Telling a story about a massive enterprise client to a small business prospect can backfire. Instead of being impressive, it often makes the prospect feel that your solution is too complex or expensive for them, and that you are simply bragging about your large clients.

An investor might correctly identify a company's flaw but still be wrong to pass, as great founders often fix those issues. This requires investors to have the humility to admit their ultimate conclusion was wrong, even if their initial analysis was correct, and be willing to re-engage with the startup.

The most challenging founder issue to identify isn't dishonesty towards others, but self-deception. When a founder genuinely believes their own illusions, it's difficult to distinguish from reality and emotionally painful to witness their talent being misapplied due to flawed core assumptions.

Persisting with prospects who are not fully committed, even if they meet some criteria, is a sacrifice of your integrity. Taking their money when you know you cannot deliver optimal results undermines your value and guarantees a poor outcome for both parties.

Instead of walking away immediately upon finding inaccuracies, quantify the risk. Rebuild your business case assuming the worst probable scenario based on the discovered misrepresentations. If the deal remains net positive even with these new, pessimistic assumptions, it may still be a viable investment.

Unlike first-time founders who struggle for attention, successful repeat founders face the opposite problem. Prospects tend to agree with their ideas due to their reputation, creating 'happy ears' and masking the truth until a payment is requested.

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.

If a deal team says, "don't bring the integration people in because they'll mess up the deal," it is a massive red flag. This indicates they are likely sugarcoating problems and painting an overly optimistic picture for the seller, virtually guaranteeing post-close surprises and failure.

During due diligence on a venture firm, asking portfolio founders why they chose that investor is critical. If the answer is simply "they had money," it implies the VC offers no strategic value—like recruiting help or corporate relationships—and is not a top-tier partner.