What does it take to raise future entrepreneurs? At The Cecily Group, we believe that true entrepreneurial spirit isn’t just inherited, but should also be nurtured. It starts with creating the right environment, offering the right kind of support, and inspiring curiosity, confidence, and resilience.
Spotting Opportunities and Taking Initiative
Entrepreneurship is often seen as a blend of finding good opportunities and having the courage to act on them. Families with entrepreneurial traditions know this well—the success stories of parents and grandparents often serve as powerful examples for younger generations. But while these stories can inspire, they aren’t enough on their own. To truly foster an entrepreneurial mindset, families must create space for the next generation to explore their own ideas, take risks, and even experience failure in a supportive environment.
How Families Shape Entrepreneurial Mindsets
Families play a huge role in shaping how children approach their careers and life goals. When a family actively encourages innovation, independence, and learning from mistakes, it sets the stage for long-term success. But this isn’t about pushing children toward a pre-planned career path. It’s about inspiring them to think creatively, stay open to new ideas, and build the confidence to pursue opportunities that match their interests and talents. Even in wealthy families, success is something each generation has to work toward in their own way, supported but not constrained by their family’s legacy.
Let Them See the Whole Picture
Children learn best by watching their parents “in action.” This includes seeing the good times, but also the tough moments of self-doubt and failure that are part of any entrepreneurial journey. While success stories are inspiring, it’s just as valuable for them to understand that setbacks happen and resilience matters. Not just from the current generation, but also for past, perhaps no longer present, generations. The ability to bounce back from failure is one of the most important skills an entrepreneur can develop.
And remember: the path to entrepreneurship looks different for everyone. The opportunities and challenges facing the next generation aren’t the same as those their parents faced. What worked before may not work today, and that’s okay.
Real Life Example: Richard Branson (Virgin Group)
Richard Branson grew up in a household where his mother, Eve Branson, was a strong influence. She didn’t hide life’s difficulties from him. In fact, she once encouraged him to find his way home alone from a young age to build independence. When his first business ventures failed—including a magazine he started as a teenager—his family encouraged him to keep going. These early failures taught him resilience, which later became a defining trait in building the Virgin empire.
Go Beyond Financial Support
While financial backing is helpful, it’s not the most important kind of support you can offer. Emotional encouragement, access to experienced mentors, and fostering critical thinking skills matter just as much, if not more. When young people know they have a safe space to explore ideas and fail without judgment, they’re more willing to take risks and pursue what really excites them.
Real Life Example: Sara Blakely (Founder of Spanx)
Sara often speaks about how her father would regularly ask at the dinner table, “What did you fail at today?” Failure wasn’t something to be feared, it was expected and seen as a learning opportunity. This mindset helped her push through multiple rejections when launching Spanx, ultimately becoming one of the youngest self-made female billionaires.
Don’t Overlook the Role of Women and Demographic Shifts
It’s also important to address gender dynamics and changing family structures. Research shows that girls often feel overlooked in family businesses and end up choosing different paths, despite having traits highly beneficial to entrepreneurial success (Schröder & Schmitt-Rodermund, 2013). Families should actively encourage and support the entrepreneurial ambitions of daughters just as much as sons.
And as families become smaller, there are fewer people to carry on the family business. That makes it even more important to create an environment where every family member feels empowered to contribute and explore their own ventures. Failure to include daughters as future leaders in family businesses due to pre-defined restrictions and decreasing family sizes may force these businesses to be sold to external investors.
Real Life Example: The Pritzker Family (Hyatt Hotels)
The Pritzker family, founders of Hyatt Hotels, offers several examples of women stepping into leadership roles despite a traditionally male-dominated family business culture. The family places strong emphasis on education for all members, regardless of gender. Many female heirs have attended prestigious institutions like Harvard, Stanford, and Columbia, enabling them to pursue careers in business, philanthropy, and public service.
- Marian “Cindy” Pritzker was a prominent figure in the family, known for her philanthropic contributions to Chicago’s cultural and educational sectors. She co-founded the Pritzker Architecture Prize and played a central role in developing the Harold Washington Library Center.
- Penny Pritzker became U.S. Secretary of Commerce and remains an influential business leader and philanthropist.
- Jennifer Pritzker, a retired Army lieutenant colonel and philanthropist, publicly came out as transgender in 2013, becoming the first and only openly transgender billionaire. She has founded several organisations, including the Tawani Foundation and the Pritzker Military Museum & Library.
The 5 C’s: A Framework of Entrepreneurial Mindset
When it comes to developing an entrepreneurial mindset, we use a simple but powerful model called the 5 C’s:
- Curiosity – Encourage asking questions and exploring new ideas.
- Commitment – Teach the importance of following through and taking ownership.
- Courage – Support them when things get tough; remind them that perseverance builds success.
- Capability – Help them develop real-world skills and build valuable connections.
- Confidence – Celebrate achievements and encourage setting new goals.
This cycle repeats itself, creating a deeper imprinting of entrepreneurial values over time.
A Legacy of Innovation and Resilience
Cultivating an entrepreneurial spirit in the next generation should be more about inspiring a mindset—one that values curiosity, resilience, and the courage to try new things— than it is about transferring wealth or handing over a business.
By creating a family culture that supports personal growth and celebrates diverse talents, we help future generations build their own paths to success. And in doing so, we can create a legacy of innovation, independence, and meaningful contribution to the world.
Reference:
Schröder, E. and Schmitt-Rodermund, E. (2013) ‘Antecedents and consequences of adolescents’ motivations to join the family business’, Journal of Vocational Behavior, 83(3), pp. 476–485. Available at: https://doi.org/10.1016/j.jvb.2013.07.006.
