Ashleigh Dempster is no stranger to interviews and generally being in the centre of all things cool. As the former Toronto culture maven (The Society) and now footwear designer (AKID brand) based out of LA, with a  brood of three boys (including a hubby she met on a flight over to NYC) this girls got it handled.

And in the time it took me to put together this post, she announced the upcoming launch of “Goodfoot” – AKID’s charitable arm that will donate 2000 pairs of shoes to kids in need for back to school. Way to go mama!

I had the pleasure of catching up with this kick ass woman and got her to share some of her biggest joys, challenges, what makes her a Rebel Mama at heart and an inspiration to us all.

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You’re juggling motherhood and entrepreneurial duties like a BOSS. How important do you think it is to do personal projects outside of motherhood? 

Thank you!  I wish I felt that way!  Re: projects, I think it really comes down to the individual.  Personally, I need that work outlet to feel balanced and happy as a whole. I always believe if you feel good, everything falls into place.

What are some things that make parenthood truly fun and fulfilling for you?

I am fascinated by their little minds.  I wish I could be that open. I love to try imagine what it’s like to see through their lenses. My kids teach me new things every day…and challenge me every day, both of which are fulfilling in their own way.

What’s one current challenge at home with the littles, and how are you dealing?

My 4.5 year old somehow changed over night from an innocent toddler to a sassy little boy.  The temper tantrums are real.  He’s constantly pushing buttons and exercising his independence. It’s a bit of a give and take thing. I’m trying to figure out when it’s OK to just let things go and when you really need to push back.

We’re all about the mom hacks around here – what has been your best / favorite life saver to date?

UBER and Glamsquad! I use UBER for everything both work and personal related.  Glamsquad is an app that I have recently become addicted to.  At times where I need to glam up a bit (blow out, makeup, nails) they will come to your home and make you look great within an hour. You can book last minute too!

Having one child is plenty, having two is a whole other deal… what was it like for you going from one to two and how did you manage it all?

I actually feel like the adjustment with my first born was harder than the second. The first time around was such a wake up call. It felt like the rug had been ripped out from under me. Not only was I getting adjusted to being a mom but I also moved to a new city when he was 4 weeks old, so I really didn’t have a support system around me. The second time around brought new challenges but for the most part, I was prepared.


If you had to choose three things that make motherhood easier, what would they be? We’re thinking wine is a given here. 


Any advice to mamas trying to “have it all” and striving for the ultimate balanced life that you seem to effortlessly exude? 

Nothing is effortless.  And the more time we spend on social media the more effortless things look when the reality is the opposite. I have yet to meet one mother who says it’s easy.  You just need to do your best and be OK with that. Don’t compare. Don’t question yourself and most importantly, do not feel guilty.

Kids really will be the ones to embarrass you most. Any hilariously awesome stories you can share that illustrate how wacky it can really be? 

Not sure where I start with this one. Little boys are obsessed with their private parts…I’ll leave it at that.

No judgment here (reality TV is one of ours) – what’s your favorite thing to indulge in when you get some time to yourself?

Those nights where I can crawl into bed at 9pm and watch an episode of Game of Thrones, Stranger Things or whatever show I’m currently into feels pretty indulgent these days!

We’ve got mad love for our city. What (if anything) do you miss most about Toronto?

I absolutely love Toronto and feel like it’s become even more exciting since I moved to LA (isn’t that always the way)! My family and some of my closest friends are in Toronto so it’ll always feel like home to me.

We can’t leave without asking a style related question, since you make being a mom look cooler than a pair of high wasted jeans. What are your Cole’s Notes on how to achieve that easy, cool-girl vibe and avoid looking like a hot mess when you’re short on time?

I stick to my basics- jeans, leather pants, t-shirt and then add a little flare with a great pair of shoes and jacket.  Layers are key in LA so I always invest in a nice jacket when I see one.

At Rebel Mama, we rely heavily on our lady tribe – mama’s or not. Describe your tribe and why you can’t live without them.

I am lucky to be surrounded by so many incredible friends. They are all so unique and special in their own way. We are all different- some are single, some have kids, some married, etc.  The common connection is we all have each other’s back and we’re really in it together.


Shop AKID BRAND at Advice from a Caterpillar & Nordstrom Vancouver.
Coming this Fall to Eaton Centre, Yorkville, Gravity Pope and more!

Shop all the styles online at
Follow AKID BRAND and ASHLEIGH on Instagram!

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Images via: 
ChildrenSalon, Broken English Jewelry and Ashleigh’s personal Instagram account.

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