A rising tide lifts all boats. The true test of a founder partnership emerges during downturns. Diligence should focus on teasing out traits like adaptability, humility, and accountability, which predict how a founder will react when plans inevitably go awry.
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In a non-control deal, an investor cannot fire management. Therefore, the primary diligence focus must shift from the business itself to the founder's character and the potential for a strong partnership, as this relationship is the ultimate determinant of success.
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.
A compressed diligence process relies heavily on projections. A superior approach is building a relationship over 1-2 years, which allows an investor to witness the company's actual execution against its stated goals, providing far greater conviction than any financial model.
The long-standing relationship between PhonePe's co-founders, built on deep trust, allows them to be interchangeable in their roles. This enables one to step back during difficult periods while the other steps in, ensuring resilience through crises.
Investor Mark Rampolla argues that a brand's potential is capped by its leader's personal development. His firm seeks self-aware founders committed to "inner work," believing this psychological resilience is a key predictor of building a billion-dollar company.
Since startups lack infinite time and money, an investor's key diligence question is whether the team can learn and iterate fast enough to find a valuable solution before resources run out. This 'learning velocity' is more important than initial traction or a perfect starting plan.
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.
While assessed during diligence, the true caliber of a founder—their passion, authenticity, and ability to "run through walls"—becomes starkly clear after the deal closes. This distinction is not subtle; the impact of a truly exceptional founder versus an average one is immediately evident in the business's trajectory.
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.
