It’s always been in my nature to follow rules while remaining unconventional. In high school, while my friends slaved away at local fast food chains, I opted to be the neighbourhood babysitter. What’s better than getting paid to watch TV, play games, and jump in the hot tub after the kids are in bed? Once I got my drivers license I turned to alternative jobs in the marketing field, like spending my summers outdoors doing the Pepsi Challenge.


Looking back I credit the notion of rule-following to my parents who were Kenyan immigrants to Canada. They insisted that following the rules always leads to success.  It seemed to work out for them. My father enjoyed a successful career as a high school chemistry teacher and my mom, a registered nurse who went on to work in hospital administration.


You can imagine my parent’s disappointment when I chose to take the path less travelled and launch a tech start-up. Naturally, I was under the impression that I just had to follow the rules and success would find me. Create a business plan. Check. Develop a MVP. Check. Get users. Check. Show proof of concept. Check. Check. Check.


So why was it that every time I reached a predetermined goal my efforts were met with a lukewarm response followed by an abrupt reassessment that ended up with the goal post moving. It dawned on me that the rules of entrepreneurship do not apply to all. I’m talking about those of us who belong to underrepresented communities in tech. Black. LatinX. Indigenous. Women.


I’m not suggesting that I did everything perfectly. However, I’ve put my 10,000 hours (x5). I’ve personally witnessed companies moving forward with just one eigth of what I was bringing to the table. Through it all, I realized that the rules do not stand alone. If you look really close there is an asterisk. It’s almost invisible to the naked eye, but it’s there. An alternative set of terms and conditions. The only way to access them is if you’re in the “inner circle.”     


It’s not all gloom and doom. Change is inevitable and is slowly taking place. There are founders, incubators, mentors, VCs, corporations, and community groups working to improve the disparities. The one thing that remains the same is the number of founders that reach to me looking for advice on how to navigate through the asterisk.


This blog is my way of sharing my personal experiences, both good and bad, in the hopes that founders can bypass the challenges that tripped me up.


Welcome to Asterisk. The fine print…from my perspective.

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