5 Reasons Companies Hate Hiring Entrepreneurs

Why Employers Hate Hiring Entrepreneurs…

For the past 7 years I had been running a niche eCommerce business, the past 3 of which I had done so full-time self employed. I started my business while working a day job and continued running it as a Side Hustle for the first 4 years. About 4 years in the business was making more than three times my salary at my day job at which point I was finally comfortable quitting my day job. My business partner had quit his day job a few months earlier and had been pushing me to do the same.

For the next 3-4 years I operated that business full-time. Without getting into specifics towards the end the regulatory landscape of our industry changed, merchant processing which was always tough got tougher. Government regulation got tougher. I decided it was time to sell the business and move on to other things.

I set aside enough money to where I could sit on the sidelines of the workforce for at least a year while I figured out my next move or tried to launch another business. A few months into this the boredom of being home alone all day coupled with frustration over my slow progress to launch something else led me to at least casually investigate the possibility of going back to work for someone else and getting a job.

What I was really looking for out of a job was not the money, though that is important, so much as to find a job that would help me acquire more knowledge and skills which would help benefit me in my own pursuits down the line whether that be other eCommerce businesses, Digital Marketing Freelancing, or starting an agency.

I went on probably about half a dozen or so job interviews and I kept finding people almost trying to talk me out of wanting to work for them. Several employers told me I would be bored working for them, or that I would feel micromanaged. Most seemed concerned with how long I would stick around. The couple who were even willing to consider hiring me were quick to ask if I’d be willing to sign a non-compete agreement. And one particularly odd interview the CEO of a web design firm slash digital marketing agency actually called me, and this is an exact quote, a “wild ass cowboy” and said I was a square peg that wouldn’t fit into their round hole.

It’ kind of funny, take a look at job postings and I’d be willing to wager at least half of them have a bullet point about wanting someone with an “Entrepreneurial Spirit” yet they don’t want to hire Entrepreneurs. And it’s not just me, I’ve seen the same experience echoed across other Entrepreneurs and self employed individuals. So why don’t employers want to hire Entrepreneurs?


5 Reasons Employers Don’t Hire Entrepreneurs

1. Entrepreneurs Make Bad Employees

This reason kind of encompasses a lot of different stuff, however most businesses feel Entrepreneurs would make bad employees. And it’s not that Entrepreneurs are bad people, but many of the things that make Entrepreneurs successful ie stubbornness, thinking outside the box, asking for forgiveness and not permission, these things right or wrong, don’t fit in with corporate culture or most workplaces.

Employers tend to think, probably rightfully so, Entrepreneurs are independent and may not take direction well. Entrepreneurs by necessity need to be efficient and will oftentimes do what works or what’s most efficient and not what they are told to do. Entrepreneurs are risk takers, and traditional business oftentimes doesn’t like risk. Entrepreneurs also need action, bureacracy will kill them.

Many Employers seem to feel Entrepreneurs may have skills and be successful but are going to be hard to reign in and manage.

2. They Worry You’ll Steal Their Business Idea

Of those interviews I went on, the few companies who seemed to at least be willing to consider hiring me all asked if I’d be willing to sign a non-compete agreement.

Here’s kind of the catch-22 of seeking employment as a former Entrepreneur or someone who was formerly self employed… Large Corporations are much more structured and are going to be less likely to hire you because of that. And small and mid-sized businesses and even start-ups, are going to be much more likely to value your skill-sets and be willing to hire you, but are also going to be worried you’ll copy their idea and start your own business.

If you’re seeking a job at Dell Computers for example, there’s little risk you’re going to start a competing computer company, but they will also be less likely to hire you because Entrepreneurs are much less likely to fit in, in a highly structured corporate environment.

Smaller businesses may actually value some of the skill-sets an Entrepreneur has, but those businesses are ones that an Entrepreneur would be capable of copying, improving, and launching their own competing business. And it’s not necessarily a crazy conclusion to come to. Entrepreneurs by nature start businesses. They also solve problems and look for and improve inefficiencies, so it’s not crazy to think they’ll do that.

My business actually began after seeing a gap in the market my previous employer wasn’t meeting and had no desire to meet so I started a business meeting that need and launched my own business and eventually left that company to run my own company.

3. They Question Your Self Employment

These days Entrepreneurship is kind of a hip and cool subject matter and Entrepreneurs actually get a bit of respect. Not too long ago Entrepreneur was viewed as kind of a nice way of saying unemployed. These days everyone seems to fancy themself an Entrepreneur, everyone has “CEO” on their Instagram profile. But what seperates the “Wantrepreneuers” from the “Entrepreneurs”? Really the success of the business.

Essentially what I’m saying here is anyone with a 2-3 year gap in their resume could theoretically just say they were an Entrepreneur. I wound up finding myself defending my success as an Entrepreneur and business owner, but short of showing these hiring managers my Paypal and Merchant processor records how do they really know if I ran a successful business or if I’m making up stories?

Another thing I found was companies or hiring managers essentially asking why I was looking for a job if I was running a successful business. I really did run a successful business, I had SEO articles ranking on page 1 of Google I could show them, my site was still live. I could for the most part easily back up what I was saying or claiming, but I still found employers questioning this.

4. Your Skill-Sets Are Too Unique

Now this really depends what type of business you were running. In my case I was running a niche eCommerce business with one partner. We had a lot of success. We started the business with $268 and within a few years were doing over 3 Million in sales per year. Because the organization was so small I had my hands in every part of it from building websites, to graphic design, to customer service, to SEO, to order fulfillment.

I found myself in the position of being a Jack of All Trades, but a Master of None. I knew a lot about a lot of stuff, but I wasn’t necessarily an expert in any one area. While interviewing for positions like SEO Specialist, they were looking for someone who’s sole focus in life was SEO and content writing, and having been a business owner and having to spread myself so thin across so many things, I was good at SEO, but it wasn’t my primary focus.

Most organizations have very specific roles for individuals. In most businesses you’re not wearing multiple hats, your expected to do one thing and to do it well, and coming from the world of Entreprenuership, you’re much more likely to be a Jack of All Trades. I had one particular CEO tell me I have a unique set of skills, and he’d like to find a way to create a position for me and work me in, but didn’t think it was likely.

5. They Worry You Won’t Stick Around

You’ve probably heard the phrase once a cheater always a cheater. I’d say it also applies to the idea of Entrepreneurship. Once an Entrepreneur always an Entrepreneur. Entrepreneurs are wired differently. From how we’re motivated, to how to work, to seeking independence and freedom. We’re a different breed of people. Because of this employers worry you won’t stick around for the long term.

Now in reality I don’t think this is a fair assessment, because the current trend in the workplace, especially in tech and digital marketing fields is people job hopping every 1.5 to 2 years or so. So in reality even most “employees” are not going to stay for the long term and be stable long term employees. Yet still Entrepreneurs are a concern to employers.

Some employers worry you’re just using them for a steady paycheck and benefits while you work on launching your next idea, while other legitimately think you’re just going to be bored and leave.

One particular role I was interviewing for a digital agency and web design company. The vast majority of the projects I was going to be working on in my role, was going to be writing content and designing landing pages for Senior Care Homes. Both hiring managers told me I’d probably be better at the job than anyone else they currently had working for them, but that they knew I would be unhappy and that I would get bored. And to be honest, they were right.


Wrapping Up

So where does this leave you, if you’re someone who’s finding yourself seeking employment after a stint of a few months, a few years, or even a few decades of having been self-employed or as an Entreprenur?

I plan on making a follow-up post, possibly even a few, discussing how to sell your experience in the best possible light. What companies and what industries you should seek out which will appreciate your background, etc, etc, etc. Stay tuned for that.

In short though, do your best to frame many of these things about you in a way which benefits the company. Comming from the world of Entrepreneurship you had no boss so you had to be a self starter. There was no manager or IT department to run to so you could work independently and became a problem solver as there’s nobody else to go to with your problems. You were self motivated. You could teach yourself things and find answers to things on your own. This along with all the actual practical skills you learned or acquired.

Have you gone back into the workforce after a stint of self-employment or Entrepreneurship? What was your experience like? Do you have any additional tips to offer? Drop a comment below and share your story.