This is a really good question and one I ask myself all the time. I also am an entrepreneur and have owned my own businesses off and on for the past 15+ years. During the times that I was looking for work, I also found myself pigeon holed because I was not the "cookie cutter" Enterprise Account Exec for Salesforce then Oracle, etc. It seemed to me that it became a detriment as potential employers see you as a flight risk. I would steer away from being overly entrepreneurial. HOWEVER, with that being said, I wear the entrepreneur title as a badge of honor. I am battle tested, been in the trenches, worked for no money at length and can walk the walk. At the end of the day it is a monetary decision. Good Luck!

The "it depends" insight you've already received in other responses here is only part of the correct answer. The full answer is "it depends whether entrepreneurship is relevant to the prospective employer."

Your CV is not really about you... it's about your prospective employer and the skills and experience you bring to them which make you uniquely qualified for a job. I've reviewed thousands and thousands of résumés and I've hired entrepreneurs galore. What mattered was the skills and experience they brought to my company, not so much where they worked.

Don't include information on your résumé which is not related to the job posting or which does not explain exactly why you're a great candidate for the job. For instance, an interest in being an entrepreneur is not relevant. What may be relevant is citing examples of how you've demonstrated an "entrepreneurial approach" if, for instance, the job posting calls for someone who can take initiative to drive new business, develop new relationships or grow an aspect of a company's business.

You may want to explain in your cover letter why you're interested in transitioning from self-employment to a role as an employee or contractor. This will help put a recruiter at ease that you're not a "flight risk" when the first opportunity arises for you to start your own business.

I'm happy to answer any additional questions you may have.

Most of the time the answer is yes it is harmful. Harmful because people who are entrepreneurs do not make good employees.

Entrepreneurs think differently than traditional employees. People who are entrepreneurs are the rock in their employers boot because they are always questioning "why" and "can't this be done better" . I am a business owner and once you are your own boss, working for someone else is very difficult. Most employers view it this way too. Most employers are going to assume and fear that you will be an extreme know-it-all pain in the ass.

You might want to say you worked FOR your company-leave it unsaid that you were the owner.

I would concur with Josh and yet add the dreaded "it depends".

Does it hurt to have been an entrepreneur?
Only if that is how you define yourself.
I'd love to talk with you about how you can define yourself by your abilities and passion, telling a story of grit that includes trying and failing. Sell the startup failure as boldness and it can actually help, because even big companies like the 'startup mindset'.

Let's chat about constructing this narrative and am sure you will actually learn something new about yourself!

Josh's answer was on the money.

In my experience "it depends" on who your target is.

In life there are always two kinds of people, whatever you are doing, and they will have these reactions:

> they will like who you are / what you're doing

or

> they won't like who you are / what you're doing.

What you've done is illuminated the failure of what I call "outdated job hunting technology." The resume and cover letter are really poor methods of looking for work.

But let's say you continue to use them.

WHO are you sending your CV to?

Whose eyes is it getting in front of?

If it's top executives, then I think you have a chance.

Yes, the format is still detrimentally old school, and we could do a lot better in that department, but at least the right kind of person is reading what you have to say.

But if it's stodgy, rules-bound HR departments, scared of making a bad decision (and their own shadow)...you probably won't pass the safety test.

Without any help, you can dramatically improve your odds by only applying to roles where you know the recipients of your information will be top executives.

They're the only people who can change the plan. Reallocate resources. Hire who they want, regardless of "the rules."

I have a Kindle book on unorthodox job hunting methods that work and radio interviews about them I'd be happy to provide. I'd post the Dropbox link here but am not sure that would be OK. (Mods, if it is, let me know and I'll do that.) In the meantime, I'll be happy to share them with anyone who messages me.

This could go one of two ways. I've had some employers hire me because of Entrepreneurial things I've done and mentioned on my resume and CV, and I've had other potential employers who either felt threatened by it or thought I wouldn't be committed to their business and would run off and start my own thing.

I think at startups and/or smaller businesses where positions tend to be less structured it's viewed as an asset that you can be a jack of all trades, your comfortable working in a fast paced and changing environment, in a more corporate atmosphere where they want you to do your job and only one specific duty it may not be seen as an asset.

You could potential tailor your CV to include or leave off the Entreprenurial stuff depending on whom you're applying with.

I thought Mary above had an interesting approach, mentioning you worked for the company and leaving off that you were the owner depending upon the position and company you're applying with.