
Matthew DiFrancesco
Financial Advisor | High Lift Financial
Matthew is a Principal and Wealth Advisor at Cornerstone Planning Group, operating under his firm, High Lift Financial & Consulting. He works primarily with closely held business owners (especially family-owned collision repair shops) providing integrated financial, business, and transition planning that brings personal, professional, and financial decisions into alignment.
Known for his thoughtful, collaborative, and highly organized approach, Matthew focuses on asking the right questions and simplifying decisions that impact families, employees, and long-term legacy. Ensuring recommendations are practical, coordinated across advisors, and aligned with what clients truly want their next chapter to look like is what matters most to him.
Matthew was drawn to this work by the unique challenges business owners face when personal lives, family dynamics, and businesses are deeply intertwined. He finds the most meaning in helping owners gain clarity and confidence during pivotal transitions – knowing those decisions shape not only financial outcomes, but families, teams, and legacies.
Beyond work, Matthew enjoys prayer, playing tennis, traveling with his family, and exploring trips centered on history, learning, and great food. He is also active in community and industry education through speaking, writing, mentoring, and hosting the Your Business, Your Life podcast.
Community Involvement

Tunnels to Towers
Since 9/11, Tunnels to Towers has been helping America’s heroes by providing mortgage-free homes to Gold Star and fallen first responder families with young children and by building specially-adapted smart homes for catastrophically injured veterans and first responders. They are also committed to eradicating veteran homelessness and helping America to Never Forget September 11, 2001.