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.
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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.
Early ventures that failed weren't seen as setbacks but as low-cost learning opportunities. This perspective, framed by his grandfather's high-risk business, eliminated fear and built foundational skills with minimal downside, making eventual success more likely.
The entrepreneurial journey is a paradox. You must be delusional enough to believe you can succeed where others have failed. Simultaneously, you must be humble enough to accept being "punched in the face" by daily mistakes and bad decisions without losing momentum.
Early ventures into legally ambiguous or "get rich quick" schemes can be an effective, albeit risky, training ground. This "gray hat phase" forces rapid learning in sales, marketing, and operations, providing valuable lessons that inform more legitimate, scalable businesses later on.
Winning in business requires three core components. First, a tangible money-making skill like sales or marketing. Second, a tenacious, scrappy mindset forged by necessity. Third, the ability to select good projects, a skill often learned by first pursuing and eliminating bad ones.
Companies like Instagram that succeed early become risk-averse because they lack experience in navigating failure. In contrast, enduring early struggles builds resilience and a willingness to experiment, which is critical for long-term innovation.
Entrepreneurs often view early mistakes as regrettable detours to be avoided. The proper framing is to see them as necessary, unskippable steps in development. Every fumble, pivot, and moment of uncertainty is essential preparation for what's next, transforming regret into an appreciation for the journey itself.
An entrepreneur's success rate dramatically shifted from 0 for 12 to 5 for 5 not because his execution improved, but because his project selection did. He stopped chasing high-risk, "one in a million" moonshots (like building the next social network) and focused on businesses with clearer paths to revenue (e-commerce, services).
In any difficult pursuit, the majority of people will try, fail, and drop out. The key is recognizing that with every failure you endure and learn from, the line of competitors gets smaller. True advantage lies not in initial talent but in the willingness to get back in line repeatedly while others give up.
You aren't competing with people who are more talented; you're competing with those willing to put in more imperfect reps. Success requires showing up consistently and learning in public, while others wait on the sidelines to be 'good' before they start. The key is persistence through the awkward phase.