Three Jedi Mind Tricks Against The Entrepreneurial Struggle

How to Stay Sane as a First-Time Founder When Things Go Wrong


So, we had just closed our first round of funding when my key employee quits. I had sold the investors on that employee's skills, and everything was horrible. I felt like a faker, and our company would never work despite the funding! That night I slowly walked to the bus with my head down and spirit even lower. I felt numb and hurt. But we found a replacement within weeks, and nobody really cared.

Three years later, I am at this conference in Manila, and we go to a bar. Those Philipinos can drink, I tell you! I had just bought new sunglasses, put them in a bag and leave it in a corner. The next hangover morning, I wake up smelling like gin and tonic receive two bad news. My COO tells me the replacement employee (who was now even more key!) had just quit. Also, somehow, I had forgotten my bag and new sunglasses at the bar.

I was really pissed. How could I be so stupid to lose my new sunglasses? I didn’t think much about the employee quitting. It all seemed like ‘just another one of those.’ Having been through the experience, I realized it was fixable.

Somehow it seems like the mind particularly freaks out the first time something bad happens. I now consider that a vaccine against future mental blow-ups. It’s better to get it early when the stakes are low.


Some months later, it’s that time of year when we run out of VC money (again!). The future is unclear. The cash balance is getting lower by the day, and so is my self-esteem. I feel agitated and thin-skinned. What I have to do is very clear. a) Work my ass off to secure funding and b) prepare for “plan b” to cut costs.

So we put together “the list.” It contains names and salaries of employees and potentially a red “X.” The horror! I feel like Harry Potter when he meets the Dementors. Finally, they will realize that it’s all a big fraud, and I’m a failure. My sandcastle is crumbling, and sadly, it’s the only place my mind occupies.

So my head is spinning, and I call my friend. He’s this big-shot entrepreneur. Maybe he’s 20 years older than me, but surely 100 years wiser. We meet for lunch. He is having a big salad, and I don’t know what the hell I’m having because I can’t get a single bite down anyway.

“Layoffs…yeah, yeah. Done tons of them. Always healthy for the company. It’s good for you, you’ll see. Make sure you cut deeply just once, and you’ll be fine you’ll see.”. He casually talks between green leaves and Diet Coke. Boredom is written all over his face. My biggest existential problem in the whole universe is just a dead bug on the windshield for him. A tiny bit annoying but ultimately no big deal.

I calmly observe him and start to relax. His boredom made me realize it’s just ‘another one of those.’ Just this time, it didn’t happen to me. It happened to my unexcited friend. Apparently, you can download someone else's mental vaccine.

Check, please.


I’m a nerd, and sometimes I think about a startup as a computer game. Like Sonic the Hedgehog, remember? That blue thing that runs at breakneck speed and jumps through hoops. I sometimes feel like him running a startup. Sonic sometimes completes the level, and sometimes he crashes with a big bang (and loses all his rings!). Then he stands up again and starts over.

“What’s the worst that can happen in a start-up?” I ask myself in one of those few, calm, clear moments. You lose all your rings and have to restart the level. Maybe the game. But you’re not actually dying.

That always gives me a calming sense of relief. In start-up land, detachment is healthy. It’s a game. You are not your company.

By the way, back to my hangover morning in Manila. I go back to the bar and — can you believe it — find my bag and my sunglasses lying around somewhere. So I’m the happiest person in the world. Still unfit but at least being able to see again. And, of course, we found a replacement for that guy who quit.

Tech founder & investor from 🇩🇪. Sharing experiences for first-time founders💡🛠🚀

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