For massive, secretive deals like a corporate headquarters relocation, confidentiality is a core requirement. A single leak to the press, against the company's wishes, can violate the terms of secrecy, trigger internal revolt, and cause a multi-million dollar opportunity to collapse immediately.

Startups pursuing an enterprise model face extreme external risks. After months of work, Sure's pivotal first B2B launch partner went out of business just one week before the go-live date. This highlights the fragility of relying on a single large partner and the resilience required to overcome setbacks outside your control.

An acquisition target with a valuation that seems 'too good to be true' is a major red flag. The low price often conceals deep-seated issues, such as warring co-founders or founders secretly planning to compete post-acquisition. Diligence on people and their motivations is more critical than just analyzing the financials in these cases.

In the Paramount/Warner bid, Larry Ellison's financial backstop used a revocable trust. This created a major risk for Warner, as the assets could be withdrawn at any time, potentially leaving them without recourse if the deal soured. This highlights a critical due diligence point in high-stakes M&A.

When an acquisition fails due to regulatory hurdles, the resulting breakup fee can be a strategic financial boon. For example, Figma received a $1 billion fee from Adobe after their deal was blocked, which functioned as non-dilutive capital to help the company re-accelerate its growth.

Drawing from his experience partnering with Apple, Solomon cautions that most large-scale partnerships fail. For a partnership to succeed, it must have 'compelling glue'—meaning deeply aligned incentives, a shared purpose, and a governance structure that can overcome the natural friction between two different organizations.

A deal failed because the acquirer rigidly insisted the target switch from Macs to PCs for compliance reasons, without exploring creative solutions. This highlights how a lack of flexible problem-solving on operational details can escalate into a deal-killing issue, masking deeper cultural misalignments.

Andy Cohen recounts walking away from a deal post-LOI after the target tried to renegotiate terms to favor preferred shareholders over common employees. Even though F5's economics were unaffected and lawyers offered indemnification, the company refused to be associated with such practices, prioritizing ethical principles and reputation over closing the deal.

After working out 22 distressed joint ventures during the GFC, the key lesson was that partner quality dictates outcomes more than the deal itself. When things go wrong, good partners collaborate to find solutions, while bad partners create conflict, making even a good deal untenable.