We all hear the “reasons why.” Industries run on them. “We prioritize X because it’s efficient.” “Our media covers Y because it’s newsworthy.” “This is the path to success because it’s proven.” For years, I nodded along, trying to fit my own entrepreneurial journey into these accepted narratives. But something always felt… off. The stated reasons rarely told the whole story. It wasn’t until I cultivated a different kind of habit — not just asking “why,” but engaging in Deep Dialogue — that I began to understand the unspoken logic, the invisible rules, that truly govern how industries operate. This wasn’t about aggressive questioning; it was about a genuine, almost anthropological curiosity explored through conversation. And it’s a habit that not only built my resilience but fundamentally shaped how I built my business, MotivBase. Many of us are taught to be skeptical, to question. But often, that just leads to a surface-level debate or makes us “that annoying person.” The real magic happens when you move beyond simple interrogation and into a deeper conversational inquiry. It’s about discussing the stated reasons to such an extent that the unspoken drivers, the basic human or systemic building blocks, naturally begin to surface. Consider the world of market research. It’s common for businesses to prioritize neat statistics over nuanced human stories when trying to understand their customers. The stated reason? ‘Stats are quantifiable and scalable.’ But if you engage in deep dialogue with market researchers and the executives they report to, you start to uncover a different layer of truth. You move past the surface justification to understand that this preference is often about the intense pressure for defensible certainty in high-stakes presentations. It’s about the severely limited time decision-makers have, and an organizational culture where easily digestible numbers are equated with analytical rigor. The unspoken driver isn’t purely about the best data; it’s deeply intertwined with professional safety, navigating internal power structures, and the need to communicate in a way that feels efficient and ‘safe’ to those in charge. Or consider tech media’s fascination with who raised how much money, often overshadowing businesses achieving steady, profitable growth. A deep dialogue reveals it’s not just about “news.” It’s about the media’s role in an ecosystem that craves unicorn narratives, their need to “call it first” for status, and a definition of success heavily influenced by venture capital’s rhythms. My own journey is littered with moments where this habit was crucial. When I was building MotivBase, an AI-powered cultural intelligence platform, the venture capital world repeatedly told me it wouldn’t scale. Their stated reasons were often variations of: “It’s too niche,” “Anthropology isn’t tech,” or “The market isn’t ready for this.” If I had just accepted those statements, or argued against them directly, I wouldn’t have gotten far. Instead, I engaged in (sometimes painful) dialogues. I’d ask, “Help me understand what ‘scalable’ looks like from your perspective?” or “What are the markers you typically see in a business you believe will achieve massive growth?” Through these conversations, the unspoken drivers began to emerge. It wasn’t just about my business model; it was about their models. It was about pattern recognition based on their past successes (and failures), the pressure they faced from their LPs to find billion-dollar outcomes, and an industry built on a certain archetype of “tech founder” and “tech solution.” The invisible rule wasn’t “your idea is bad,” but “your idea doesn’t fit the template that minimizes our risk and maximizes our specific kind of reward.” Understanding this unspoken logic didn’t necessarily make them invest. But it did something far more valuable: it gave me clarity and resilience. It helped me understand that their “no” wasn’t always a reflection of my venture’s potential, but often a reflection of the invisible rules governing their world. This understanding allowed me to seek alternative paths, to bootstrap, to build credibility through evidence and client success, rather than solely through external validation that wasn’t designed for a business like mine. It allowed us to focus on what truly mattered: solving real problems for clients who did see the value, eventually leading to a successful exit. This habit of deep dialogue isn’t about winning an argument. It’s about understanding the terrain. It’s about seeing the hidden currents that shape what people believe is possible, valuable, or credible. It’s a cornerstone of navigating the often-unspoken, invisible rules I explore in my upcoming book, “Invisible Rules: How to Outsmart the Entrepreneurial Game.” It’s a practice that allows you to move with empathy, to build strategies grounded in a deeper reality, and ultimately, to carve your own path, even when the well-trodden ones don’t seem to lead where you want to go. Want early access to my book? Join the Inner Circle Join the Inner Circle

The Startup Playbook Is a Lie. Ask Better Questions.

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