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.

David Vélez found that adopting big-company management practices made Nubank feel like a big company, killing its startup urgency. The goal is not to become a traditional CEO, but to pair a founder's vision with light processes and a strong, agile team.

Bootstrappers should avoid modeling their processes after companies like Apple or Basecamp, who have near-infinite time and resources. Instead, look to other successful solo founders or small teams who operate under similar constraints for more relevant and applicable strategies.

As startups hire and add structure, they create a natural pull towards slower, more organized processes—a 'slowness gravity'. This is the default state. Founders must consciously and continuously fight this tendency to maintain the high-velocity iteration that led to their initial success.

Founders often start scrappy out of necessity and dream of lavish resources. However, once successful, many realize that small, lean, and scrappy teams are more effective. This creates a paradox where the most successful entrepreneurs intentionally revert to the resource-constrained mindset they once tried to escape.

Founders often chase executives from successful scaled companies. However, these execs can fail because their experience makes them overly critical and resistant to the painful, hands-on work required at an early stage. The right hire is often someone a few layers down from the star executive.

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.