Despite immense success with his wife Cass, founder Mike Lazaro calls his next venture—started without her—the 'biggest mistake of my life.' He admits ego and hubris led him to ignore her doubts and partner with someone else, resulting in failure. The lesson: past success doesn't invalidate a trusted partner's intuition.
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The most significant founder mistakes often arise from abandoning one's own judgment to do what is conventionally expected. Jason Fried notes that these errors feel worse because you aren't just failing, you're failing while trying to be someone else, which undermines the core identity of your company.
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.
The founder’s 76-year-old partner, having been "screwed over" in past deals, acted out of extreme self-preservation. This past business trauma led him to prioritize his own financial security at all costs, even if it meant reneging on promises to his trusted partner.
A key warning sign was when the founder's business partner stopped communicating with him directly and began consulting his accountant instead. This communication shift signaled a change in priorities from collaborative building to self-interested financial maneuvering before the exit.
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.
Beyond financial incentives or strategic differences, a primary driver for a successful partner to spin out from an established firm can be pure ego. The desire to build something independently and prove one's own success is a powerful, albeit rarely admitted, motivation for starting a new venture.
The intense, unreasonable passion that fuels hyper-growth is the same trait that can lead a founder to make reckless, company-threatening decisions. You can't have the creative genius without the potential for destructive behavior. The same person who clears the path can also blow everything up.
Home Depot's founder, Bernie Marcus, walked away from a crucial $2M investment from Ross Perot over minor control issues, like what car he drove. He prioritized partner alignment over immediate capital, believing a bad partner would inevitably doom the venture, regardless of the money.
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.