First-time CEOs often change their entire strategy after talking to a few investors. This is a red flag signaling a lack of conviction. Investors want to see a CEO who listens and evolves but ultimately sticks to their core, well-researched beliefs, especially when faced with disarming questions.
Related Insights
Storytelling is inextricably linked to strategic thinking. If a founder struggles to articulate their company's narrative in a simple, compelling way, it's often because the underlying strategy is weak or inconsistent. The difficulty isn't in the telling, but in the story itself.
A new CEO’s first few months are best spent gathering unfiltered information directly from employees and customers across the business. Avoid the trap of sitting in an office listening to prepared presentations. Instead, actively listen in the field, then act decisively based on those firsthand insights.
Limited Partners (LPs) value fund managers who are willing to listen and internalize market feedback, even if they ultimately follow their own strategy. This openness is a key positive signal, while a refusal to listen is a major red flag that often appears early in the relationship.
A founder must simultaneously project unwavering confidence to rally teams and investors, while privately remaining open to any evidence that they are completely wrong. This conflicting mindset is essential for navigating the uncertainty of building a startup.
A successful startup often resembles a cult, requiring a leader who communicates their vision with unwavering, first-person conviction. Hiding the founder behind polished PR spokespeople is a mistake; it neuters the contagious belief required to recruit talent and build a movement against impossible odds.
Experience taught Herb Wagner that great leaders consistently surprise on the upside. He now weights leadership quality far more heavily, assessing CEOs not by interviews or charisma, but by their verifiable track record and through trusted backchannel references who have worked with them directly.
A CEO is always selling their company's story—to investors, hires, and customers. An investor's first filter is whether the CEO can get them interested and excited in the first 30 seconds. If it takes a 35-slide deck to explain the vision, the opportunity is likely already lost.
While it's crucial to listen to markets and clients, founders must also be prepared to stick to their convictions when investors, who may not be specialists in their niche, offer conflicting advice. Knowing when to listen and when to hold firm is a key startup skill.
Great founders turn a pitch into a collaborative discussion by asking investors to identify business weaknesses. This signals curiosity, strength, and a desire for genuine feedback over just presenting a perfect picture. It demonstrates a coachable leader who is focused on gathering data to improve.
An effective manager evaluation technique is to recognize that everyone presents their polished "best self" initially. An allocator's primary job during due diligence is to actively investigate beyond this facade to uncover the manager's "true self"—how they operate under pressure and handle failure—before committing capital.