Fooled by Rationalism

How Descartes Effortlessly Killed Your Entrepreneurial Dreams

The Quantified VC
The Startup
7 min readSep 22, 2018

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When you start living the life of your dreams, there will always be obstacles, doubters, mistakes and setbacks along the way. But with hard work, perseverance and self-belief there is no limit to what you can achieve.

— Roy T. Bennett

In France, people pride themselves on what is known as the Cartesian method, named after their renowned 17th-century natural scientist and philosopher René Descartes, who was the quintessential methodist (in the Chisholmian sense of the word). He developed a problem-solving approach founded on the principle of suspicion: You start with a hunch that things may not be as simple as they seem, which helps you identify a problem, and you refuse to accept anything as true until you know it as such without a single doubt. Then you break it down into parts, prioritize the steps of your solution, and systematically march forward from the simplest to the most complex, taking care not to overlook any part of the whole. This clear and distinct approach led Descartes to significant discoveries in analytical geometry, modern algebraic notation, optics and philosophy.

I doubt, therefore I exist.

~René Descartes

Descartes’ doubt is universal — he attacks his beliefs all at once by attacking their foundations — and it is hyperbolic, extreme to the point of being ridiculous, e.g. the possibility of an evil demon whose whole aim is to deceive you. Certainty, as Descartes understands it, is not a feeling; it involves a type of rational insight.

However, if beliefs must be in some way infallible and if you go after only beliefs that you are certain of, many ideas wouldn’t have come to fruition. How many times have you heard stories of successful people talking about how they never knew in the beginning that they could succeed at all?

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How Airbnb Started

Years before Airbnb turned the hotel industry upside down, many A-list investors doubted — and some were even horrified by — the idea and its potential. Fred Wilson and Union Square Ventures notoriously rejected the nascent startup. Chris Sacca did, too, and later lamented:

“Airbnb, multi-billion-dollar business, right? I was one of the first people to see the Airbnb page. And I pulled them aside and said, guys, this is super dangerous. You’re renting out a room in somebody’s house while they’re still there? Somebody’s going to get raped or murdered, and the blood is gonna be on your hands. There’s no way this’ll succeed. That’s a $10 billion business today that I’m not an investor in.”

Even Airbnb’s first investor Paul Graham also admitted to have some initial doubts:

“I thought the idea was crazy. Are people really going to do this? I would never do this.”

Almost everything about Airbnb at the time was riddled with doubt. And it wasn’t just Airbnb’s business model that posed a concern. When Joe Gebbia and Brian Chesky — both Rhode Island School of Design alums — were initially seeking funding for their startup, investors found their background incredulous and jarring. If the founders doubted themselves or their idea just as much and gave up, Airbnb never would have prevailed.

A lot of innovations started out as ideas and are built on doubt, such as Bitcoin and the ensuing cryptocurrency movement. A lot of investment decisions are made on doubt, too, because investors often don’t have all the facts and/or are unable to completely rule out their biases.

Bitcoin Magazine, Issue 1

Fail Before You Even Get to Start

Anyone can have an idea, but most people automatically apply the Cartesian method and doubt that their ideas will ever work or that they will ever be able to make their dreams a reality. If you break down your ideas into many parts, attack each part relentlessly from every possible angle, search for all their weaknesses and vulnerabilities, and seek to account for every possible reason why they won’t work, your initial enthusiasm yields to an intense skepticism — and you may end up stuck in the pit of self-doubt with all of your attention consumed by it. You create the elephant in your head, and you give up without even starting. Ideas are worthless until you’ve developed or executed them. Overcoming self-doubt and moving forward with your idea is crucial — and each step you take improves your odds of success.

This is not to suggest that you should drink your own Kool-Aid and blindly fall in love with your ideas. You may discover that, after basic research, some of your ideas aren’t viable. Don’t focus on the negatives — turn the challenge into an opportunity. Look for ways around your difficulties and keep pushing for a solution. There’s a fine line between stubbornness and conviction. If you are stubborn, you are on your own island and you close your mind to all other possibilities because you can’t possibly be wrong. On the other hand, if you have strong conviction you will be receptive to new information and able to embrace other possibilities.

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Doubt kills more dreams than failure ever will.

— Suzy Kassem

Asking for advice and validation can be dangerous, especially if you ask the experts in a given domain. Experts know everything about how their industries run today, so they may assume that your idea can’t possibly work because it has never been done before. However, many newcomers can sometimes see opportunities that veterans can’t. When you are trying to do something disruptive or groundbreaking, there are going to be naysayers. You need just enough information to know that your idea is possible and move forward quickly.

Acting on a new concept or an unproven idea has never been easier. You can have an idea for a company or a product today and show something to users tomorrow. Keep on iterating, learning and tweaking. Many ideas will almost certainly need to be changed, modified and tweaked multiple times based on the market’s reaction before they are ultimately successful. Therefore, there’s no point spending inordinate amounts of time and money developing every detail of your concept and adding all of the bells and whistles.

Conviction is Your Best Defense Against FUD

Once you’ve tested your idea and the market, the hard — and the least controllable — part about this is the human part. It’s about having your own conviction and transmitting that conviction to others through enthusiasm and optimism to reach a common goal. It’s about convincing people to come together and work hard to achieve the extraordinary and the improbable.

Conviction is in short supply because our brains are wired to overreact to uncertainty with doubt and fear. As uncertainty increases, the brain shifts control over to the limbic system, where emotions such as anxiety and panic are generated. This brain mechanism worked well eons ago, when cavemen entered unknown wilderness and didn’t know what sort of dangers might be lurking behind the bushes. Overwhelming caution and fear ensured survival, but that’s no longer the case today, where uncertainty rules and important decisions must be made every day with minimal information.

By nature, entrepreneurs are visionaries. They are always immersed in the improbable. Building startups isn’t about $100-million rounds or “unicorns.” Too often it’s an anxiety-ridden, lonely, frustrating process filled with uncertainty, improbability, crippling self-doubt, and personal tolls on all your other relationships. You constantly get into a psychic wrestling match with a little voice in your head that chips away at your confidence and dials up your doubts:

What if I mess up?

What if I’ll make a fool of myself?

What will other people say?

I’m simply not good enough, smart enough, talented enough, capable enough, experienced enough?

I don’t have a superpower that sets me a part from others?

And you run into scenarios which shake you up, like when you find a competitor having extraordinary growth, when an advisor doubts your idea or tells you how difficult or how long the path is, or when people tell you that startups and venture capital have peaked. The easiest thing for you to do, then, is to over-analyze the situation and start going off on a tangent.

I’ve watched startups dither and make “decisions by indecision.” I’ve watched founders seek “air cover” for hard decisions by getting too much input from their teams or boards. I’ve watched leadership teams hedge risk by building multiple products and spreading resources too thinly instead of having strong conviction in their core ideas.

It’s all too easy to let FUD sabotage your chance for success and marginalize your ability to lead. A weak entrepreneur infects the entire team with his/her uncertainties and self-doubts very quickly, and this can have snowballing consequences on the health of a young company. Pessimism in an entrepreneur is highly visible to everyone. When you are building a company, there are so many chances to make adjustments and so many ways to realize your vision — but only if the key players firmly believe in that vision.

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The Quantified VC
The Startup

building the future with open source robotics | devil's advocate & intergalactic mathemagician | venture capital & startups 🔢 calculus > statistics