A founder's real boss is their customer base. While keeping a board happy is important, some CEOs become so consumed with managing up that they lose sight of the product and customer needs, ultimately driving the company off a cliff despite running perfect board meetings.

Even a marquee, hyper-growth customer can be a net negative. AppDynamics chose to part ways with Netflix when its scaling demands consumed the entire engineering roadmap, preventing the company from serving its other 199 customers and building new features.

Preparing a company for acquisition can lead founders to make short-term decisions that please the acquirer but undermine the brand's core agility, setting it up for failure post-sale. The focus shifts from longevity to a transaction.

A board member's role includes flagging strategic risks, including geopolitical exposure that could drastically limit future acquirers or prevent an IPO. Advising a CEO to relocate teams from a high-risk country is not operational meddling, but a core governance duty.

Unlike standard corporate M&A, an innovation incubator's acquisition criteria are different. Cisco's Outshift ignores a startup's revenue and business metrics, focusing solely on the technology, talent, and cultural fit to accelerate its own strategic objectives.

All founders make high-impact mistakes. The critical failure point is when those mistakes erode their confidence, leading to hesitation. This indecisiveness creates a power vacuum, causing senior employees to get nervous and jockey for position, which spirals the organization into a dysfunctional, political state.

When a founder faces a major acquisition offer, the pivotal question isn't just about valuation, but temperament. A board member should ask, "Are you built to be a public company CEO?" The intense stress and public scrutiny aren't for everyone. Pushing a founder who isn't an "IPO guy" to reject an offer can be a disastrous long-term decision.

The most lucrative exit for a startup is often not an IPO, but an M&A deal within an oligopolistic industry. When 3-4 major players exist, they can be forced into an irrational bidding war driven by the fear of a competitor acquiring the asset, leading to outcomes that are even better than going public.

When a company like Synthesia gets a $3B offer, founder and VC incentives decouple. For a founder with 10% equity, the lifestyle difference between a $300M exit and a potential $1B future exit is minimal. For a VC, that same 3.3x growth can mean the difference between a decent and a great fund return, making them far more willing to gamble.