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How to bootstrap a company with a part time job

In my previous article, Setting priorities for your business I interview Kareen Aristide of Convergence Plus, whose business provides personal development training and coaching for individuals and families. When faced with a re-design of her business, she had to learn how to bootstrap a company by taking a part time job to finance her business.

For some entrepreneurs who have already had a business, taking a job might be seen as a step back. After all, the dream is to be free of working for someone else. While a regular paycheque is nice, it does come with strings that involve your time and loss of freedom.

If you follow Kareen’s strategies, bootstrapping your company with a job doesn’t have to be painful.

1. Know why you’re getting a job
First define what you want to get out of the job and how long you intend to hold the job. If you’re taking the job to further your skills, determine before hand what skills you intend to get.

2. Research first and choose a company that is open to entrepreneurs
Kareen says, “I told them that I was a business owner, and entrepreneur but was looking to supplement my income until I was able to go full time with my business.” In addition, Kareen was upfront about the sort of hours she was able to give, what sort of work she wanted to do, making sure these matched her current skills.

How do you find a company willing to go along with your plans? The key is research. Kareen would look for companies that already matched her priorities and values. She would also research their needs, and present her proposal to the employer in a way that her skills met their needs. “I was able to show them some of the things that I could do. I’d tell companies I love your vision, your philosophy, I want to help, so use me in anyway you see fit.”

3. Define yourself: Are you an employee or an entrepreneur?
Kareen details her experience at her part time job. “When I approached this particular employer, I approached it as a business owner first. You have to really define, am I an entrepreneur or an employee? If you decide you’re an entrepreneur, then, you have to look for organizations that you’d like to partner with or offer your services to. Approach them as a business owner, instead of approaching them as an employee. Find out what their needs are, and offer to partner with them. Like, “I’m willing to work as an employee for you in order to complete this hole that you have, then, once I’m able to do exactly what I want to do with my business to take it to a full time level, these tasks are what I will continue to do for you on a consulting basis.”

“When you bootstrap a company with a job, the most important thing is to take charge. Instead of waiting for a job that’s being advertised, target the companies that you want. Go meet with the decision maker. Conduct an information interview, where you interview the employer. Ask them what they do, what their needs are. Once you have that information, you have the upper hand. Then you can tell them what your services are, what your offer, and determine your terms.”

4. The employer is not your enemy

Kareen emphasizes, “a lot people don’t define their life according to what they want. They think that they’re at the mercy of the job market and the employer. The reality is, the more you know what you want and how you want to achieve it, the more you will get it and the more the employer is willing to work with you in order to get it. But if you don’t do your homework first, if you just say, ‘I just need a job,’ you’re not building your own dream. Most employers have their dream that they’re building and they’re using you as a resource to do it.”

5. Relationships matter

Sometimes when you go into a job declaring that you have other interests, employers might feel threatened. Some might even go to the extent of monitoring your work. For Kareen, it depends on the sort of relationship you build and the trust you can offer the employer. Kareen believes, “If an employer is looking over your shoulder, it’s because they don’t trust you. The reason they don’t trust you is because of something you project or something you’ve done in the past to make them not trust you.

“It’s important that the employer knows that you’re dedicated to their business and can show results. If you show results they will never feel threatened by anything you do. You need to show that you have their business at heart. That’s why doing your homework and choosing the right company from the start is key. Don’t look at the job as you earning an income. It’s more that you are helping the company move forward.”


If you’d like to learn how to bootstrap a company, contact Convergence Plus. Kareen provides training to help you define yourself and build better relationships.

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