Month: January 2026
Growing up in a Family Business with Joshua Gentine (Ep. 14)

Growing up in a Family Business with Joshua Gentine (Ep. 14)

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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
  • And more

Resources:

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Connect with Joshua Gentine:

About our Guest: 

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.

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The Power of Uncles: Mentorship, Mischief & Meaning with Connor Crown (Ep. 12)

The Power of Uncles: Mentorship, Mischief & Meaning with Connor Crown (Ep. 12)

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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
  • And more!

Resources:

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Connect with Guest:

About our Guest:

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.

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