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Stuart Gentle Publisher at Onrec

Should You Really Hire an Ex-Entrepreneur? Pros and Cons

As an employer, it is your duty to source for the best talents in your industry and to set up a team that can effectively set your company on the path of growth and prosperity.

But with today’s fast-revolving business world, it is hard to find employees who are qualified and dedicated to work on your ideas and goals to fruition.

At Techtiq Solutions, we find it extremely hard to hire client facing staff that are both commercially and technically sound at the same time to help out clients in strategising, building and launching web and mobile apps.

And after going through hundreds of CVs, we find a rare breed of resumes that show past entrepreneurial activities that either failed, or in some way the candidate just exited the business and is now looking to get back to being an employee.

If you are like many people, however, you probably are skeptical about this approach. If you are, this article will help you to understand the pros and cons to expect should you hire an entrepreneur. Please read on.

7 Proven Benefits of Hiring an Ex-Entrepreneur

Entrepreneurs understand everything around business risks, potential opportunity and failures

Most ex-entrepreneurs are people who took bold risks before; risks that probably led to the collapse of their businesses. And because they didn’t fail on their very first day in business, they must have had their fair share of entrepreneurial success at some point. What they bring to the table, therefore, is an all-around experience of both failure and success and a zeal to take on experiments and risks.

An ex-entrepreneur knows the benefits and dangers of early-tech adoption, for example, so they will help you to decide which tech products to acquire and when. He will help you in deciding on how and when to launch new products, and which marketing strategies would work best for your company.

And this skillset you might not from any other hire you will make.

They focus a lot more on the “bigger picture” than on petty workplace politics

A former entrepreneur will only apply for a job in your company if your vision and mission align closely with his/her growth objectives. This goes without saying: All that person needs is a chance to redeem himself from past failures and to bring to life the great ideas he couldn’t actualize in his own company; probably due to financial constraints, lack of resources, or just mistakes that they’ve learnt from.

If you hire an entrepreneur, he will spend most of his time working for the company’s big picture and less time participating in petty employees’ squabbles. Issues like who occupies which office and who deserves what compensation are not really important to such an employee for as long as you give him the chance to grow his entrepreneurial skills within your organisation.

Ex-entrepreneurs are great fits for leadership positions

Ex-entrepreneurs comes with tons of experience in strategizing for big projects, outsourcing funds, building and managing teams, and solving complex business problems. Maybe that person was a competitor of yours- regardless of how small his company was- so he probably has done enough research about your company and the industry as a whole. He definitely understands what your company needs to do to shake off the competition.

Ex-entrepreneurs also understand the art of hiring new talents and firing dead weight. If you give them the freedom to hire their own crew and make important departmental decisions, you can bet that they will thrive in their job. And because they learned from real-life business experiences, they are confident in their management tactics, unlike some classroom-trained managers who keep second-guessing their own decisions.

They never get comfortable

For your company to grow, you need people who are able and willing to take your ideas and make them better. As a matter of fact, an employee who implements your ideas to the latter without tweaking and improving them will never give your brand the competitive advantage it needs to become an industry leader. Regrettably, employees who lack the entrepreneurial spirit easily get comfortable in their status quo and shut off innovation and creativity for as long as their paychecks keep coming.

Ex-entrepreneurs are nothing like that. They are so dedicated to correct their past mistakes that they cannot afford to get comfortable. Their endgame is, in most cases, to learn more about key aspects of running a successful business: marketing and promotions, managing budgets, and raising capital, etc. They are always hungry for more and, with the right strategies, your company can really benefit from that hunger.

They are relentless in their pursuit of success

When a potential business lead presents itself, entrepreneurs jump on it faster than everyone else and pursues it to fruition. They aren’t quitters. If you assign a task force to them, they will get the best out of every talent and skill under their management. And even when the available resources seem to be insufficient, a former entrepreneur will always maximize every penny until the end goal is achieved.

Also, ex-entrepreneurs will inject the sense of urgency when everyone else in the company advocates for the pursuance of slow, steady growth. By improving the speed of existing operations, other employees will be forced to work extra harder in order to keep up with the pace. That means higher productivity and increased company revenue.

They know how to nurture healthy business relationships

Employees who go beyond their job descriptions to attend to customers, engage in community service, and network with potential investors on behalf of their companies are priceless for any employer. As a matter of fact, many employers these days are training their staff on the importance of relationships at different levels of business. But, in this regard, you don’t need to train someone with an entrepreneurial mindset because he/she intuitively values healthy business relationships.

They are versatile

If you hire someone who previously managed a startup company, that person will come with actionable experience on literally every aspect of running a business. Why so? Because startup entrepreneurs are basically jacks of all trades. You will find a small business owner doubling up as the social media manager, helping in designing the website, customer relations officer, human resource manager, technical manager, or even the tech expert. This is the versatility that you need for seamless flow of operations between departments.

 Cons of Hiring Entrepreneurial Employees

They can be dreadful future competitors

Someone with an entrepreneurial spirit will not rest until he/she succeeds as an entrepreneur, possibly not as an employee. He will help you to actualize your ideas, alright, but he will equally be learning your wits and strategies in readiness for his future business ventures. And because of his intimate understanding of your company, such a person would be your nightmare competitor.

Ex-entrepreneurs will even use your company to experiment on different unexplored territories within the industry, mastering the dos and don’ts in the process. After all, he will lose very little if your company collapses due to risky experimentation.

Potential anti-establishment

Former entrepreneurs are good team leaders but when they aren’t in charge, they can be horrible team players. They are too confident in their ability and decisions that they often struggle to follow set processes. They are probably too creative to be doing the same each passing day or to be restricted to a cubicle for hours on end.

To motivate such a person, you will have to give him a seat at the decision-making table and act on his ideas in the most convincing way.

They are prone to over-ambitiousness

As we mentioned earlier, one of the reasons why a former entrepreneur took your job offer was because he/she wanted a chance to redeem his/her unfruitful entrepreneurial ambitions. Sometimes these ambitions boil over to uncontrollable, unrealistic levels which, in turn, lead to frustration.

 If, for example, your company is unable to raise enough resources to implement the employee’s ideas, chances are that he will get demotivated to the point of never giving his 100% to the company ever again.

They are constantly on the move

Entrepreneurs get bored with daily routines way faster than other employees. If your company is growing at an acceptable slow rate, an entrepreneurship-minded employee will feel like his talents are being wasted and so he will bolt out.

Another case is when he feels like he has learned or accomplished everything he wanted in your company so he chooses to move on to find new, bigger challenges.

Also, a potential entrepreneur might move on to start his own company the very moment he raises enough funds for business capital.

Prone to irreparable mistakes

Entrepreneurs are bold risk-takers, which makes them great assets for any industry. But sometimes that boldness results in unimaginable losses, particularly if your company is struggling financially.

And again, how can you be sure that they will not import the problems that collapsed their own companies into yours?

They don’t get comfortable

This is both a good and bad thing. Although comfortable employees aren’t as innovative as their entrepreneurial counterparts, at least you are sure that their lives start and end with the company. Such people will rarely think of starting any side hustles.

Entrepreneurs, on the other hand, will never be contented with their monthly paychecks. They will establish small businesses on the side, consequently burning themselves out.

Final thoughts:

Even with all these pros and cons, it is worth noting that they aren’t all applicable to every ex-entrepreneur out there. People are different and so are the entrepreneurial employees. It is therefore incumbent upon every employer to device a foolproof recruitment process in order to get the right employees for their existing processes and objectives.


Chris Kimera is the founder of Techtiq Solutions, a digital agency in London that specialise in innovating, designing and development of websites and mobile applications that solve traditional business problems.