The Exit Paradox: Balancing Fear and Greed to Maximize Value
Presented By: Graystone Consulting from Morgan Stanley
When considering selling a business, there are two primary emotions at play: fear and greed. On one hand there is fear—fear of loss, fear of uncertainty, fear of making the wrong move. On the other hand, there’s greed—the desire to maximize value, to capture every last dollar the business can command. These two emotional forces often pull owners in opposite directions. But the truth is, the right approach isn’t about choosing one over the other—it's about balancing both. Join us as we dive deeply into why the most successful business exits come from understanding and navigating this paradox thoughtfully and deliberately.
Moderator:
Vice President, Private Wealth Advisor
Graystone Consulting
Matthew Gurwin is a Vice President, Private Wealth Advisor, and Certified Exit Planning Advisor (CEPA®) for Graystone Consulting at Morgan Stanley. He specializes in advising business owners and families considering substantial liquidity events due to the sale of a privately held business. A veteran of the financial services industry, Matt draws on his 25 years of experience, helping entrepreneurs maximize the value of their business, take their personal and personal financial plans to the next level, and be prepared for what adventure comes next after transitioning their current company.
Panelists:
Principal
The Sixth Level Collaborative
Rachel Wallis Andreasson, MBA, a Principal of The Sixth Level Collaborative is committed to creating a culture no one wants to leave. Rachel is a second-generation owner of Wallis Companies and has a proven track record of building sustainable infrastructure and governance systems. Rachel is known for her ability to unlock individual and group potential, making her a transformative force in every endeavor she undertakes.
COO
Viscogliosi Brothers
Rob Grimaldi is chief operating officer of Viscogliosi Brother's LLC, a single-family office that is a global leader in medtech and biotech investing and innovation, with a long heritage of creating new markets, commercializing innovation, addressing clinical unmet needs while changing standards of care in the neuro-musculoskeletal medical device industry. In addition to his experience in family office leadership, private equity and venture capital, Rob has advised many entrepreneurial led companies acorss multiple industries through various stages, from formation to exit. Rob is a co-founder of Ad Infinitum, a bio-preservation solution and co-founder of diagQ, a diagnostic company.
Founder & Investor | Head of Corporate Development
The Fintex Group
Maia Monell is a leader in health technology and financial innovation. She is the Head of Corporate Development at The Fintex Group, following its 2025 acquisition of Nav.it, the financial health app she co-founded in 2019. Prior to Fintex, Maia was a founding team member of Bridge Athletic, the prescriptive Al technology delivering world-class performance training to athletes worldwide.Beyond her operator experience, Maia is an allocator focused on advancing healthcare, sustainability, and economic development. She is the President of MALIAM a multi-generational family office and investment firm dedicated to the future of human flourishing.
President & Founder
EdgePoint Capital
Tom serves as the President of the firm, managing client transactions, overseeing its day-to-day management and executing strategic initiatives. Tom uses his extensive business and financial experience to assist business owners in completing transition events, acquisitions or recapitalizations. His diverse experiences range from executing corporate divestitures for General Electric to assisting small closely held businesses in executing family ownership transitions Tom is also an advisor and board member of several private and public companies.