Family Hustle: Ashleigh Dempster & Matt George

When it comes to business partnerships, your relationships can get tricky. Luckily, for Ashleigh Dempster and Matt George, they know how to keep the lines between business and personal from getting blurry. In this edition of Family Hustle, our Behind The Hustle team explores their individual career lanes and how they both bring dimension towards a new journey they’re embarking together.

 Ashleigh Dempster

Ashleigh, highly successful in the marketing and branding industry, humbly claims she still has a long way to go. Her journey began when she first started working and found a gravitational pull towards the marketing industry. With every step forward, Ashleigh believes each opportunity lead her closer to today. Despite the differences in the jobs and positions from one to the next, they all came with a lesson applicable for the journey ahead and subsequently opened other doors for Ashleigh.

7 years prior to her partnership with her husband Matt, Ashleigh had already experienced a business venture with someone close, her best friend.

Starting a new company together, they both experienced growing pains as partners and friends. To keep both relationships thriving, Ashleigh claims a need for clarity on roles; it’s all about dividing and conquering as a unit. When you run a small business, you will often find yourself wearing many hats, and it’s always important to remain conscious of the hat you’re wearing. Being one of the most incredible learning experiences for Ashleigh, she shares how essential it is to celebrate the small successes together. Whether it be the first sale or the first deal, little reminders are necessary to keep you focused for the longer road ahead.

Matt George

Harder to pinpoint, Matt began his journey at the age of 19 when the first concept came to fruition. Surrounded by smart, interesting, and hardworking people, ideas bounced around and a venture in retail began. Proving to be successful, Matt became a retail owner of spaces like Saint Alfred, Nomad, and Goodfoot. Continuously trying for new ideas and keeping it moving, Matt has also been on numerous projects; Ransom by adidas as an example. Looking back at his career, Matt feels the road to his success had no intentional plan; instead, it’s been an organic journey of opened opportunities inching towards an ultimate idea. While this ultimate idea has yet to be defined, over the course of time, the path has become more focused.

Through Matt’s experience with retail, one thing has proven to be true: the value of culture in a business model. In any business that’s growing, in order to thrive, a culture must exist. Because human interaction must naturally manifest as a collective whole, one cannot assume that their business will drive, force, or create a culture. Rather, the characteristics of a community will determine whether or not your business will survive. Simply put, culture does not rely on a business; businesses are dependent on the culture.

AKID: A Family Affair 

Individually successful in their own lanes, this power couple comes together to advance their careers towards new horizons.

Originally a fun project, it quickly morphed into Matt and Ashleigh’s first business together, children’s footwear. Having children of their own, they noticed there was a void in the marketplace. Hardly finding anything appealing, they would typically gravitate towards one or two brands. Often times, brand giants like Nike take their best selling item and make it kid size. For Matt and Ashleigh, they felt the need to have something special for kids’ wear, marking the start of AKID.

With Matt’s extensive career in footwear and Ashleigh being a shoe fanatic, they had a good sense of direction where to go. Fundamentally, they wanted a high quality product while maintaining a good price point. At the same time, they wanted to stay away from being too “kiddy” and have a more adult feel and look. However, with adult shoes having an edgier feel, Matt and Ashleigh wanted to take a minimalist approach. Playing on numerous ideas, simple and easy resonated for AKID.

In the testing phases and deciding what products to produce, it’s good to walk in the shoes, check for places where it hurts, and seeing if the shoe will last. Learning that the best feedback comes in always trying out the product, Matt admits without the kids, it wouldn’t be possible – the children will always be the main inspirations.

Ashleigh even reveals one of their lines inspired through the lens of the firstborn son, Jasper – bandana print shoes with each foot a different color. Becoming a family hustle, their boys are contributing to the business without even knowing. Hence, it was only fitting to incorporate Jasper into the campaign. At the same time, Matt and Ashleigh have tons of friends with gorgeous children and they naturally became the models for AKID. Organically, it just becomes a story that invites everyone to take part.

Learning from AKID, it’s good to disrupt the marketplace to make yourself standout. Sometimes, you just need to take a chance to shake up the traditional business model and pave your own road towards success.

The Couple

While the journey with AKID is merely beginning, Matt and Ashleigh can attest that working together has been interesting and different, but overall good. Coming together in their first business partnership, both Ashleigh and Matt can agree on the importance of communication.

Just like any other relationship, in order to successfully thrive, the lines of communication must be open. Matt adds having a clear understanding of each person’s responsibility is vital, while Ashleigh expresses the necessity of having the same goal. Of course, there will be differences and disagreements, but you have to learn to respect each other’s role. In some relationships, there are falls outs or you may want to escape a conversation, but in a marriage and a business, there is no other option but to work it out. In addition, one has to be careful in keeping their workspace and home life balanced; leave work as work and family as family.

Through it all, you have to be honest with yourself and with each other. Be prepared from the beginning to make the objectives clear. Things will shift, but that’s okay; you just have to trust each other.

Hustling on their own accord, Ashleigh Dempster and Matt George have proven they are their own movements, but together as a family, they truly become a force.


by Janine Yoro  | |  Read more articles by Janine here

Photos by Don Kang  | |  Follow him at @donjkang