Olivia: Alright Jackson, pop quiz. You're a Silicon Valley VC. A founder pitches you their 'pre-revenue, paradigm-shifting' startup. What's the one word they'll use at least 17 times to sound impressive? Jackson: Oh, that's easy. 'Scale.' They want to 'scale' everything. Scale the user base, scale the culture, scale their lunch order. It's the most overused, least-understood word in business. Olivia: Exactly! It’s become this magic word that’s supposed to signal massive success, but most people using it don't even know what it means. And that's why we're diving into 'Do Scale' by Les McKeown. He argues that most people using that word are, frankly, wrong. Jackson: Who is this guy to call out all of Silicon Valley? What's his story? Olivia: That's the fascinating part. He wasn't some academic in an ivory tower. McKeown was a serial entrepreneur who launched over 40 businesses before he was 35. He built and sold companies, consulted for giants like Microsoft and the US Army, and distilled all that brutal, real-world experience into this roadmap. This book is the result of seeing it all go right, and more importantly, go wrong. Jackson: Okay, so he's got the scars to prove it. I'm listening. If everyone's getting 'scaling' wrong, what's the right way to think about it?

Olivia: Well, McKeown starts by clearing the deck. He says the first step is to understand that not all growth is scaling. He uses this great analogy of a skateboarder. You see someone zoom past you on a skateboard. You can think, "There goes someone on a skateboard." But a moment later, you hear a crash and a muffled swear word. Jackson: Ah, I see. There's a huge difference between being on the skateboard and actually knowing how to ride it. Olivia: Precisely. Just because a company is growing fast doesn't mean it has the ability to scale. Scaling, according to McKeown, is the ability over time to sustainably grow your organization to the size its industry will allow. The key words there are 'ability' and 'sustainably'. Jackson: That word 'sustainably' feels important. I feel like a lot of startup growth we hear about is anything but sustainable. It's burning through cash to get users, hoping for a buyout. Olivia: You've just hit on the first major distinction he makes. He separates growth into three buckets: Linear Growth, Flipping, and true Scaling. Linear growth is what most healthy businesses do. They grow, they're profitable, but their primary focus isn't just to grab market share at all costs. He tells the story of a luthier, a guitar maker named Jim. Jackson: A guitar maker? I like this already. It’s not another software company. Olivia: Exactly. Jim made these incredible, world-class guitars. He got so famous that his business started to grow exponentially. He was on the verge of becoming a major guitar manufacturer. But he had a moment of crisis. He realized his passion wasn't managing a huge factory and supply chains; his passion was crafting perfect guitars. Jackson: So what did he do? Olivia: He sold the rights to his business to a large manufacturer and went back to his workshop, happily making just a few masterpieces a year. He chose his passion and a healthy, linear growth model over the headache of scaling. He wasn't a failure; he made a conscious choice. Jackson: That’s a powerful idea. That scaling isn't the only definition of success. But what about that other bucket, 'flipping'? That sounds more like the stories we hear about today. Olivia: It is. Flipping is maximizing market share as fast as possible without the constraint of sustainability. The goal isn't to build a lasting company; it's to get acquired. He gives two brilliant, modern examples. First, a guy named Vijay who created an add-on for a popular CRM software. Jackson: Okay, a classic tech story. Olivia: Vijay's goal was explicit. He told the author, "I want to get so big so quickly that [the big CRM company] just has to acquire me." He gave away free copies, offered huge discounts—he bought market share at a loss. And it worked. The big company acquired him. He successfully flipped it. Jackson: And the second example? Olivia: RXBAR, the protein bar company. The co-founder, Peter Rahal, used to walk into coffee shops and gyms and just give his bars away for free. He said, "We didn't care. We just wanted people to start trying them." They created a massive, rapid user base. Less than two years later, Kellogg's bought them for $600 million. Jackson: Hold on. That sounds like amazing success. Why is that not scaling? They got a huge payout! Olivia: Here's the crucial distinction McKeown makes. It's about intent and structure. Flipping is a valid strategy, but it's a short-term play. You're not building the systems for long-term, independent, sustainable growth. You're building an attractive asset for someone else to buy and then plug into their scaling machine. True scaling is building your own machine that can last. Jackson: Okay, that clarifies it. It's the difference between building a house to live in for 50 years versus building one to sell in 6 months. The foundation, the plumbing, the very structure is different. Olivia: Perfect analogy. And deciding which one you're building is the first, most critical choice a leader has to make. Because if you decide you want to build that 50-year house—if you truly want to scale—the biggest obstacle is almost always the person holding the blueprints: the founder themselves.

Jackson: That makes so much sense. The decision to truly scale sounds like a massive commitment. It feels like the biggest hurdle isn't the market, but the founder's own psychology. Olivia: You've nailed the "Founder's Paradox." McKeown argues that the very traits that make an entrepreneur successful in the beginning become their biggest liabilities when it's time to scale. The primary culprit? What he calls the "Golden Gut." Jackson: The Golden Gut. That intuitive, seat-of-the-pants decision-making that gets the company off the ground. Olivia: Exactly. In the early days, the founder is close to everything—the customers, the product, the team. Their gut instinct is fed by real-time, high-quality information. An anecdote from one customer is probably representative of many. But as the company grows, a gap emerges between anecdote and data. One angry customer might be a statistical outlier, not a trend. The founder's gut is now operating on faulty, incomplete information. Jackson: It's like a superpower that works great in your small hometown, but once you move to the big city, relying on it just gets you into trouble. You can't possibly know every street corner anymore. Olivia: That's it. And this is where the founder's ego gets bruised. They've built their identity on being the one with all the answers. Admitting their gut is no longer golden feels like a personal failure. This leads to what McKeown calls the "curse of knowledge." The founder thinks, "No one can do this as well as I can." Jackson: Oh, I've been there. You try to delegate something, but you're so deep in it that you can't even explain it properly. It's like trying to teach a fish to ride a bicycle. You just end up grabbing the handlebars yourself. Olivia: And that's a recipe for burnout and a bottleneck that chokes the whole company. McKeown's advice here is beautiful. He uses the analogy: "When is the best time to plant a tree? Twenty years ago. When is the second-best time? Today." You have to start training someone else today, even if it's painful and slow, because that's the only way the organization can grow beyond you. Jackson: But it’s more than just delegation, right? It feels deeper, more destructive. Olivia: It is. This is where McKeown introduces his most powerful concept: the two faces of every visionary leader. There's the Visionary, who inspires and creates. But there's also a destructive alter ego he calls the Arsonist. Jackson: The Arsonist! I know that guy! That's the feeling of 'this is crushing my soul, I need to blow something up to feel creative again.' It's a terrifyingly accurate description of that self-destructive impulse. Olivia: He even scripts the internal monologue. First, the founder faces a mundane but necessary scaling task, like rewriting job descriptions. They think, "OK, this is boring, but I'm an adult, I can do it." Then, after a while, it's, "Jeepers, this is crushing my soul." And finally, the Arsonist takes over with the rationalization: "This isn't right! We're successful because I'm a visionary, not a bureaucrat! This whole system is wrong!" And they light a match. Jackson: And they dismantle the very processes that were meant to save them, all in the name of "getting back to their roots" or "being authentic." It’s tragic. Olivia: It is. They sabotage their own success because the discipline required for scaling feels like a cage. The freedom they started the business for feels like it's disappearing. Jackson: So how do you fight the Arsonist? How do you build the cage so it doesn't feel like a prison? Olivia: You build something that feels completely counterintuitive to a visionary founder: a machine. A boring, predictable, sleep-inducing machine for making decisions.

Jackson: A machine. You're kidding me. The secret to massive, explosive growth sounds like a government form. What's the secret sauce, some kind of killer app? Olivia: The secret sauce, McKeown reveals, is an acronym so boring it's almost funny. It's HQTBDM. Jackson: H... Q... T... B... D... M? Come on. That can't be real. That sounds like a compliance code for a tax document. Olivia: (Laughs) High-Quality Team-Based Decision-Making. I told you it was sleep-inducing! But he argues this is the absolute, non-negotiable key that unlocks scaling. To understand why, you have to understand the chaos of early-stage companies. He calls it "flockball." Jackson: Flockball? Like little kids playing soccer, where the entire team just swarms the ball in one big, chaotic clump? Olivia: That's the exact image. In a startup, a crazy order comes in—he tells a story about having to ship 500 cases of Elderberry Spring Water to Beijing by Thursday. It's an impossible task. So what do they do? Flockball. Everyone drops what they're doing and swarms the problem. They pull it off through heroic effort and sheer willpower. It creates this legend, this "golden age" myth within the company. Jackson: But you can't run a hundred-million-dollar company on flockball and heroics. People would burn out in a week. Olivia: You can't. Eventually, you hit what he calls "Whitewater." The complexity becomes too great, and the flockball approach starts failing. Orders get missed. Customers get angry. The heroes are exhausted. This is the point where you either shrink back to a simpler size or you build the machine. Jackson: And that machine is HQTBDM. So what is it, practically? Is it just more meetings? Olivia: It's about building a structure for smart, repeatable decisions. And the foundation of that machine is something most people ignore: the organizational chart. Jackson: The org chart? That dusty diagram that's always out of date? Olivia: But it has to be a living org chart. McKeown says you have to fix it ruthlessly. No ambiguous reporting lines. No dysfunctional structures. And most importantly, you have to define the roles based on "hats," not "heads." Jackson: Hats not heads. What does that mean? Olivia: It means you define a job based on what the business needs that role to do (the hat), not based on what the current person in that role happens to be doing (the head). This detaches the role from the person, allowing you to design the perfect structure for the future, even if it means admitting the current people aren't the right fit for the new hats. Jackson: Wow, that's a tough conversation to have. "Hey Bob, we love you, but we're redesigning your hat, and it doesn't fit your head anymore." Olivia: It's brutal, but it's necessary. The final piece is what he calls Lateral Management. In a traditional company, a manager's job is vertical—they manage their team. In a scaling company, a manager's primary job becomes lateral—making decisions that are best for the entire enterprise, not just their own department. Jackson: Ah, so this 'machine' is what protects the company from the founder's 'Arsonist' side. It replaces the Golden Gut with a collective, structured brain. The boring org chart and the clear roles become the guardrails that keep the visionary on track. Olivia: Exactly. The machine isn't sexy. It's not a magical algorithm or a disruptive technology. It's mechanics. It's process. It's the mundane, disciplined work that allows for extraordinary, sustainable growth.

Jackson: So when you pull it all together, the journey he lays out is pretty profound. It’s not really a business book in the traditional sense. It feels more like a psychological roadmap for a leader. Olivia: I think that's the deepest insight. Scaling isn't an external action you take; it's an internal transformation you undergo, which is then reflected in the organization's structure. You have to evolve from being the company's hero to being its architect. Jackson: The hero relies on their gut, on instinct, on personal charisma. The architect relies on blueprints, on systems, on a team that can build without them standing over their shoulder. What got you here won't get you there. Olivia: That's the phrase he comes back to. The skills of the startup founder—the risk-taking, the improvisation, the heroic flockball—become toxic at scale. The journey is about letting go of that identity to embrace a new one. It's about trading the thrill of the heroic sprint for the discipline of building an engine that can run a marathon. Jackson: It makes you wonder, for any leader listening, which mode are you in right now? Are you the hero, or are you building the machine? And are you showing up to work as the Visionary... or the Arsonist? Olivia: That's the question to sit with. And it's a constant battle. We'd actually love to hear from our listeners on this. Have you had an "Arsonist" moment where you almost blew up a good system out of frustration? Or a time your "Golden Gut" led you completely astray? Share your stories with us on our social channels. Jackson: It's a vulnerable question, but I think every leader has a story like that. This was fantastic, Olivia. A really clarifying look at a word we all use but rarely understand. Olivia: It’s a hidden gem of a book. Practical, sharp, and deeply human. Jackson: This is Aibrary, signing off.