Chronicle Stories
“The lack of succession and contingency planning posed a huge risk for my business. With Chronicle’s help, we are now much better protected and prepared.”

Challenges
Robert*, now in his mid-50s, married, with 3 independent, adult children, has built a very successful, profitable operating business that is currently valued at ~$30 million. The earnings generated from his business have allowed Robert to accumulate significant investment capital, acquire a luxury home in Toronto, and a vacation property in Ontario’s cottage country. With a strong focus on driving growth, and managing day to day operations, Robert realizes that he has lost sight over other important aspects of his flourishing empire. With his children pursuing careers in various professions, there is currently no identifiable “successor” to continue the business in the future. There are no clear transition or contingency plans in place if Robert was to become ill or pass prematurely. Beyond exposure to these business risks, there are now investments spread across multiple advisors and the absence of a coherent financial strategy.
As these issues accumulate, Robert has become increasingly anxious about his ability to manage his expanding list of challenges, including:
Contingency and Succession Issues
- Identifying and developing the appropriate people to manage critical business issues in the event that Robert were to be suddenly ill or die prematurely
- Determining whether to transition the business to a family member or prepare for a 3rd party sale
- Ensuring that sufficient capital will be available to allow the business to persevere through the loss of a key person
Investment & Financial Strategy
- Improve coordination between professional advisors (i.e. accountants, lawyers) and investment managers to improve issue identification, reporting obligations, and enhance collaboration
- Develop a due diligence process to effectively evaluate the merit of investment opportunities, including venture and direct private allocations
Family Financial Issues
- Understanding how and when to educate family members on estate, financial, and business matters important to the various members
- Determining how to provide financial support for his children without impairing their desire to become financially independent and to earn their own success
Tax and Estate Planning
- Identifying prudent opportunities to reduce income tax and enhance net annual income retention
- Ensure that sufficient liquidity will be available to fund future deemed disposition taxes and eliminate the need for forced asset sales
- Develop an estate distribution plan that integrates strategy to fund specific philanthropic objectives in a manner that maximizes future income tax benefits
How we are helping
We collaborated closely with Robert, his spouse, and other professional advisors to develop and implement a structured financial and business continuity plan that addresses his key concerns. This included:
Centralized Advisory & Financial Planning
- Established a lead advisor to coordinate financial, tax, legal, and investment strategies
- Identified key blind spots and developed solutions to mitigate risks
- Conductied regular financial reviews to ensure alignment with evolving circumstances
Business Contingency & Succession Planning
- Created a strategic plan to protect the business from unforeseen events
- Defined leadership roles and potential succession pathways
- Clarified options for business sale versus family succession to ensure maximum value preservation
Investment Strategy & Opportunity Evaluation
- Developed a structured process for analyzing venture and direct investment opportunities
- Integrated tax-efficient investment strategies with portfolio management
- Implemented consolidated reporting and asset mix analysis for a clear financial picture
Estate & Tax Planning
- Provided strategic guidance on estate distribution
- Updated estate plans, including tax-optimized wills
- Developed a long-term tax mitigation strategy to optimize financial security
Philanthropy & Legacy Planning
- Explored philanthropic options aligned with Robert’s long-term values and interests
- Provided guidance on balancing philanthropy with wealth transfer to family members
*Name changed for privacy purposes.