Insanely Simple

When was the last time you looked at something complex—your inbox, your company’s strategy, or even your phone—and thought, “Why does this have to be so complicated?” Ken Segall’s Insanely Simple: The Obsession That Drives Apple’s Success argues that this craving for clarity isn’t a quirk; it’s a competitive advantage. Segall, who spent over a decade as Steve Jobs’s ad creative partner at NeXT and Apple, insists that Simplicity isn’t just an aesthetic choice—it’s a business weapon. It’s what made Apple the most valuable and beloved company on Earth while rivals drowned in bureaucracy and jargon.

The book explores how Apple’s “religion of Simplicity” under Steve Jobs became its secret operating system. Jobs wielded what insiders half-jokingly called “the Simple Stick,” using it to smash unnecessary complexity—in meetings, in products, in marketing, and in processes. Simplicity, at Apple, was never about cutting corners. It was about stripping away the nonessential until only what truly mattered remained. As Segall reveals, this pursuit of purity influenced everything from the design of the iMac to the wording of an ad, from the size of a meeting to the architecture of the company itself.

The Philosophy of Simplicity

Segall frames Simplicity as a universal human preference—people, animals, and even amoebas respond better to simple solutions. The irony, he says, is that while everyone craves it, few are willing to fight for it. Complexity is seductive because it masquerades as sophistication. In truth, it’s “simplicity that looks easy but is hard as hell to achieve.” This is why Jobs called Apple’s products “insanely great”—achieving that level of clarity required insane discipline. Segall argues that the difference between companies like Apple and Dell or Microsoft isn’t talent, but an unrelenting obsession with staying simple in philosophy, design, and behavior.

The Ten Elements of Simplicity

Drawing from 17 years of experience with Apple and other tech giants, Segall identifies ten core elements or “weapons” of Simplicity, each explored in a separate chapter: Think Brutal, Think Small, Think Minimal, Think Motion, Think Iconic, Think Phrasal, Think Casual, Think Human, Think Skeptic, and Think War. These aren’t abstract mantras but actionable lenses to simplify how you lead, create, and decide. They show how Apple avoided bureaucratic traps, how Jobs kept teams tight, how he made decisions quickly but decisively, and how he connected emotionally with customers through marketing that spoke to humans, not engineers.

Throughout the book, Segall contrasts Apple’s methods with those of Intel, Dell, and IBM—the “bozos,” in Jobs’s phrasing. These companies, he shows, constantly succumbed to their love of process, committees, and focus groups. Apple, by contrast, empowered a small group of smart people led by a clear decision-maker, with no committees or layers. Where Intel tested every ad, Apple relied on instinct and craft. Where Microsoft named its products Centrino or Zune, Apple chose iMac and iPod—short, memorable, human. Each decision reaffirmed Apple’s DNA: make things for people, not programmers.

Why This Matters to You

Segall’s central message is both business philosophy and personal challenge: anyone can wield the Simple Stick. Whatever your field, simplifying what you do—your meetings, your writing, your customer experience—is how you stand out. Simplicity, he writes, “isn’t available with a switch; it needs a champion.” You become that champion when you insist on honesty (Think Brutal), focus on essentials (Think Minimal), and talk like a human (Think Human). The payoff is clarity, creativity, and stronger relationships—with customers and colleagues alike.

In the end, Insanely Simple offers more than behind-the-scenes anecdotes about Steve Jobs or Apple’s marketing. It’s a manifesto for clear thinking in a complicated age. It shows how the world’s most admired company thrived not through complexity but by doing the hard, unglamorous work of keeping things simple. As Thoreau said, “Simplify, simplify.” Or as Apple would edit him: “Simplify.”

Ken Segall opens with his first jarring encounter with Steve Jobs: after complimenting the agency’s TV ads, Jobs smiled and said, “The print is really shit.” In that blunt opener lies Apple’s first rule of Simplicity—brutal honesty clears the clutter. Jobs wasn’t being cruel; he was cutting through the politeness and partial truths that waste time and dilute ideas. Segall calls this the art of “Think Brutal”: say what you mean, hear what’s true, and move forward. Simplicity can’t breathe in a fog of diplomacy.

Radical Candor over Politeness

Jobs’s style wasn’t for the faint-hearted, but Segall insists it worked because it created clarity. Everyone knew where they stood. There was no guessing what Steve thought—he’d tell you, instantly. This brutal transparency made decision-making faster and teams more focused. In contrast, the author recalls working with Intel and Dell, where endless intermediaries softened feedback and buried good ideas in emails. “Varnished truth,” he writes, “is complexity’s favorite disguise.” Brutal simplicity, by contrast, keeps teams honest and creative energy flowing.

Standards That Don’t Bend

Jobs’s bluntness was tied to an ironclad refusal to compromise. “Good enough is not enough,” as Chiat/Day’s old T-shirt read. Segall describes Jobs rejecting whole campaigns, products, even people, if they didn’t meet his standard. That perfectionism may sound tyrannical, but it was how Apple kept integrity intact. The author himself learned this the hard way: once, he presented an ad he didn’t truly believe in—only for Jobs to spot it immediately. “So you put the B team on this one?” he said flatly. Segall never made that mistake again. Brutal honesty, he learned, doesn’t just protect the company; it preserves your credibility.

Brutality with Style

Jobs’s reputation for fierceness often overshadows his humor and humanity. Segall shows both sides: the same man who could torch an idea could also laugh about it moments later. When NeXT’s first ad campaign failed spectacularly, Jobs erupted—then calmly dissected what went wrong, gave each team member a “letter grade,” and ended the meeting by promising to do better together. In Segall’s words, “being brutal and being respected are not mutually exclusive.” It’s only unbearable when cruelty replaces purpose, and Jobs’s brutality always served the work.

Thick Skin and Clear Minds

You can’t practice simplicity if you can’t take a punch. Segall argues that thick skin and intellectual honesty must go hand in hand. Creative people need feedback that stings, not flattery that slows them down. Apple’s culture institutionalized that belief: problems were addressed directly, meetings were concise, and the truth was blunt. In his words, “Clarity propels an organization—pervasive, 24-hour, in-your-face clarity.” This is “Think Brutal”—honesty as both shield and sword, pruning away the unnecessary so excellence can grow.

How many people does it take to kill a great idea? Usually more than seven, Segall jokes. “Think Small” means narrowing the circle to a small group of smart people—the only way to keep Simplicity alive. Steve Jobs famously threw people out of meetings, literally. “Who are you?” he once asked a newcomer at Apple headquarters. When she explained her role, he said, “I don’t think we need you in this meeting, Lorrie. Thanks,” and resumed speaking. Cold? Maybe. Efficient? Absolutely.

The Small-Group Principle

Segall recalls that every Apple–Chiat meeting included only those who mattered: Jobs, Phil Schiller, Jony Ive, and a few creatives. There were no “mercy invites.” Everyone had a voice; no one could hide. In such rooms, ideas moved quickly and decisions stuck. Compare that to his post-Apple experience at Intel, where one idea could pass through dozens of managers and focus groups before dying of asphyxiation. Jobs liked to say, “We’re the biggest start-up on earth,” and to make that true he banned committees and layers. Even Apple’s executive retreat was called “Top 100”—because that was the maximum number of people Jobs could know by name.

Process vs. Progress

Other companies love processes; Apple loved results. Segall contrasts this with Dell and Intel, where meetings came with rulebooks, golden muffins, and PowerPoint templates. Apple’s meetings were whiteboards and conversation. Jobs insisted that decision-makers be present in every major meeting—no “approval chains.” If the CEO’s too busy to join, he said, “You’re too busy to do it right.” The fewer hands an idea passes through, the less likely it will get watered down. This insistence on direct connection allowed Apple to operate with the speed and creativity of a garage start-up even as it scaled globally.

Efficiency Born of Trust

Simplicity thrives in teams that trust themselves. Apple’s creative partner, Chiat/Day, worked this way as well: small, flat, and fiercely collaborative. Steve’s rule—“no one sees the agency’s work before I do”—ensured unfiltered communication and built mutual confidence. At Intel, by contrast, Segall saw fear masquerading as process: focus groups, endless data, and quarterly “report cards” rating the agency. “When process is king,” he writes, “ideas never will be.” Jobs, meanwhile, loved spontaneity—rewriting ads mid-shoot if a better idea came up—and expected others to love it too. To him, creativity wasn’t a chain of approvals; it was a chain reaction.

When you shrink your meetings, flatline your hierarchy, and empower your smartest thinkers, you unleash speed, clarity, and passion. “Think Small,” Segall writes, “because small is where big ideas are born.”

In 1998, Apple was gasping for breath. When Jobs returned, the company had dozens of computer models—Quadra, Performa, PowerBook, LC—and none of them sold well. His remedy was a simple chart with four quadrants: consumer and professional, desktop and portable. Four products. One focus. Segall calls this the “Reduction Act of 1998,” the moment Jobs proved that minimization can save a company. The result? Fewer models, higher quality, clearer choices, and a rebirth symbolized by the new iMac.

The Discipline of Saying No

“I’m as proud of what we don’t do as what we do,” Jobs once said. Minimizing, Segall explains, requires courage. It’s easier to add than to subtract, to please everyone rather than disappoint some. But every time you chase more products, features, or ideas, you add friction. Jobs’s model was radical focus—cut the “crappy stuff,” he told Nike’s CEO, and perfect the rest. The result wasn’t less creativity but more: engineers and marketers could pour energy into bold innovations rather than maintain a sprawling catalogue.

When More Hurts Sales

Segall compares Apple’s two laptop choices with Dell and HP’s twenty-plus models. He quotes confused Dell customers and even sales reps who couldn’t explain differences between machines. Complexity, he writes, “masquerades as choice,” but when customers feel overwhelmed, they flee—or regret their purchase. Apple’s “less is more” retail experience, online or in-store, reinforced its message: buying a Mac feels easy because it is easy. Simplicity sells itself.

The Courage to Minimize Process

Minimalism wasn’t just a product principle—it guided Apple’s marketing. Intel, obsessed with “zero-defect advertising,” over-engineered its creative process with endless testing and revision. Apple didn’t test at all. Segall says Steve trusted “a small group of smart people” to decide, then ship. This trust trimmed months off project timelines and produced iconic campaigns. Minimal teams, minimal steps, maximal impact.

To minimize, you must confront your own clutter—projects, emails, meetings, metrics. Ask, “Does this move us forward?” If not, hit it with the Simple Stick. The less you carry, Segall reminds, the faster you move.

Apple’s greatest ads, Segall argues, are more than marketing—they’re symbols. From “1984” to “Think different,” Apple used iconic imagery to define what it stood for. The Think different campaign, created by Segall’s team with art director Craig Tanimoto, turned two words into a global slogan. Its black-and-white portraits of Einstein, Picasso, Gandhi, and Dylan became visual poetry of innovation. Simplicity spoke louder than specs.

Selling Ideas, Not Products

Jobs’s 1997 brand presentation remains legendary. “Apple is about people with passion who can change the world,” he said. No talk of megahertz or RAM—just values. The ads honored the “crazy ones,” implying that Apple designed for them. This emotional truth restored Apple’s identity and morale when it was near collapse. Segall contrasts this with Dell’s 2008 brand disaster, run by committees that couldn’t even agree on a logo. Apple’s single heartbeat—clarity of message—became its unfair advantage.

Icons in Product Form

When the first iMac appeared—translucent, colorful, handle-topped—it was itself a “Think different” sculpture. Jobs said, “The back of our computer looks better than the front of theirs.” Visual simplicity became marketing. The same theory drove iPod’s famous “Silhouettes” campaign, conceived by Chiat/Day’s Susan Alinsangan: featureless dancers with white earbuds, pure motion and joy. The product barely appeared, yet became instantly recognizable. Even the iPhone’s single button, Jobs insisted, was an icon of simplicity—proof that design was communication.

Segall’s takeaway: the most powerful way to simplify is to symbolize. One image, one phrase, one feature—if it captures the essence of your story, you don’t need more words. Think different did it with two.

What makes Apple’s devices irresistible isn’t their power—it’s their humanity. Segall’s chapter “Think Human” begins with Steve Jobs weeping over an iMovie project he made of his kids. That moment, he told Segall, was “the first time a computer made me cry.” It proved his belief that technology should touch the heart before it touches the brain. From iPod to Siri, Apple built machines that help people feel. The secret? Design for emotion, not specification.

Emotion as Simplicity

Early PCs forced humans to act like machines. Macintosh flipped that by letting machines act like humans. In the 2000s, iPod, iPhone, and iPad deepened that bond—each simplifying interaction until technology became intuition. Jobs’s “1,000 songs in your pocket” said more than any spec sheet. Siri later gave devices literal voices, proving that simplicity can be conversational. Segall notes that Apple “removed the barrier of technology” where rivals added complexity in pursuit of features. The result wasn’t just innovation—it was affection.

Human Language, Human Brand

Apple’s marketing, like its design, speaks human. It says “It just works,” not “Now with 4 GB RAM.” Segall explains that Jobs banned jargon because “people don’t talk that way at dinner.” The company inherited this “human-speak” from its earliest ads (“Simplicity is the ultimate sophistication”) and kept it through every new medium. Even Apple’s minimal web address—just “apple.com”—reflected respect for the customer’s time. That tone built trust, turning buyers into evangelists.

Simplicity, Segall reminds, is empathy systematized. It’s what happens when you stop talking to audiences and start talking to people.

To keep things simple, you often have to fight experts who complicate them. Segall’s “Think Skeptic” shows Jobs defying lawyers, engineers, and conventional wisdom in equal measure. When Apple attorneys warned that an ad comparing PowerPC chips to Intel’s might cause a lawsuit, Jobs’s email reply was crisp: “F*** the lawyers.” The ad ran. Intel grumbled—and Apple won attention. Skepticism, Segall explains, doesn’t mean ignoring counsel; it means putting advice in context and defending what matters.

Courage over Compliance

Jobs’s boldest act of skepticism came with the iPhone name. Cisco owned that trademark, but he unveiled “iPhone” anyway, daring Cisco to sue. Within weeks, Apple negotiated rights to the name. The lesson? Simplicity sometimes requires dissent. Where most executives seek safety, Jobs sought elegance—and was willing to gamble for it. Segall contrasts this with Intel’s nervous retreat from its “Yes” campaign after minor legal challenges: its fear of risk became complexity incarnate.

Fighting Bureaucratic No’s

Jobs’s skepticism wasn’t rebellion for its own sake; it was a shield for creativity. When told an idea was impossible, he pressed harder until someone proved him right. Segall recounts a holiday ad Apple delivered to Time magazine in two weeks after being told it was impossible—because Jobs threatened to give the project to a rival agency. At Dell, executives made similar demands without the passion or clarity, resulting in rushed failures like the Adamo laptop. Skepticism without Simplicity, Segall notes, becomes chaos; with it, it becomes innovation.

To think skeptically is to believe in your instincts more than other people’s fears. That’s how Apple turned “can’t” into “done.”

The final principle, “Think War,” shows Simplicity as not just a value but a weapon. Apple’s 1998 “snail ad” mocked Intel’s slow chips, taunting a giant with humor and confidence. Jobs grinned, imagining the headlines if Intel sued. For him, good marketing wasn’t polite—it was warfare waged through clarity. Segall writes, “When ideas face life or death, the last thing you want is a fair fight.”

Picking the Right Enemies

Apple’s wars—against IBM in 1984, Intel in 1998, Microsoft in 2006—focused attention. Even Jobs’s partnership with Bill Gates was strategic: accept investment, drop lawsuits, then aim higher. Later, the Mac vs. PC campaign personified competition as a humorous exchange between two characters—amiable rivalry without arrogance. By simplifying the enemy, Apple simplified the message: choose freedom over frustration, creativity over conformity.

Overwhelming Force Through Passion

Jobs believed that half-measures kill ideas. He used every weapon available—alliances, headlines, even presidents. When Nelson Mandela declined to appear in the Think different campaign, Jobs had Bill Clinton personally call his office to ask. It didn’t work, but his relentlessness made the point: “Never use a peashooter when you have a howitzer.” His howitzer was Simplicity itself, concentrating Apple’s story into irresistible forms. When iPhone launched, it wasn’t the first smartphone; it was the first simple one—and that won the war.

Segall closes with Jobs’s own rule of battle: never stop peeling away complexity until you reach elegance. Simplicity, when defended fiercely, becomes the most powerful weapon any company—or individual—can wield.