Financial education isn’t a one-time talk. It’s a lifelong practice shaped by family, values, curiosity, and resilience.
In this episode, Joline Godfrey welcomes Kirby Rosplock, CEO and founder of Tamarind Learning, for a conversation about financial fluency across every age and stage. They explore why families need ongoing learning, how values and money conversations belong together, and why curiosity matters in a fast-changing financial environment.
Kirby also shares how AI can support learning without replacing judgment, effort, and human connection.
Kirby discusses:
Why families need repeated financial learning instead of one-time education events
How curiosity, values, and moral judgment shape better financial conversations at home
Why schools and programs fall short when learning isn’t reinforced over time
How AI can support learning while still requiring human thought, judgment, and privacy care
Why children and adults build resilience when education includes effort and hard things
Kirby Rosplock is the founder of Tamarind Learning, a platform focused on financial fluency, wealth education, and lifelong learning for families and advisors. She works closely with families to help them build stronger conversations around money, values, responsibility, and decision-making across generations. In her conversation with Joline Godfrey, Kirby shares insights on adult learning, resilience, family systems, and the role curiosity plays in helping individuals grow into thoughtful financial stewards.
Parenting can feel harder when kids have more voices, more information, and more pressure than ever before.
How can parents guide children without shutting them down?
In this episode, Joline Godfrey talks with Jennifer Fox, a coach and former wealth management executive, about how parents can use coaching skills at home. Jennifer shares how listening, asking better questions, and checking your own reactions can help children feel heard, challenged, and supported. She also explains why human connection matters more as kids grow up surrounded by technology.
Jennifer shares:
How coaching helps children develop their own voice while still receiving thoughtful guidance
Why asking if kids want to be heard, helped, or hugged can shift hard conversations
How parents can pause reactions and respond in ways that build confidence over time
Why families may need shared language around parenting goals and changing needs
How human connection gives kids a stronger base when technology keeps changing
Jennifer Fox is a purpose-driven, inspirational, and innovative leader in the financial services and wealth management space. Known for her authenticity and transparency, she fosters trust and collaboration to create meaningful impacts for clients, teams, and the community.
With a proven track record of crafting and executing strategic visions, Jennifer has consistently transformed organizations, driven remarkable growth, and safeguarded financial and reputational risks. Her reputation as a thought leader is underscored by her ability to identify emerging trends and capitalize on growth opportunities.
Jennifer’s extensive experience extends to seamlessly interfacing, collaborating, and building enduring relationships with C-suite executives, board members, investors, team members, and strategic partners. Her intellectual rigor and leadership have made her a respected figure in the industry.
What if the biggest risk to your family’s wealth isn’t the money, but the silence around it? The conversations that never happen, the assumptions that go unspoken, the lessons we hope our kids just “pick up” along the way.
In this episode, Joline Godfrey sits down with estate planning attorney and author Mark Shiller to explore a question many families quietly carry: how do you support your children financially without unintentionally holding them back? Together, they dig into what it really means to prepare the next generation, not just financially, but as thoughtful, capable humans.
Joline and Mark discuss:
Why families often come in for technical help, but what they really care about is how money impacts the people they love
The growing shift over the past 5 to 10 years, with more families opening up conversations that once felt off-limits
Why parents and grandparents cannot outsource these conversations, and need to take an active role in guiding their children
A powerful metaphor of the apple tree, reframing legacy as something that grows and continues, not just something that is consumed
Mark works with individuals, couples, and families in connection with their estate, tax, and business planning. His clients are typically business owners, professionals, and senior executives who appreciate his thoughtful and creative approaches to their often complicated personal, tax, and financial planning challenges.
Mark has been quoted in such publications as Smart Money and Worth and has been a frequent speaker on estate planning topics. He is a Fellow of the American College of Trusts and Estates Counsel, former Chair of the Board of Governors of the Real Property, Probate and Trust Law Section of the State Bar of Wisconsin, Past President of the Milwaukee Estate Planning Forum, and Past Chair of the Estate and Trust Law Section of the Milwaukee Bar Association. Mark also served as an adjunct professor at the University of Wisconsin Law School for four years, teaching a course on estate and business planning for a privately held enterprise.
What if the “random stuff” your kids collect is actually shaping who they become?
In this episode, Joline Godfrey and Kit Hinrichs, founder and Creative Director at Studio Hinrichs, discuss the unexpected power of collecting as a tool for raising curious, confident, and connected kids. Joline and Kit, a renowned designer and lifelong collector, explore how collecting begins in childhood and evolves into a meaningful way to build identity, resilience, and connection. Through stories from Kit’s extensive collection of Americana, including historic flags, toys, and artifacts, they highlight how every object carries history, geography, and personal meaning.
Joline and Kit discuss:
Why does collecting often start earlier than parents expect
How collecting builds intellectual, social, and human capital (FISH)
The role of storytelling in helping kids connect to history and values
Kit Hinrichs is one of America’s most respected graphic designers and a renowned collector of American flags and historical artifacts. With a career rooted in branding and visual storytelling, Kit has spent decades exploring the intersection of design, history, and culture. His collection spans traditional flags, textiles, folk art, and unique Americana, each piece carrying a story of craftsmanship and national identity. He is also the author of Broad Stripes, Bright Stars, a graphic history celebrating America’s 250th anniversary.
Families today face a rapidly changing future, where raising resilient and thoughtful children matters more than ever.
How can parents prepare kids for a future filled with uncertainty and opportunity? And what role does financial education play in shaping problem-solvers?
In this episode, Joline Godfrey speaks with Jason Wild, Co-Founder and CEO of Wild Innovation & Strategy Excellence, Inc., and co-author of Genius at Scale, about applying leadership and innovation principles inside the family. They explore how parents act as “bridgers,” translating financial concepts into everyday lessons children can understand. The conversation highlights the F.I.S.H. framework, the importance of culture and values at home, and why raising adaptable problem-solvers may be the may be one of the most valuable legacies.
Jason shares key ideas, including:
Why parents serve as “bridgers,” translating financial ideas into practical lessons children can understand
How the F.I.S.H. framework expands wealth beyond money to include intellectual, social, and human development
Why meaningful parent-child conversations matter more than technology for building financial understanding
The role family culture and values play in raising resilient, adaptable children
Why problem-solving skills will matter more than predicting specific future careers
Jason Wild is a strategist, advisor, author, and growth executive with more than two decades of global experience helping organizations build cultures of innovation and achieve transformative growth. His career began in Chicago and led him to work with admired companies, including IBM, Salesforce, and Microsoft, where he has built and scaled growth, solutions, transformation, and strategic marketing teams that help enterprises translate ideas into meaningful impact.
Throughout his career, Jason has focused on forging long-term relationships based on trust across business ecosystems. He is recognized for applying artificial intelligence solutions to help organizations create competitive differentiation through efficiency, innovation, and growth. Over more than 20 years, he has worked on the ground in over 40 countries, helping organizations develop operating models that encourage innovation while building the next generation of high-performance leaders.
Jason is the co-author of Genius at Scale: How Great Leaders Drive Innovation, written with Dr. Linda A. Hill and Emily Tedards. Published by Harvard Business Review in March 2026, the book draws on a decade of research with Fortune 100 CEOs, transformative startups, and leading nonprofit organizations to explore the leadership mindsets and behaviors that unlock innovation at scale.
At Salesforce, Jason co-founded Ignite and led the program globally. Under his leadership, the initiative grew from a small US-based team into a global organization of 250 members that influenced more than $2 billion in annual contract value over five years. Ignite became a key driver for strategic opportunities and earned recognition from organizations including Fortune, Gartner, and Harvard Business School.
His career impact includes influencing more than $6 billion in enterprise deals across IBM, Salesforce, and Microsoft. He also co-led Microsoft’s largest non-government deal in Spanish history and created Microsoft’s first unified global sales methodology, which contributed to more than $100 billion in incremental revenue. Jason has delivered strategic programs for more than 100 global enterprises, including Disney, NATO, AT&T, and Unilever, operating across dozens of countries while helping organizations bridge business strategy and technology transformation.
Today, Jason focuses on building strategic capabilities that help organizations stand out in complex, high-stakes partnerships and pursuits. He advises CXOs on modern leadership practices and works closely with executive teams to shape strategy and long-term growth plans. His work centers on building meaningful relationships, inspiring change, and helping organizations shape a stronger future.
Money lessons often start later than they should, yet children are absorbing messages about wealth, work, and values long before adulthood.
How can families and schools work together to help kids think critically about money, opportunity, and responsibility?
In this episode, Joline Godfrey speaks with Earl Walton, Director of the Ross Roeder Institute at Shorecrest Preparatory School, about how financial education and financial parenting can reinforce each other. They explore how early exposure to money concepts helps children develop confidence and curiosity. The conversation also touches on expanding career awareness, building ethical decision-making around wealth, and creating programs that grow with students from kindergarten through high school.
Key takeaways from the conversation:
Why financial literacy programs work best when they evolve with students from early childhood through high school
How parents and schools together create stronger financial understanding and practical life skills
Why repeated exposure to money concepts builds confidence and curiosity in young learners
How expanding career awareness helps students see opportunities beyond familiar professions
Why ethics, responsibility, and values should be part of every conversation about money
Earl Walton is the Director of the Ross Reader Institute at Shorecrest Preparatory School, where he leads a K–12 program focused on financial literacy, economics, and entrepreneurship. Drawing on his background in business and entrepreneurship, Earl helps students develop practical life skills that prepare them to actively participate in their financial future. His work centers on building a curriculum that grows with students over time, introducing core money concepts early and reinforcing them through real projects, critical thinking, and exposure to a wide range of career paths.
Parents often wrestle with one universal question: “Will my kids be okay?”
This episode uncovers how that loving concern connects deeply with emotions, family values, and the power of community.
In this episode, Joline Godfrey speaks with Christi Rae, host of The Great Canadian Piggybank podcast, about helping parents build confidence around money conversations. Christi shares how her journey from gaming to financial education led her to foster community, balance technology with nature, and encourage families to talk openly about money.
Key takeaways:
The universal parental worry about children’s financial future and why it stems from love
Helping parents feel comfortable admitting what they don’t know about finances
The importance of community and connection in learning about money together
How financial literacy is tied to emotion, family values, and resilience
Christi’s transition from gaming to creating The Great Canadian Piggybank and East Van Seeds to spread joy and community
Christi Rae is the creator and host of The Great Canadian Piggybank, a podcast that helps parents feel more confident about teaching their kids money skills within a Canadian context. With over two decades of experience in the gaming industry, leading major franchises such as Fortnite and Gears of War, Christi brings creativity, empathy, and community-building to everything she does. She is also the founder of East Van Seeds, a community initiative promoting sustainability and connection through shared gardening resources.
It’s a bridge between generations, a tool for financial learning, and a way to preserve family stories.
In this episode, Joline Godfrey welcomes Douglas Dreier, founder of The Collection Connection, to discuss how collecting ties memory, history, and financial skills together. From comic books to baseball cards, collecting not only nurtures curiosity but also teaches kids valuable life lessons.
Douglas shares:
How collecting preserves stories and strengthens family bonds
Why nostalgia drives people to reconnect with childhood joys through objects
Ways parents can use their child’s interests (like comics or Pokémon) to build bridges
How collecting teaches financial lessons like bartering, budgeting, and valuing assets
The role of passion-driven collections in fostering social connection and lifelong learning
The Collection Connection founder, Douglas Dreier, has spent his entire life cultivating the art and understanding the power of collection. With over 15 years spent managing a private museum dedicated to sharing a wide variety of items and collections, Douglas has amassed a variety of iconic items that not only tell a story but portray a unique aspect of human history.
At the core of Douglas’s mission lies a love for learning and teaching. Before managing his family’s museum, Douglas earned his Master’s Degree in Instructional Design from the University of Maryland, Baltimore College before teaching in low-income areas of Baltimore, Maryland and Albuquerque, New Mexico.
Now, Douglas has ventured into the business and consulting side of collecting with The Collection Connection. His vision is to make a community in which he can share his knowledge of museum ownership, investor relationships, curating exhibits, and understanding historical significance. Douglas seeks to inspire others with his passion for collecting. Be it natural history, documents, books, sports, entertainment, and anything else, Douglas believes such items have the power to excite our imaginations, transform our understanding, and bring us closer together.
Douglas is on the board for the Smithsonian Institute Traveling Exhibition Services (SITES), the Smithsonian Regional Council for Los Angeles, and the Santa Barbara Museum of Natural History.
What happens when families lead with curiosity instead of control?
In this episode, Joline Godfrey is joined by Josh Gentine, founder of Bench Consulting and member of the Sargento Foods family, for a deeply personal and practical conversation.
Together, they explore how healthy communication, intentional leadership, and emotional awareness shape thriving families, especially those managing wealth across generations.
Josh discusses:
How growing up in a legacy business shaped his view of family expectations and personal autonomy
Why families struggle with communication, and how business frameworks like personality assessments and family meetings can help
The tension between stability and innovation in multigenerational families
How vulnerability from the leading generation fosters trust and growth in younger members
The importance of preparing families emotionally and structurally for the transfer of generational wealth
Josh Gentine is a coach and family business advisor, helping individuals, entrepreneurs, families, and boards of directors maximize impact. Josh is accredited as a Hogan-Certified coach, Gallup-Certified Strengths coach, and an ICF Certified coach. Josh’s background as an entrepreneur, advisor, corporate board member, and third-generation family business owner gives him a range of perspectives to draw from when advising clients. Josh focuses his time on helping family businesses transition leadership from one generation to the next, coaching family members, entrepreneurs, and senior leaders, and supporting talent strategies across organizations. Josh sits on the board of directors at his family’s company, Sargento Foods, as well as a $700 million ESOP auto dealership group. Additionally, Josh runs family executive round table groups for middle-market and large-cap family-run companies, and he is currently a part-time instructor with UNC Kenan-Flagler Business School’s Family Enterprise Center.
Prior to starting Bench, Josh served as a Manager at Deloitte Consulting, where he focused on mergers & acquisitions as well as co-designing Deloitte Consulting’s global talent operations.
Josh earned his undergraduate degree in Finance from the University of Notre Dame and his MBA from the University of North Carolina, Chapel Hill. Josh returned to Notre Dame following his MBA to study philosophy and theology in the seminary with the intent of becoming a Catholic priest. Josh and his wife, Meredith have two young children, Henry and Juliette, and live in Charlottesville, VA.
What if the most powerful mentor in a child’s life isn’t a parent, but an uncle?
In this episode of Raising Financially Fit Families, Joline Godfrey sits down with Connor Crown, Co-Founder and Managing Partner of Expanse, and uncle to 10, to explore the often-overlooked influence of uncles in multigenerational families. Through stories both heartfelt and hilarious (including a surprise Easter Bunny appearance), Joline and Connor unpack the rich, informal role uncles can play in a child’s development, identity, and understanding of family values.
Joline and Connor explore:
How uncles become role models, messengers, and mentors
The balance between being the “fun uncle” and a steady adult presence
Why storytelling matters and how it becomes a powerful tool for passing down values
A hilarious Easter Bunny story with a serious life lesson in accountability woven in
Why making space for these roles can strengthen family connection and legacy
Connor is the Co-Founder and Managing Partner of Expanse, an asset management firm built with a family office perspective. Connor’s upbringing and investment experience instilled in him a profound understanding of the principles behind long-term, organizational growth, which he used as the foundation for building Expanse. Expanse’s venture arm is proud to partner with a diverse portfolio of businesses on the forefront of enabling technologies powering the future of finance, healthcare and commerce including OneHealthGroup, Zocks and Release Recovery.
In addition to his commitment to growing innovative businesses, Connor is deeply passionate about philanthropy and driving positive change. As the Co-Chair of the Gun Violence Prevention Committee at Crown Family Philanthropies, he’s dedicated to making the city of Chicago safer for future generations. With Expanse, Connor actively seeks partnerships with founders dedicated to making a meaningful impact on the world through their products and services. Expanse’s vision extends beyond financial gains, aiming to create a mutually beneficial ecosystem for families and partners with a shared long-term perspective.
Prior to founding Expanse, Connor spent over five years advising global financial services and insurance firms on enhancing B2C operations and client management. He serves in advisory and board roles for multiple early-stage companies, including Hamsa and ThriveNaturalCare. Connor graduated from Duke University with a BA in sociology and a certificate in marketing/management while also being a member of the varsity track team. He continued his education at Northwestern University’s Kellogg School of Management, where he received his MBA with a major in finance and a focus on venture capital. Connor and his wife Alyssa live in Chicago.
