Last week, I was talking with an entrepreneur who’s built an incredible business. Later in the conversation, I asked if the idea he started with was the same one that ultimately made him successful. I’ve asked this question many times before, knowing that most entrepreneurs pivot or iterate multiple times before finding what works.
In this case, the entrepreneur said his original idea was the one that worked, and that it had to be, because his goal from the start was to build a large, scaled business. Reflecting on this, I realized he had aligned his personal ambitions with the potential of his startup idea.
Many entrepreneurs are happy creating a company that provides freedom, flexibility, and financial stability for their families. For them, the size and scale beyond those needs …
Last week, I was talking with an entrepreneur who’s built an incredible business. Later in the conversation, I asked if the idea he started with was the same one that ultimately made him successful. I’ve asked this question many times before, knowing that most entrepreneurs pivot or iterate multiple times before finding what works.
In this case, the entrepreneur said his original idea was the one that worked, and that it had to be, because his goal from the start was to build a large, scaled business. Reflecting on this, I realized he had aligned his personal ambitions with the potential of his startup idea.
Many entrepreneurs are happy creating a company that provides freedom, flexibility, and financial stability for their families. For them, the size and scale beyond those needs aren’t really important. Others have a different drive, a bigger chip on their shoulder, and dream of building something much larger in scope and impact. Of course, there’s no right or wrong answer; everyone has their own aspirations.
Personally, when I started out, I just wanted to be an entrepreneur. I wanted to create something from nothing and build a business that worked, though I had no clear definition of what “success” meant. After some modest early wins developing a software product and landing a handful of customers, I set a new goal: to make the Inc. 500 list of the fastest-growing private companies in the United States.
After achieving that, my next goal became building a business with enough potential to raise venture capital and operate at scale in the software world. I still didn’t have a clear definition of success, but I figured that if investors were willing to back it, the idea must be big enough to matter.
I wouldn’t necessarily recommend this approach to other entrepreneurs, but it’s an example of how my thinking evolved over many years of introspection and experimentation. My advice to entrepreneurs, especially those early in their journey, is to align their ambition with their startup idea.
If your goal is a great lifestyle, there are countless opportunities to build a business that supports that. If your goal is to create something transformative with a major impact on your city or industry, the idea needs to be correspondingly more ambitious and scalable.
The best part is that none of this is fixed. Some entrepreneurs start with an idea that grows far beyond anything they could have imagined, and that’s the beauty of putting yourself in the arena.
Published by David Cummings
Entrepreneur View all posts by David Cummings
Published November 8, 2025