“It will be harder than any job you’ve ever done before”

It will be harder than any job you’ve ever done before. I had the sense that based on my past work experience I would be well-positioned to handle the entrepreneurial world. While I think I was well equipped, I underestimated the foundation, support and infrastructure that existed at my previous jobs. When you’re starting from scratch there is no existing equity, brand love, no HR department, no IT support. It’s all you. You’ll need to figure all that out as well as build and maintain a product or service that is competitive within your industry.

As part of our interview series called “5 Things I Wish Someone Told Me Before I Became A Founder”, I had the pleasure of interviewing Andrew Knight & Kieran O’Briene, Co-Founders of Rebel & Thorn.

Andrew Knight — Originally an “Ad Guy” by Trade, Andrew merged his passion for strategy and business with the creative arts, cutting his teeth in the account service and strategic planning departments of Ogilvy & Mather and J. Walter Thompson. He was eventually persuaded to shift client-side and began running the media and strategy department within Diageo Canada, and now is the Co-Founder of Rebel & Thorn. Andrew is also a husband, father and dog fanatic.

Kieran O’Beirne — Originally a mechanical engineer, Kieran has extensive international experience in operations, project management, and brand strategy. Kieran shifted his career into innovation and later into marketing after completing his MBA while working abroad in Dublin, Ireland, and is now the Co-Founder of Rebel & Thorn. Kieran is also a husband, father, enthusiast of all things automotive, an avid DIY / home renovator, and holds a Diploma in Brewing.

Andrew, can you tell us a story about what brought you both to this specific career path?

Andrew: Like most entrepreneurs I’ve spoken to, the path wasn’t exactly linear. I had been working at Diageo for several years managing their strategy and media department and with the rise in digital / programmatic buying, I had committed to learn more about how it worked behind the scenes. Without going into too much detail, I was shocked by how opaque the practice was. There was no transparency or willingness to help clients learn how their money was being spent and, most importantly, how it could be done more efficiently. We challenged our agency at the time, but as a large multinational, a “custom” approach for individual clients is difficult to achieve. I shared many of my findings with Kieran and he was also surprised at the borderline fraudulent way in which media is managed. That was probably the tipping point for many subsequent conversations on how we could potentially create a business designed specifically to help clients achieve better business results in media with a focus on transparency and superior service.

Can you tell us a story about the hard times you faced when you first started your journeys?

Andrew: In the 4 years since starting Rebel & Thorn we have been incredibly blessed with the support and success we’ve experienced. However, getting to this point has, at moments, been incredibly challenging. I think for any small / start-up endeavor, trying to convince clients to take a chance on working with an unknown partner is tough. In the case of media, many of the larger Canadian companies are bound to Acknowledgement of Receipt relationships because of North American or Global deals, so even getting a smaller project can be difficult. Just trying to get someone to listen to our pitch and offerings was our biggest challenge. We knew once we started a working relationship they would see the value, but in the early days without existing clients, revenue, and the like, it was tough going.

Where did you both get the drive to continue even though things were so hard?

Andrew: I think both myself and my business partner are incredibly passionate about the work we do and derive true enjoyment from it. We are students of this industry and have always been keen to learn and grow with this dynamic area of the media landscape. We also knew the product we were selling was superior and if given a chance we could demonstrate that.

Kieran: I believe ‘drive’ or ‘grit’ or ‘perseverance’ are often qualities people inherit, or learn early in life … so some credit probably goes to our upbringings as well. We’ve learned that lows are temporary, and there is intrinsic reward in sticking with things to their resolution.

Kieran, how are things going today? How did grit and resilience lead to your eventual success?

Kieran: Right now, things are great. 2020 was our best year yet, and for 2021 we’re on track to at least double the size of our business. A huge part of our success has been due to our willingness to learn and our belief that we can figure out just about anything. Every time we take on a challenge or overcome an obstacle it builds our collective skill set, experience, but most importantly confidence. At this point, we rarely stop to worry about whether we’ll be able to do something, we just get down to figuring it out.

Can you share a story about the funniest mistakes you made when you were both first starting? Can you tell us what lessons you learned from that?

Kieran: In the beginning we weren’t always busy with ‘work’, but we had tons of stuff to do. There were a few weeks in 2018 where we spent more time building and installing a kitchen in our office than we did working on client projects. I’d come home covered in dirt and sawdust, and my wife would wonder what kind of ‘media’ company we were building. We also worked in an office with almost no heat during our first winter … everyone in the office would literally wear all their outdoor winter gear at their desks, and rotate between typing and wearing gloves to warm their hands back up.

Can you tell us what lessons you learned from that?

Kieran: We, our whole team, need to be flexible. Thankfully we’re too busy to be building kitchens these days, but the mentality that a small, nimble, organization needs to be filled with ‘enablers’ has stuck. We can’t afford to have anyone be precious about what is or isn’t their job, and we know that what any of us are working on could change quickly. It’s our responsibility as leaders of our organization to figure out the best way to manage resources, but we also know we can rely on our team to stretch themselves, and do or learn things they hadn’t anticipated when they started.

What do you think makes your company stand out? Can you share a story?

Kieran: Caring too much. We care a lot about our integrity, our performance, and about doing things right. One of our biggest challenges is often struggling with doing what we’re asked to do, rather than what we believe we should do, or what’s actually in our client’s best interests. Our team spends countless hours trying to do things perfectly, while often the vast majority of that work is opaque to our clients, who would never know the difference. In long-term client relationships, this pays off, because eventually all the little things are noticed, and you gain a sort of trust that is elusive for ‘order takers’ or ‘yes-people’.

Andrew, which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Andrew: I think you need to find what works for you and build your company, structure, and support around that. A lot of people are not very good at self-reflection, but it’s essential to running a small/scale-up business if you want to stay sane. One thing I will say, but don’t always follow myself, is trying to remind yourself that everything can’t be an emergency. When you are a small business, it can feel at times like you can’t say no to a client request, but sometimes that ‘no’ is exactly what you need to do for the health of your business as well as the client’s.

None of us are able to achieve success without some help along the way. Kieran, is there a particular person who either or both of you are grateful towards who helped get you to where you are? Can you share a story?

Kieran: I think first and foremost it’s family. Starting our own venture and funding a cash-intensive business took, and continues to take, a huge amount of support and faith from our wives and families.

We got a huge leg up when we started from former colleagues who’d moved on to new roles and businesses. These were the people that became our first clients. Knowing our capabilities, and getting us in the door to pitch on media and projects helped us accelerate out of the gate.

After that, I’d say some of our tech / media partners. The existing relationships we had with some large media vendors and technology platforms enabled us to get meetings and agreements that would otherwise have simply been off the table for a startup, or even many medium-sized enterprises. We were extremely lucky to have been able to build these relationships while still working on the client side of the business, managing large brands and portfolios.

Finally, friends of ours, and owners of the production company ‘The Juggernaut’, deserve a firm nod from us as well. They adopted us in our early days, and let us work out of their offices for free for the first few months to help us legitimize ourselves with clients who could visit us in ‘our’ offices … it was an important leg up for a company that then, consisted of two people, two laptops, and a dog.

How have you used your success to bring goodness to the world?

Kieran: Environmentally continuousness and action spread like wildfire in our office as our team grew. Specifically related to carbon footprint and waste reduction. Pre-covid all the take-out places around the office knew our team because we were always bringing bags of our own containers to fill up with our orders. Our team have changed their diets, bought electric cars, and generally become much more purposeful about understanding the role we all play in working to reduce our footprint… I don’t know that this would have proliferated the way it has without the culture our business developed.

Closer to our professional endeavors, we’ve been able to go after clients we believe are aligned to this way of thinking and, for various not-for-profits and similar organizations, we’ve been able to reduce or eliminate our fees to support the work we do with them.

Andrew, what are the “5 things you wish someone told you before you started leading your company” and why. Please share a story or example for each.


  1. It will be harder than any job you’ve ever done before. I had the sense that based on my past work experience I would be well-positioned to handle the entrepreneurial world. While I think I was well equipped, I underestimated the foundation, support and infrastructure that existed at my previous jobs. When you’re starting from scratch there is no existing equity, brand love, no HR department, no IT support. It’s all you. You’ll need to figure all that out as well as build and maintain a product or service that is competitive within your industry.
  2. Don’t underestimate the value / importance of your past job. I tend to hear “don’t you wish you’d started a company years ago?” a great deal from friends, clients, and colleagues. Despite our early success at Rebel & Thorn, to assume that this wasn’t directly linked to the skills and experience acquired from previous positions would be foolish. The reason we can have conversations with senior decision-makers and are trusted allies to our clients is that we are able to draw on the wealth of our previous work experiences. Without that experience we’d just be another opinion, and probably one you shouldn’t listen to.
  3. Launching a company is hard, but so is scaling. One of the biggest challenges of the past few years has been maintaining our standards and commitment to business excellence as we grow and bring on new employees. In any new company, when there are only a handful of employees, keeping an eye on everything is relatively straightforward, but as more clients and more bodies join the company it can become challenging to give up some of that control. You need to be choiceful on your hires so they can allow you to focus on growth but maintain the culture and workplace standards you’ve been successful with.
  4. As a business owner, no task should be “beneath” you. Especially in the early days, you’re going to need to realize that some days, weeks or months will be full of different levels of tasks. As Kieran mentioned, when we started Rebel & Thorn, we basically built our entire office and kitchen during our lunch or afterhours.
  5. Find a business partner who compliments your skill sets. I think we got lucky here. Over the past four years I don’t think there’s ever been a significant argument between Kieran and me. One of the main reasons is that, while we both fundamentally agree on the same principles and practices of how we’ll run our business, our strengths and weaknesses are different and very complimentary. Sometimes the temptation when starting out is to find colleagues and partners who are very similar people to you and therefore a more comforting choice. While that may work for some, I can no longer imagine working 60 hours a week with someone exactly like me.

Can you both share a few ideas or stories from your experiences about how to successfully ride the emotional highs & lows of being founders?

Andrew: This might be another piece of advice that can at times be personally challenging for me to follow. When you’re running a company of any size, there will be good days and bad. But I try to remind myself to stay balanced. Remember that the good is probably not a good as you think and the bad is likely not quite so bad.

Kieran: To add to that, having an equal business partner is a huge advantage in my mind (equal share, control, dedication, and capableness). This might be difficult to find for some people, but I think describes our situation well. We are often diametrically opposed in our views or interpretations of situations (high or low), and this works extremely well in balancing each other out.

You are people of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be?

Andrew: I’m not sure this qualifies, but something we’ve talked about for years is to create a coalition or collective of Canadian small businesses and establish a practice that whenever there is an RFP or agency search, at least 1 independent candidate is considered. Far too often the “big guys” make up the pitches for meaningful business, which means the diversity of thought and certainly the opportunity for local Canadian companies to break through and show their mettle are constrained. I think encouraging large multinationals to give Canadian small business a shot to impress would help nurture a culture of entrepreneurs domestically and push greater innovation in the industry.

How can our readers further follow your work online?

Follow any of our businesses or products on LinkedIn

Thank you so much for this. This was very inspirational, and we wish you only continued success and good health!

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