Disclaimer: 9to5gadgets.com is a participant of the Amazon Services LLC Associates Program. Any valid purchases made through clicking on the links on this site (when directed to Amazon) will garner us a commission.

Hiring an Entrepreneur: The Pros & Cons You Need To Know

I've been an entrepreneur for most of my adult life. In fact, I can confidently say that except for a brief stint answering phones I've worked for myself setting my own hours for the past decade. I'm what's known as an entrepreneur. 

You might hear that word and go straight to Elon Musk, Bill Gates, and Steve Jobs. However, the truth is that in the US alone there are 31 million entrepreneurs - 16% of the workforce - according to the Global Entrepreneurship Monitor, and most of us don't make splashy headlines and don't go on to become eccentric billionaires. 

The normal route for an entrepreneur is to start off with a "normal job" and then transition to being an entrepreneur. However, in some cases, entrepreneurs will also enter the workforce and send their CVs. They aren't your normal CVs and they aren't your normal employee. I know this because I am one and I did enter the workforce as an employee so today I'm going to explain to you firsthand the pros and cons, risks, and benefits your company can have when hiring an entrepreneur.

It goes without saying that this is my own personal experience and my own personal view on the subject and it may not apply to all entrepreneurs since we are a very mixed set of profiles by default.

The Pros and Cons of Hiring an Entrepreneur

I always like to know the bad news first and then the good. I'm going to take the same approach here and we will start with the cons of hiring an entrepreneur.

Cons of Hiring an Entrepreneur

They aren't used to company politics and don't speak the "company language"

While most candidates you may consider for a job will have previous company experiences where they've had to learn how to adapt and learn company politics, entrepreneurs like myself are new to this. 

I found it difficult while working in company X to understand when my manager was saying one thing and meaning another. When you're an entrepreneur you are very direct with your feedback and you don't mess around because time is money. This doesn't mean being blunt but you can expect an entrepreneur to be more direct. 

One of the first challenges I had to overcome when starting to work at a company was learning to read between the lines and that what's being said is almost or equally as important as what isn't being said. 

Also, while company politics play a big role for most people, for entrepreneurs they really don't matter all that much. When my manager or boss would talk to me about future performance reviews it wasn't as important to me as it might be to some of my colleagues simply because I took the job to learn and that's my driving force, not anything else. 

They need to be nurtured and need more feedback than traditional employees

While it's true that as an entrepreneur I'm used to wearing multiple hats and being comfortable with every decision I made I found that my behavior as an employee was quite opposite to that. I took the job to learn, grow, form relationships, and get out of my comfort zone so that means that I needed perhaps more feedback - especially when starting out - to know that I'm doing the best possible job. 

Because ultimately, that's my goal. To do the best possible job and reach that point in the shortest amount of time. In the entrepreneurial world time is money and if you don't move quickly and adapt you can lose out on big opportunities.

That's why when you hire an entrepreneur you should consider that you might need to dedicate a bit more time to give him feedback and nurture his talents as well as his weaknesses. That might not be very attractive for a company depending on their policies.

They aren't "worker bees"

You can't hire an entrepreneur to do the same exact task over and over again or constrain him to do just one or two things because the chances that he will leave are far greater than those of a regular employee who could be more used to having to handle long periods of doing repetitive and "petty work".

They will also hate having to go through office politics and jump a ton of hoops to get their job done. For example, if I know that a small payment is needed to help the company grow I'm unlikely to feel comfortable having to get that approved with all the bureaucracy that it might entail. Especially when you're used to making that decision on your own.

An entrepreneur needs to feel a sense of control as well as a sense of autonomy to make decisions that will help him do the best possible job. 

They can struggle with the 9 to 5 life

I will admit, this is perhaps one of the biggest challenges and why I joined company X because they had a flexible work schedule. 

An entrepreneur is used to being the owner of his time and knows how to use it at his own discretion. This doesn't mean that they won't show up for meetings or anything like that but that they are not used to selling their time and will do better in a more flexible goal-oriented position.

This also applies to vacation days. As an entrepreneur, you decide when you work and when you don't want to work. Having to request permission to not work can be a really different experience. Surprisingly this is one that I actually took on with less difficulty than expected. 

What I struggled with the most was with sick days. Again, when you're working for yourself and you don't feel well you don't need to justify to anyone that you're taking a sick day. However, in a company that's not how things work and you do need to let them know and essentially ask for permission to be sick. 

They can bolt if things don't work out

An entrepreneur will always be an entrepreneur. You can place him at a 9to5 job but that doesn't mean he stopped being an entrepreneur, that's something you're basically born with. This means that your entrepreneur will likely have a side hustle or be working on one in his spare time. This also means he is most likely confident enough to leave if things aren't working out.

While a regular employee will generally fully depend on the company's salary to meet their financial needs, an entrepreneur will likely have a backup plan - or three - in place if things don't work out and won't waste his time if that's the case.

Your entrepreneur will likely leave if you have a toxic work environment if you aren't nurturing his desire to learn, if you are giving him repetitive tasks and if he has to deal with awful office politics. If this set of conditions happens and your entrepreneur is confident and/or ready to move on he won't give it a second thought. Especially if he is not particularly strapped for cash. 

Money is not their main motivator

Again, while most employees will be working to get a paycheck at the end of the month and dreaming about getting a promotion for an entrepreneur the motivation needs to come from a sense of fulfillment. This doesn't mean they don't care about the financial aspect but it's less relevant since for them this is also a learning and social experience

Additionally, entrepreneurs know what it's like to go through tough financial times and it's rare if you find one that hasn't had a rough patch at one point or another so they aren't as scared of this because they know all too well that they can weather that storm and use coupons if that's what it takes to get back on the horse and see their vision come true. 

Freedom will always be more important to a true entrepreneur than money. As Lori Grenier once said, "Entrepreneurs are the only ones who are willing to work 80 hours a week to avoid working 40 hours a week ".

Pros of Hiring an Entrepreneur

They are excellent managers

Entrepreneurs are used to dealing with lots of different types of personalities and will ergo be a perfect choice for a management position. They know how to get the best out of everyone

They know what buttons to push to get the best possible performance out of their workforce and with enough autonomy will push through to achieve the company's goals under budget and ahead of time. 

Place them in a repetitive role and they will die but if you place them in a position where they need to make decisions and engage with people and strategize, they live for that, that's their bread and butter.

They will give you their all

As an entrepreneur, I'm not used to having a work schedule. I work when work needs to get done. As a consequence of this, I noticed fairly quickly into entering company X that I was giving them my all. Once I understood and believed in the mission and had enough autonomy to work without much oversight I found myself reaching a whole new level of productivity. 

Also, as I mentioned before, we are not creatures of the 9-to-5 lifestyle. Therefore If answering an email at 10 PM with a client that's in a different time zone will move things along faster than I'm prone to doing. My co-workers found this behavior odd since when they check out they've CHECKED OUT but I don't really have a "check out" time. My brain is constantly thinking of ways that I can deliver more, be more, do more, and get more.

They are natural negotiators and will save you money

To be a successful entrepreneur you have to have good negotiating skills. While this is something most people find uncomfortable for entrepreneurs it feels like a game. I found it strange that most of my co-workers would not really negotiate the prices with our collaborators. 

They would just accept them. Fortunately, as an entrepreneur who had to deal with a rough patch, it's in my DNA to negotiate and always try to get a better deal than what's on the table.

I would do this even if the price offered was well within our scope. Worst case scenario the client will say there is no room for negotiation and you'll end up paying the original price or not accepting at all if the price is far beyond the company budget. Typically I would get 25-30% discounts just by asking and that's something that ultimately does count on the bottom line. 

They bring a whole new set of ideas along with them

As an entrepreneur you need to hustle and squeeze the most out if every penny invested into the business which means you will learn new ways of doing things and new tools to get things done. Unlike standard employees who will typically be accustomed to doing things in a fashion that is popular amongst medium and big companies, an entrepreneur will deliver a new set of tools and ideas to streamline processes when he joins your company. 

That does not mean he can't adapt to new ways of doing things - he will want to learn after all - but he can offer a new perspective.

They think outside the box

Again, to drive home the previous point. An entrepreneur is used to seeing the big picture and tracing a path to getting to their ultimate goals which means they look at things from the big picture. That's why they are excellent in leadership positions where they need to be in charge of executing ideas that help the company reach their end goal. 

They aren't thinking about sticking out a job for a paycheck, they want to learn and acquire valuable skills that could later be of value to him so thinking small is not part of their DNA.

They are very honest and that allows you to take the temperature on a department

I once had someone say in company X that I was the "most honest person he has come across in the work environment, for better or worse". This is great for the HR team since they will get a real picture of what's going on in a department when they talk to the entrepreneur in that department. It's not that they are very blunt but they don't view the experience of working in a company as the sole option they have for survival since they typically have a few options up their sleeve. 

In that sense, the entrepreneur has little to loose and a lot to gain by being honest and doing his part to make the work experience as positive as possible for everyone involved. Sure, this might upset his superiors but that's not something that is particularly worrying for an entrepreneur since the worst case scenario is that he will be fired and continue with his entrepreneurial efforts, a return to the previous status quo. 

And quite honestly, being fired for being honest about what's working and what's not working within a company should be a reason to leave that company altogether, regarthless of you being an entrepreneur or not. That's not really a positive climate where you will thrive.

Conclusion: Should You Hire an Entrepreneur?

The answer to this question after evaluating the pros and cons of hiring an entrepreneur should be clear by now depending on your company structure, company climate, the role you are looking to fill and the type of person you need for the part.

If you're going to hire an entrepreneur to do a repetitive job where he has little chance of learning and growing within his job then honestly don't bother since he will be the first one looking to get out. And we are talking about a very quick turnover rate here, not several months or years. 

If you have a company culture that doesn't align with the entrepreneurial lifestyle then you still have a good chance of him being a good employee as long as you keep nurturing his need to grow and learn. 

Obviously it's also critical that you have the resources - ie: time - to properly train him on the tasks he is not accustomed to performing since otherwise that could be a train wreck waiting to happen. A solid time frame for an entrepreneur to get confident in a new job is typically along the three months so you need to be ready to offer him that. 

And, of course, if your company REALLY values initiative, new ideas, thinking outside the box, doesn't have rigid structures in place, offers a nurturing environment where the entrepreneur can feel free to ask questions and suggest chages and your looking to fill a role in a department where the entrepreneur will get a chance to connect, discuss and grow then you should definitely consider hiring an entrepreneur since he could very well be the very best fit for the role.