STACK SHORTS + Eva Redpath

“It takes 30 days to create a habit, 60 days to see progress, and 90 days to see results. So I think it’s very important – from the mental, the physical and the financial – to really give it some time. “

Eva Redpath is a fitness entrepreneur and all-around badass. As Canada’s first Nike Master Trainer and founding trainer for Barry’s Bootcamp Canada, she’s learned that physical, mental and financial health are connected and can’t thrive in isolation.




STACK is a smarter way to manage your money. STACK Shorts is part of our mission to help you free your money by starting honest financial conversations. 


STACK SHORTS + James Hinchcliffe

“It’s all about the long game. It’s not just about what you’re doing right now, it’s what you’re doing in the last lap. You always have to plan ahead. “

Born a racing fanatic, James Hinchliffe earned one of his first paycheques behind the wheel of a car. Now he’s front of the pack in one of the most dangerous (and expensive) sports in the world. From building his love of racing into a thriving brand and how his own definition of success guides his choices, he tells us how he followed his own course out of debt and onto a track that balances his need for speed with his long-term goals for the future.




STACK is a smarter way to manage your money. STACK Shorts is part of our mission to help you free your money by starting honest financial conversations. 

STACK SHORTS + Georgie Greville

“Women need to help other women get in positions of power. Straight up.”

Growing up all around the world gave creative director and entrepreneur Georgie Greville a uniquely non-traditional approach on how to make her art into her career. In her early days as a female writer and director she faced sexism and pay inequity head on. Now, as co-founder and brand leader at Milk Makeup, she tells us how she actively fosters female leaders, challenges outdated beauty ideals and works to inspire young creators to stand up for what they’re worth.



STACK is a smarter way to manage your money. STACK Shorts is part of our mission to help you free your money by starting honest financial conversations. 

STACK SHORTS + Humble The Poet

“I was the happiest guy with a zero bank account, because it meant I was no longer in debt.”

Well-known as a rapper, poet, artist, author and MC with a massive YouTube following, Kanwer Singh (aka Humble the Poet) is rich in wisdom and, luckily for us, happy to share it. His own experiences with debt, defining success and the true value of self-worth have given this artist we love a wealth of mindful and candid straight talk about money.



STACK is a smarter way to manage your money. STACK Shorts is part of our mission to help you free your money by starting honest financial conversations. 


STACK Stories + Humble The Poet

Well-known as a rapper, poet, artist, author and MC with a massive YouTube following, Kanwer Singh (aka Humble the Poet) is rich in wisdom and, luckily for us, happy to share it. His own experiences with debt, defining success and the true value of self-worth have given this artist we love a wealth of mindful and candid straight talk about money. Along the way we were inspired by his vulnerability, dedication to speaking his own truth and willingness to use his personal story to expose the hidden, personal shame at the centre of bad financial habits… and how to use it to become truly rich for the first time.

We knew that while chatting with Humble the Poet we’d be met with some serious wisdom, but we didn’t anticipate the number of mind-blowing ah-ha money moments that he was about to drop on us. As a professional wordsmith and former teacher, we shouldn’t have been surprised. With the straight talk of an MC and the clarity of a poet, Humble is so in tune with the core truths of what he wants to share that our first-time meeting was filled with deep realizations around just how personally our finances impact us and what we can do to make sure that the relationship is nourished and not ignored.

As authentic as he is artistic, Humble’s path led from passing the days as an elementary school teacher with a comfortable gig and predictable pay cheque to finding the courage to pursue his creative passions and become an artist and beloved YouTube star. (Being BFFs with Lilly Singh didn’t hurt, either.) On the way he learned about the complexities of career and finances the hard way and came out the other side finding a voice of incredible insight and eloquence. Now he’s discovered that the bravery he found to pursue his creative passions also crosses over to a willingness to speak openly about the shame associated with debt and the discomfort that, if left unspoken, can turn hard conversations around money into full-blown debt disasters.

Photo: Bella Francis

From humble beginnings

Humble’s career journey is undeniably unique but starts where many kids find their first financial lesson and adolescent income source: a paper route. The child of immigrant parents, his upbringing was a constant lesson in smart saving and even smarter spending. He watched as his father paid off the mortgage quickly and celebrated with one of the family’s rare splurges: a pizza party. Growing up in the Toronto area of Rexdale, Humble’s friends came from a wide variety of income brackets. Some friends had to work to help their parents cover the bills while others got to choose what car they were going to drive to school that day. His early worldview was formed early by seeing firsthand just how differently people experienced and understood their own relationships with money.

“You can always focus on people who have more than you, but you can also choose to appreciate where you’re at based on those people you know, too.”

Humble’s own relationship with money wasn’t always so wise. Like a lot of young people early in their careers, he spent cash as quickly as he made it. A natural storyteller, he was making a decent living as a full-time teacher, but, lacking a strong financial education, the way he budgeted didn’t allow for much long-term saving. When he made the life-changing decision to leave the security of his traditional job path and take the chance on his creative dreams, things weren’t easy. He had no idea how to make a living as an artist, and, thanks to some unclear contracts and bad management decisions, over time he landed himself $80,000 in debt. That’s when his real education began…


On changing habits to change yourself

Humble had an eye-opening moment when he hit financial rock bottom: he finally admitted to himself that ignoring the problem and hoping for a miracle wasn’t going to work. Instead, he would have to be realistic and face some of his greatest fears. Starting these honest conversations with himself and determining where he truly found value in his life brought him to a much happier, more truthful place. He took inspiration from his past and thought back to his father and how he paid off that mortgage so quickly, celebrating with just a pizza. He knew that he had to get real with himself before anything else.

Humble’s new mindset led to meaningful actions. He made a lifestyle switch and actively embraced minimalism, selling what he didn’t truly need and focusing all of his time and effort on work. After four years he was able to get back to zero and felt “richer” than he ever had before. Through his experience he learned invaluable lessons and immediately knew not to celebrate by spending like he had before. He patted himself on the back, maintained his current minimalist lifestyle, and was eventually able to turn what was once a black hole of debt into an upward spiral of savings. That financial security and increased confidence fed his creative momentum and led him into a new world of artistic opportunities that led him to the creative career he had always dreamed of.

Photo: Bella Francis

“Your immediate company matters. Find people who share your priorities.”

Changing your relationship with money starts as a journey for one but grows to include decisions on how you’ll need to interact with everyone in your life to maintain your newfound habits. Instead of heading back to the same old friends that preferred his (former) baller lifestyle, he chose friends who more closely shared his new values as his role models. His modest and financially savvy father, of course, but also some friends you might not suspect: artists and entrepreneurs on the Forbes’ list. People who, despite having the finances to spend millions, mindfully chose to live simply and valued their relationships with people over their ability to buy stuff. Humble has met billionaires whose approaches to life and money has taught him one of his most valuable lessons: that true wealth is not feeling the need to show off how much money you have.

“What you feel on the inside won’t get resolved by what’s going on on the outside”

As much as he could see it was a cliché, he also had to admit that the more he pursued what he loved and the less he cared about an ego-driven need to make money (sound the cliché alarm…) he began to make more money. By saving, spending within his means and knowing that placing value in what you spend your money on isn’t a true representation of your worth, he found that financial security followed. He created his own definition of success and that’s what he achieved – personally, spiritually and, eventually, financially.

The direct connection between financial and mental health

Humble knows firsthand the impact money has on self-esteem. When your finances are out of control and you start to tie this to your own experience of self-worth it’s a slippery slope to begin questioning what you deserve from your life overall. For Humble, this manifested in wondering if he deserved to have fun or be with his friends. Did he even deserve to be pursuing his own art? In the middle of his most challenging days he was solely fixated on his debt and nothing else, forgetting the importance of self care and physical health. He lost 20 pounds and one day was just “a beard and his two front teeth” – proof that stress can eat away at you both mentally and physically.

“When you’re not feeling good there are so many options to address that – go to the bar, a movie, shopping, buy something, medicate the way we feel, but it’s all short-term.The best thing I do is just go for a bike ride. Focus on staying mindful.”

When he began to focus on protecting his inner-peace he found this naturally led him to spend less. Small steps toward saving money made him feel better about his choices and more confident in his own ability to control his life. As his self-awareness grew and his situation improved he was able to pull himself out of debt but admitted that, even years later, he still felt shame. Only now is he able to to talk about it openly, but with an excellent motivation: the hope that his story can empower others.

Humble is highly aware of the power he gained by asking for help, reaching out, and being vulnerable. Nothing can be gained from keeping quiet and avoiding hard personal conversations. In fact, doing so can set you back even further. The moment you open up you’re able to live life on your own terms, which is exactly what Humble is doing now – both grateful for how far he has come and defining success on his own terms as he continues to grow.

“Live the life you want. Live a simple life, maybe a life of routine. The only way to be successful is to know yourself, figure out what gets your juices going, and pursue your enthusiasms. You have to know yourself and practice a life of gratitude and appreciation”

Header image created by Max Rosenstein for STACK Sessions. All other photography created by Bella Francis. Video courtesy of Kanwer Singh.

STACK is a smarter way to manage your money. STACK Stories is part of our mission to help you free your money by starting honest financial conversations. 


As @Hatecopy, Maria Qamar blew up her groundbreaking brand of pop art on Instagram while smashing stereotypes. She manages her finances as creatively as she lives her life. As a multi-disciplinary freelancer with projects in progress around the world, she’s learned that money might be nice but the only currency she really cares about is creativity.

While growing up, Maria Qamar, a.k.a. Hatecopy, faced an endless stream of “friendly” suggestions about following a practical career path. Her parents thought she should be a doctor or a pharmacist, but Maria had her sights set on a different future. And she was right. Her decision to follow her creative instincts unlocked the freedom to pursue her real passions. And she’s never looked back. 

From Instagram darling to international artist, Maria’s artistic career has been a long series of success stories. With over 130,000 Instagram followers, she’s now a thriving Toronto artist, a published author (with her Trust No Aunty an instant cult-classic) and a magazine-cover star, with a celebrity fan club that includes Mindy Kaling and Lena Dunham. Despite the Insta-worthy shine of her success, her story has been anything but smooth-sailing. No matter what life throws at her, she stays on course by staying true to her vision and following her heart.


Photo: Warren Credo / A Beautiful World

On boldly being yourself paying off

All her life, Maria has been focused on creative pursuit. Moving to Canada from Pakistan at the age of nine, she turned to art when she felt alone or misunderstood. After a day of being teased at school, she would come home and sketch comic panels of what had happened. These nascent comics would always end the same way: with Maria the conquering heroine (foreshadowing, anyone?). This theme of triumph through self-reflection has continued throughout Maria’s career as an artist, evident in all she does.


Through her work, Maria is speaking to women and men like her, who have grown up in western society with eastern roots. Her creative work, and often comedic commentary finds a way to speak to the balance and nuances of the two cultures, engaging new fans along the way. Maria’s artwork has been heavily in demand since she first started posting it on Instagram – proving to her parents (and all the other doubters) that a life in the arts can more than pay off. Inspired by pop artist Roy Lichtenstein and South Asian soap operas, she has created a style that’s all her own. As her artistry has evolved, so has her career. What started as casual Instagram posts has transformed to live beyond the screen and canvas, producing clothing, dinnerware, eyewear, tattoos, murals and much more.

“I didn’t realize that all you needed to attain clients was the confidence to post your work, good or bad, online. It’s all I ever did and it helped me to partner with some amazing brands and businesses.”

Photo: Warren Credo / A Beautiful World

On believing you can do it and actually making it happen

Though many would-be artists fear the stereotypical ‘starving artist’ life, Maria never allowed a fear of failure to prevent her from giving it her best shot. She refused to believe that art wasn’t a sustainable career option, believing instead that anything is possible if you’re creative enough to find a way to make it happen.

While her art is her main source of income (and has been for the past three years), the financial side of her business has never dictated how Maria creates. The financial incentives are nice, obviously, but rarely the main motive for a true artist. Sure, we all need to eat, pay rent, get around and splurge out at the spa once in a while, but Maria believes money should never dictate good creative. That being said, she always makes sure her clients understand the time, effort and physical labour that go intoeach custom piece and advocates accordingly for a price tag to match.

“Since [art] was a passion that became a profession, money never mattered much. Whatever I make from my artwork goes right back into creating more, so I’ve got a sustainable way to live as a happy creative now.”

On using your own rules to define your worth

Having never known a life that didn’t include a stream of “friendly advice,” Maria was often getting ‘suggestions’ – often on her choice of career – from her family and large network of “aunties” (read: female family members and friends, often full of often-unsolicited counsel). The stigma towards the arts that many parents cultivate in their families can keep kids from pursuing creative fields altogether. Maria was encouraged to attend business school as a way to stay away from the arts, and follow a career path that her family viewed as more stable, despite the knowledge that women and especially women of colour receive less pay than their male counterparts in this supposedly stable corporate world. In fact, the money she earned as a copywriter wasn’t much to begin with, proving that the safest road isn’t always the most profitable (and almost never the most fun).


Photo: Warren Credo / A Beautiful World

Maria’s story is an anecdote for the ages, showing the true value of putting stock in yourself. She’s never used her bank balance, job title, or relationship status to gain a sense of self or define her worth. It’s always been about her ability to creatively solve problems. It’s that creativity that has helped contribute to her success, and allowed her the financial freedom to travel and invest in new tools and experiences that will help her to create new art, a self-fulfilling prophecy that will sustain her for years to come.

If Maria had a nickel for every piece of aunty-advice, she may never need to pick up a paintbrush again. But the one piece of advice she holds firm is never forget your identity. Words of wisdom worth more than any corporate pay cheque or hefty commission. And if she ever needs a little extra financial advice? She can always turn to one of the many accountants in the family.

“I always knew I was going to be an artist and I always knew I would find a way to express myself to the world. I just didn’t know when. The confidence in my work and the support from my community pushes me every day to be better than the day before.”

All artwork created by Maria Qamar. All photography created by Warren Credo / A Beautiful World for STACK Sessions.

STACK is a smarter way to manage your money. STACK Stories is part of our mission to help you become the master of your money by starting honest financial conversations.

ASA: Solo In Splitsville

Hi STACK. I love my friends, and I want to keep loving them even after we go out to eat, but I usually want to murder one or more of them when the time comes to figure out how to pay the cheque. We all have different jobs, make different amounts, and are on various parts of the “I’ll just have water” to “I’ll have a sixth martini” scale of drinking preferences. Help me not murder my friends. What’s the best way to make this work better?
Solo In Splitsville

Hi friend. There are few financial danger zones that cause as much stress as the dreaded moment when you decide how to pay the bill with a group of friends. A lot of our most common money worries – sticking to a budget, keeping up with your crew, not wanting to hate that one guy who doesn’t pay his share – are all on full display when it’s time to split the bill in a crowd.

The specifics of our own financial situation, lots of which we might not have talked about openly, are fuel for the fire. Our friends don’t necessarily know if money is tight at the moment, and expecting them to behave they way we secretly want to is a recipe for disaster. Like lots of things in life, the key to harmonious bill paying is some good ol’ open conversation first.

After talking to experts and combing through academic studies (yeah… there have been full-blown University studies on split-the-cheque-stress), Forbes reported that there are lots of reasons why it’s fair to pay less if you eat less.

Don’t hope for the best

We know that nobody wants to be that first person who kills the vibe by bringing up how you’re paying the second you sit down. But we think it’s time to flip the script on that. Instead of worrying about coming off as a cheapskate, think of how much stress you’re saving by deciding up front how you’ll manage the bill. By addressing what everyone else is thinking, you’ll be the toast of the table, and by having these convos more often you can make them less awkward for everyone. The only thing worse than planning ahead is going with the flow and then being saddled with an extra helping of resentment at the end of the night.

Take Charge for Yourself

If you’re on a budget or have already decided how much you want to spend, then like OpenTable suggests let your server know right when you sit down that you’d like a separate bill. You’ll need to be careful that you don’t get your hands into any shared apps or bottles of wine that you’re not helping to pay for, but it’s the easiest way to give you total control over what you’re spending that night. Waiting until the end of the night (after you and you friends have had a few), makes it harder on your server to separate you out and easier for your friends to think you’re being a jerk.

Trick or Treat

If you’re heading out with someone who usually picks up the bill (your one really rich friend… your Dad… your boss…) and you want to avoid post-meal awkwardness it’s totally fine to confirm before you order how you’re going to be paying. If they offer to cover the tab, it’s a nice gesture to ask to pay for the tip. They’ll probably turn you down, but it shows you respect that they paid and really appreciate it.

Common Cents

There are no hard and fast rules about how a lot of money situations should work, but a lot of the time they go south because people aren’t openly communicating what they think. A little bit of consideration can go a long way and, like Thrillist points out in How To Split A Cheque Without Losing Friends, no two situations are the same. Common sense and open, honest discussion about how you want to handle paying a cheque will make sure your BFF status is still intact at the end of the night… 

Have a question? We’ve got answers. Send you own ASA to us below and our money management experts will get you the advice you’re after.

STACK SHORTS + Fred VanVleet

“My daughter will be the hardest working princess there ever was.”

Fred VanVleet’s relentless spirit and toughness on the court have helped him persevere in all aspects of his life. From the silliest $700 he’s ever spent to how he’s raising his baby daughter, “Steady Freddy” knows that lessons from his past are helping him to own his future.


STACK is a smarter way to manage your money. STACK Shorts is part of our mission to help you become the master of your money by starting honest financial conversations. 

STACK Shorts + Coco Rocha

“It is still awkward to say what you’re worth, but the way I’ve gotten around that is by having those conversations over and over, to the point that it’s boring.

From supermodel to super-entrepreneur, Coco Rocha’s early career has already given her a lifetime of experience. Her dedication to staying true to her personal values reflects her belief that every person, in every industry, should know what they’re worth and be able to ask for it.


STACK is a smarter way to manage your money. STACK Shorts is part of our mission to help you master your money by starting honest financial conversations.

STACK Shorts + Mey

“I have immigrant parents. being very academically inclined, they were telling me to be a doctor. So I went to school to be a doctor. Halfway through i realized, i don’t actually want to do this, so i switched into a double major in computer science.”

Mey Iduwe, a Senior Backend Developer at STACK, made a major pivot in his professional life and never looked back. Along the way he’s figured out how to make a budget he can live with and what he’s willing to sacrifice to get what he really wants. (Hint… it’s probably not what you think.)


STACK is a smarter way to manage your money. STACK Shorts is part of our mission to help you become the master of your money by starting honest financial conversations.