You can go far if you wish upon a star (and don’t get cancelled)

Sam Gibb
endeavourventures
Published in
5 min readJun 30, 2021

Starting anything requires a leap into the unknown, making the assumption that you can create something that for a great majority of people is the first time that they have embarked on this specific journey. There might be some dots that you are able to connect that would suggest that you might have the ability to follow the trajectory that you’ve set out for yourself, but to a large degree you are going to be feeling your way in the dark. This is the same for whatever you’re beginning to attempt.

There are two competing forces that need to be balanced here: Firstly, the doubt and uncertainty that comes with embarking without a complete map of the territory. Secondly, the confidence that’s required to act with conviction to propel the concept into a business. The best entrepreneurs are able to straddle this dichotomy well. If you have too much hubris, it’s likely that you won’t be able to adjust your course when you get feedback. Too much doubt and it’s unlikely that you’ll ever set out at all.

Look into the distance
To be able to balance uncertainty and confidence, you need to have a vision of the future and how you can influence it into being. You can make adjustments to the overall direction as you make progress based on the feedback that you receive (having an element of doubt helps to weigh external voices) but you need to have an overarching North Star otherwise you’re likely to be swayed by the winds of popular sentiment (having faith in a long-term vision).

This is similar to snowboarding off-piste, you need to be focused on positive targets ahead of yourself and let the corrections take care of themselves. If you are too reactive or focused on the negatives that you need to avoid, you’ll likely find yourself up against a tree. There’s no way for you to know about all of the issues that you’re going to face when you begin, the best course of action is to set a course and adjust to deviations as necessary.

Start with a large surface area
To begin with, it helps if the idea that you’re trying to build is based on helping a large potential pool of customers. It’s good to start with a specific solution to an identifiable problem but if you are only focused on one specific problem, you might miss the larger jobs to be done. However, if you start with a broader problem, you maximise your potential surface area, giving yourself room to pivot and manoeuvre if you’re not receiving sufficient positive feedback.

Failing to have a sufficiently large opportunity set is also an issue for investors and how they evaluate early-stage companies. In my experience, the problem is that a lot of early-stage investors don’t have any specific view of the future, they haven’t identified problems that affect a broad cross-section of people or companies. They don’t have any conviction about what the future will look like or how they can influence their immediate environment to make that potential future a reality. This results in a lack of conviction and reliance on external indicators of validity (e.g. strong lead investor, high levels of traction, endorsements from well-known brands). The best investors have a view on what will happen and actively seek out opportunities that will enable that view to materialise. I know that this is how I approach partnering with and investing in early-stage teams.

It’s difficult to succeed without failing at least once. For example, the recently cancelled popular children’s author, Theodor Geisel, also known as Dr. Seuss, had his first book rejected by more than twenty publishers (maybe they knew what was on the horizon 80 years in the future…). Regardless, he went on to publish forty-six children’s books (40 now?).

A number of teams that I’ve worked with have managed to pivot their original business models based on feedback, while still remaining focused on their original goal and vision.

Dunning-Kruger
The original story of misperceived confidence had to do with a bank robber, who tried to rob two banks while his face was covered in lemon juice, based on the misunderstanding of the chemical properties that made it useful as an invisible ink. A lot of the time, when younger entrepreneurs begin a venture, they misperceive the requirements and institutional hurdles that they’ll be required to cross.

This isn’t necessarily a negative because without it, we would be left with industry professionals who only want to make incremental differences to the status quo. Assuming that they don’t already have so many entrenched interests that prevent them from taking any action at all. Without a level of misperceived confidence, there would be no paradigm shifts in industries.

Those that are inexperienced are able to approach new fields with a beginner’s mindset, starting from first principles to understand why things are so.

The performance artist Marina Abramović puts it directly: “If you start believing in your greatness, it is the death of your creativity.” Ego is the Enemy

Not having any preconceived notion of what the result will look like can be a strength. While daunting, starting with a blank canvas allows you to plot a novel course. This no doubt leads to a number of dead ends with the wasted time and energy that it entails, that experience would have avoided. However, any temporary setback enables adjustments to be incorporated, which makes future success more likely.

The Dunning-Kruger effect is characterised by having higher levels of confidence at low levels of knowledge and correspondingly lower levels of confidence with high levels of knowledge. To deal with this, it’s useful to adjust where confidence lies at different stages of the journey.

Conclusion
At the beginning of a venture, it’s prudent to have high levels of confidence in the eventual outcome with significant amounts of humility around what the execution will look like. As you pick up momentum and knowledge, you can have confidence in the processes that you’re creating and decisions that you’re making. The confidence can be transferred to micro aspects without getting lemon juice on your face. Go forward with conviction and adjust the course as necessary, don’t wait to be told what your world can become.

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