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Interviewing Toronto Entrepreneur: Kim Orlesky

Welcome to our Friday Feature: Toronto Entrepreneurs segment, where we bring you insights, experiences, inspiration, and advice from prominent entrepreneurs in the Greater Toronto Area!

We’ve interviewed business leaders who have been kind enough to take the time to share their experiences with us on what it’s like starting their very own business (and nurturing it as well)!

We believe that these stories would be valuable to other aspiring or established business leaders. On behalf of, we hope that you enjoy reading this as much as we enjoyed creating it! Feel free to share this story with your networks.

Introducing Toronto Entrepreneur: Kim Orlesky, President of KO Advantage Group

Company Profile

Company name: KO Advantage Group

What does your company do? Sales Training for Entrepreneurs and Small Businesses

Year launched: 2017

Number of employees: 5


The Interview

1. How did you get the idea to start your business? After leaving my corporate sales career to travel around the world for 6 months, I decided I wanted to create a life that would allow me to have more freedom and flexibility in my life. I knew I was great at sales, specifically in high-value business-to-business services, and realized this was an under-served market in the entrepreneurial space. Many companies will spend tens of thousands of dollars in 3-day sales training, and that budget and time didn’t work for the hardworking entrepreneur and small business. I wanted to not turn business owners into sales people, but rather teach sales skills.

2. What's the best/worst thing to happen since you started your business? The best thing was being named Startup Canada’s female entrepreneur. This was at a time I would consider to be the worst time of my business. I was feeling low and not seeing things happen as fast as I would have liked. I was feeling a lot of self doubt that my program and sales training would ever really take off. I saw it as a sign from the universe to keep pushing through, and I’m glad I did. Business continued to really take off after that.

3. What are some of the challenges you’ve faced as an entrepreneur? As I continued to build my team I didn’t realize how much more of a manager I would become than a visionary. I am grateful I have a wonderful team that is willing to work with me and come up with amazing ideas. What I realize is that more often than I would like to admit the answers to many of their questions is, “I don’t know. We’ll have to figure it out”. I think it is a wonderful thing to be humble as a leader and be willing to empower the team to come up with solutions with you.

4. What are some lessons you’ve learned as an entrepreneur? Be much more conservative with cashflow than you would like to be. I consider myself to be a risk taker and am willing to spend my last $100 to potentially make $1000. However take into account that it could be longer than 30 days to see that money come in. Now that we’re coming through our first full fiscal year I am seeing the cyclical nature of the business and feel much more prepared for conserving cash flow for the slow summer months.

5. What are the best parts about entrepreneurship? The same reason everyone gets into it - the freedom! I have an 18-month old son and I don’t take any in-person meetings, and limit myself to less than a handful of phone meetings on Fridays, because that time is dedicated to him and me. My husband and I also have a summer place that we love leaving on Thursdays and returning mid-day Monday. It allows us to calmly go there and back. There is no job in the world that would allow me to have that flexibility and feel like I’m still making an impact on the world. Happiness starts at home, and I make sure they always get the best of me first.

6. What has been your most effective form of advertising? Hosting events. There is no comparison when people are able to meet me in person, hear me speak, tell my story, and build a strong relationship. I have had people attend for the first time and buy or see me at different events and then decide to invest. Don’t discount your local geography or the opportunity to meet people in person. Face-to-face is the best way to create value for your premium service.

7. Who are the entrepreneurs you look up to? When I build my business I wanted it to be a mash of Grant Cardone and Marie Forleo. I love that Grant has a sales school that is recognized by so many people. His latest 10X Conference bring tens of thousands of people from around and it really builds people up. Marie Forleo created a great name for herself and built it around the reasons why you want to be an entrepreneur.

8. What goals have you achieved for your business so far? The moment we had our first student sign up and have the course taught, without any intervention from me was a MAJOR milestone. I actually shed a tear in that moment. It solidified the idea that we have a great course and the content, not the teacher was what students were looking for. It also was the first moment that I realized I was building something bigger than myself and I was creating a business that was independent of myself.

9. What are your goals for your business in 2018? Being a young business still, almost every goal is revenue related. We want to hit the elusive $1M mark (and definitely believe this is within arm’s reach) and want to consistently fill two entrepreneurial student classes and teaching two small business teams once per month.

10. Where do you see yourself and your business in 5 years? I would love to see the team continue to expand. I want to have our sales training recognized across all of Canada and the eastern and western seaboards of the US. I would love to have my next book become an international bestseller. I would love to host a weekend conference helping to empower more entrepreneurs on the power of slowing down and creating more connection in the sales process and away from online and marketing-only activities.

11. What upcoming projects are you working on? Currently writing my third book, which will be all sales focused. This has been a project that has been in the works for far longer than it needs to be and I am excited to have it completed. I know that no matter if people are ready to invest in sales training or not, they all need to read this book and understand why the sales conversation needs to happen BEFORE the marketing conversation.

12. What trends are you seeing in your industry? Everything is moving online, but I think there is a hybrid between being completely hands off with an e-course, and instead using technology to create a stronger connection. We do our courses online and with an instructor. This allows us to fill the course from people all across North America and create powerful student relationships. More and more training companies are going to be moving towards our model and I know we only have the advantage for a slight period of time, so our ask in every one of our quarterly strategy sessions is how do we constantly make ourselves better?

13. What business advice would you give yourself if you were to start all over? Be quick to fire and slow to hire. When I knew I needed a person to help me build my business I was so lost when it came to hiring. I hired the first person that checked most of the boxes. In the end this was not the best hire for the company and because I had already invested so much time I kept trying to nurture the employee instead of deciding to let it go. In the end I was grateful that she decided to part ways with me, but it cost my company FAR MORE than if I would have just ripped off the bandaid. Now I vet every hire with the entire team and we know that it may take a month or two to find the best fit, but they will work with the team as we grow, not just be stuck in a role that is likely to evolve and expand in a short period of time.

14. Last but not least, let’s end off with a fun fact! What might we be surprised to know about you? Before graduating from university with a degree in Finance I really wanted to become an actor and was actually in school for Drama.

Social Media

Let's get social. Follow Kim Orlesky on social media!

YouTube - Facebook - LinkedIn -

Twitter -

Many thanks to Kim for sharing her story with us! Stay tuned for our next featured Toronto Entrepreneur!

Do you have someone in mind who should be on our Friday Feature – Toronto Entrepreneurs segment? If so, email

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