TLDR;

Still asking 'why' like a broken record and getting nowhere? Shocking. This piece hands you the keys to unlock what actually drives your prospects and your industry – the juicy, unspoken stuff no one admits to. Stop swimming in the shallow end of surface-level BS. We're giving you 3 concrete ways to start having "Deep Dialogues" that expose the invisible rules. So you can stop guessing, start outsmarting, and maybe, just maybe, build something that doesn't suck (and actually sells). You're welcome.

In this issue, we'll tackle:

• Why your current 'why-asking' strategy is probably just making people want to avoid you at office parties.

• The surprisingly potent art of "Deep Dialogue" – and no, it's not a new mindfulness fad.

• Three actionable (and slightly sneaky) ways to start uncovering these invisible rules TODAY.

• Hilarious (and painfully true) examples of "invisible rules" in market research and tech media.

• My own glorious, sometimes cringeworthy, journey of making VCs understand that "anthropology" isn't just for academics with elbow patches.

Let's dive right in.

We’ve all been there. Stuck in meetings, nodding along to the corporate jargon buffet: "We prioritize X for maximum efficiency!" "Our media strategy is laser-focused on Y because it’s ‘newsworthy’!" "This is the optimal pathway to success because, well, it’s ‘proven’!" For years, I played this game, trying to pretzel-twist my entrepreneurial ambitions into these pre-approved narratives. But let's be honest, something always felt… off. Like wearing a suit two sizes too small. The "official" reasons rarely painted the full picture; mostly, they were just good PR.

It wasn't until I developed a rather peculiar habit – not just incessantly asking "why" like a caffeinated toddler, but diving headfirst into what I call Deep Dialogue – that the real, juicy, unspoken logic started to surface. These are the invisible rules, the hidden puppet strings that actually dictate how entire industries operate. This wasn't about staging aggressive interrogations or becoming "that guy" who derails every conversation. Oh no. This was about cultivating a genuine, almost anthropological curiosity, explored through actual, you know, conversations. And this little habit? It didn't just toughen me up; it fundamentally sculpted how I built and eventually sold my company, MotivBase.

Many of us are conditioned to be skeptics, to question everything. Noble, right? Except it often just devolves into a surface-level squabble or, worse, makes you the office pariah. The real alchemy happens when you graduate from simple questioning to a more profound conversational inquiry. It’s about dissecting the stated reasons with such Sherlock Holmes-level intensity that the unspoken drivers – those fundamental human or systemic gremlins – just can't help but reveal themselves.

Take the glorious world of market research. It’s practically a religion for businesses to worship at the altar of neat statistics, often sacrificing nuanced human stories in their quest for customer understanding. The stated reason? ‘Oh, stats are quantifiable, scalable, and look fabulous in a pie chart!’ (They never say the pie chart part, but we know). But, if you engage in some deep dialogue with the market researchers and the executives they nervously report to, a far more entertaining truth emerges. You swiftly bypass the flimsy surface justification and realize this obsession with numbers is often fueled by the crushing pressure for defensible certainty in those high-stakes, career-defining presentations. It’s about the ridiculously limited time decision-makers possess and an organizational culture where easily digestible numbers are fetishized as analytical rigor. The unspoken driver isn’t purely about uncovering the best data; it's a tangled mess of professional self-preservation, navigating treacherous internal power dynamics, and the desperate need to communicate in a way that feels efficient and, crucially, ‘safe’ to the overlords. So, less about insight, more about not getting fired. Got it.

Or consider the tech media’s breathless obsession with who just raised a gazillion dollars, often completely overshadowing businesses that are, you know, steadily and profitably growing. A bit of deep dialogue there reveals it’s not just about "news." It's about the media's symbiotic, slightly dysfunctional relationship with an ecosystem that desperately craves unicorn narratives. It's about their pathological need to "call it first" for a fleeting hit of status, and a definition of "success" so heavily skewed by venture capital’s boom-or-bust rhythms it’s a wonder anyone still takes it seriously.

Okay, Smarty Pants, So How Do I Actually Do This "Deep Dialogue" Thing?

Glad you asked. It’s not about having a PhD in social anthropology (though it clearly doesn’t hurt, ahem). It’s about being a bit more cunning in your curiosity. Here are three ways to start prying open the clam of industry silence:

1. Ditch "Why," Embrace "What's the Real Job Here?": Stop with the anemic "Why are you doing X?" It’s tired. Instead, try the more potent, "Help me understand the expectations on you/your team that make X the logical (or perhaps, only) choice right now?" People spill way more beans when they're talking about the cages they’re in and the pressures they face, not just their flimsy post-rationalizations. Think less interrogation, more "tell me about this straightjacket, and who’s holding the buckle?"

2. The "Espionage for Entrepreneurs" (aka The Junior Circuit): Forget trying to corner the VP in the elevator with your brilliant insights. Your real intelligence goldmine? Their direct reports, the people in the trenches. These folks are often refreshingly candid (off the record, over a casual coffee you’re buying, of course) about the actual anxieties, unspoken mandates, and political landmines their bosses are really navigating. They see the stated vs. the unstated play out daily. Listen more than you talk. It's amazing what you'll unearth when you’re not talking to the person whose primary job is to spin you.

3. Play "Spot the Stated vs. Unspoken": Channel your inner detective. Listen intently to the official, polished, "stated" reasons for why things are the way they are. Nod politely. Then, with a charmingly innocent (but secretly razor-sharp) curiosity, start asking questions that poke at the context and unspoken pressures. "That's a fascinating focus on scalability. What's the internal weather like that makes this such a critical factor right now?" or "I hear you on prioritizing X. What are the invisible goalposts you're aiming for that we might not see from the outside looking in?" The Grand Canyon-sized gap between the official story and the contextual reality is precisely where the juicy invisible rules reside.

My own entrepreneurial saga is littered with moments where this habit of deep dialogue was the difference between "game over" and "level up." When I was wrestling MotivBase, an AI-powered cultural intelligence platform, into existence, the venture capital wizards repeatedly told me it wouldn’t scale. Their stated reasons were a delightful cocktail of: "It’s too niche, darling," "Anthropology in tech? How quaint!" or the ever-popular, "The market simply isn't ready for this level of genius."

If I’d just meekly accepted those pronouncements, or worse, tried to argue them head-on with PowerPoint slides, I’d still be selling artisanal kombucha at a farmer's market. Instead, I plunged into (often excruciatingly painful) dialogues. I’d innocently ask, "Help a humble entrepreneur understand, what does ‘scalable’ look like from your esteemed perspective?" or "What mystical markers do you typically observe in a business you believe is destined for world domination (and a massive ROI for you)?"

Slowly, through these verbal chess matches, the unspoken drivers crawled out of the woodwork. It wasn't just about my quirky business model; it was about their models. It was about their addiction to pattern recognition based on their past wins (and spectacular flameouts), the immense pressure they faced from their LPs to unearth billion-dollar lottery tickets, and an industry fundamentally built on a very specific, often very narrow, archetype of "tech founder" and "tech solution." The invisible rule wasn't really "your idea is objectively terrible," but more like, "your idea doesn’t fit the pre-approved template that minimizes our perceived risk and maximizes our very specific, very large, kind of reward." How charmingly self-centered.

Understanding this unspoken, often unacknowledged, logic didn't magically make them shower me with cash. But it did something infinitely more valuable: it gifted me clarity and a rhino-hide level of resilience. It helped me internalize that their "no" wasn't always a damning indictment of my venture's potential, but frequently a reflection of the bizarre, invisible rules governing their peculiar world. This epiphany allowed me to seek out alternative paths, to bootstrap like a maniac, to build credibility through actual evidence and ecstatic client successes, rather than solely chasing an external validation system that clearly wasn't designed for a business as wonderfully weird as mine. It allowed us to laser-focus on what truly mattered: solving actual problems for clients who did see the profound value, eventually leading to a rather delightful and successful exit.

This habit of deep dialogue isn't about winning arguments or being the smartest person in the room (though that’s a fun side effect). It's about understanding the goddamn terrain. It’s about spotting the hidden currents, the rip tides of assumption that shape what people believe is possible, valuable, or even credible. It's a foundational skill for navigating the often-unspoken, frequently infuriating, invisible rules I dissect with anthropological glee in my upcoming book, “Invisible Rules: How to Outsmart the Entrepreneurial Game.” (Yes, that was another shameless plug. You’re welcome.)

It’s a practice that empowers you to move with a peculiar blend of empathy and cunning, to build strategies grounded in a deeper, often hilariously absurd, reality, and ultimately, to hack your own path, even when the well-trodden ones look suspiciously like they lead off a cliff.

A fascinating chat with FoodHero CEO, Jonathan Defoy

Ever been so head-over-heels for your own brilliant idea that you accidentally wore blinkers to the market's actual needs? In my next newsletter, I'm dissecting a refreshingly honest chat with Jonathan Defoy, founder of FoodHero, who candidly shared how his early entrepreneurial "love affairs" with his ideas were a fast track to failure—one even costing him a million dollars. He'll reveal the critical shift in mindset, moving from passionate attachment to data-driven validation and "smoke and mirror" legitimacy building, that paved the way for FoodHero's impressive ascent. It's a masterclass in entrepreneurial tough love and a crucial insight into an invisible rule many of us stumble over: sometimes, the first person you need to get critical feedback from is yourself, especially when you think you're holding a "Steve Jobs" vision.

PS: I’m distilling every one of these hard‑won lessons into a new book that is salted for launch in Spring 2026!

Want draft chapters, behind‑the‑scenes notes, and launch‑day perks before anyone else? Join the early reader list here.