How I asked my old boss to start a business with me

Man pressing a start button

Emma Petroulas shares how she plucked up the courage to ask her former boss to go into business with her.

I love business. Especially small business. I grew up in my mum’s pharmacy and always had a passion for how things could be done better in business. Because I never got the whole science thing, and didn’t follow my sister into pharmacy, I became an accountant which was my pathway into small business.

Deciding to make the most of my accounting degree, whilst studying I worked full-time in an accounting firm and was drawn again to doing work for small businesses. It was here that I met Mark, my first real boss. By this stage, mum also had me doing the pharmacy accounts. She probably thought it was only natural that I did them. This was almost 10 years ago.

Mark was a good accountant and liked to work hard. In fact, I always thought he was a workaholic. Like me, he spent a lot of time in the family small business so he understood what I was passionate about. I loved working on small businesses, but I always felt that my wings were being clipped a little. The stuffiness of working for an accounting firm didn’t give me the freedom to express the way I thought accounting should be done for small business.

Having wanted to do some further study, my small business horizons were to change very quickly when my studies led into a lecturing position in small business accounting at the University of Technology, Sydney. My passion was satisfied and I was able to talk all day about a topic that I loved: small business. It’s still a position that I love and am passionate about. I have researched and published articles about small business and some of my former students now run multi-million dollar businesses.

My very own small business

But it was now my turn to create a small business. And I came back to where I started, accounting. All I could see was a market that still hadn’t changed considerably with the rise of technology; an industry that wanted bigger clients, not smaller ones. I just wanted to focus on small business and give them something that really worked for them. Just like what I used to do for mum.

For me, the issue I had was that even though I was really good at small business accounting, I loved chatting to small businesses even more. I needed a business partner that could compliment my skills so we could provide the best service to small businesses. They needed to be passionate about what they did and needed really good small business tax skills.

I created a list of all the people that I thought I would enjoy working with, and most importantly ones that had a love for small business. One name kept on coming up again and again. My old boss Mark. I would catch up with him every so often but him working with me for an idea that I wanted. It just wouldn’t happen. No, it couldn’t happen.

Why would a guy who I had worked for almost 10 years ago want to now work with me? Plus, he was on the road to becoming partner in the large city firm he was working in. And he had two kids so he couldn’t afford to start in a new business with no salary. All the reasons kept on coming as to why he couldn’t work with me. So I put it on ice. To be honest, I was a little bit scared of what he would say because the odds were so stacked against it happening.

Approaching my old boss

But the more I thought that he wouldn’t agree, the more I thought he was the best person for my small business accounting idea. I knew what he was capable of, he had spent many years taking care of the tax for small businesses, plus he was down to earth, someone who I could easily laugh with and feel at ease with.

I had to bite the bullet if I wanted this to get off the ground. So I caught up with Mark for a coffee. I put on my best suit. How else do you dress for your former boss?

In the corner of my local coffee shop, I gave my most passionate explanation of my small business accounting idea and why I thought it would succeed. The idea was a bit radical, a bit different, something that wasn’t available in the market for small business at affordable rates. Would he even believe it was viable? He didn’t give much away. The only thing he said was that he would think about it and we should catch up for a coffee again in 2 weeks. Was that it? After all of that.

I didn’t quite know what to feel. Was it a form of subtle rejection? He didn’t want to break my spirit so he was letting me down gently. After all, he once was my boss. Did he still think he was my boss and so was beyond working alongside me. I couldn’t quite work out how to feel.

It was a long two weeks before we met up for coffee again. He told me that for him, the two weeks had been even longer. He loved the idea, but he loved the passion that I had for small business even more. He said he hadn’t slept properly but was leaning towards saying no because he had to think of the kids and some of the other obstacles that I had thought might be there.

I knew I had to give this one more crack whilst I had his attention. I had refined the idea and my spiel over the previous two weeks and gave it to him again, the refined version. I finished. He paused over his coffee and asked a few questions. Things like number of clients, marketing, all types of questions about whether the small business market would like what we did. I gave my best shot. What was there to lose? He had already said it probably wouldn’t work for him.

And then he said yes. What could I say? My dream was becoming reality.

What I learnt from this experience was:

  • Respect is crucial in any relationship. Mark was able to see beyond our previous working relationship which meant we could discuss the business idea as equals. So, if you’re contemplating asking someone to start a business with you, don’t let a previous working relationship hold you back
  • Own the idea. Ensure you have done your research first and understand the market before you approach a potential business partner
  • Have a brief discussion first to gauge a potential business partner’s interest. If it’s not going to work, you’ll find out pretty quickly
  • Passion for the idea must be mutual. It is important to choose a business partner who has a passion for the business you are starting and the clients you will be working with. Also make sure your skills complement each other
  • No doesn’t always mean no. If a potential business partner says no but you can see they are passionate about your concept, don’t give up immediately. Listen to their concerns and see if there is a way of addressing them together. It’s amazing what a bit of passion can do.

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