In my role as Director at Engenesis Ventures, I’ve had the privilege of leading and contributing to our collective work with hundreds of founders and over 2,400 companies across industries. One thing we’ve consistently seen is how easy it is to feel stuck—especially in the early stages of stepping into something new. Whether it’s a business, a new phase of growth, a career shift, or even a creative pursuit—this is often where the real friction begins.

You’re ambitious. You care. You’re willing to work hard. But then, somewhere along the way, you find yourself tangled in a web of unexpected challenges and mental puzzles you didn’t anticipate.

One founder we worked with recently wanted to launch YouTube videos to grow his business. His questions weren’t unusual: What should my studio look like? What clothes should I wear? What should I speak about?

But it wasn’t the questions that were the problem. It was the creeping sense of paralysis—because deep down, he felt like it was supposed to be easy. Everyone else made it look effortless. So why did it feel uniquely difficult for him?

That’s where the real pain begins—not from lack of drive, but from the quiet belief that something must be wrong with me.

Where This Shows Up: Painful and Personal Examples

This isn’t a one-off scenario. This pattern shows up in many places:

• “It seems so easy for others to market themselves. Why is it so hard for me?”
• “Other products go viral. I can barely convince one person to buy mine.”
• “If only a generous investor would spot my talent...”
• “Why is my team so dysfunctional while others seem to run so smoothly?”

These aren’t surface-level frustrations. They create emotional weight—doubt, burnout, shame. You’re working hard, but the results don’t match the effort. And often, it comes down to one powerful distinction.

The Outsider Illusion vs. Insider Reality

The terms Outsider and Insider aren’t fixed categories or personality types—they’re not about who you are, but how you’re currently choosing to show up in your entrepreneurial journey. Being an outsider doesn’t mean you’re less capable—it simply means you may still be engaging with the domain from the surface. Becoming an insider is not about being “let in”—it’s a shift in posture, from observing to immersing, from projecting to building. It’s a choice available to anyone willing to face the real game.

The outsider is someone who engages with a domain from a distance—observing, theorising, or admiring what others are doing, often without real immersion in the complexity behind it. Their understanding is based on visible outcomes, not the invisible systems or nuances beneath them. Outsiders rely heavily on what’s shown—websites, media articles, social media posts, product launches—mistaking the visible for the whole. They often believe success is linear, simple, or dependent on being discovered by the right person. Outsider thinking isn’t wrong—it’s superficial and incomplete.

The insider, on the other hand, has stepped behind the curtain. They are actively engaged with the actual mechanics of how things work. Insiders know the backstage mess: the trade-offs, failures, nuance, and invisible labour. Their metacontent—the underlying cognitive structure that shapes how we interpret, make sense of, and respond to reality – including our initial observations, perspectives, perceptions, paradigms, and more— is shaped not by appearance, but by lived experience, informed by repeated cycles of feedback, mistake, and correction. They’ve moved beyond mimicking what looks good and into constructing what functions. They don’t romanticise the work—they inhabit it.

Most inexperienced entrepreneurs start new ventures as outsiders. From that vantage point, things look deceptively simple.

Netflix? Just appeared and crushed Blockbuster.
Facebook? Dorm room to billion users in no time.

But here’s what you don’t see:

• Netflix started in 1997 as a DVD-by-mail company.
• Facebook was university-only for over two years and took eight years to reach a billion users.

From the outside, it looks like a magic trick. But any stagehand will tell you: there’s a trapdoor under the magician’s table.

What’s Really Happening: Looking to Our Metacontent

What separates outsiders from insiders isn’t just time—it’s Metacontent: the underlying mental framework that shapes how you see and interpret everything.

The terms Outsider and Insider aren’t arbitrary—they stem from how we make sense of reality through what Ashkan Tashvir calls Metacontent, and more specifically through the Nested Theory of Sense-Making. According to this model, how we interpret any situation is deeply influenced by the Domain we are engaging with and the Paradigm or framework through which we approach it.

In entrepreneurship, the Domain is not just about having an idea or building a product—it has its own principles, dynamics, and nuances. For instance, genuine entrepreneurial practice requires engaging with a real, observable need that exists within a group of people—one that must be validated and meaningfully addressed. While there are multiple paradigms or approaches to entrepreneurship, there are still deep-seated principles, feedback loops, and lived realities that govern this Domain.

If someone isn’t willing to immerse themselves in the nature of this Domain—or worse, insists on operating based on surface-level impressions or ideological fantasies—they remain on the outside. They haven’t entered the Domain with sufficient depth, nor are they translating accurate sense-making into aligned decisions, behaviours, and action. That’s why we call them Outsiders. In contrast, Insiders engage with the Domain from within. They learn its language, understand its structures, test their assumptions against reality, and adapt accordingly.

For example, imagine two founders both building an app. The outsider believes the key to success lies in having the most features and a beautiful UI—they focus on polish, brand identity, and raising hype pre-launch. Their metacontent is shaped by what they’ve seen work after others have succeeded.

Meanwhile, the insider knows that distribution, user behaviour, onboarding, monetisation, and feedback loops matter far more early on. They launch faster, talk to users sooner, and iterate constantly—even if it’s messy. The difference isn’t just experience—it’s how they see the game itself.

If your metacontent is built on observing success from the outside—the launch videos, the branding, the hype—you’re absorbing a partial and distorted picture.

But ask any founder who’s been in the trenches:

“A great product is just the beginning. That’s not even 20% of it.”

The rest?

• Understanding psychology Building trust Failing gracefully Making hard trade-offs Persisting without applause

The Fantasy That Kills Startups

Here’s where the real danger lies. You can spend years, even millions, building a perfect product—and still have no customers. We’ve seen it. One founder we met had built for 14 years, raised millions, and never earned a cent.

It’s a prime example of active insistence—relentlessly building and optimising something that should never have existed in the first place.

That’s not vision. That’s delusion.

The Being Framework calls this an unhealthy relationship with persistence — doubling down on delusion instead of adjusting to reality.

And the emotional toll?

• Burnout 
• Shame 
• Isolation 
• The quiet belief: Maybe I’m just not cut out for this.

When Outsiders Critique You

To make things worse, outsiders often chime in:

• “Why aren’t you rich yet?”
• “You should try this article I read on scaling.”

Well-meaning, but misaligned. They don’t see the trapdoors, sleight of hand, or sweat. Insiders do. They’ll nod. They’ll share their scars. They get it.

But here’s the deeper issue: some people stay outsiders forever. They criticise. They analyse. But they never build. Because building is vulnerable. It exposes you to failure and truth.

And staying on the outside feels safe. But it costs you real growth, impact, and fulfilment.

Being an Insider Is a Choice

Being an insider isn’t about innate talent, charisma, or having exclusive access. It’s a choice. A posture. A turning point.

It’s the decision to drop fantasy and face the real contours of the game you’re playing. To stop looking for shortcuts or applause, and start building metacontent rooted in reality, not replication.

This shift begins with honest reflection. Start by asking:

• What assumptions am I still holding? 
• What invisible work is really happening?
• What do I need to unlearn?

Becoming an insider means choosing depth over decoration. It means stepping into ambiguity and feedback instead of waiting for permission or validation. It means staying in the room when it’s uncomfortable—and letting the work refine you. It may require rounds of transformation of your existing sense-making framework (metacontent).

You’ll know the shift is happening when you stop trying to appear like a founder… and start being one. When your questions get sharper. When your sense-making becomes more precise. When you stop chasing illusions and start crafting real strategy, one hard-earned layer at a time.

Because while the path of the insider isn’t easy—it’s the one that actually leads somewhere.

For Those Ready to See the Real Game

If you're ready to stop guessing and start seeing clearly, there is support.

At Engenesis Ventures, we didn’t want to just share anecdotes—we wanted to provide structure. So we developed the Genesis Framework through our interviews and work with over 2,400 companies—mapping expert-level mental models so you don’t have to guess.

Today, that framework is helping entrepreneurs around the world build better, faster, and with more clarity. Whether through tailored support or self-directed learning, it’s here to help you make the leap from outsider to insider.

Final Thought

At some point in every founder’s journey, the illusion begins to crack—and what remains is clarity:

This was never meant to be easy. It was meant to be real.

Becoming an insider isn’t a single leap. It’s a series of reckonings. You begin trading applause for patience, fantasy for grounded insight, and surface-level advice for frameworks rooted in lived reality.

And in that process, you discover something important:

You’re not the only one making that shift.

That’s why we built the Engenesis Platform—not just to teach frameworks, but to foster a space where founders can walk this path together. Because becoming an insider doesn’t mean going it alone. It means choosing to see with sharper eyes, to build with deeper conviction, and to grow in the company of those who get it.