Increasing your net worth from $1 to $100 is not hard, even a homeless junkie could do that without much effort. But going from $1 billion to $100 billion, or even just to $2 billion, is a whole different story.
I wouldn't agree entirely that your analogy suits the Bitcoin context and even with the general economic sense of upscaling from a $1 point to $100, I Believe it's always more deficult at the starting point than it becomes when you've witnessed some level of growth and have gained a wide range of trust accross the globe like what has happened in the Bitcoin scenario.
You would be right if we were talking about growth in terms of the actual amounts of money flowing into the market, in such case - yes it's more difficult to attract big money at the start.
But I'm talking purely about ratios (e.g. x10, x32, x100 etc). There's almost zero difficulty in making high ratios at the start. You could literally create a shit coin this afternoon, start trading it at say $0.00001 and just buy it from yourself for $1. Congrats, you just made a x100,000 return, but good luck repeating that when there's a real market with big volume.