Building a business takes years of hard work, sacrifice, and vision. Transitioning that business—whether to family, management, or a third-party buyer—requires just as much care. At Mastroianni & Associates Private Wealth Management, we focus on guiding business owners through every stage of business succession. Based in Windsor, we’ve earned the trust of entrepreneurs and families across southwestern Ontario by providing disciplined planning, clear strategies, and hands-on support that makes even the most complex transitions feel manageable.
Confidence through structure
When it comes to business succession planning, clarity matters. Owners need to know exactly how their exit strategy will unfold and what it means for their wealth, their family, and their business legacy. We provide that clarity by digging into the details—shareholder agreements, corporate structures, capital gains exemptions, and tax optimization strategies. Every plan we create is structured to minimize tax, maximize value, and reflect the unique goals of the business owner. This isn’t guesswork; it’s disciplined planning designed to bring peace of mind during a period of change.
Focusing on what matters most
Selling the business or passing it on is never just a financial decision—it’s a personal one. For many owners, their business represents decades of effort and a legacy built for their families. We work closely with accountants and lawyers, sitting in the same room to ensure all voices are aligned, so owners don’t feel caught in the middle. By coordinating every piece of the puzzle, we make sure your values and priorities are at the heart of the transition. Your legacy deserves more than efficiency; it deserves to reflect who you are and what you’ve built.
Maximizing the value of your exit
When the time comes for a private business sale or family transition, you want to be confident that you’re receiving everything your hard work has earned. Our process begins with analyzing the core of your business, uncovering opportunities to boost profitability and improve efficiency. We then position the business for its next stage, highlighting strengths and potential for growth. From there, we design an exit strategy that incorporates tax reduction, succession planning, and legal alignment. Whether you’re selling the business to outside buyers, transitioning it to loyal managers, or preparing children to lead, we make sure your exit strategy protects and enhances value.
More than numbers, it’s your legacy
A business is more than balance sheets—it’s the people, the stories, and the impact it leaves behind. As part of our business succession planning, we help you shape the legacy that matters most to you. That might mean creating a charitable endowment, supporting scholarships, or structuring trusts that carry your values forward. For many families, it’s also about harmony and continuity. With a younger multi-advisor team, we provide continuity of service, giving both current owners and their children confidence in the future.
Business succession planning strategies that work
Our strategies are tailored to each client but often include:
- Family succession planning to ensure expectations are aligned and relationships remain strong
- Guidance on selling to management or third parties with airtight agreements and maximum tax efficiency
- Tax-smart planning that leverages exemptions, income splitting, and capital gains strategies to keep more wealth in your hands
- Exit strategies that prepare businesses for smooth transitions while minimizing disruptions to operations