Joe: What if the most powerful tool in a multi-trillion dollar company wasn't a piece of technology, but an imaginary 'stick' used to beat back complexity? In the book Insanely Simple, author Ken Segall, who worked with Steve Jobs for over a decade, reveals that this was the secret to Apple's success. Jobs wielded what Segall calls the 'Simple Stick'—a ruthless, obsessive focus on simplicity that he used to reject ideas, challenge his teams, and forge a culture that changed the world. It wasn't about making things look nice; it was a weapon. Lewis: And that's what makes this book so fascinating. Ken Segall wasn't a biographer watching from a distance. He was the creative director at the ad agency for NeXT and then for Apple's legendary turnaround. He was in the room. He got the midnight phone calls from Steve to debate a single word in an ad. So he saw, firsthand, that this obsession with simplicity wasn't a myth; it was the operating system of the entire company. Joe: Exactly. And today, we're diving deep into this philosophy from three angles. First, we'll explore the 'Simple Stick' itself and what it really means to weaponize simplicity. Lewis: Then, we'll discuss the controversial culture required to sustain it—thinking 'brutal' and 'small.' This is the part that makes most corporate managers sweat. Joe: And finally, we'll look at the iconic results of this obsession, from product names that defined an era to world-changing ad campaigns. It’s a masterclass in how focus creates magic.

Joe: So let's start with that 'Simple Stick.' The best story to illustrate this, right from the book's introduction, comes from a packaging meeting. Picture this: a team of talented package designers at Apple have been working for weeks, maybe months. They've designed beautiful packaging for two different versions of the same product. They’re proud of their work. They walk into the conference room to present to Steve Jobs. Lewis: The moment of truth. Every creative person knows this feeling. You’ve poured your soul into something, and now you’re about to show it to the ultimate decision-maker. Joe: The team lays out the designs. They're sleek, they're elegant, they're very Apple. And Steve looks at them, and you can just imagine the silence in the room. He doesn't critique the font, he doesn't critique the colors. He just looks at the two boxes and hits them with the Simple Stick. He asks a question that cuts through everything: "Why are there two boxes?" Lewis: (Chuckles) That’s it. That’s the whole thing. Joe: The team is stunned. They probably start explaining, "Well, Steve, there's the pro version and the standard version, they have different features, so they need different boxes..." And Steve just cuts them off. He says, "No. This is too complicated. Just make one product. Combine them. Then you only need one box." The project leader later told Segall, "Steve hit us with the Simple Stick." And they all realized, in that moment, that his solution was simpler, faster, and just… better. They couldn't believe they hadn't thought of it themselves. Lewis: And that's the core of it. The Simple Stick isn't about incremental improvement. It's not about making the existing thing 10% better. It's about radical reduction. It's about challenging the premise of the project itself. Most companies would have spent the next hour debating the shade of gray on the two boxes. Jobs questioned the existence of the second box. It’s a fundamental shift in thinking. Joe: It really is. And you see the opposite of this everywhere. Segall brings up a fantastic example: Microsoft's Zune store. When they launched it to compete with iTunes, Apple had a simple, one-click, 99-cent price per song. It was dead simple. What did Microsoft do? Lewis: Oh, I remember this. It was a masterclass in unnecessary complexity. They invented "Microsoft Points." So you couldn't just buy a song. First, you had to buy a block of points with your real money. Then, you had to do the mental math to figure out how many points a song cost. It was intentionally confusing. It created a cognitive tax on the customer. Joe: Exactly! They added layers. They made the customer work harder. And Segall's central thesis, which Jobs understood instinctively, is that people prefer simplicity. Given the choice between a straight line and a meandering path, people will always choose the straight line. Businesses that create those straight lines win. It sounds obvious, but almost no one actually does it consistently. Lewis: Because complexity is the natural state of any organization. It's entropy. As Sam Walton used to say, if you don't actively fight bureaucracy, you will get it. Period. You don't even have to try. The Simple Stick was Steve's tool for fighting that entropy. It was his cultural weed whacker. He was constantly asking, "Do we really need this? Is this essential?" And if the answer was no, it was gone. No committees, no discussion, just gone. Joe: It’s a powerful idea. It’s not just a design philosophy for products; it’s a business philosophy for everything. And to make it work, you need a very specific, and some would say very difficult, kind of culture.

Lewis: Right. You can't wield a Simple Stick in a culture that values politeness over truth. And that's where things get... uncomfortable for a lot of people. This leads us to the book's next big idea: to achieve simplicity, you have to 'Think Brutal.' Joe: And Ken Segall experienced this on day one. He tells the story of his very first meeting with Steve Jobs at NeXT. Segall had just been hired as the creative director for the account. He's nervous, he's heard all the stories about Steve. Steve walks in, shakes his hand, and says, "I've seen your work for Apple. Your TV commercials are great." Segall is feeling pretty good. And then, without missing a beat, Steve adds, "But your print work is shit." Lewis: (Laughs) Welcome to the team! No sugarcoating, no corporate-speak, just pure, unadulterated feedback. Joe: But Segall says something really important. He said it wasn't delivered with malice. It was just a statement of fact, as Steve saw it. And the effect was immediate clarity. Segall knew exactly where he stood and what he had to fix. There was no ambiguity. He didn't have to spend the next three weeks trying to decode what "we have some opportunities for enhancement in our print vertical" actually meant. Lewis: Exactly. Ambiguity is the enemy of speed and quality. This 'brutal' honesty, as Segall calls it, is actually the ultimate form of respect for people's time and focus. It says, "I trust you're professional enough to handle the truth, and I'm not going to waste your time or mine dancing around it." It creates a high-velocity environment where everyone knows the standard. Joe: And this culture of clarity was enforced everywhere. Which brings us to the principle of 'Thinking Small.' Segall tells this incredible story about a regular marketing meeting at Apple. The room is filled with the usual key players. But Steve walks in and spots a woman he doesn't recognize. Her name is Lorrie. He stops the meeting before it even starts and asks, "Who are you?" Lewis: Oh, this is a legendary story. Joe: Lorrie, a bit flustered, explains that she's from another marketing team and was asked to join because some of the projects overlap with her work. It's a perfectly reasonable explanation in any other company on Earth. But Steve just looks at her and says, "I don't think we need you in this meeting, Lorrie. Thanks." And he just waits for her to pack up her things and leave. Then he starts the meeting. Lewis: It sounds incredibly harsh. But again, think about the principle. The principle is: everyone in this room must be essential. There are no 'mercy invitations.' There are no spectators. This isn't personal; it's about maintaining the focus and quality of a small, smart group. He was protecting the meeting's integrity. He famously said Apple had "zero committees." He wanted to run it like the biggest startup on the planet. Joe: And you see the stark contrast when Segall talks about working with other big tech companies, like Intel. He describes a culture that was the polar opposite of Apple's. At Intel, the relationship was 'managed.' They had a formal, quarterly 'report card' system where the agency and client would grade each other on performance. Lewis: A report card! That's the definition of big-company behavior. It's creating a process to manage a relationship instead of just having an honest relationship. It’s a system built on mistrust. Joe: And it gets worse. The CEO of Intel at the time, a company of brilliant engineers, gave a mandate for "zero-defect advertising." He wanted the creative process to be as predictable and error-free as manufacturing a microchip. Lewis: Which is a complete misunderstanding of what creativity is! Creativity requires the risk of failure. It requires imperfection and experimentation. A "zero-defect" mandate is a recipe for safe, boring, and utterly forgettable work. You can't spreadsheet your way to a great idea. Apple's culture, by being 'brutal' and 'small,' was designed to protect those fragile, brilliant sparks of creativity from the crushing weight of corporate process. Joe: So you have this philosophy of the Simple Stick, and you have this brutal, small-group culture to protect it. What does that actually produce? It produces things so simple they become iconic.

Lewis: This is where the magic happens. This is where the internal philosophy becomes an external reality that customers can touch and feel. And it starts with the most fundamental thing: a name. Joe: The story of naming the iMac is one of the best in the book. So, Apple is about to launch this revolutionary new computer. It's the product that's supposed to save the company. Internally, it has a code name, but they need a real name. Steve Jobs has his own idea. He's a huge admirer of Sony and their iconic 'Walkman.' So, he wants to call the new computer... the 'MacMan.' Lewis: (Groans) Oh, it's so bad. It sounds like a superhero sidekick from the 1980s. It’s clunky, it’s derivative… it’s the opposite of simple. Joe: The agency team, including Segall, is horrified. But Steve is the client, and he loves it. So they have to go back and come up with alternatives. They work and work, and eventually, they land on five options. One of them is 'iMac.' They present the list to Steve. He looks at it and says, "I hate them all. 'MacMan' is better." Lewis: The ultimate rejection. So what do they do? Most agencies would just give up and start designing the 'MacMan' logo. Joe: But they believed in their idea. Segall explains that they used a clever tactic. They came back a week later with new ideas, but they also re-presented 'iMac.' The rule was, as long as you have new thinking to share, you can always bring back an old idea. They broke down the logic for Steve: the 'i' stands for internet, which was the computer's main selling point. It also stands for individual, imagination, instruct. It was simple, it was elegant, and it was forward-looking. Lewis: And this time, it clicked. Joe: It took a while, but he eventually came around. And that single, simple letter created a phrasal template for an entire product empire. 'iMac' led to iMovie, which led to iPod, which led to iTunes, iPhone, and iPad. It's a simple, repeatable, and infinitely scalable branding framework that built a dynasty. That is the power of getting the name right. It wasn't just descriptive; it was evocative. Lewis: And that's the key difference. 'MacMan' describes what it is. 'iMac' suggests what it can be. It’s a platform for a bigger idea. And that same principle of distilling everything down to a single, powerful idea is exactly what they did with their advertising. Joe: Absolutely. The 'Think Different' campaign is the ultimate example. When Steve came back, Apple was dying. They needed to remind the world what the brand stood for. They didn't create an ad showing off the processing speed of their computers. They didn't list a bunch of features. Lewis: They didn't throw five crumpled balls of paper at the audience. Joe: (Laughs) Exactly. They threw one. The campaign was just black-and-white photos of icons—Einstein, Gandhi, Picasso—with two words: "Think different." That's it. It was a campaign about values, not products. It was a simple, powerful idea that connected with people on an emotional level. Lewis: And it perfectly illustrates how the whole system works together. That world-changing campaign was conceived and created by a small, trusted team—Steve and his agency—moving at incredible speed because of that culture of brutal honesty and focus. The philosophy of the Simple Stick led to the culture of 'Brutal & Small,' which in turn produced the iconic output of 'Think Different.' It’s a perfect, closed loop.

Joe: So when you step back and look at the whole picture Ken Segall paints, it's this incredible chain reaction. It starts with a ruthless, almost religious philosophy of simplicity. Lewis: That philosophy is then protected and enforced by a culture that values brutal honesty and small, elite teams over process and politeness. Joe: And that culture, in turn, produces these iconic outputs—products, names, and messages—that feel so simple and effortless to the outside world, but are actually the result of an intense, almost violent, process of reduction and focus. Lewis: It's a powerful lesson. Simplicity isn't the absence of complexity; it's the mastery of it. It's not the easy path; it's the harder path. As Steve Jobs himself said, "Simple can be harder than complex. You have to work hard to get your thinking clean to make it simple." Joe: But the book proves it's worth it in the end. Because once you get there, you can move mountains. Lewis: And that really leaves you with a challenge. The book makes you ask: where in our own work or our own life are we tolerating complexity? Where are we designing two boxes when we only need one? Where are we writing a long, meandering email when a blunt, five-word sentence would do? And more importantly, do we have the courage to pick up the Simple Stick and do something about it?