Success brings knowledge, but it also creates a bias against trying unconventional ideas. Early-stage entrepreneurs are "too dumb to know it was dumb," allowing them to take random shots with high upside. Experienced founders often filter these out, potentially missing breakthroughs, fun, and valuable memories.

Many established marketers are ineffective because they rely on outdated strategies. A newcomer, free from this baggage, has a competitive advantage because they can bring fresh, unbiased perspectives to solve problems. This reframes imposter syndrome as a potential strength.

True growth and access to high-level opportunities come not from feigning knowledge, but from openly admitting ignorance. This vulnerability invites mentorship and opens doors to conversations where real learning occurs, especially in complex fields like investing, which may otherwise seem like a "scam."

Bizzabo's founders, being new to the events industry, used their lack of preconceived notions to their advantage. They could question established norms and identify problems that insiders overlooked, leading to innovative solutions. This "beginner's mind" is a powerful disruptive tool.

In a crowded market, the most critical question for a founder is not "what's the idea?" but "why am I so lucky to have this insight?" You must identify your unique advantage—your "alpha"—that allows you to see something others don't. Without this, you're just another smart person trying things.

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.

Countering conventional wisdom, Shopify's design leader argues that deep, long-held context often leads to incrementalism. He believes designers can onboard to new problems quickly, and their resulting naivety and fresh perspective are more valuable assets for driving true innovation.

Finding entrepreneurial success often requires a decade-long period of trial and error. This phase of launching seemingly "dumb" or failed projects is not a sign of incompetence but a necessary learning curve to develop skills, judgment, and self-awareness. The key is to keep learning and taking shots.