Livelii Member Spotlight: This Founder built a startup from her basement

Running a business takes time. It’s not just what you do for others, it’s what you do to support yourself that contributes to success. Shantae Cunningham, a Toronto-based expert in Finance and Accounting and a member of Livelii, shares her story on how she took her business, Cobella Financial, from her basement to the big times.

  • Why did you want to get into the financial services industry and start Cobella Financial?

I wanted to get into Accounting since a business class I took in high school during grade 12. I always loved going to that Business class and learning about how Accounting worked. We had an Accounting executive from Pepsi come into the class as a guest speaker and he talked about his work and his journey. I’ll be honest he glamorized the life of an Accountant and I ate it up. From there, I decided to go to school and pursue a career in Accounting and Finance at Seneca College and enjoyed everything I was learning about business, accounting, and finance. I would always go home to my grandparents who were immigrants to Canada and tell them what I’ve learned and ask why they didn’t do this or that. Ultimately, they just didn’t know and I soon realized that having the available resources and financial literacy can change the trajectory of your approach to things in life. During and after college, I took on many Accounting related jobs.

While working full-time at a public accounting firm in Toronto as an Enterprise Bookkeeper, I was also working as a freelance bookkeeper as my side hustle. I was the go-to person for my friends and family that were starting their businesses to navigate through finance and bookkeeping-related questions as well as navigating the waters with the Canada Revenue Agency. With their business growth, I grew with them and ultimately decided to take a bet on myself, quit my job and start my own company. Then, Cobella Financial was born and I haven’t looked back since.

  • Tell us a little bit about the name and its significance, because that means a lot to you as well. And also I love the story behind it and what it represents.

I originally had the vision to create an online blog called Bomm Cobella that would blend beauty, lifestyle, and finance for the everyday woman. This blog would give digestible information and tips around financial literacy and equip women with resources while discussing familiar topics with them. I had even created a YouTube channel on it for a bit. This was a passion project of mine for a while that ultimately was never launched. Cobella Financial was built from the idea of Bomm Cobella. To me, the name Cobella was a play on words of the word “head” from the word “Cabela” which in Spanish means hair. The idea of Cobella was to think with your head about all aspects of your life, and finances.

  • A lot of entrepreneurs can become married to the vision of their business. Talk to us about how you approached this when starting up.

I instill the vision of Cobella Financial to new clients that I met, had a consultation call or discovery call with. Not only did this help me with my elevator pitch but it also helped me to meet other business owners that aligned with that vision. It also helped me to create a vision for where I see Cobella Financial in the next 1 year to 5 years and start the roadmap to meet them.

  • Talk to us about some of the lessons and maybe some of the shortfalls or failures that you faced that taught you a lot in this journey.

Every “L” I took was not a loss but a lesson. A few of the speedbumps I’ve experienced on my journey were thinking I could do it all alone and almost risking burnout. Frankly, I was spreading myself too thin to wear every single hat at Cobella Financial during our season of growth. Also, in the beginning, in the process of growing my company and of course making ends meet financially. I had said “yes” to a lot of projects and clients that I should’ve said “no” to. This helped me though, to understand the type of clients and industries that I love working with. People-pleasing is a top issue among many entrepreneurs, especially those just starting. This feeling passed as I built my confidence as a business owner and shut the door on “imposter syndrome” to know my worth.

  • Looking forward, what are some exciting projects that you can share? And what else are you doing to scale Cobella Financial to the next level?

There are very exciting things in the works with Cobella Financial for 2022! A lot of which hasn't been announced yet. We’ll be launching a masterclass this year that will help business owners that are in the earlier stages of their business, just starting, or have a side hustle they hope to make a full time. Details around the masterclass will be released soon! We’re also hoping for some in-person events now with the Covid restrictions in Canada settling to educate and meet our community in person. We’re also working on a program for youth to give the tools of Financial Literacy and Entrepreneurship.

  • What is one area of the business that you would dedicate all of your time and efforts to if you could?

I’d love to be able to dedicate all of my time and efforts to Social Media and other Marketing efforts. This would help me have more time to create more interactive video content and build a larger online community with Cobella Financial. Owners of Accounting firms are rarely seen to dominate with their online presence or be known as The Best Marketer. However, as a business owner, it’s best to recognize when it’s time to outsource some of your weaknesses and have an amazing social media manager on my team.

Get in touch with Shantae - Instagram | Linkedin | Website

About Livelii Livelii comes together as a group to tackle challenges, reduce fees, remove barriers, and provide transparent pricing each calendar year. As a groundbreaking first-ever platform in Canada, Livelii is focused on building a community of Independent workers in Canada to provide Health, Dental & Life Insurance coverage without bias. Visit to learn more about Livelii and our mission.

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