Authority Magazine: 5 Things I Wish I Knew Before Becoming a CEO

This interview between Kevin Collins and Charlie Katz was originally published by Authority Magazine on August 13.


Don’t define yourself by how much work you can get done in a day. We live in a productivity-obsessed world that encourages us to define our worth by the volume of work we’re able to accomplish in any given day. I have fallen into that trap myself, but I now believe that the true value we get out of life is in direct proportion to how well we’re able to prioritize the aspects of our lives that we enjoy most, whether they’re professional or personal.

As part of our series called ‘Five Things I Wish Someone Told Me Before I Became A CEO’ we had the pleasure of interviewing Kevin Collins, CEO and Founder of

Kevin is the CEO and Founder of Charli AI, a unified workspace for your digital content and cloud apps. A serial entrepreneur who has experienced serious highs and lows throughout his career, Kevin is passionate about helping workplace professionals put more life back into their work-life balance.

CK: Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

KC: Earlier in my career I worked in various senior management and executive positions across a number of sectors, including telecommunications, professional and financial services, and consulting. From 2008 to 2016, I was the CEO of Bit Stew Systems, where we developed a platform to solve the data-integration challenge in the Industrial Internet of Things. In 2016, General Electric acquired Bit Stew in a US$153 million deal — one of the biggest tech acquisitions to take place in Western Canada in a decade.

As a result of that acquisition, I lost my executive assistant — and that’s when I understood how much work and stress my EA had shielded me from by keeping me organized and on top of things. Having to take on tasks like scheduling and accounting myself left me feeling exhausted and burnt out. I realized that I, and other working professionals like me, needed an effective way to take those sorts of tasks off of our plates so we could focus on the critical areas of our business — and also free up time for the things that really matter. That’s when I came up with the concept for my latest business venture, Charli AI.

CK: Can you share the most interesting story that happened to you since you began leading your company?

KC: One of the more interesting aspects of my role at Charli versus other leadership positions — including as CEO at an industrial-focused company — is the intersection between my private life and business life. Charli is more consumer-focused than any of the projects in my past and this means surfacing more of my private life in the form of experiences and lessons learned. One of those is linking the lessons learned in Overlanding and how they help with startup life. Something will inevitably go wrong at some point when you’re Overlanding. You have to expect it. In fact, it’s kinda the name of the game when you’re off-roading in the backcountry; you need to be prepared for every scenario and you need to think on your feet. I’m sure you can see the parallels here but, what I’ve taken away is that the key to long-term survival is to be prepared for a bumpy ride and have contingency plans for when things don’t go your way.

CK: Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

KC: It doesn’t fit into the category of the “funniest mistake”, but it’s certainly a head-scratcher — a “what were you thinking?” moment.

Not long ago we were trying to figure out the best user experience for everyone using Charli. We didn’t have much to go on but did have some experience with early mobile users and had some ideas. Although these ideas were great in our heads, they didn’t translate well to the reality of what we developed. Our goal was to create an experience that was super simple and easy to use. What we ended up with was a far cry from that and would eventually go on to be called the “Curated Experience”.

At some point we’ll put this UI in the museum and laugh at ourselves. And we have to learn to laugh at ourselves as we’re innovating and making mistakes from time to time. Even though we’ll make these mistakes, they are fantastic learning opportunities and this “head-scratcher” was no exception. We learned about the real value in the product and how to surface the interactive abilities of Charli in a much better way than we ever had beforehand. We also developed new capabilities that allowed us to experiment with features in real time while not impacting our existing users. We would likely not have the “assisted UI” or “command line” features in the product if it wasn’t for this experience. Moreover, we may not have the “content canvas” in our product or even a content focus if it wasn’t for this fortuitous mistake. Innovation requires experiments, mistakes, and learnings.

CK: None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

KC: I’ve been fortunate enough to have a lot of great people in my life who have helped me along the way. These people have been instrumental in my life and business learnings, especially when I’ve made mistakes and have needed some help. One person who really helped me in my early days and passed along some life lessons that I carry to this day is a former boss, now friend.

Mike became my new boss while I was at my first real job, only three years into my career. He noticed that I had some bad habits around execution, focus, and self-discipline. We butted heads a lot in those days but he must have recognized some potential, so he persevered. After a few heated exchanges, I did smarten up, and Mike ended up becoming one of the best mentors I’ve had in my career. I give him full credit for helping me develop the ability to stay focused, work effectively with a team, establish achievable goals, and execute on plans. He even taught me the value of diversity in the team and how important that is to making better decisions. I worked with Mike as my boss for another five years before moving on in my career. He is now a good friend and someone that has impacted how I operate to this day.

CK: As you know, the United States is currently facing a very important self-reckoning about race, diversity, equality and inclusion. This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?

KC: People from different backgrounds bring a wealth of lived experiences that can give them perspectives that you might never be exposed to otherwise. This is hugely valuable in a business sense, but I would argue that it is equally important on a person-to-person level. Having a diverse team in the executive suite can help cultivate the sort of outside-the-box thinking that business leaders are always striving for.

On the business level, diversity lends itself well to remaining competitive and being innovative. New ideas come from the seeds that are planted through experiences, discussions, debates and deliberations. Business leaders often talk about innovation and for companies in traditional businesses, getting left behind is not an option. Diversity is an essential ingredient.

Read the interview in full here.

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