Entrepreneurship as a Path to Empowering and Equipping the Next Generation for Leadership and Success

“Give a man a fish and you feed him for a day; teach a man to fish and you feed him for a lifetime.” 

While the context may be outdated, the principle remains deeply relevant. Especially with the largest wealth transfer in history underway, families are increasingly focused on how to prepare rising leaders not just to inherit wealth, but to steward and grow it in meaningful ways. 

Entrepreneurship offers one of the best vehicles for this kind of preparation. It equips next generation family members with real-world experience in risk assessment, decision-making, problem-solving, team-building, and value creation - all critical skills whether they eventually take on leadership roles within the family enterprise or forge their own paths. 

But you’ve seen what it looks like when it goes wrong. The son of the wealth creator wants to chart his own career path and launches a business with no business plan, and no one offering accountability; Dad tells him it’s a terrible idea and the business ends up losing a half a million dollars; Dad believes the failure validates his skepticism…and what’s worse, the relationship becomes strained or even fractured. 

So, it’s clear that this approach doesn’t work - how can we do better?

Killing Two Birds with One Stone: Entrepreneurship as Leadership Development 

Entrepreneurial endeavors within a family aren’t just about launching new businesses, but about developing the mindset and capabilities that define strong leadership. Families that support next-gen entrepreneurship often find that it has a dual benefit: 

1. Preparing Future Family Leaders - Running a business, even on a small scale, helps rising generation family members develop the skills they’ll need to lead within the family enterprise, manage investments, or take on governance roles. The experience of hiring a team, managing finances, and navigating uncertainty builds confidence and resilience, qualities that are essential for leadership in any capacity. 
2. Developing Investment Acumen for Venture & Growth Strategies - Many family offices now include a venture or direct investment arm, making entrepreneurial experience especially valuable. By launching and managing their own ventures, next-gens gain firsthand insight into what makes a business viable, how to evaluate opportunities, and how to assess risk. This experience makes them far better equipped to participate in investment decisions - whether in early-stage startups, growth-stage companies, or strategic acquisitions that align with the family’s broader portfolio. 

Entrepreneurship as a Bridge Between Generations 

For many families, wealth was originally created by an entrepreneurial founder:  someone who took a bold risk, built something from the ground up, and turned it into lasting value. 

Whether this entrepreneurial founder (Mom, Dad, Grandmom/Grandpop) is still operating the business or has transitioned into other areas of leadership, it’s very hard for them to also become a coach to other family members with entrepreneurial ambitions;  s/he is an entrepreneurial superhero and for a rising gen family member venturing out on his/her own, that can be quite intimidating. 

For rising-gen members, starting their own ventures can serve as a bridge to that entrepreneurial legacy. It offers them a direct connection to the character, mindset, challenges, and perseverance that defined the family’s original success. This not only fosters a sense of identity and purpose within the family, but also helps them develop a deeper appreciation for and connection to what it takes to sustain and grow a legacy over generations. 

But this bridge between generations can become rickety or even break when a rising generation entrepreneur experiences the failure of a business that had plenty of encouragement from Mom and Dad, but far too little support, education, and coaching at the outset. 

Creating the Right Conditions for Entrepreneurial Success within the Family and Family Office 

The most effective families create an intentional ecosystem of support that provides the right mix of structure, mentorship, and accountability. Key elements include: 

• Education and Exposure - Providing learning opportunities through workshops, mentorship programs, and exposure to different industries. 

• Advisory and Mentorship - Connecting next-gens with experienced entrepreneurs, investors, and operators who can offer guidance while still allowing them to make independent decisions. 

• Structured Capital & Support - Investing in a way that encourages responsibility and long-term thinking, rather than simply acting as a financial cushion. 

• Leveraging the Family Office Infrastructure - Developing a subcommittee within the Investment Committee that focuses on direct investment opportunities; creating cohorts of family members with entrepreneurial ambitions and building educational and support programs to foster development. 

A Key Component: Third-Party Support for Next-Gen Entrepreneurs

Any parent knows that an outside voice can carry far more influence with family members than the voice of Mom/Dad/Grandpa/Aunt. And those who leverage the support of advisors inside their family office or family wealth advisory to offer entrepreneurial coaching to their rising entrepreneurs often find the same dynamic at play. Families looking to foster strong engagement and entrepreneurship development in their family members often find that the support of a neutral external coach can offer a space for the family member to thrive and develop in a way that feels uniquely their own. In this context, they receive the right balance of structure and flexibility, offering them the guidance they need while allowing them to build and grow on their own terms. 

These bespoke coaching programs support family members and complement existing family office infrastructure, while allowing family members in the leading generation to simply enjoy the role of advocate and supporter. 

Building a Legacy Beyond Wealth 

At its core, fostering entrepreneurship within families isn’t just about financial returns, it’s about equipping the next generation with the tools to lead, innovate, and make decisions with confidence. It’s about ensuring that wealth isn’t just passed down, but actively grown, shaped, and leveraged for future impact. 

As families navigate this critical turning point, the opportunity isn’t just to preserve what’s been built, it’s to empower the next generation to create something of their own. In doing so, they don’t just carry on a legacy, they make their own unique imprint on it, evolving it for the future. 

About the Author

Rebecca Brown is the founder and lead coach at Core Satellite Partners, an advisory firm offering strategic mentorship, hands-on guidance, and tailored support to rising generation family members pursuing entrepreneurship. Core Satellite Partners helps next generation founders navigate the complexities of launching and scaling businesses while balancing family wealth, legacy, and personal identity and ambition. From validating ideas to structuring funding and executing growth strategies, CSP provides the expertise and perspective needed to turn vision into reality. With deep expertise in startups, venture, growth strategy, and family dynamics, CSP equips rising generation founders with the tools and insights to explore and pursue their entrepreneurial journeys.