Welcome to Transcedentrepreneurship! If you’re keen on Tech, Product and Business like me, you’re in the right place! No fluff, just my philosophical blend with a pinch of quirky allegories!
From hunting in the savannah to managing remote teams across time zones, one force has driven our rise: communication.
But not all communication is equal. Animals can warn each other of danger or signal there’s a source of nutrition nearby, like the wiggle dance bees use to signal the location of nectar. Humans, however, do something different. We use symbols—words, gestures, metaphors—to share abstract ideas, imagined futures, and collective myths. It's not just language that made us powerful. It's the ability to share imagined realities—money, laws, religion— that lets us cooperate as empires, not just tribes.
Still, not everyone communicates with equal power. Some struggle to express themselves, while others inspire action with a few well-chosen words. Environment plays a role, our upbringing, our culture, our media, but, in the end, communication is a skill. And like any skill, it can be practised, refined, and mastered.
Before we move to action, we need understanding. And that begins with better questions. Communication isn't just output, it's how we gather signal in a noisy, complex world. The right question reveals context, exposes assumptions, and points to leverage. In environments of uncertainty, like entrepreneurship, questions are your most underrated tool.
Sun Tzu, the famous Chinese military general, strategist, philosopher, and the author of The Art of War, created the military doctrine of asymmetrical warfare. According to it, an attack on the enemy should begin only after the enemy has no opportunity to either defend or counterattack.
I see entrepreneurship as asymmetrical warfare, where you should only pursue an idea if the ROI is non-linear. Additionally, not all battles are yours to fight.
Most founders attack too early, without intel, and get crushed. They move fast and break things. Notwithstanding this popular narrative among thought leaders on LinkedIn, the key is to move smart and build leverage, then act decisively. You can’t just charge in. You need to study the terrain, intercept communications and find the weak points. Your questions are your surveillance drones. They are how you map emotional terrain, spot buying triggers, and understand what people will actually pay for. Asymmetric entrepreneurs ask questions so sharp, the winning move reveals itself in the answer.
You’re building a productivity app. Users say, “I wish I could tag tasks!” So you build tagging. But usage doesn’t move. Why?
Wrong question: “Do you want tags?”
Better question: “When you lose track of tasks, what happens?”
This gets you the real problem, task overload, not poor tagging. Maybe the answer is not tags, but smart filters or decluttering defaults.
You’re launching a SaaS tool. You ask, “Would you pay $20/month?” Some say yes. You launch. Crickets.
Wrong question: “Would you pay for this?”
Better question: “What do you already pay for that this would replace?”
This uncovers not just pricing elasticity but also positioning. If your tool isn’t replacing anything yet, it’s not solving an urgent problem.
You’re targeting freelancers because they’re “everywhere.” You assume: large audience = great opportunity. But sales lag.
Wrong question: “Is this a big market?”
Better question: “Who is most desperate to solve this right now?”
Size is a vanity metric. Desperation is a buying signal. Maybe the optimal target is Ops leads drowning in spreadsheets, not carefree freelancers.
Most founders ask for validation. Asymmetric founders interrogate reality. Entrepreneurship isn't about certainty, it's about timing, leverage, and clarity. You don’t win by charging in. You win by knowing something they don’t—and that starts with a question.
In asymmetric entrepreneurship, your mind is the katana. One well-placed question cuts deeper than months of code.
Until next time, build nothing... until the question makes it obvious.
DB