Money, Meet Meaning

What happens when artificial intelligence meets ancient wisdom?

In this episode, hosts Tom Levinson and Amber Hacker talk with Colin Evans, a tech innovator and AI investor whose journey spans Buddhist monasteries, Catholic churches, and Silicon Valley boardrooms. Colin shares how his spiritual roots inform his work at OpenAI, and why he believes AI has the power to free people–not just to do more or make more money, but to live more meaningfully.

From saving money on school supplies with ChatGPT to exploring whether efficiency is a spiritual value, the conversation dives into how technology can both challenge and deepen our faith. Along the way, Colin reflects on the “missionary” founders shaping AI’s future and the spiritual questions that surface when machines free us from work.

About Colin:


Colin Evans is a tech innovator, investor, and AI advocate whose career has spanned roles at StubHub, GameTime, and OpenAI.

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After their conversation with Dr. Che “Rhymefest” Smith, Amber and Tom return to a provocative line attributed to Quincy Jones: “When money walks in the room, God walks out.” Is that true – or does money simply expose what already has our attention?

Drawing on listener responses, spiritual traditions, and pop-culture moments like We Are the World and “Man in the Mirror,” they explore whether money is a rival to faith or just a tool – and why the real question may be what sits at the center of our lives.

They consider real-world dilemmas: what do you do when funding threatens to soften your message? How do you use influence without losing integrity? And how might  PEMDAS (that’s right: Please Excuse My Dear Aunt Sally) provide us with a roadmap?

It’s a thoughtful, wide-ranging conversation about money, power, and the courage it takes to keep meaning at the center – especially when the stakes get high, and the commas increase.

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From the South Side of Chicago to global stages, Dr. Che “Rhymefest” Smith has lived at the crossroads of art, money, and spiritual searching. Amber and Tom sit down with the Grammy- and Academy Award-winning songwriter, educator, and public servant to explore what happens when inspiration intersects with industry and calling becomes responsibility.

Rhymefest reflects on cultural currency, Hip-Hop, commerce, and the spiritual roots of creativity. He shares unforgettable stories: being broke in Brazil, an accountant instructing him to spend $10,000 in a week, and navigating an industry that rarely teaches artists how to steward success.

The conversation moves beyond music to public service, as Rhymefest describes his work on the Chicago Board of Education as a form of ministry – overseeing billion-dollar budgets while staying grounded in community and purpose.

It’s a wide-ranging, soulful conversation about art as a vocation, money as a tool, and the responsibility to use both in service of something bigger.

About Dr. Che Rhymefest Smith:


Dr. Che “Rhymefest” Smith is a Grammy- and Academy Award-winning songwriter and recording artist. He is also an educator and public servant, currently serving on the Chicago Board of Education, helping to oversee a $10 billion budget for more than 300,000 students.

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After their conversation with financial expert Bobbi Rebell, Tom and Amber return to a surprisingly thorny question: How much should we tell our kids about our money? From sharing your income to explaining a budget cut, they explore the delicate balance of authenticity, care, and preparing kids for the real world of money.

Drawing on listener stories, family dynamics, and wisdom from spiritual traditions, Tom and Amber unpack how age, maturity, personality, and values shape these decisions. They wrestle with what transparency looks like in practice — and when discretion might be the more loving choice.

Along the way, they dive into real-life dilemmas: correcting a kid’s misconception about your wealth, responding to bragging, making generosity visible, and deciding what your kids need to know about inheritances.

It’s a thoughtful, practical guide to the conversations that shape how kids understand money — and themselves.

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Every parent wants to raise financially confident kids – but between peer pressure, TikTok trends, and our own money baggage, how do we actually do that? In this episode, Tom and Amber sit down with Bobbi Rebell, Certified Financial Planner® and author of Launching Financial Grownups, for a candid conversation about what kids really need from us when it comes to money.

Bobbi shares the single biggest mistake parents are making and how controlled failures build financial resilience. The group talks about the influence of family dynamics, divorce, and faith traditions on financial independence, and tackles practical dilemmas like credit cards, first cars, prenups, and whether your kids should know how much you earn. Bobbi also jumps into a lightning round of the ever-popular game, “Kosher – Or No, Sir?”

Grounded, practical, and fun, this episode offers a roadmap for raising kids who are capable, centered, and ready for the real world – without parents feeling like they’re getting it all wrong.

About Bobbi Rebell:


Bobbi Rebell, CFP®, is the founder of Financial Wellness Strategies and the author of Launching Financial Grownups: Live Your Richest Life by Helping Your (Almost) Adult Kids Become Everyday Money Smart. She is a financial wellness educator, speaker, conference host, and moderator. 

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