Lessons Learned From Running My Own Business


by Anna Collard, SVP of Content Strategy and Evangelist at KnowBe4 Africa

I always enjoyed drawing, and as a kid you would have seen me sitting in class doodling cartoon versions of my teachers. More or less by accident – during an internship at Deutsche Telekom in Singapore – I fell into the information technology and, ultimately, cybersecurity field.

Because I never studied computer science (I went to an international business school), I was driven by imposter syndrome to work as hard as I could and keep on studying in order to keep up with my mostly male engineering colleagues.

Ten years into my security consulting career and while on honeymoon, I started combining what I learned in the security space with my love for cartoons.

Sitting at a beach in Zanzibar, I drew a storyboard for a cartoon animation teaching people basic cybersecurity skills, featuring characters like Fraudy Skimbag and Robin Yodata.

To cut a long story short, this storyboard became a cybersecurity e-learning product, and Chris and Kelly, our incredibly talented animators, gave the characters their final look and made them come alive.

Old Mutual, one of South Africa’s leading insurance companies, was our first customer and where my entrepreneurial story really began. Here are some of the things I learned along the way:

  1. Involve your customers from the start

I was fortunate enough to have built good relationships through the network while working as a security consultant. It was these contacts that I reached out to in order to get their input about my idea.

Instead of developing a fully-fledged product, I showed them initial drawings, shared my vision, and thereby was able to adjust to their needs. This ensured that we built something that was relevant to the market demands at the time. It also allowed me to ask them for advice rather than trying to “sell” them anything.

Ironically, this actually resulted in sales, as the customers perhaps developed a sense of ownership of the product when their input was taken into account.

  1. Be aware of your own unconscious biases

In the beginning, the Popcorn Training team consisted mainly of women who were all of similar age (my age) and new mums. Without being consciously aware of this, I hired people who were similar to me and to whom I could relate easily.

This is great when you are in the start-up phase, as you have to be able to really gel with your team. However, at some point, it becomes too one-dimensional and you need to look for team members that break the mold a bit.

A more diverse team makes for better problem-solving, innovation, and increased productivity. It is even healthy to have some conflict as long as this can be resolved maturely and people feel the psychological safety to disagree.

  1. Don’t waste your time on vanity stats

Vanity metrics are statistics that look spectacular on the surface but don’t necessarily translate to any meaningful business results. Examples include the number of social media followers.

These stats often take a lot of effort to achieve and your limited time and energy should rather be spent on real business creation, such as sales or product development. The same applies to spending too much time initially on your logo, website, business card (nobody uses these anymore), or social media presence.

Sure, at some point, you need these things to be put in place, but it’s much more important to work on your prospective customer relationships and your product or service offering.

  1. Cut your losses quickly

Sometimes things don’t work out. That’s just life, and it’s nothing personal, but perhaps the supplier you chose is not reliable or the hire you made turned out to be a sociopath. (By the way, I found that, on average, one in 7 hires turn out to be problematic). As soon as you realize that things don’t work out by your intuition – your “spidey senses”- move on.

It’s better to terminate a relationship early on instead of dragging things out. Also, be careful about the sunk cost fallacy — only because you spent a lot of time or money on something or someone doesn’t mean that it is still worthwhile pursuing. Rather write that money off as a learning cost.

  1. Learn to become laser-focused

There are a million things that want to distract you from doing what really matters. Our time is our most precious resource, and when running your own business while juggling family life, I quickly realized how little time we actually have.

Books such as “Productivity Ninja” by Graham Allcott, “Deep Work” by Cal Newport, and “Essentialism” by Greg Mckeown really helped me to develop my focus skills.

For example, each Monday morning, I take the time to write down my annual, monthly, and weekly goals. This helps me program my mind to focus on what’s important and urgent and to say No (“no, thank you”) to things that are not.

  1. Self-care is not optional

Having to deal with the multiple demands that come with running an operation, dealing with customers, people, compliance, finance, as well as new ownership, means having to cultivate ways to re-energize, stay healthy, and ultimately be more productive.

This led me down a path of self-discovery, self-improvement, and rituals such as meditation, yoga, breathwork, and other modalities, without which I couldn’t imagine living today.

For example, I used to subscribe to Calm for each of our employees and go on silent mediation weekends with the leadership team. I still have a long way to go, but these tools help tremendously in achieving levels of high performance and becoming a better version of myself.

Would I do it again?

Absolutely. Running my own business allowed me to meet amazing people and made me learn so many additional skills not just for my professional life but for life in general. It was not an easy path but definitely a very rewarding and joyous one, and despite the challenges, the path most aligned with my soul.

About Anna

Anna Collard is currently SVP of Content Strategy & Evangelist for KnowBe4 Africa where she drives security awareness across the African continent.  Collard founded security content publisher Popcorn Training, which was acquired by KnowBe4 in 2018.

Anna won the Women in Tech Innovations Throughout Africa 2020 Award for Southern and Central Africa. She featured in the Top 50 Women in Cybersecurity – Africa 2020 as well as the Top 100 Women in Cyber 2020 and 2021 globally by Cyber Defence Magazine.

She was awarded the ISACA South Africa prestigious President Award for 2020, featured in UK’s IT Security Guru 21 Most Inspiring Women in Cyber in 2021 as well as IFSEC Global Influencer in Security for 2022.





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