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What launching my first business taught me about failure, strategy and mindset.

I have a love/hate relationship with Facebook. I love it because it is still the best place to shop second-hand and to find events happening in my community. It is also still the place where most business people go to host groups. So I remain.

What I resent about it (and in saying this I recognize that I gave my permissions away by posting there in the first place) is that it’s hard to download old videos or photos that you’ve posted in past years. Which is why I no longer do this. That said, I do appreciate it when they show me pictures from my past on my feed. This is what popped up today.

Our first winter carnival!

It was a nice little trip down memory lane. It took me back about ten years ago to when I launched my first business. An online community for families with kids under the age of 5 who needed a place to find events and activities happening in our community. (no longer in existence) was a labour of love. I was on maternity leave with my first child and had been looking for a business I could run and raise my family on my terms. I came across a similar business model happening in another community and saw a need in our own. I had felt the isolation of being a new mom and craved opportunities to take part in activities with other new moms. I found it very challenging to these activities as there was no central events calendar.

I made it my personal mission to bring all these events together in one place to make it easier for parents to connect.

I threw myself into learning how to build a website using WordPress. I created a Facebook page and posted the events I’d found to generate a buzz amongst parents so that I’d have a stream of people ready to visit my site. By the time I’d launched (three months after the idea was born) I had over 100 parents following me on Facebook. The website and community immediately began to grow from there and experienced a steady increase in monthly traffic.

I knew that if I was going to make this a viable business I had to monetize it at some point. Because of the traffic I’d built, I was able to build a business directory into my website. I reached out to businesses that catered to kids and family and offered them a way to reach their target market through a directory listing on the site.

Fast forward a year and a woman I knew through a business development group reached out to me to partner up. She had an idea for a blog on parenting and wanted to work together. I welcomed her on board because I appreciated her vision and admired her gregarious nature. I felt she had complementary skills to my own and together we could take this business to the next level.

We incorporated the business.
We launched a blog and six digital publications.
We published an annual print magazine.
We produced a trade show for new and expectant parents.
We produced a holiday event.

We were on fire!

We had managed to build an online community that generated over 40k visits per month at one point.

We raised thousands of dollars for local causes.

Our Facebook covers to promote our trade show

Best of all, we provided businesses with an audience on almost all forms of media – print, online and in-person.

You would think we had it all figured out. Because of my family situation, I was able to leave my full-time job at Disney to focus on the company full-time. This was about two and a half years into the business. My partner was still working full-time in her career and part-time in our company. We even hired a part-time sales rep to help sell advertising space.

We spent more time talking to each other than our own husbands, we often joked. I am so proud of what we created together. I will forever be grateful to her for this experience.

Things started to fall apart around the three-year mark. The writing was likely on the wall before this, but I didn’t see it (or refused to). I was working tirelessly and that had an effect on my family and friendships. I was also pregnant with my second child.

We sought out mentoring and guidance from a local tech accelerator program. This seemed like a promising move because we identified gaps in our knowledge. Our mentors agreed that there was potential for this to be a scalable business model.

Despite the promise of growth, the issues that were present prevented us from making it a sustainable business on a local level.

Four years in, my frustrations and stress-level had increased to a breaking point. I sat my partner down and let her know that I couldn’t continue to operate the way we had been. Something needed to change.

We agreed that she would take over the business and I would exit. My marriage was also ending at the same time and I needed to find a way to continue to support myself and my family.

What ensued was a year-long process of exiting the company from a financial and legal perspective. It was messy and uncomfortable. It impacted our friendship for years afterwards.

I call this first business my most successful failure because I learned some valuable lessons along the way.

While there were many things we did well, there was a lot we could have done better. I’ll share these with you now.


Avoid failure by paying yourself

I figured that we would pay ourselves with the net profit in the company. There often was very little. We made almost no income from this business. For four years we poured blood, sweat and tears into this with very little compensation. I’m grateful to my ex-husband for supporting us financially during this time so I could pursue my dream. It certainly wasn’t easy for him on many levels.

I knew nothing about raising capital and was against taking out a business loan to fund this venture. Had I done some more research in the beginning and equipped myself with more knowledge, things might have turned out differently.

Burnout is real.

Avoid failure by creating a financial + strategic plan

Our mentor at the tech accelerator introduced us to the cash flow forecast. We had only been operating on rough budgets for the first three years and did not know how to project into the future.

Cashflow forecasts are integral to planning out your business. Establishing a solid strategic plan based on the cash flow is imperative to make sure that you realize your financial goals.

Get it in writing

If you are going to form a partnership with one or more individuals… Get. It. In. Writing.

Draft up a solid partnership agreement. Write out all the potential scenarios that the partnership can dissolve. Outline how each potential scenario will be handled. Write out the division of work. Document the compensation agreement. Get it all down on paper and sign it. This will help prevent friendships from potential ruin. I say this from experience both in how they can be a total failure and from how they can be salvaged.


Lean into the fear

This is important on so many levels. I was afraid of cold calling. I was afraid of going into businesses to pitch my idea and generate new clients. I held many limiting beliefs about myself that prevented me from generating the revenue required to make this sustainable.

I was afraid of failure.

When I leaned into the fear I had more success. I grew by leaps and bounds. When I gave in to the fear I became stagnant.

Don’t focus on just the hard skills
I’ve always considered myself as someone with a growth mindset. But I spent more time learning new hard skills and didn’t pay enough attention to the soft skills. This held me back and kept me feeling small for way too long.

Always. Invest. In. Yourself. In becoming 10% better every day. Develop your emotional intelligence so that you have a solid action plan on how to balance your strengths and weaknesses.

Entrepreneurship a gateway drug to personal development.

Bump & Beyond Magazine

Launching and growing this business was one of the most challenging, rewarding and humbling experiences I’ve ever had. I’m forever grateful to my business partner in this for the shared experiences and lessons.

My hope in sharing this story with you is that you find something that resonates. Not all failure is bad! I think failure is necessary in life to help us grow and become better people.

Or, that you simply enjoyed getting to know a bit more about some of my entrepreneurial adventures and failures!