Dichotomy of Entrepreneurship

Leander Märkisch
4 min readJul 21, 2020

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How entrepreneurs combine diverging concepts and strive under uncertainty

Photo by Alex on Unsplash

TL;DR Unlearn to rely on single thought patterns when founding a company

Building a scalable, repeatable, profitable business is a year-long search process under resource-constraints and uncertainty. Since each journey of an entrepreneur is different and highly contextual, conventional advice is of limited usefulness to navigate the chaotic system.

Deep discussions with entrepreneurs who have been there, research on not-so-standard literature, and my own (limited) experience in venture-building, led to the emergence of unusual patterns.

Oftentimes you hear the advice of systematically analyzing business opportunities (Jobs-To-Be-Done), while many great companies started out of an entrepreneur’s side-project based solely on intuition (Facebook, Paul Graham).

You create a compelling vision to change the world while starting with a solution to a hyper-specific problem for a very small group of people.

You need to believe in yourself and ignore the critics while listening empathetically to them simultaneously because the critics might have a valid point.

The list goes on. There numerous contracting combinations that are both right.

Diverging concepts, merged.

We are often stuck in our default thought-patterns, thereby missing out on what we do not know. We have the tendency to either follow a process-oriented structure or listen to our gut. Why not both?

Disillusioned clarity

Steve Jobs is famous for his reality-distortion-field. Simply by ignoring conventions on how things should be done, he was able to push his engineers to develop products in an unbelievable short time.

On the other hand, 42% of startups identified the “lack of a market need for their product” as the single biggest reason for their failure. Simply put, they were not clear enough about who their customers are and what they want.

Saket, former VC turned founder, explains that entrepreneurs need to be disillusioned on a high-level that they can create a company beyond their wildest expectations while being clear on a low-level, turning implicit assumptions into facts.

Stay disillusioned on your mission and communicate with clarity on all abstraction levels.

Humble boldness

Elon Musk envisions the human race as an interplanetary species. Being part of something that stretches beyond one’s individual needs is a strong motivational force and can foster unprecedented progress. Visionary thinkers are bored with minuscule progress, a prerequisite to executing the vision, and are often trapped in recurring thought patterns without taking action.

Humbleness refers to the ability to accept one’s own mistakes and imperfection. Humility is essential to learn from others and becoming aware of things that do not work out. But humbleness itself fails to Zen Buddhism’s concept of a Beginner’s Mind

In a famous parable, three construction workers are asked what they are working on. Their answers range from ‘laying bricks’ to ‘building wall’ to ‘building a cathedral’. All of them are right.

Be stubborn on the vision, flexible on the details. And do things that do not scale.

Analytical intuition

Thinking and acting are in constant conflict. More information reduces uncertainty in decision-making and therefore prevents possible mistakes. Too much thinking prevents taking any action since the pursuit of complete information and certainty is asymptotic — steadily advancing but never definite.

Wild, impulsive action drives progress and leads to concrete experiences which in turn provide new insights. But headless working towards an undefined destination is barely beneficial.

Basecamp copes with this dilemma by taking considered bets. After 2-week refinement process called shape-up, 6 weeks of development and deployment follow. While the time- and resources-scope is limited (never extend the deadline or increase the number of people working on it), the outcome-scope (result) is flexible and often decreases throughout the work process.

Improve your ability to think by connecting science & art, analytics & intuition.

Conclusion

These three points are somehow intertwined. After the discussion on the importance to combine concepts from both ends of the spectrum, there is a clear need for concrete action steps.

Daniel Gross advises in his YCombinator talk to expand one’s awareness, essentially moving from 1st person to 3rd person gaming experience. Regular meditation and reading philosophical texts accelerate development. Daniel’s mental model is based on Robert Kegan’s theory of Adult Development and various mental models. Both worthwhile resources to investigate.

“The test of a first-rate intelligence is the ability to hold two opposed ideas in mind at the same time and still retain the ability to function.” — F. Scott Fitzgerald

Become aware that two or more approaches are right and might ultimately lead to the same outcome, assuming sufficient time and persistence. Your odds of success are directly proportional to the number of tools you can evaluate and apply.

Thanks for reading,

Leander

The futurist Alvin Toffler states that “the illiterate of the 21st century will not be those who cannot read and write, but those who cannot learn, unlearn and relearn.”

Google gave us the opportunity to acquire any knowledge. I prefer to take the contrarian approach by removing out-dated knowledge. Welcome to Unlearned.

Each Sunday, I’ll dissect a random topic and add a new perspective. Curious? Join a tight-knit tribe of thought-provoking individuals and sign-up for the email bulletin here.

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