Hindsight is a complex word because of the way it is commonly used.
It is important to understand the phrase "Hindsight is 20/20", because it is the most common usage of the word, and that meaning is almost always implied when the word is used alone. "20/20" is a 'perfect' score on a vision test, and is used here to mean both insight and understanding. Hindsight is 20/20 because events always seem obvious and simple when you reflect on what has already happened. It is also used as a reminder that foresight is difficult and complex.
Because of this, "Hindsight" is often used when discussing an action that should have been taken, especially if the consequences are much more obvious now. For instance, someone undergoing a painful dentist appointment might remark "In hindsight, I should have flossed my teeth."
Your example about Steve Jobs doesn't quite work, for a few reasons.
"Steve Jobs just builds things he believe it's great first, then people will understand his products and his ideas later in a hindsight"
There are three ideas here:
Steve Jobs builds things he believes are great. (Since there are many things, we want to use the plural for believe and it's here.)
People will understand his ideas and products later. (We can group the ideas and products together because they are both "his")
[Steve Jobs' decisions will make sense] in hindsight.
To improve this sentence, we want to make it clear that we are talking about one thing - not things, ideas, and products. It should also be clear that the people who understand later were confused at the beginning.
If we use the definition of "hindsight" to mean something that was only obvious later, we might say:
Steve Jobs made a lot of shocking decisions, which in hindsight were understood to be genius.
By saying his decisions were shocking, we establish why people thought they were not genius.
We could say "only later" instead of "in hindsight" here, and it would mean nearly the same thing. However, there is a slight implication when we use "hindsight" that the answer could not have been known at the time, because we do not share Steve's genius.
Best Answer
Yes, both of your sentences are correct. "Stagger" can be used both in a literal sense (having trouble walking) and in a metaphorical sense (struggling to grow a new business).
Both of your sentences are clear in their meaning, but I think in order to be 100% correct, you need make some tweaks. "Stagger" means most commonly (in my personal experience) "to walk or cause to walk unsteadily as if about to fall". It has a lot of nuances in its meaning, but for the most part, someone who is staggering is already standing up and walking (though not well).
For that reason, I would be more likely to say:
Staggering is more what he would do after he managed to get himself standing.
n.b.: Be careful in the second sentence: "staggering" can be an adjective, meaning "causing great astonishment, amazement, or dismay; overwhelming". Starting a "staggering new business" probably means that the business is unexpectedly doing very well, not that it is struggling. You want to be sure to include a word like "forward" that shows movement, like the business is going forward on shaky legs.