Preparing a Company to Survive Diligence
Show Notes
Gary Shields, CFA, has spent three decades advising founder-owned companies through exit processes across financial services. In this conversation, he explains why the deals that fall apart in diligence almost always show warning signs a year earlier, and what owners should fix before a process ever begins.
Key Takeaways
- 1Most failed deals show the same warning signs twelve months before diligence begins.
- 2Buyers discount uncertainty far more than they discount bad news that is disclosed early.
- 3A management team that can run the business without the founder is worth a real premium.
- 4The right advisor relationship starts well before a company is ready to sell.
About Gary Shields, CFA
Gary Shields, CFA is chairman and managing partner at Nassau Street Partners, and joined Capital Founders Forum to discuss exits and valuation within financial services.
Never miss a conversation
New episodes on capital, growth, and exits — every two weeks.
Related Episodes

What Strategic Buyers Actually Pay For
Why most founders overvalue their business, and the three diligence issues that kill deals in the final stretch.
Andy Harris
STS Capital Partners

Insurance M&A After a Decade of Consolidation
An acquirer of eleven insurance agencies on what actually drives multiple expansion.
Daniel Cross
Harbor Underwriters

Why Wealth Clients Need to Feel Seen Before They Need a Plan
A wealth advisor on why founders, athletes, and multi-generational families need to feel heard before they need a plan.
Amanda Castellano
Moors & Cabot
