Sheena Macrae (she/her) is an artist-turned-entrepreneur with a passion for educating children. For nearly eight years, Sheena’s worked on a storybook brand called Ollie Club that inspires and motivates young kids on their journeys with food wellness.

When beginning, Sheena didn’t think her brand would expand past the book. But today, Ollie Club has entered the homes of millions of families and is sold globally from Canada to Australia. And as the brand’s founder and CEO, Sheena is leveraging the power of community to take her company even further.

Sheena, could you talk a little about your film and art background?

I studied as a filmmaker and contemporary artist for years, and that cemented how I look at things. In art, you’re trying to make things that people can see in not-so-obvious ways and have them develop conversations. That grounding as an artist let me see projects in different ways. Out of that, I had the opportunity to start making films in the educational space that focused on kids learning.

Once you make a film for someone and translate that into visuals, you’ve become the translator of someone’s vision. You gain insights into that field by doing so.

How did your background in art help spark the beginning of Ollie Club?

I ended up running an educational company making videos, books, websites, etc., and that’s how I started. One of the projects that begat Ollie involved working with educators that focused on children’s health in one of the poorest areas in Europe. We realized we needed to make this material more appealing to people. We had to get the kids, parents, and teachers involved, and I thought writing a storybook would be the most accessible way.

The brand revolves around Ollie, the world’s pickiest eater – and with the help of his magic spoon gets hilarious food superpowers. The storybook was commissioned into a TV series, and now we’ve got 52 episodes, over 13 hours of broadcast TV animation grounded in educational best practices.

My strategy has always been about getting kids engaged with the conversation. People love Ollie the character and can use him to motivate their children to try new foods.

Why do you think the story of Ollie has taken off so well?

I think it’s done well in part because of our accessibility. My impetus is always trying to see something from a different point of view. We had all this amazing content in a book, so why not make it into a broadcast program? And once that takes off, why don’t we try to bring Ollie into the family kitchen and gamify the kitchen? Ollie takes shape in many forms and is available to anyone at any time.

My strength has been in seeing educational content from the point-of-view of ‘who needs to change and why would they?’ What would make a child want to eat something? Well, a magic spoon is a fun and playful way for kids to get into imaginary play.

We’ve been able to tap into places where people can free their imaginations and become something else. We create a space where moments can be made and we’re trying to create new opportunities for loving things to happen within families.

When starting out, did you think Ollie would develop from a children’s book into this full-blown media brand?

I had no idea we would explode like this. When we launched in 2016, we were purely focused on providing educational content that we couldn’t see the rate at which we were expanding. In fact, it wasn’t even on the radar because I remember a woman in publishing who once said to me, “there is no way this is going to work; you have a one-in-a-million chance.”

It took years, but we had a tipping point where people started to validate it. I realized that you don’t do anything alone. There are a thousand fingerprints on the Ollie brand. I worked hard, but there were many, many people who came and lent a hand and believed in Ollie as much as I did.

What kept you going through the difficult times?

Since starting with Ollie, I’ve struggled and had loads of doubt, but it always felt like the right thing to do. It felt like something that needed to exist in the world, and we had an idea to bring it there. I think part of it is being comfortable with the discomfort of failing. It validates every tough day when you’re at a low point but still know that what you’re doing is the right thing.

The other component was acknowledging that we’re all in this together. Artwork and entrepreneurship are all about the communities you build and lean back on when you go through setbacks.

What are some of the challenges you’ve encountered? 

There have been a million ups and downs throughout our journey. Creating educational content for children is unique because you’re trying to get everyone involved – the children, their parents, and their teachers.

We’ve had to be OK with adapting and changing. First, we were an education company trying to sell to educators, but then we became a TV company. Now, we’re a digital subscription, direct-to-consumer company, and we need new skills to support our next chapter.

If there’s anything I’m good at, it’s that I’m innately curious, and I’m OK with feeling disappointed. I don’t have all the answers or ideas but I know how to surround myself with people who believe in what we’re doing and can brainstorm solutions with me.

How did you first get involved with StartOut?

I learned no hard skills about entrepreneurship through my art training. When I began working at my first educational company, I learned as I went. I would reach out to people who knew a little bit more than I did, and I’d ask questions over and over again.

Since the beginning, I’ve pursued ongoing education, constantly taking online courses to better my entrepreneurship skills. During that time period, I found out about StartOut through Lorenzo Thione. I’ve learned so much through the organization; they’ve helped me build an entire support system. You can feel isolated starting your new thing and need a community to get through it.

I’m so thankful for everyone who’s had a hand in making Ollie this global initiative. We’re constantly thinking ahead, and the future of Ollie and his magic spoon feels brighter than ever.

As part of our Educational Founders campaign, Sheena and Ollie Club will offer free subscriptions for parents with kids 6 and under this month. Connect with Sheena on LinkedIn to learn more and get the latest updates on Ollie Club. Follow our blog on Medium for monthly founder features.