Founders Paradox

Everyone in the startup world knows the famous line, often attributed to Elon Musk: "Starting a company is like eating glass and staring into the abyss." We hear it and we nod. We think we understand. We brace ourselves for the brutal competition, the 100-hour weeks, and the terror of watching our bank balance dwindle. We prepare to eat glass. Hell, we may even look forward to the pain.

But what I was never prepared for, and what I see so little content around, is that the abyss isn't just the market, the risk of failure, or the financial whirlwinds. The most consuming abyss is a profoundly human one: the inescapable loneliness of being the person in charge.

The hardest part isn’t the work; it’s the fundamental separation that comes with the role.

And the pain when you don't respect the need for separation.

Your Team Aren't Your Friends

This might sound harsh, but it's a truth I'm coming to accept: the people you spend 12 hours a day with, the people you build, struggle, and win with, cannot be your best friends. There's an invisible, structural wall between a founder and a team member.

The power imbalance is real. At the end of the day, you sign their paychecks. You are responsible for their career growth, their performance reviews, and ultimately, their employment. This creates a dynamic that can never be a true peer relationship. You can be friendly, respectful, transparent, and have fun, but the hierarchy is always there. And at times, I've been reminded of this in some shocking and hurtful ways. To my shame, I'm sure I've reminded others just as harshly.

It creates a mismatch of stakes and motivations. For you, the company is an all-consuming vision. It's what you think about in the shower and what wakes you up at 3 AM. For a great employee, it's hopefully a mission they care deeply about, but it's also a job. Their primary focus, understandably, is to execute their tasks well and be recognized for that execution. This leads to a subtle but crucial divergence. You need the vision executed. They need their contribution to be visibly excellent. Sometimes, the effort spent on making the work known can overshadow the nuance of getting the work done right. And as the founder, you're the only one who feels the weight of that tiny gap.

If there is something I feel I'm failing at more than anything, it is this: knowing what to do when the project, task, or role isn't being executed.

The Internal Monologue

The moment you see a deliverable that misses the mark is one of the most isolating experiences I know. Before any conversation happens, a silent, frantic monologue begins inside your own head.

Step 1: Immediate Self-Blame. "Was my brief unclear? Did I not provide the right context? Let me re-read the Slack messages... Oh shit, I didn't get this in writing. Why do I always give tasks via calls and not written?" You instinctively assume the fault is yours because you bear the ultimate responsibility for clarity.

Step 2: Confusion and Frustration. But let's assume the worst case. You review your instructions, rack your brain on the conversations, and realize they were, in fact, crystal clear. And not only were they clear, this project is one that this role shouldn't even need instructions on. It's fundamental. The monologue then shifts: "Okay, so what happened here? Is this a one-time slip? A skill gap I wasn't aware of? Is this person just not listening? Do they not care?" Then, almost immediately, the "friend-first" approach kicks in as a defense mechanism: "Oh man, I wonder if they have something going on in their personal life. I should give them a break. Let it slide. I'll catch them on the next one."

Step 3: The Weight of Solitude. You can't turn to the person next to you and vent, "Can you believe this?" because that person is either the one who did the work or their close teammate. You can't share the full weight of your disappointment, so you carry it alone. And your real friends, those not related to the business? They don't deserve to hear the day-to-day struggles of a startup founder. They have their own problems; they don't need to hear mine. Nor can they truly impact the situation—they only have a small window into my world.

Swinging Between Fire and Friendship

Once you’ve processed the issue, you’re faced with a paralyzing choice: how do you respond? My mind often swings violently between two poles, and frankly, I despise both of them.

One option is the "Scorched Earth" Impulse.
This is the desire to be brutally, almost savagely, direct. "This is not acceptable. It completely missed the point. It needs to be redone from scratch, now." This approach feels powerful and decisive in the moment, a way to channel frustration and ensure standards are met. But it comes at a huge cost: it erodes psychological safety, creates a culture of fear, and damages the long-term relationship.

The other is the "Preserve the Relationship" Impulse.
This is the opposite extreme. You soften the blow, start by praising the effort, and gently coach them toward the right outcome. The fear here is that in your effort to be kind, you become unclear. You risk ambiguity, allowing mediocre work to pass as "good enough" and blurring the lines between a leader and a friend.

The worst part is the whiplash of feeling both impulses at once. It's an exhausting internal battle. It's not about choosing a path; it's about wishing you didn't have to walk this tightrope at all. And, for better or for worse, although I swing between the two, I have the biggest desire to go scorched earth. It's channeling frustration into direct feedback. It's clean, to the point, and in a way, I don't need to mess with those things called feelings. It's emotionless. Damn, maybe I am German.

Redefining the Abyss

So, what’s the neat, tidy conclusion here? There isn't one.

This is a constant work in progress. If I had to take a stab at it, I would say I'm learning to find that third path: the one where I can be direct, kind, and effective all at once.

But one thing I know for sure, and one thing I have to get right, is getting the thought of being great friends out of the picture. It only muddles the already murky waters of running a startup.

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