: China Summit, New Fed Chair, AI Revenue

32:55 AI Picks & Shovels — How Trinity Finances the Infrastructure Boom

37:37 John Coleman: Bullish on the US Economy & AI Long-Term

40:52 Luke Roush: Global Capital Flows Favor the US

42:53 Kyle Brown: A Golden Time to Build, Invest & Worship Freely

43:58 Expansion of Private Markets Fuels Innovation & Growth

45:16 Rapid Fire: What Is God Teaching You in His Word?

47:47 Kyle Brown on “Oodles” — The Economic Unit of Enjoyment

49:34 Closing Remarks

What does it look like when a wealth advisor doesn’t just manage your portfolio — but your legacy? Kyle Kutz, Senior Partner and Private Family Office Director at Blue Trust, joins Luke Roush to talk through the real work of faith-driven stewardship: building a financial finish line, navigating multi-generational wealth, unleashing generosity, and ultimately achieving peace of mind that only comes from stewarding God’s resources His way.

Blue Trust serves 11,000 families with $60 billion in assets under advisory — and last year alone, their clients gave away over $450 million. Kyle unpacks how that culture of generosity was built, what it means to be the “comprehensive financial quarterback” for complex family wealth, and why independence from greed matters far more than independence from financial need.

Luke and Kyle also tackle the tension between business capital and family capital, the “home-going plan” tool Blue Trust uses to prepare families for legacy, and how the firm thinks about equipping next-generation family members to discover their unique calling — even when it has nothing to do with the family business.

CHAPTERS

00:00 Introduction & The Financial Quarterback

01:06 Welcome and Blue Trust Overview

01:59 Getting in the Game: Who’s on Your Team?

03:29 Defining the Quarterback Role as a Family Office Advisor

04:59 Being Proactive: The Financial Finish Line Concept

07:29 Financial Independence vs. Dependence on God

08:43 Biblical Wisdom and Independence from Greed and Fear

10:34 First Building Blocks for Faith-Driven Families

11:14 Clarity → Alignment → Peace of Mind Framework

13:27 Pattern Recognition and the Role of the Advisor

14:55 Wealth Creators vs. Wealth Inheritors: Same Principles, Different Dynamics

16:44 Everyone Is Gen 1 in Something

17:25 Leaving Opportunity on the Table

19:05 Tax Leakage, Fee Inefficiency, and Estate Planning Gaps

21:32 Business Capital vs. Family Capital

24:02 Navigating Family Dynamics Across Generations

25:00 The Tent Analogy: Growing the Family’s Giving Vision

27:43 The Home-Going Plan

29:35 What Makes a Faith-Driven Family Office Different

32:03 Non-Financial Capital: Spiritual, Social, Relational

33:41 Two Practical Steps to Start the Journey

35:22 Unleashing Generosity: $450M Given in One Year

37:41 How Generosity Conversations Deepen Client Relationships

38:32 What God Is Speaking to Kyle Right Now