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The Glory of Serial Entrepreneurship

Great idea? Check. Prototype? Check. Flip flops & hoodie? Check.



I was 29, I unbuckled my seatbelt, flashed the peace sign to the other passengers staring at me in shock and flew out of the plane, with the goal of building another flying machine.

You need to be a bit insane to step away from the womb-like comfort & the morphine-drip of a steady paycheck. That initial energy that propels you towards the glitzy lifestyle of an entrepreneur doesn’t last.



The first jump is magical, and the post-funding / post acquisition / post-IPO life is also magical, for those who reach it. Not much of the entrepreneurial dream that is sold covers what lies between the two. And now that I’m on my second startup, I understand why:

The middle part sucks, but it’s where the real journey begins.

“Everyone has a plan until they get punched in the face.” - Mike Tyson

Coming from an engineering background, I had pretty much zero respect for everything that didn’t involve coding & algorithms. Like many other engineers, to me the equation was simple:

Great idea + well-developed application = buying the house next toJay Z and Beyonce in a year or two.

But this is not how it works.

Ego level: 100%

You start as an energy ball. In one massive month-long session, you develop your code, underpay a freelance designer for a logo & interface, launch your prototype and immediately go on the networking circuit. Once you try to explain your product to someone, in over an hour, trying to prove how it’s important., you feel that something is wrong.



Soon enough, your fears are confirmed. Others are slowly moving away so they don’t end up joining a really bad conversation, and then feel compelled to nod politely: “Very interesting, good luck!” before they rush off.

Ego level: 80% remaining

“OK, I’ll work more on code”, you think. “I’m going to go into my cave, devise a super marketing plan all by myself-I’m a genius.”



“Then I will announce ‘People of Earth! I am graciously presenting you…this!’ Everyone on earth will lose their mind.”



But as you’re off to present your idea,  confidently running to the stage, you see your audience: three people in the audience, one of them is playing Candy Crush on his phone.

Google Analytics? Refresh. No hockey stick. Your Facebook ad campaign, which was basically the heart of your marketing plan, causes more bounces than an all-star game. You thought you could build a startup monk-style, without talking to anybody.



“That’s not how it works, son,” the universe responds. You choose to ignore the universe.

Ego level: 50% remaining

“Of course things aren’t taking off, I have no funding!” You tell yourself.  “How am I supposed to fly if I don’t have wings?”



Most entrepreneurs are hammered with the idea that funding equals success. It has become the ultimate goal and a way to escape questions about how well the product is actually doing.

You start a pitch with pride, but an investor points out that you have no traction. You, in a few moments, become a sad miserable beggar.



- “Can I have your money, please?”

- “No, go away.”

Ego level: 25% remaining

“Investment is for silicon valley brats. I don’t need it”



You evaluate everything that has not gone as expected. You conclude: the product needs better features. You dedicate your remaining energy to a completely new iteration. You decide to shell out top dollar for an interface that makes any website look like a plain piece of paper.



Success is guaranteed now. This product is incredible. You are incredible.



Make sure your travel documents are ready, there’s nothing more embarrassing than missing an acquisition meeting with Mark Zuckerberg due to visa issues.



Launch day, Massive PR campaign. Google analytics. Spike? Crash? Nope, flat line.



Something must be wrong with the technology. Everything turns out to be working fine. You do a focus group, for the first time, to uncover why people aren’t using your product. Maybe the ‘call to action’ button colour reminds people of bad childhood memories.



Finally, you see it: Great product. It’s amazing how you solved a problem. It’s just…this problem is not what people really care about.

Ego level: 0% remaining

Old school boxers insist that you aren’t a boxer until you get your nose broken. Tasting that pain & humiliation makes you fearless so that you’re not afraid to build a simple MVP to test your assumptions and possibly be proved wrong as early as possible.



So that you’re not afraid to ask for help and criticism when you need it because you can’t do everything on your own. So that you’re not afraid to try and build a profitable business without the support of a millionaire or big clients from day one. So you’re not afraid to get hit because getting hit is part of the game.



Provided, of course, that you have the guts to rise up again.

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