Headlines about high AI pilot failure rates are misleading because it's incredibly easy to start a project, inflating the denominator of attempts. Robust, successful AI implementations are happening, but they require 6-12 months of serious effort, not the quick wins promised by hype cycles.
Tech culture, especially during hype cycles, glorifies high-risk, all-in bets. However, the most critical factor is often simply surviving long enough for your market timing to be right. Not losing is a precursor to winning. Don't make existential bets when endurance is the real key to success.
Don't just ask customers about their business—independently verify it. When launching Uber Eats, the team couldn't get clear answers on restaurant economics. So they ordered food, weighed the ingredients, and built their own model, giving them the "ground truth" needed to confidently propose their pricing structure.
Co-founding Scour with Travis Kalanick taught Jason Droege that business has no fixed playbook. From wild VC negotiations to legal battles, he learned that if you can imagine a path and align incentives, you can negotiate your way through almost any obstacle.
Use gross margin as a quick filter for a new business idea. A low margin often indicates a lack of differentiation or true value-add. If a customer won't pay a premium, it suggests they have alternatives and you're competing in a commoditized space, facing inevitable margin compression.
Early AI training involved simple preference tasks. Now, training frontier models requires PhDs and top professionals to perform complex, hours-long tasks like building entire websites or explaining nuanced cancer topics. The demand is for deep, specialized expertise, not just generalist labor.
Off-the-shelf AI models can only go so far. The true bottleneck for enterprise adoption is "digitizing judgment"—capturing the unique, context-specific expertise of employees within that company. A document's meaning can change entirely from one company to another, requiring internal labeling.
Instead of replacing leaders at each growth stage, the Uber Eats management team was built like an "organism" with complementary strengths and was kept largely intact from launch to a $20 billion run rate. This proves a cohesive team that can learn together is more valuable than constantly hiring for "scale experience."
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.