“The problem is that the game was rigged before I was born…” 🤔🫣😮‍💨🫥👶🏻🐣🧑🏻‍🍼

Two Years In: The Unseen Cost of the Bootstrap Dream

They talk about the hustle, the grind, the sleepless nights fueled by passion and cheap coffee. They tell you to bootstrap, to build lean, to prove your concept without outside money. And you listen, because it sounds like the purest form of entrepreneurship – building something from nothing, driven solely by belief in your idea.

For two years, that’s been my reality. Two years of pouring every ounce of energy, every spare moment, every last bit of mental and emotional bandwidth into bringing a vision to life. Two years of “no money down,” which really means “all of your money down,” or more accurately, “no money coming in, ever.”

The pain isn’t just financial, though that’s a constant, gnawing ache. It’s the pain of watching friends and peers hit milestones, buy homes, take vacations, while you’re calculating if you can afford the cheapest hosting plan for another month. It’s the pain of explaining, again, what you’re doing, only to see a flicker of polite scepticism in their eyes when they hear “still working on it.” And that’s among those that didn’t dropout of high school with the lowest grade – these are the people in your home town. They mean well, but understand almost nothing, and know even less. They fill their lives with the lowest common denominator of dreary scripted idiomatic/idiocratic reality TV entertainment, booze, and nicotine vapes. They defend the indefensible actions of billionaires, not realising that as human beings, they are equals, as we all are mortal.

The time commitment is absolute. Weekends cease to exist as leisure time; they become development sprints, marketing deep dives, or desperate attempts to network. Evenings aren’t for unwinding; they’re for catching up on the mountain of tasks you couldn’t squeeze into the day job (if you’re lucky enough to still have one). Every hour feels like it must be productive, leading to a relentless, self-imposed pressure cooker.

And the effort… oh, the effort. It’s not just coding or designing or selling. It’s the administrative slog, the legal hoops, the endless customer support queries (even when you only have a handful of users/clients/projects). It’s the mental gymnastics required to wear ten+ different hats simultaneously – CEO, CTO, Lead Developer, Accountant, HR, Porter, Engineer, Science Advocate, Physicist, Head of Marketing, Customer Service Rep, and janitor. You learn skills you never knew you needed, push boundaries you thought were insurmountable, and discover reserves of resilience you didn’t know you possessed.

But the struggle is perhaps the most insidious part. It’s the constant battle against doubt, both internal and external. It’s pitching your heart out, presenting a meticulously researched business case, showing clear market potential and a viable path to profitability, only to be met with polite rejections, radio silence (ghosting), or the dreaded “come back when you have more traction [etc].”

You refine the pitch, tweak the model, gather more data, show early signs of adoption, however small. You believe, fundamentally, that this should work. The logic is sound, the market need (nay, the human species need) is real, the solution is elegant, profound. Yet, despite the undeniable effort and the seemingly solid foundation, the appreciable success remains elusive. The traction isn’t enough, the growth isn’t exponential, the investors aren’t biting.

Two years. From late ~2023. It feels like a lifetime and a blink of an eye all at once. You’ve built something real, something functional, something you’re genuinely proud of. But the world hasn’t embraced it in the way you envisioned. The dream isn’t dead, not yet, but it’s certainly battered and bruised.

This isn’t a story of failure, not definitively. It’s a story of the brutal, unvarnished reality of the bootstrap journey when the stars don’t align perfectly. It’s a testament to the sheer willpower required, and a sober reminder that sometimes, even with a sound plan and relentless effort, the path to success is longer, harder, and more uncertain than any blog post or startup guru will ever fully prepare you for.

And you’re left standing, two years in [turn the page], wondering what comes next, and how much more [the engine’s failed again] you have left to give…

My little dark age… 🎶🎵🎼