08. Why the Best Startup Moves Don’t Always Make Sense at First
- Ben Steenstra
- Jul 16, 2025
- 5 min read
Updated: Jul 7
Lesson 8 of 8 in the Startup Course.
Watch the video version of this lesson here:
A lot of founders want to make smart decisions.
That sounds obvious.
But in startups, some of the smartest decisions do not look smart in the beginning. They look strange. Uncomfortable. Premature. Risky. Hard to explain. Sometimes even wrong.
That is what this lesson is about.
Because some of the strongest startup moves happen before the room agrees with them. Before the logic is obvious. Before the market can clearly explain why the move works.
And founders need to understand that, because if they only make decisions that already look reasonable to everyone else, they will usually stay trapped inside the expectations of everyone else too.
The Strange Move That Changed the Game
In 1980, something unusual happened during a chess championship in Sweden.
On one side of the board sat Anatoly Karpov, the world champion. He was disciplined, admired, and deeply associated with structure, control, and consistency. He represented the system at the highest level.
Across from him sat Tony Miles, an English grandmaster who was much less expected to win.
And then something happened that matters far beyond chess.
Miles responded to Karpov with a move that looked unusual enough to disturb the entire rhythm of the game.
It was not random.
It was not chaos.
It was not rebellion for the sake of rebellion.
It was a deliberate departure from expectation.
And it worked.
That is the startup lesson.
Not every powerful move looks impressive at first glance.
Sometimes it looks odd precisely because it does not fit the inherited script.
Founders Often Lose by Following the Expected Script
Startups are full of invisible scripts.
How you are supposed to pitch.
How your deck is supposed to look.
How a founder is supposed to sound.
How a product is supposed to launch.
How a market entry is supposed to happen.
How traction is supposed to be explained.
How pricing is supposed to work.
How growth is supposed to look.
These scripts are useful up to a point.
They help people recognize patterns.
They reduce confusion.
They make communication easier.
But they also create imitation.
And imitation becomes dangerous when a founder starts following the script so closely that the startup loses what makes it distinct.
That is when “best practice” becomes mediocrity in disguise.
Because best practice often describes what worked before, not what is about to work next.
Not Every Good Decision Looks Good Immediately
This is one of the hardest truths for founders to live with.
You can make the right move and still look wrong for a while.
The market may not understand it yet.
Investors may hesitate.
Advisors may call it unclear.
People around you may prefer something more familiar.
That does not automatically mean your move is correct.
But it does mean that external confusion is not reliable proof that you should stop.
Many founders are too dependent on immediate validation. If the response is not quickly enthusiastic, they retreat to something safer. Something more conventional. Something easier to explain.
That instinct is understandable.
But it often destroys originality before originality has time to prove itself.
The Difference Between Weird and Wise
This lesson is not about being unconventional for the sake of being unconventional.
That is not strategy.
That is performance.
Founders do not win by trying to look edgy.
They win by seeing something real that others do not see yet and having the courage to act on it carefully and intelligently.
That is a very different thing.
A weird move without substance is just noise.
But a move that looks strange because it breaks a false assumption can become a breakthrough.
That is why independent judgment matters so much.
A founder has to ask:
Does this move only look strange because it is weak?
Or does it look strange because it is early?
That distinction changes everything.
Why Courage Matters More Than Early Applause
One of the most underrated founder skills is the ability to stay grounded while a good decision still looks uncertain from the outside.
Not every important move gets instant confirmation.
Sometimes the strongest signal is not applause.
It is internal clarity.
That clarity does not come from ego.
It does not come from stubbornness.
It does not come from refusing feedback.
It comes from having thought deeply enough, listened carefully enough, tested honestly enough, and understood the opportunity well enough to move before consensus fully forms.
That is what courage looks like in entrepreneurship.
Not recklessness.
Not noise.
Not posture.
Courage is what allows a founder to move first without needing everyone to agree first.
Startup Progress Often Starts with Rhythm Breaking
That is another reason the Tony Miles story matters.
Great moves often break rhythm.
They interrupt expectation.
They disturb the pattern.
They force the system to respond differently.
This is true in chess.
It is true in markets.
It is true in branding.
It is true in product strategy.
It is true in positioning.
Many founders stay invisible because they are too committed to being understandable in familiar ways. They say what everyone says. Offer what everyone offers. Pitch how everyone pitches. Price how everyone prices. Design how everyone designs.
Then they wonder why nothing moves.
But nothing moves because nothing shifted.
Sometimes the startup does not need a better version of the expected move.
Sometimes it needs a move that resets the board.
Five Founder Lessons from This
1. Best practice is not always best timing.
What worked before may be too crowded, too late, or too generic now.
2. Some strong startup moves look strange before they look smart.
Do not confuse unfamiliarity with weakness too quickly.
3. Originality requires independent judgment.
You cannot build something distinct while constantly waiting for approval from people who prefer the familiar.
4. Weird is not enough. The move still has to be true.
Unconventional only matters when it reveals a better path, not when it only creates noise.
5. Sometimes the right move breaks the rhythm before it creates the result.
Founders need the patience and courage to survive that gap.
The Question for Founders
So here is the question behind this lesson:
What move are you avoiding right now because it still looks too strange from the outside?
What are you already sensing but still not doing because it is hard to explain?
Where are you following the expected script even though you know it is making you more generic?
Where do you need more applause before you allow yourself to move?
Because in startups, the best decision is not always the one that looks smartest immediately.
Sometimes it is the one that changes the whole board.
Startup Course: All Lessons
- 08. Why the Best Startup Moves Don’t Always Make Sense at First
Related Reading on BenSteenstra.com
Note: This video was created with the help of AI so these lessons can be shared clearly in languages Ben does not speak natively.
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