Does entrepreneurship become easier or stay the same?

It gets easier. The more projects you start, the higher the chance that you get lucky and something catches on. If you also account for the fact that you will be learning from your mistakes, acquiring new skills, growing your network, and therefore building better businesses (and building them faster) as you go on, the case for serial entrepreneurship becomes downright optimistic.

I like to think of it like this: Everyone has a number. The number of business you'll have to start before you succeed. For some that number is 1. For some it might be hundreds. Regardless, it's just a matter of pushing until you get there.

Some advice for hitting that number sooner:

• Always be a student. Don't stop consuming stories, don't stop reading, don't stop learning.
• Work on small things. If it's taking you longer than 3 months to build something, then it's probably too big. I'd personally aim for launching v1 in under a month.
• Focus. One project at a time, that's it.
• Do what you need to do, not just want you want to do. So many failures result from founders just doing their favorite activities all day as opposed to the activities their businesses actually need.
• You probably want to start with a content-based business. It's just faster and easier.
• Ideas matter. Don't let anyone tell you they don't. IMO your idea should include not just your product or service, but also your target market, your plans for reaching them, and your business model. And you should think about all of this before you start.

Good luck!

It definitely gets easier, you become less naive, learn along the way and figure out what works best.

A business is a journey, not just about the product, but one for you as a person too. Often ideas seem great until you start doing them, but you have to experience it to understand that.

I'm not sure if it ever becomes easy, but easier yes.

It gets unbelievably easier. I probably have over 40+ projects. In reality most of them are failures, but many of them are very successful.

The first failure is really hard, but once you accept failure is part of the process and start accumulating scar tissue, you realize there is nothing impossible.

Will smith says it better on this video: https://www.youtube.com/watch?v=Ks0GWwU50Ag

Fail fast, fail often, fail forward.

I don't know that it gets easier. Depends on the person.

But it does shatter illusions, so you at least know what kind of work is required to be successful. That means I spend less time writing apps because I know that other stuff will take just as long, or even much longer.

I think one of the best things you can do is grow a following wherever you're most comfortable (blog, newsletter, social) - because that following does make things easier. Your next project already has an audience that will see it, even if it's not 100% related. And the project after that, etc.

It depends. If you can rely on the knowledge, resources, and contacts from your previous businesses then it could be a lot easier to launch something new.

You might just talk to a few people to confirm interest, sign contracts within a week to get your first sales, and call up someone who has the right skills to handle the work.

But if you're going into a completely different market or industry then it's like starting over again.

After over 10 years working in tech I launched a business in an industry that I was unfamiliar with (apart from pretty much everyone needing it). Wow did it throw some new challenges at me!

I knew a lot of people work hard and I don't think I was underestimating what's involved. But I didn't know all the details of the problems that would come up and how deep I would have to go to solve them. At this point it would be a lot easier to launch related ideas or extend that business because I learned how to deal with it.

If I choose to go into another new industry in the future, I know I'll be a beginner again.