Chet Pipkin reflects that his company's biggest missteps occurred when they abandoned their own unique, effective internal systems to adopt "the right way" as prescribed by outside experts. He advises founders to trust their intuition and the bespoke processes that work for their specific business, rather than blindly following conventional wisdom.
Related Insights
When your business no longer feels aligned, trust your instincts to make a change. The required pivot may be disruptive and risky, especially if the current model is commercially successful, but your internal wisdom is the most reliable guide for long-term fulfillment and integrity.
Brian Halligan reflects that as HubSpot grew, he was coached out of his natural 'founder mode' instincts (e.g., many direct reports, public feedback) and into conventional 'manager mode' (weekly one-on-ones, private criticism). He now regrets this shift, believing his initial, more unconventional approach was more effective.
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.
Founders with deep market fit must trust their unique intuition over persuasive, but generic, VC advice. Following the standard playbook leads to cookie-cutter companies, while leaning into the 'weird' things that make your business different is what creates a unique, defensible moat.
In school or corporate jobs, the 'rules for success' are provided. Founders enter a world with no such rubric and often fail because they don't consciously develop their own theory of how the world works, instead defaulting to shallow, unexamined beliefs about what founders 'should' do.
Jason Fried advises founders facing inflection points to trust their own instincts rather than seeking external playbooks. An outsider can't replicate the founder's deep, irreplaceable knowledge of their business's history and decisions. The only path forward is to continue "making it up" based on that unique context.
Chomps' founders learned not to blindly copy the strategies of successful brands. They advise founders to gather wide-ranging feedback but to ultimately analyze it through their own company's unique context, as what works for one brand is not a guarantee of success for another.
Activities like discovery interviews and seeking design partners often feel productive and validating. However, they are frequently designed to make founders feel comfortable and avoid the difficulty of real selling and deep immersion. True progress comes from uncomfortable, direct actions, not feel-good processes.
Founders often start with strong intuition but lose it after achieving success. This occurs because long-held societal conditioning, which teaches individuals to distrust themselves and outsource authority to experts, resurfaces and mutes their inner voice.
While it's crucial to listen to markets and clients, founders must also be prepared to stick to their convictions when investors, who may not be specialists in their niche, offer conflicting advice. Knowing when to listen and when to hold firm is a key startup skill.
