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Navigating Entrepreneurship and DEI in the Workplace: an Inspiring Interview with Andrew O’Brien


Meet Andrew O’Brien, the founder and CEO of Obie & Ax, the largest and first-to-market podcast production firm. He has spearheaded the pioneering of a company like this, working with esteemed clients such as the FBI, Walmart, and even the Toronto Police on building their own podcast series. Andrew himself has a strong background in business entrepreneurship, building and selling tech companies, even partnering with Michele Romanow, who also is a Dragon on the show ‘Dragons’ Den’.

Obie & Ax’s core values are built on Diversity, Equity and Inclusion, talent acquisition, and community relations. They ensure these values are upheld not only externally, with a diversified application process, marketing, and KPIs tailored for diversity, but also internally with company-wide Think Tanks and feedback procedures. Feedback is essential, not only to improve workplace performance, but to cultivate a place of safety and appreciation, where employees will be happy in their roles and want to come to work.

Within the community, Obie & Ax are dedicated to these beliefs through educating their clients. They are partnered with Sonya Holt, who recently retired from her position leading the CIA’s Diversity and Inclusion Office, and she helps to educate every single client on DEI, to give them a foundation to take their podcast and make changes across the globe. Andrew draws attention to how it is key to teach companies how to lead by example to make change. “Hope is nothing without action,” he states.

As a seasoned businessman, Andrew had a lot of words of advice for us, specifically the hardships that come with entrepreneurship. He paints a picture of the reality of starting a business without the rose tinted shades. “You need to be prepared for hardships and excited to go through them to get to the clear sky. You have to love thunder and lightning…because I know when I get through that, I'm much stronger and powerful and there’s so many great things on the other side of the storm.” He continues by emphasizing the importance of being realistic and hard work. “If you’re not willing to put in the work and underestimate [the struggles] it will make you a worse person.”

However not all is as bleak as it seems, and Andrew highlights that by facing your struggles head on, you can overcome it too. Identify, isolate, and execute, is the three-step process he conveys. “Take [that issue], drag it to the surface and battle it head on,” is what he says. “That is what will build strength and allow you to find positives from negative behaviour. Negative behaviours are only dormant positives, just pointed in the wrong direction.”

As we near the end of our interview, Andrew recommends we learn from people, but instead of looking at their path to success, analyze what also leads them to their failures. “Sitting back and understanding what somebody did to make them fail is one thing we don’t look at in our society. I know what I do well, but I need to be better where I’m weak. And that is the best advice I can give to anybody.” And as a finishing note, he suggests finding self-motivation in what you do. “Get away from that doing something for others mentality,” Andrew voices. Getting yourself excited and discovering that inner-drive is the true key to success, as you are the only one aware of your true capabilities.

For students who may be interested in getting involved with Obie & Ax, as an official partner of Schulich, they are always taking applications and looking for new talent, full-time or even for co-op.

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