Ideally, aspiring entrepreneurs should work for a start-up AND a large company before starting up on their own.
Working with a startup and working with a large company offer very different learnings and experiences for an aspiring entrepreneur.
For example, working in a startup helps an aspiring entrepreneur understand how to make things work in a resource constrained environment; how to hire people when you are not a known brand; how to be flexible and nimble, etc. Working in a startup also helps aspiring entrepreneurs understand how business models evolve; how a gradual ramp-up is implemented; how a business plan has to be adjusted; how quickly things can change… and how assumptions are tested and hence, adjustments made in goals, strategy and implementation plans.
On the other hand, working in a large company helps aspiring entrepreneurs learn about the power of processes and systems; the challenges of working at scale; the way to handle HR issues when there are multiple layers in an organization when, (unlike a startup), you don’t know your colleagues by name. Working in a large company also teaches aspiring entrepreneurs about focus, being goal & objective oriented and about increasing profitability. At scale.
In effect, both environments – large company and startups – offer experiences that are varied and very useful when you yourself will start your own venture. However, irrespective of what type of organization you work in, my advice to aspiring entrepreneurs is that they should keep their eyes, ears and senses open to understanding the overall ‘business’ of the company rather than just the function they are assigned to.
Also, if you are clear that you want to be an entrepreneur, I would recommend you to take up a sales job. Any company, any where… take a job that requires you to go out in the field, meet customers, pitch your product, negotiate and sell.
Selling teaches you many things about the practicalities of business life. Rejection by customers teaches you to be modest about your assumptions on conversions. Dealing with rejection teaches you to deal with failure and challenges.