Instead of defaulting to skepticism and looking for reasons why something won't work, the most productive starting point is to imagine how big and impactful a new idea could become. After exploring the optimistic case, you can then systematically address and mitigate the risks.

Conventional definitions of risk, like volatility, are flawed. True risk is an event you did not anticipate that forces you to abandon your strategy at a bad time. Foreseeable events, like a 50% market crash, are not risks but rather expected parts of the market cycle that a robust strategy should be built to withstand.

Firing decisions should be a function of both incompetence and business constraint. Not all underperformers are equal priorities. Some are like a "trash can on fire in the driveway"—a problem, but not the company's main bottleneck. Focus firing efforts on roles that are the direct constraint to growth.

AI models tend to be overly optimistic. To get a balanced market analysis, explicitly instruct AI research tools like Perplexity to act as a "devil's advocate." This helps uncover risks, challenge assumptions, and makes it easier for product managers to say "no" to weak ideas quickly.

When facing an existential business threat, the most effective response is to suppress emotional panic and adopt a calm, methodical mindset, like a pilot running through an emergency checklist. This allows for clear, logical decision-making when stakes are highest and prevents paralysis from fear.

Before starting a project, ask the team to imagine it has failed and write a story explaining why. This exercise in 'time travel' bypasses optimism bias and surfaces critical operational risks, resource gaps, and flawed assumptions that would otherwise be missed until it's too late.

When reviewing a shared business case, look for red ink—comments, changes, and edits from the buying team. This signifies ownership and conviction. A document with zero changes indicates shallow discovery and a lack of internal buy-in, making it a powerful negative signal for the deal's health.

A simple framework for assessing financial products involves checking for three warning signs. If it's too complex to explain to a 12-year-old, seems too good to be true, or lacks proper auditing, it's a major red flag. This heuristic helps investors cut through hype and avoid potential blow-ups like MicroStrategy's.