An entrepreneur at heart, Gwen Elliot has recently hit pause on her many media-focused projects to zoom into a new career with eCommerce platform Shopify as a course producer. Her new position puts her next to some brilliant coworkers, who are instilling a refreshing sense of freedom in Gwen as they allow her to own her role and take part in many exciting projects. One such project she’s enjoying working on is the Shopify Academy, which aims to teach aspiring entrepreneurs how to start and grow a profitable business. This side-gigging hustler has worked in the TV industry and coached entrepreneurs while also applying her creative forces to marketing, blogging and even co-developing a program that gives business people all the tools they need to get noticed by media and also leverage that attention for bigger opportunities. In the midst of her entrepreneurial endeavors, her goal to successfully do everything on her own didn’t end up feeling quite right, and eventually she felt so bankrupt that even money wasn’t going to get her out of bed. Gwen has since pulled back the sheets and exposed some truths about her obsession with chasing the self-made title. She has discovered that happiness is an inside job and continues to focus on what makes her tick, swearing by practicing martial arts as one of the guiding factors in her pursuit of satisfaction. Her perspective has drastically changed and she’s come to realize that starting something big doesn’t have to be done totally independently.


A Course in Miracles Book

Each day I do a lesson from the workbook!

Yeti Microphone

My favourite way of creating, interviewing and communicating.

Krav Maga Equipment

When I wear my equipment, I feel that “warrior-mode” is activated.

My Tea Collection

I’m working on making more of an effort to enjoy healthier beverages (less alcohol FTW!) and having a ton of tea encourages me to drink it in the evenings to relax.

Saje Natural Wellness Diffuser

I love when my house smells like ‘Celebration’ or ‘Liquid Sunshine’.

Epsom Salts

SO necessary after a Krav Maga class 😉

Coffee from a local coffee shop

I love supporting local coffee shops! The coffee’s just amazing, and it’s fun to get to know the baristas!

Go with Your Gut Cookbook by Robyn Youkilis

I am working on learning how to cook more delicious, healthy meals and I love Robyn’s book because it makes it so easy!

My fave lunch on the go

The almond lime bowl from Kupfert & Kim.

Intention Decks

I love using these decks (I have decks from Gabby Bernstein, Tiny Devotions, Doreen Virtue) to help me focus on what question I want to get answered and choose a card (that I believe will help me with the answer). Yes, this is highly ‘woo-woo’ and I find it fun!


Before we talk about your new career, let’s get some background on your entrepreneurial past - what type of work were you doing?

I called myself a mediapreneur, so I developed media strategies for small businesses and solopreneurs to help them use the media to grow their businesses; I also ran events. I got to work with and coach entrepreneurs from all over the world who found me online or through word of mouth. I enjoyed helping them get into media outlets for a while, but eventually it just wasn’t fun anymore – I hit that breaking point. That was my side business for about five years, and although it was always my dream to go full time on my own – and I did – it just didn’t end up being the dream I’d imagined.

If that was your side business, what else were you doing?

I worked in the TV world in pretty much every role there is. I went from starting as a researcher to creating my own local cable show called Start Something Big to producing a show that aired on the Oprah Winfrey Network in Canada. I also worked in marketing for a tech company for a while. I wanted to have a side business because when I launched Start Something Big it was for fun – I wasn’t actually getting paid for creating the show. I thought there had to be a way to learn how to get paid to create media content, and that’s when I discovered an entrepreneur named David Siteman Garland; he’s an American online entrepreneur who I discovered when I found his website therisetothetop.com by Googling ‘how do you turn media into a full time gig.’ I learned that he was selling podcasts, online courses, and video interviews, and the whole online course world got me really excited because I saw the possibilities; it really laid the foundation for me wanting to create the Media Method Program, which I founded with a good friend and mentor last year.

Can you tell me about the Media Method Program?

We designed the program for entrepreneurs to piece together everything they need to know to get their business in the media: how to ace the interview once they get it, how to leverage that media for sales, and how to turn that media attention into new opportunities, like getting a book deal or speaking engagements. It’s a DIY course that you can take at your own pace. I’m just really proud to have something out there that I feel is really helpful. It’s available now and we plan to keep updating it and also add a new live coaching component to supplement the foundation of courses.

Do you have a background in media?

Yes; I went to Ryerson University for radio and television but to be honest, the PR side of it was completely self taught. I just found that when I was first starting out, after graduating from university, and when working on Start Something Big, I had this spark, this ‘hey, why not try to share this in the media and spread the word.’ I started to teach myself how to do media, learning as I went from working in the TV world and learning from others about what was really good and what was really crappy. Suddenly there were some big breaks and people were starting to ask me to help them; I took on small contracts and then they just kept on getting bigger and bigger.

Would you agree that media advisement is an area in which many professionals need help?

Yes; there are so many people starting businesses and media is one of the fastest ways to build your credibility, acquire customers, and boost confidence. Once you get that media hit, it’s like ‘wow, maybe I can do this’ for a lot of people. It really builds their community as well, and also that buzz – once you get featured in the media, people start to see you in a different way; they see you on TV and see that you’re informed and relevant. I’m proud to be able to help teach people this in a simple format.

What other work accomplishments are you proud of or have brought you joy?

What comes to mind is quite recent and really exciting; I worked for a company called Female Funders, a company that teaches women how to become angel investors, with the founder Katherine. I was there from the very beginning, when she first had the idea, and then she hired me on to do media and events for the company, and now just in the last couple weeks it’s been acquired by another tech company. I helped her build her community and credibility really fast and I think that really lent a hand in getting her company bought. I’ve helped entrepreneurs get into a lot of different media outlets, like Forbes, New York Times, Virgins, TechCrunch, Market Launch, CTV and a lot of different Canadian TV shows. I helped get myself into Cosmopolitan through a side project I have with my three younger sisters called Mo’ Money Mo’ Progress, where we’ve been trying to figure out our financial situation and also blogging for a couple years.

How many side gigs have you had at most?

I’m a hustler. I mean, there were times where I was working on five different things at once, some of them paid and some of them unpaid. For example, Mo’ Money Mo’ Progress is completely unpaid but it’s fun; it’s something that I’d hoped to turn into something one day but yeah, I think five is the most. I’d be working on Mo’ Money Mo’ Progress, working in marketing for the tech company, working on a show called The Naked Entrepreneur and then also handling my side business. OK, maybe four.

So you worked on your side business for five years before you decided to go after the dream full time?

Yes, but here’s the true story: I was working in marketing for this tech company because I got burnt out working in TV. I needed to figure something else out and then this opportunity to work at a company called ShopLocket came up. Next that company got purchased by a larger company and, after a couple years, they ended up laying off our entire Toronto office. While a lot of my colleagues were really sad about the layoffs, I was secretly thrilled because I was wanting to quit, wanting to start my own thing – but I was scared. I didn’t know how I could leave. The day after getting laid off, I ended up getting the biggest media and events contract of my life with an entrepreneur and it was just a total confirmation that I could do it and was okay on my own.

Having a side gig turn into viable full time work is often the dream for many entrepreneurs, but you said earlier you went from being excited to realizing it wasn’t working for you. Can you speak to what happened?

I would say I was emotionally, spiritually, mentally, and financially bankrupt. I kept pushing when I knew it wasn’t the right thing to do anymore. I’d do whatever it took, I’d max any credit card, I wouldn’t ask for help; I just couldn’t. Every time I’d go for coffee with someone, I’d just start crying when they asked how I was. To me it wasn’t the money part that was as scary as just not knowing what to do at all – it was the first time in my life that I had no clue what came next. It was just the end. I truly had to surrender and stop pushing for the first time in my life, and instead really focus on living in alignment and feeling better about myself before I took any next steps.

So what came next?

Right away I realized I probably had to get a more conventional kind of job. It was the worst; I was even in denial for a while. My mom eventually said ‘Gwen, you can’t live like this, you’re miserable, you need to be around people again because you’re a people person.’ When I started at Shopify they had me take the Myers-Briggs test, and I found out that I’m 90 per cent extroverted and with the way I’d set up my business, I was only talking to people 10 percent of the time. Entrepreneurship really does teach you self awareness, so I basically went right into trying to figure out what to do next to remedy the situation. I applied to a bunch of random jobs I found online but nothing stuck. I got interviews, I got an offer from one company, and I got to the fourth round of interviews for another company, but I didn’t get the job. I was feeling defeated and like none of these felt right. In December, I took the holidays off; I decided I was just going to pause and figure this out and maybe – who knows? Maybe I’d start my entrepreneurial journey again…it was just time to stop pushing from all sides. It was soon after that I got the impulse to check out the Shopify site and saw a posting for a course producer role. I don’t know if you’ve ever experienced that full body feeling like ‘yes, like this is it, this is exactly the job I’m meant to do!’ – that’s how I felt.

Did you internally resist leaving entrepreneurial work life at all?

I was so resistant to joining a company. I bought into the message that the only way you could have freedom in your life is to be an entrepreneur, but that’s a lie. I feel more free now as an employee than I ever have. I think I was just really afraid to rejoin a team, because I was worried someone would be micromanaging me. Little did I know that it’s possible to find a company that aligns with what you believe in; when you’re trusted to be able to do the work yourself it can really be an enjoyable experience – I was blown away.

Your perspective seems to have changed a lot in a short time. Does the word entrepreneur still seem as powerful to you?

The entrepreneurs that I know who have made it just don’t give up, and in a way I technically gave up on the dream, but I still feel very entrepreneurial. I’ve studied that word a lot, and I think that some of the most successful people have an entrepreneurial nature. However, they also have self awareness that lets them realize they aren’t meant to be with a certain company or they aren’t meant to create a product or service in the world at a given time. So I guess the answer to your question is that I don’t know. The word is still super jazzy and glamourous and I don’t think that’ll go away.

Your ultimate reality was that when you were doing it on your own you had to work extra hard without having much - if any - team support though, right?

Exactly. Entrepreneurship is the best personal development course in the world. I truly believe that; you’re accelerated in understanding who you are and what you’re good at and what you’re terrible at, and you have to be able to take that information and adapt. If you can’t do it fast enough, your business isn’t going to be successful. It’s okay to fail as long as you’ve learned something, because then you’ll be able to figure out a new way to go about things for the next business that you start. I learned that I will never be a solopreneur again in the future. If I start another venture, there’s going to be other people involved – that was a really important lesson.

What was the transition like for you going back to a so-called regular job with a company?

Once I saw the job posting, I was all-in; it took six interviews to get hired here. It was a real test of patience because I saw something and thought, ‘oh, I would love to do that,’ but then suddenly it’s not as easy to achieve as it appears. It really helped me tie up my loose ends though, and focus on a job that I didn’t feel the imposter complex about when I started. I think the reason I didn’t – and still don’t – really feel it is because of the incredible amount of time and effort that it took to get in the door here. I mean, just from the number of people I spoke to during the process it’s likely somebody would have seen right through me if I couldn’t do the job; that actually helped me to just decide to trust I could do it.

What kept you strong and steady during this time of change?

I got really into going for long walks, meditation, working on eating a bit better and being honest with people. I had just started dating somebody when I discovered the Shopify job posting and I made a decision to not only be myself but also be as honest as possible with this person. I told him that I was going through a very rough time and trying to figure out my next step in life and luckily he was great at listening and being supportive and we’re still together now. He’s so sweet. During the harder times, I went to see a spiritual therapist. I also went to these monthly events in Toronto called Goddess Nights, which are run by a friend of mine. She brings together these awesome women to have real, meaningful conversations; I actually volunteered at them so I could meet and talk to more people. Whatever I could do, whatever was out of the box, I did it.

How crucial is it to take that time to decide what you want next before you set out job hunting?

I’ve found taking a pause to be the most important part of finding the right opportunity. A friend of mine actually wrote a book called Pause that’s really amazing. She used to work at Google and has been an advocate for people taking pauses instead of flat out quitting. I think it’s so important. Too often in life we’re just rushing from one opportunity to the next and not taking a minute to reflect on the experience, and I feel like it was taking that pause over the holidays that really helped me understand what I was looking for in the next opportunity. For me, it was absolutely crucial. I want all those hustlers out there to know that’s it’s okay to take a break and be still, and to not be in hustle mode all the time; it’s not always sustainable or fun.

How did you decide that Shopify was right for you?

I actually ran a media event for Shopify three years ago. They let me use a space to run events and they didn’t charge me a dime; that planted the seed to get me thinking, ‘wow, what a beautiful company, what a beautiful office space.’ I’m really inspired by their mission to help create more entrepreneurs by helping people work in a way that’s profitable and really changes the lives of these people and their spouses, families, communities and even possibly the world. I was really aligned with the course producer role; I strongly identify with education, especially since I was coming off a bit of a failure. To be able to weave my own experiences into these courses and not make entrepreneurship seem like it’s only shiny and fun is invaluable. I help to cast the people who teach the courses, and that includes ensuring they are real people who are going to tell the truth about the entrepreneurial journey. It really just seemed like the perfect opportunity for me.

Could you expand on what your role as a course producer entails?

Right now we’re working on creating Shopify Academy, which is made up of online courses – they’ll be free to start – that teach aspiring entrepreneurs how to launch and grow profitable businesses. What I’m doing is actually writing the scripts and casting the teachers, as well as being on set and helping produce every shoot. I’m also helping with the edits and basically being a jack of all trades in a way. When I first started, we also created 14 online courses for a group that are in the Build A Business competition for people who are making between $1 to $50 million dollars. We created courses on wholesale strategy or conversions that will really help people who are already making a certain amount of money to grow even faster.

You’re obviously really enjoying your new position - what do you love about it?

I would say number one is the level of trust that my boss and team have in me. The project I’ve been assigned is a pretty big undertaking and I’m fully trusted to make it happen. It’s not like I’m out there alone of course, we have meetings to figure out challenges together, it’s just the confidence they have in me is great. I’ve only been at Shopify for a couple months but we work so fast – I’ve already put out 14 courses and have more in production, it’s crazy! It’s a really exciting environment to work in, and the people are all really passionate and smart. I always feel like the dumbest person in the room, and there are a lot of rooms – and again I mean that in an exciting way. I am humbled at every meeting.

You mentioned finding happiness internally in order to facilitate external happiness and good opportunities. Could you expand on that?

I would say happiness is an inside job, meaning that you don’t need to rely on external circumstance to make you happy. It’s all about cultivating that feeling internally – just sitting and appreciating the little things in life that bring you joy. When I’m having a bad day or people aren’t treating me super well, I try to remind myself that it’s not about me. Their bad day or negativity shouldn’t ruin my day. It’s a challenge and so it’s something that I work on all the time. If somebody says something kind of snarky at the coffee machine I try not to think ‘God, do they hate me?’ Getting all worried about that is a waste of time. Doing things that make you feel better, even a little bit, make a big difference – you’ll be amazed at how your external world starts to reflect the way you feel internally in every way, from your bank account, to relationships, to the way you treat your body through food and exercise. I feel like I did a complete 180 from the way I was living; at my darkest time, I couldn’t get out of bed. I was just dreaming that I’d melt into my bed and maybe just quietly disappear, and now I’m excited to see people and so excited to be alive. It’s amazing for me to say that considering where I was six months or so ago, and so every day I’m really working on just being appreciative of where I’m at. It’s amazing how things just keep getting a little better.

I understand that martial arts is important to you - is it more than a casual hobby?

Martial arts is my joy – I can’t believe I didn’t mention it yet! I love doing Krav Maga, which is an Israeli martial art that focuses on self defence. It’s really one of the most practical of the martial arts because it enables you to defend yourself. I’ve been doing it for just over a year; I just got my green belt last week, which I think is the sixth belt up, so I’m about halfway to my black belt. Doing martial arts is now the framework in which I live my life. I go a couple times a week, and I have this new little family of fellow martial arts enthusiasts. I highly recommend everyone have a hobby or something outside of work that you can make progress on; the belt system in martial arts makes it easy to measure achievements that aren’t work-related. I honestly feel like developing a fighter spirit has helped me during some of the really rough times, and having a physical activity in your life that gets you moving is also really important, especially if you’re not feeling great.

To come full circle, you said that entrepreneurship was the dream and in speaking to you it’s clear you’re still passionate about it - what originally attracted you to it?

I think it was the fun that people looked like they were having, and the apparent freedom and ability to create your own opportunities and income. For years I was totally swayed by things like Facebook ads – all those adverts that said things like ‘make six figures in six months following my four-step system.’ I totally bought into the flashiness, not realizing that anyone who was able to do something like that must’ve had failures along the way too. It’s not part of the selling feature that these people very likely learned the hard way before they were able to create success for themselves. All the positive things about being an entrepreneur were very exciting to me, but I know now that a lot of them are also very possible in other avenues – like being employed at a company. In the end it doesn’t really matter where you work, you can still have success.

Is entrepreneurship all that different than a conventional job?

What comes to mind is that I no longer care about the title of employed versus entrepreneur, whereas before I was very interested in being labeled an entrepreneur. At the end of the day, I’m just trying to build a life that is an extension of who I am; it just so happens that right now, it’s being with a company. I think many people are like the old me, just very obsessed with the entrepreneur title, or even a little ashamed if they’re at a company and have a side business. We all need to let go of these labels and just focus instead on how we feel about the work that we’re doing and on how much of an impact we’re able to make. I think in my role now, I’m able to make such a bigger impact and affect so many more people than I did working alone – so I’m right where I need to be.