A significant motivation for Steve Jobs at NeXT was revenge against Apple. This led to poor strategic decisions, like running attack ads with no product to sell, wasting resources and focus that should have been dedicated to product development and achieving product-market fit.

Upon his return, Jobs found Apple's product line of over 40 confusing machines incomprehensible. He scrapped nearly everything, replacing it with a simple two-by-two matrix: Consumer/Pro on one axis, and Portable/Desktop on the other. This radical simplification focused the entire company on just four great products.

The young Steve Jobs famously vilified IBM in the iconic "1984" ad. However, upon returning to a failing Apple, the older Jobs recognized his own operational weaknesses. He hired a wave of talent from IBM, including Tim Cook, to instill the discipline in logistics, procurement, and manufacturing that he had previously disdained.

Sierra VC Shashank Saxena finds Steve Jobs most inspiring not for Apple's initial founding, but for witnessing its dramatic reinvention with the iPod and Mac. This perspective highlights that a leader's ability to execute a successful turnaround can be a more powerful source of inspiration than their original vision alone.

Reluctant to become Apple's CEO, Jobs called his mentor, Intel's Andy Grove, for advice. Grove's blunt response, "I don't give a shit about Apple," served as a jolt. It made Jobs realize that he, in stark contrast, cared deeply, prompting him to accept the interim CEO role.

When confronted with Apple's live voicemail feature, reps should avoid panicking and delivering their full pitch. The goal is to spark curiosity with a brief, value-led statement. Mentioning results for similar companies and suggesting an easier follow-up channel makes it more likely the prospect will engage.

Steve Jobs despised the enterprise software market, but it was the only thing that made his company NeXT profitable—and only after he stepped back, disinterested. This same enterprise-grade OS, NeXTSTEP, ultimately became the foundation for macOS and iOS, saving Apple.

Jobs' attempt to overthrow CEO John Scully failed because he confided in a rival, Jean-Louis Gasset. Gasset promptly warned Scully, leading to the plan's collapse and ultimately Jobs' ousting. This highlights the danger of misplaced trust in high-stakes corporate politics.

The historic acquisition of NeXT by Apple was not initiated by executives, but by a single, proactive phone call. A NeXT product manager, seeing Apple was looking for an OS, simply asked "why don't we just freaking call Apple?" and cold-called their CTO, changing tech history.