A product team saved $150 million in margin improvement not by building new features, but by decommissioning a long tail of customized, on-prem legacy products. This "unsexy" work eliminated significant operational drain from support and maintenance, directly impacting the bottom line in a way new features rarely can.

The decision to move from Arc to Dia was less about Arc's limitations and more about the founders' profound conviction that AI was a fundamental platform shift they had to build for from scratch. The pull of the new technology was a stronger motivator than the push from the existing product's challenges.

True innovation requires building features customers don't yet know to ask for. Bloomberg's success came from providing functionality users hadn't imagined was possible with computers, rather than just reacting to their explicit requests.

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.

When fundamental market changes make your business model obsolete, incremental changes aren't enough. You must consider how your underlying talent and expertise can be repackaged into a completely different business, like turning a tech platform into a consulting service.

Pivoting isn't just for failing startups; it's a requirement for massive success. Ambitious companies often face 're-founding moments' when their initial product, even if successful, proves insufficient for market-defining scale. This may require risky moves, like competing against your own customers.

Many founders become too attached to what they've built. The ability to unemotionally kill products that aren't working—even core parts of the business—is a superpower. This prevents wasting resources and allows for the rapid pivots necessary to find true product-market fit.

Numi launched a line of silk blouses that developed its own cult following. However, it created a second, competing brand identity and diverted focus. They phased it out to double down on their core competency—women's undershirts—where they were the undisputed market leader.

The Bloomberg terminal's breakthrough was not simply displaying data, but integrating the tools needed to analyze and act on it. It was built around the user's entire workflow—calculating, graphing, and messaging—which existing data screens completely ignored.