Facing the same blocker repeatedly—in Kalshi's case, government rejection—is uniquely demoralizing. It causes the team to question the core strategy and leadership's judgment, leading to significant attrition and a collapse in faith that is harder to recover from than varied challenges.
Calling a "code red" is a strategic leadership move used to shock the system. Beyond solving an urgent issue, it serves as a loyalty test to identify the most committed team members, build collective confidence through rapid problem-solving, and rally everyone against competitive threats.
The most common failure mode for a founder-CEO isn't a lack of competence, but a crisis of confidence. This leads to hesitation on critical decisions, especially firing an underperforming executive. The excuses for delaying are merely symptoms of this confidence gap.
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.
Leaders who always have the right answer often create an environment where others feel devalued and excluded. The blocker's real cost is not the accuracy of their ideas, but the damage done to team connection and collaborative decision-making, which prevents the team from arriving at the best solutions together.
Mandating new processes, like reducing meetings, is ineffective if the collective beliefs driving old behaviors (e.g., lack of trust) are not addressed. To make change stick, leaders must first surface, discuss, and realign the team's shared assumptions to support the new structure.
Companies like Instagram that succeed early become risk-averse because they lack experience in navigating failure. In contrast, enduring early struggles builds resilience and a willingness to experiment, which is critical for long-term innovation.
Instead of dismissing harsh criticism, extract the underlying truth. A brutal investor rejection focused Gamma on intertwining product and growth from the very beginning, acknowledging the difficulty of competing against incumbents. This became a foundational part of their strategy.
Managers cannot just be soldiers executing orders. If you don't truly believe in a strategy, you cannot effectively inspire your team. You must engage leadership to find an angle you can genuinely support or decompose the idea into testable hypotheses you can commit to.
Before labeling a team as not resilient, leaders should first examine their own expectations. Often, what appears as a lack of resilience is a natural reaction to systemic issues like overwork, underpayment, and inadequate support, making it a leadership problem, not an employee one.
The number one reason founders fail is not a lack of competence but a crisis of confidence that leads to hesitation. They see what needs to be done but delay, bogged down by excuses. In a fast-moving environment, a smart decision made too late is no longer a smart decision.