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The Calin Family
The Calin family embodies the American Dream. In the 1980s, George and Lila, the family’s matriarch and patriarch, built a thriving oil business from the ground up. After selling the business, they secured generational wealth and established a family office, bringing together a trusted team of advisors who became like family themselves. This close-knit team helped the Calins navigate investments, estate planning, and other complexities, building a legacy of trust and stability.
As the family grew and evolved, so did their needs. George and Lila’s three children, now adults with families of their own, sought to create their own legacies, build businesses, and explore new opportunities. However, the family office—built around the first generation’s priorities—struggled to adapt. Outdated systems and methods that prioritized loyalty over innovation created a growing sense of frustration among the second generation.
The Challenges
The family office was run by a small internal team: a bookkeeper, an executive assistant, and a property manager, all overseen by George and Lila. Though this system had worked for decades, cracks were beginning to show:
The Bookkeeper’s Resistance:
The bookkeeper, a steadfast figure since the early days of the business, resisted change and tightly controlled their work. They dismissed calls for modernization or succession planning, saying, “I’ll be here as long as I’m needed.”
This created significant roadblocks. Processes were undocumented, and critical information remained siloed, making it nearly impossible to introduce modern tools or build redundancies. While the family valued the bookkeeper’s loyalty, they knew the lack of transparency was unsustainable.
The family relied on a CPA, an estate planning attorney, and several banking and investment advisors. However, these external advisors operated in silos, communicating only when necessary. This disjointed approach made it challenging to produce an accurate, comprehensive financial picture.
For example, the family banker noticed discrepancies between conversations with the family and the documents they provided. The CPA and estate planning attorney, both in their mid-80s, handled tasks reactively, further complicating efforts to manage the family’s wealth.
The family relied on a CPA, an estate planning attorney, and several banking and investment advisors. However, these external advisors operated in silos, communicating only when necessary. This disjointed approach made it challenging to produce an accurate, comprehensive financial picture.
For example, the family banker noticed discrepancies between conversations with the family and the documents they provided. The CPA and estate planning attorney, both in their mid-80s, handled tasks reactively, further complicating efforts to manage the family’s wealth.
The second generation sought transparency, modern technology, and structures to support their ambitions. Meanwhile, George and Lila remained committed to stability and loyalty, viewing their long-standing advisors as irreplaceable. This dynamic created tension and risked undermining family unity.
Our Approach
Understanding the sensitivity of the situation, we prioritized building trust with all stakeholders. We approached the bookkeeper with respect and curiosity, asking questions and documenting workflows wherever possible. While the bookkeeper remained resistant to change, every piece of information gathered helped lay the foundation for new systems.
Using input from the internal team, we began creating processes that could operate independently of any single individual. Key initiatives included:
We also focused on improving communication among external advisors. By hosting regular meetings with the CPA, estate planning attorney, and financial advisors, we broke down silos and fostered collaboration. Initially hesitant, these advisors came to appreciate the clarity and efficiency these meetings provided.
The journey with the Calin family is ongoing. While the bookkeeper remains a challenge, we’ve built systems around them, documenting workflows and creating redundancies. The family understands the risks of relying on one individual but has chosen to let the situation evolve naturally, trusting us to be prepared for any eventuality.
Progress has been incremental but meaningful. The second generation is gaining the transparency and tools they need to build their own legacies, while George and Lila feel reassured that their trusted advisors remain valued and respected.
The Calin family’s story highlights the importance of balancing tradition with progress. While loyalty and trust are vital, they must be paired with modern systems and strategies to meet the needs of future generations.
For families facing similar challenges, the lesson is clear: transformation doesn’t have to mean disruption. By working collaboratively, respecting relationships, and meeting families where they are, it’s possible to create a family office that honors the past while preparing for the future.
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