Focusing only on trendy sectors leads to intense competition where the vast majority of startups fail. True opportunity lies in contrarian ideas that others overlook or dismiss, as these markets have fewer competitors.

Startups often fail to displace incumbents because they become successful 'point solutions' and get acquired. The harder path to a much larger outcome is to build the entire integrated stack from the start, but initially serve a simpler, down-market customer segment before moving up.

Breakthrough companies often succeed not by iterating endlessly, but by 'planting a flag'—making a strong, often contrarian bet on a core thesis (e.g., email-first media) and relentlessly executing against that vision, even when it's unpopular or lacks momentum.

Startups often fail by making a slightly better version of an incumbent's product. This is a losing strategy because the incumbent can easily adapt. The key is to build something so fundamentally different in structure that competitors have a very hard time copying it, ensuring a durable advantage.

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 a rapidly evolving space like AI, being the first mover can be a disadvantage if you bet on the wrong technical approach (e.g., fine-tuning vs. application logic). Second movers can win by observing the market, identifying the first mover's flawed strategy, and building a superior product on the correct technical foundation.

Instead of creating a market expansion strategy from scratch, ServiceUp explicitly copied the playbook of DoorDash, a successful three-sided marketplace in an adjacent vertical. This involved entering a new city and simultaneously acquiring customers, suppliers (shops), and drivers, accelerating growth.

While massive "kingmaking" funding rounds can accelerate growth, they don't guarantee victory. A superior product can still triumph over a capital-rich but less-efficient competitor, as seen in the DoorDash vs. Uber Eats battle. Capital can create inefficiency and unforced errors.

Pursuing a genuinely non-obvious idea feels risky, not just uncertain. This feeling of danger—the fear of wasting years on a potential failure—is often a signal that you're working on something truly contrarian and valuable, as it deters others.