Since the pandemic hit, Deb Day’s been holding a daily virtual meeting with her team that’s been like no other marketing and digital content studio has conducted. They open with a wellness check-in and bookend with a gratitude practice. There’s no talk of clients, projects, or deadlines. Instead, they talk about priorities and everyone shares one thing they’re grateful for. It could be anything: supportive partners, the roof over their head, coffee, a good TV series to pass lockdown leisure hours.

“The team’s not worked in the office since March 13, so it was a priority for me that we adapt our connection with each other,” says Day, who founded the Toronto-based strategic marketing enterprise, Innovate By Day, in 2010. “Virtual meetings can be very  transactional — ’just get ’er done.’ It’s a bit soul destroying, so we’ve put systems in place to connect with each other more and differently.”

Indeed, Day stirs up a lot of “business as usual” approaches, which has helped the company innovate to meet the challenges of the pandemic — surviving without having to lay off a single person.

When she launched, she even resisted the term “strategic marketing” for what her company does as it’s associated more with capitalism and consumerism than the feminist and social-justice values at the heart of her studio.

Innovate By Day primarily works within the cultural industry — film, television, art, music, publishing, nonprofits and broadcasters — building online communities and creating audiovisual content such as TikTok videos, Instagram lives, company sizzle reels. Day’s thoughtful about who she works with, teaming up with clients who align with her company’s values. “We would never do something that was pornographic or overtly racist or provocative for the sake of being provocative. I have to be able to align with them at some level, as does the team.”

To accompany the CBC documentary Girls’ Night Out, based on the Ann Dowsett Johnston’s book Drink, the company created the #RethinkTheDrink campaign, a cross Canada peer-to-peer talkback tour and impact campaign at colleges and university campuses featuring custom content and marketing materials. It also created a legacy toolkit to keep the conversation going to combat binge-drinking culture after the in-person tour wrapped.

On another campaign, Day’s team was engaged to support the discoverability and online conversation of the powerful six part documentary series Enslaved: The Lost History of the Transatlantic Slave Trade for and its international release on specialty channel EpixHD in the US, BBC Two in the UK and CBC in Canada. Their role was to curate content, write messaging and moderate the conversation online on the selected social media channels. 

“Those projects are meaty and they’re really, really satisfying,” says Day. “Sure, we’re not making the same money as someone who’s selling iPhones and cigarettes, but we’re okay with that. Our goal is to not become bigger and massive. It’s to do meaningful work. We love empowering new businesses and new projects to really define who they are and to reach their audiences.”

Day has taken the same approach internally, empowering her employees with a human-centric, feminist approach to the way she runs her studio. They embrace anti-oppression and anti-racist values, supporting staff to be their best and truest selves.

Early on, Day developed an employee benefits package by asking her team what kind of coverage they wanted. As a result, the company developed a package that includes health and dental insurance and more sick days and time off than Ontario’s minimum employment standards — in an industry that often relies on freelance “gig” workers.

She also flattened the hierarchy. Employees aren’t pigeonholed into defined roles and responsibilities. Being a smaller team helps. So does encouraging people to stretch themselves in different ways based on their interests and abilities. For instance, a UX/UI designer became the lead coordinator on a project completely unrelated to their role. A social media specialist produced content outside their skill set. Says Day: “Due to the nature of our company, we have to be flexible and really lean into how we can evolve ourselves at the same time as we’re evolving what we’re offering to the clients.”

She adds that anyone who wants to work a regular nine to five schedule and stick to a job description wouldn’t want to work for her company. “We have to be far more agile and adaptive especially in these times.”

On the other hand, anyone who wants to be playful and innovative can thrive. Four years ago, the company secured their own IP to evolve their offerings for their clients, leading to the development of one of their most successful projects yet, the “Innovate Prediction Game Engine.” Teaming up with some of the biggest reality television franchises in Canada, the studio created an online game that lets people bet on who they think will get knocked off of The Bachelor Canada or who they think will win the Head of Household on Big Brother Canada.

Evolving is something the company has had to do a lot this past year. When the pandemic hit, 50 percent of the company’s business was either paused or cancelled. They battened down the hatches as COVID-19 cases went up while marketing spending went down. They applied for every funding program they qualified for. They checked in on their clients and contractors to see how they were doing. They teamed up with a business coach to ensure their cash flow was stable. They put a plan in place in case someone got sick. And it all paid off. The company retained all of the staff, including nine full-time and four part-time employees, as well as a handful of contractors.

Day says that none of it would’ve been possible if she hadn’t taken care of herself first. As an entrepreneur with a teenage daughter, a husband, and father living in a care home, she often finds herself pulled in many different directions. And as an extrovert cooped up indoors with little contact with people, she’s found working virtually challenging. What keeps her going are those daily gratitude practices and daily walks, which are non-negotiable. “It’s really important to take care of myself because I won’t be able to take care of others,” says Day.

She remembers the early days of having to convince clients that marketing was worth spending money on. It’s easier now convincing clients the value of connecting with people, not only because the pandemic makes that so difficult but also because it’s a value that is deeply rooted within the company itself.

“I’m building a company that I would’ve loved to have worked for,” says Day. “A company that feels supportive and is respectful and collaborative.”

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Publishers Note: Fifth Wave Labs is Canada’s first feminist accelerator program for women in digital media. It is a year-round program offered by CFC Media Lab and its partners to support the growth and development of women entrepreneurs in the digital media sector in southern Ontario. All enterprise founders in the Fifth Wave community are selected for both their potential and commitment toward weaving intersectional feminist ideals of equity and social justice into sustainable and scalable business growth strategies. Fifth Wave Initiative is committed to 30% participation by members of underrepresented groups. The Fifth Wave is a LiisBeth Media partner and ally. Interested? Apply here.e

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Feminist Art Conference 2014, OCAD University, Toronto

The process for art-making can boil down to something like this: Make art, get feedback, make art better. Sounds easy, right? It wasn’t for Ilene Sova. In 2012, the Toronto artist-activist was painting portraits of women who had disappeared in Ontario for her Missing Women Project. She wanted to talk about the hard issues she was tackling in her art—patriarchy, misogyny, systemic racism, violence against women—but there wasn’t a group of fellow feminist artists to turn to, at least not a formally organized one.

Sova put out a call for submissions and volunteers and got a rush of responses, including from people in Kenya and Colombia. On International Women’s Day in March 2013, she launched the first Feminist Art Conference (FAC), a multidisciplinary event that brought together artists, activists, and academics of different gender identities, ages, nationalities, and feminisms so they could show their work and use it to spark discussions around important feminist issues.

The conference sold out in two days, attracting 120 participating artists and 150 attendees. “Clearly what I had been missing in my own social practice was something that others in our creative communities were also yearning for,” says Sova. FAC’s subsequent annual conferences have been equally as successful, especially the 2017 event that happened the day of the Women’s March.

‘Ashaba’; No human can look at her directly by Karen White explores unseen oppression. By covering her face while staring straight at the viewer, the artist makes us feel both complicit and engaged in the exploration of colonialism and imperialism.

 Art That Moves

Feminists have been long fed up with the fact that women’s art continues to be undervalued, underrepresented, and often completely ignored. The feminist activist group Guerrilla Girls have been calling out the gender and racial inequality in the arts since 1985 when they picketed the Museum of Modern Art in New York for featuring only 13 women out of 169 artists.

That inequality persists today. Female visual artists earn just 65 percent of the annual income of their male peers, according to a 2018 report by the Ontario Arts Council. Since 2013, women have only accounted for 36 percent of solo exhibitions at Canadian galleries; it’s dramatically less for non-white women. Gender disparity also exists in the performing arts space, which FAC attempts to redress in their events.

FAC has heard all the reasons why feminist work is often shut out of commercial spaces and public institutions. It’s not mainstream or universal (i.e., not male). It’s too angry and personal (i.e., too female) to be good. No one (i.e., men) will buy it. FAC’s response? Carve out spaces to showcase intersectional work that might be deemed taboo elsewhere, for instance, on topics such as rape culture, transphobia, racism, ableism, domestic violence, missing and murdered Indigenous women and girls, media representation, cultural appropriation, environmental degradation, and Islamophobia. Nothing is off limits. FAC featured a graphic novel about trauma and abuse, Girl in the Attic by Hyein Lee, which contains such difficult subject matter that FAC added its first-ever content warning.

Girl in the Attic by Hyein Lee explores themes of trauma and abuse by drawing the viewer into the narrative.

According to Sova, people attending FAC events say they are really touched because the art reflects current social issues that affect them. “This creates a very impactful experience for those viewing art or experiencing a performance,” says Sova.

After hosting four conferences, FAC changed its name to the Feminist Art Collective to reflect its expanding mission. It now hosts artist residencies on the Toronto Islands. And its next event—the Feminist Art Festival, March 5 to 7, 2020, at OCAD University—will include a reception, conference, performances, film screening, makers’ market, and a two-week exhibition featuring the work of visual artists.

The Art of the Action

Since day one, FAC has operated as a grassroots organization run entirely by volunteers. Currently, the core team consists of 30 people from a variety of backgrounds and experiences.

Carissa Ainslie, who took on the coordinator role after Ilene Sova became the Ada Slaight Chair of Contemporary Painting and Drawing at OCAD University, describes their current organizational structure as non-hierarchical. “We try to be intersectional in terms of who we’re including in the conversations that we’re having,” says Ainslie. “Ensuring that everyone has a voice at the table is really important regardless of what their experiences have been.”

FAC’s biggest challenge is finding the time and money to put on events, particularly without a physical office or paid staff. It didn’t help that the Ontario government slashed arts sector funding from $18.5 million to $6.5 million earlier this year but, before that, FAC did not have much success getting grants as their conferences are so unique they don’t “tick all the eligibility boxes.” Instead, they’re exploring other options such as sponsorships with companies that align with their values.

For now, FAC relies on in-kind donations for printing services, food and beverages for receptions, and space rentals (OCAD University is a signature partner and hosts the festivals as well as committee meetings). Ticket sales (with pay-what-you-can options) and their annual Made by Feminists market at the Gladstone Hotel also brings in funds.

Despite budget constraints, FAC continues to grow. Submissions for the 2020 festival were up to 187 from 130 in 2017, coming in from Australia, South America, Europe, United States, and Canada. Ainslie says the political landscape has changed since their last conference in 2017 with the #MeToo movement encouraging people to talk openly about sexual harassment and gender inequality.

A voting committee of 11 people (artists, curators, activists, community members and academics) will select the final artists to participate at the festival, through a selection process that considers social justice issues, intersectionality, the collective’s mission and, of course, the strength of the art itself rather than the artist’s professional record.

Not Missing, Not Murdered by Amanda Amour-Lynx features the shirt the artist wore the night she was sexually assaulted. Photo: Black Umbrella Photography, Rebecca Tisdelle-Macias

With FAC serving as a spring board, past participants have gone on to show or perform their work in other venues and countries, collaborated with artists they met at FAC events, and even started conferences (see Black Futures Now and M.I.X.E.D) as well as a literary magazine (Living Hyphen).

Says Ainslie: “The world is a bit ridiculous and I hope people can come together and have some good conversations. We try our best to support the artists the way we can. We can’t always do that with funds but we can by creating a space where artists can build their CV and present work that may not be welcome anywhere else. We just want the best for all the artists involved.”

The Feminist Art Festival runs from March 5 to 7, 2020 in Toronto. Get your tickets here. 

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This article was made possible thanks to the generosity of Startup Toronto.

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Takara Small is good at many things, but perhaps her greatest strength is being able to compartmentalize microaggressions so she can go on about her day. As someone who runs a non-profit, writes about technology, appears on radio and TV, and hosts two podcasts, she has little time to ruminate on the racism and sexism she encounters.

For instance, at a recent tech conference that she was covering for a leading publication, she was asked odd questions. Where is the bathroom? What floor is the event on? “I was so confused,” says Small. “Then I realized they thought I was staff because the only Black people at the conference were staff workers. They assumed anyone who was Black was not media or not a speaker.”

As a form of self-preservation, she adopts a “forgive but never forget” mantra and channels her energy into creating opportunities for others facing barriers in tech and STEM education.

In 2017, Small, 31, started VentureKids Canada, which brings free coding, financial literacy, product building, and entrepreneurship workshops to young people from low-income and underserved communities in urban and rural Ontario.

VentureKids turns common barriers into non-issues. Can’t afford a coding class? It’s free. Don’t have a laptop? They’ll provide you with one. Couldn’t pack a healthy lunch? Food is taken care of. Worried you’ll be the only girl? Classes are gender-balanced. The non-profit has even given students face time with big tech reps from Microsoft, LinkedIn, Google, and Twitter—an encounter that’s super rare if you’re a teenager from rural Ontario.

Says Small: “There’s a misconception that everyone owns a laptop and has access to the internet. That’s not true. In Canada the cost of data is quite high, and the cost of laptops and phones can be prohibitive for some people. I wanted to make sure I was creating free programs that would help people from financially sensitive backgrounds be able to work in an industry that desperately needs workers.”

Desperate is right. Tech leaders have been going on and on about how they want to attract more diverse talent. The research has made it abundantly clear that a diverse workforce leads to more open-mindedness and innovative ideas. According to studies, it’s also just plain profitable. Still, women, Indigenous peoples, some racialized minorities, and LGBTQ+ workers are less likely to be included in the tech economy compared to men and non-racialized workers. Even if they’re in, they don’t always feel included.

Bias is to blame for the lack of diversity, but so is a leaky educational pipeline that limits some people’s exposure to computer science careers at an early age. With VentureKids, Small is determined to patch up parts of that pipeline by showing marginalized kids that they too can be entrepreneurs and tech workers. Often, she’s one of the only people to show them these possibilities.

 Paying It Forward

When LiisBeth’s editor put out a call for pitches about Toronto feminist entrepreneurs advancing social justice, Small was the first person I thought of. Full disclosure: She’s a good friend of mine. We met at Ryerson University as journalism students. Even back then, Small was striving to make a difference, and this made her very, very busy. Now, on top of running her non-profit (she does not pay herself for this work), she hosts two podcasts: I’ll Go First for The Globe and Mail, and Dial Moving for #MoveTheDial where she talks to leaders about all the things that affect underrepresented groups in tech. She also makes her living as a public speaker and journalist for various media outlets including the CBC, The Globe and Mail, and Refinery29.

Small’s upbringing informs much of the work she does today. She was raised by a single mother in Toronto before they moved to Cobourg, Ont. Thanks to a combination of scholarships and financial aid, she was able to move back to Toronto to attend university and eventually break into the tech and media sector. Her journey hasn’t been easy, which makes her more determined to ease the path for the next generation of marginalized folks. “Not everyone can afford to go to college or university. If I really wanted to make a difference, I knew I had to start VentureKids for the kids and families who don’t have the means to pay for coding programs,” says Small.

This past summer, VentureKids launched its first rural-city program thanks to some sweet partnerships with Northeastern University Toronto, Microsoft Canada, the Town of Cobourg, and loyalty program company Points, along with individual donations. As a result, VentureKids secured free space, talented mentors, breakfast and lunch, and roundtrip train tickets for 20 students from eastern Ontario. Every Friday for three months, students aged 14 to 18 took basic web development classes and brainstormed ways technology could solve a specific problem in their community.

A teenager from a rural farm came up with the idea to start an equipment-sharing website where farmers could connect with other farmers to share the cost of expensive equipment and maintenance fees. The idea took off. Now, she’s getting interest from clients outside of her farming family.

Small says students developed several other promising ideas and everyone stuck with the program, despite the up to six-hour roundtrip commute in one day (some had to wake up as early as four in the morning). That tells her underserved youth are hungry for this opportunity. Says Small, “Not every student will create a business that gets funding, and not all startups end up lasting, but the fact that we have students interested in thinking about entrepreneurship is a success.”

Looking to the future, one of VentureKids’s goals is to expand its rural-city program to northern Ontario so that it can reach out to Indigenous and new Canadian students.

Raising a Village to Raise Tech Kids

Running a non-profit is hugely time consuming. Consider this recent tweet from Small: “Seriously thinking about changing my bio to simply read ‘tired’ lol.”

Small does a lot of networking, reaching out to volunteers, experienced teachers, and community partners to donate their time, money, space, expertise and even their laptops. Workhaus lends VentureKids a complimentary office space in their downtown Toronto location. Carole Piovesan of INQ Data Law provides free legal help. Says Small, “One thing I have learned is that there are people and allies who are willing to donate their time and services because they care about our mission.”

In the New Year, Small faces the enormous task of putting a volunteer board of directors together. The five directors don’t have to have a tech background per se, but a diverse set of skills and experiences certainly helps.

In the two years since becoming a non-profit founder, Small has learned a few lessons. She’s learned to seek volunteers who are reflective of the people they’re serving and who understand the difficulties of breaking into the tech sector. By contrast, one well-known business leader offering unsolicited advice clearly didn’t get the program when he suggested cutting the free breakfast and diverting the money to other things. Says Small: “That advice doesn’t really match with how we operate. I think it’s well meaning but when you consider the fact that the populations we’re serving don’t have the resources, then it doesn’t really make sense.”

It’s a hard slog, for sure, but Small says the benefit of a non-profit is being able to focus on the communities and youth they serve instead of worrying about making as much money as possible to please investors and shareholders.

“Finding ways to keep yourself optimistic is really important and VentureKids helps with that,” says Small. “It’s a ray of hope and it keeps me excited about the future.”

Recommended Listening

On top of hosting two podcasts, Takara Small listens to a few herself. Here are her faves:

Harvard Business Review: HBR has a variety of podcasts on leaders in business, women in the workplace, and advice on work dilemmas.

Blacticulate: A British podcast featuring interview with young Black professionals.

Oprah Super Soul Conversations: Oprah’s personal selection of interviews with thought-leaders, best-selling authors, spiritual luminaries, as well as health and wellness experts.

Science Vs: This podcast explores fads and trends to find out what’s fact and what’s not.

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In the span of four months, Cherry Rose Tan was involved in a major car accident, lost her brother unexpectedly on Christmas Day, and found out her mother had stage three cancer. Her grief was unlike anything she had ever felt before, so she decided to turn to her colleagues in the tech industry for support. But she didn’t know where to go or who to talk to. That’s when she realized the sad truth: Nobody in tech talks about this stuff.

So Tan, an executive coach in Toronto who helps entrepreneurs get past their personal and professional roadblocks, started For Founders By Founders in 2018. She defines it as a movement to get tech founders, investors, and executive directors to talk to her about their mental health struggles—and agree to publish their story online.

“There’s some serious mental health breakdowns and emotional suffering that happens in my industry,” says Tan. “People come to a point in their success where they’ve spent so long in a place of drive and doing and achieving more, that they’re really disconnected from their emotions and what it means to be human.”

Tan wanted to end this systemic silence, but prompting entrepreneurs to open up about their struggles wasn’t easy. Says Tan: “One investor said to me, ‘I love what you’re doing, but I need to be real with you. I don’t think you’re going to get a single person to pledge their mental health story.’”

She refused to believe that. “We don’t have to settle for an industry where the best we can do is have founders cope with alcohol and drugs and do their healing in bathrooms.”

Tan knew she was tapping into something huge. Research by psychiatrist Dr. Michael Freeman, who specializes in mental health issues and illnesses among entrepreneurs in the US, found that 72 percent of entrepreneurs struggled with mental health. They were also twice as likely to suffer from depression and experience suicidal thoughts than non-entrepreneurs.

People may go into entrepreneurship for the freedom it can offer, but what’s rarely discussed is how often that journey comes with seemingly insurmountable stress, burnout, and crippling loneliness. Stigma and shame around mental health often keeps people from getting treatment when they need it.

To start her venture, Tan reached out to a few people she knew had gone through something deeply personal and asked them if they were willing to talk about it in a one-on-one interview. It took four months before she secured her first subject (or champion, as she likes to call them); within a year and a half, she had convinced 65 people to share their stories, including CEOs of multi-million-dollar companies. Tech leaders opened up about an array of challenges: abusive families, postpartum depression, eating disorders, painful divorces, losing a parent, the immense pressures of running a company, and being responsible for so many people’s livelihoods.

So far, Tan has published 20 of those stories online at pledgeyourstory.com. She is currently working on a podcast slated for release in November, which will feature one-hour intimate conversations with tech entrepreneurs about their personal mental health experiences.

Says Tan: “One of the most impactful stories was from a founder who I really respect. Super accomplished, serial founder. This person shared with me a story about their breakdown, a time when things were so, so, so bad that they didn’t know if they would survive until the next day. This person told me the reason they’re alive and doing the work they do is because of one person who changed their life and said, ‘I’ll be the person who will hold the space and listen to your story.’ It just reminded me that this work really matters.”

As a for-profit social enterprise, Tan is able to do this work while generating revenue by crafting mental health strategies for founders and investors, speaking at companies and conferences, and providing mental health training at the executive level.

Tan’s forum is particularly useful for female founders who often face even more pressures. They struggle with being taken seriously, securing funding, finding a supportive network, combatting discrimination, coping with imposter syndrome—you name it. For Founders By Founders gives women entrepreneurs an outlet to openly talk about their struggles without shame, judgment, or guilt. Says Tan: “There’s a lot of masculine energy in this industry, and I feel like that’s why so many people are suffering is because they don’t have a connection to this softer side of themselves.”

Throughout her interviews, Tan noticed other patterns emerging. For instance, she discovered that anxiety and imposter syndrome tend to creep up when founders raise their first round of funding. And when founders exit their company, they often feel like they’ve lost their sense of identity and fall into depression and grief.

So now Tan is creating a playbook for tech founders that will lay out a roadmap of what to expect with their emotional and mental health journey from startup to acquisition.

“I’m really excited about this playbook,” says Tan. “I want to show people the way out of emotional suffering.”

If you are in an emergency, in crisis or need someone to talk to, please use these hotlines or call 911 immediately.

Cherry Rose Tan’s Reading Recommendations:

The Surrender Experiment

“Life-changing book. It talks about a nine-figure tech founder who decided to let go of control (as a paradigm for success), and how his life transformed on every level because of it. What happens if we start trusting ourselves and life, instead of fighting it? I found it powerful for shifting my perspective with adversity.”

The One Thing

“One of my favourite mindset books of all time. Written by the founder of the world’s largest real-estate firm, it explores the question: What is the one thing I can do such that by doing it, everything else will be easier or unnecessary? It has been important for my mental health and in keeping me focused on what is most important.”

This article was generously sponsored by Startup Here Toronto

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Reena Rampersad makes a killer cannabis-infused chimichurri sauce. Not only does she drizzle in some cannabis oil, she incorporates the non-psychoactive leaves to give it more texture and a boost of antioxidants. As the owner of the High Society Supper Club, Rampersad creates private dining experiences featuring all kinds of micro-dosed dishes – from amuse bouche (or is that amuse bud?) to infused butters, dressings for salads, sauces for mains, and fudge and cookies.

“It took me some time to experiment and figure out my menu,” says Rampersad, who lives in Hamilton, Ont. where her business is also based. “I asked friends on their day off if they could test out my recipes. That’s how I figured out how to dose properly. We started doing unofficial dinner parties. Then we did larger dinners and started bringing them to Toronto.”

Over the past several years, she has catered more than 100 supper parties for all sorts of clients, from corporate beverage companies to owners of resplendent mansions to family dinners. Buffets start at $55 per person, while table service is $65. She gets two to three bookings a week and has eight people on her payroll.

But there’s just one problem: Even though recreational cannabis is legal in Canada, it’s not yet legal for establishments to produce and sell cannabis-infused food and drinks. That legislation comes down October 17, 2019. So, for now, Rampersad runs the High Society Supper Club as a complementary service to her Limin’ Coconut catering company, which specializes in Indo-Caribbean cuisine. She had a license to operate since 2015. If a clients request an infused item, Rampersad must get them to provide their own cannabis while she provides the infusion service—at no extra charge.

“This is how we have to do it for now,” says Rampersad. “The irony is that the High Society is really what’s been taking off. People are interested in seeing what infused dining is all about. But I can’t officially operate as a business, which has been so hard because I could be paying my bills really, really well right now.”

It takes guts to run a business that occupies in such a quasi legal area, especially if you’re a woman of colour. Out of the 99 licensed cannabis companies in Canada who have public information available, only eight are headed by women.

Rampersad, who is the daughter of Trinidadian parents, says she’s often one of the only minorities at the cannabis conferences and panels she gets invited to, and, to her disappoint, discovered that there is not even much talk about diversity and inclusion. “All too often it’s a message that people are trying to censor out or don’t care about or are trying to silence,” says Rampersad. “When we talk about implementing change and creating an equitable industry, I don’t see how that’s possible if we don’t have that from the top down. If we only have one narrative being represented, that’s going to carry out everywhere else in terms of the images that are being marketed and the policies that are being created. It’s actually very alarming since cannabis is slotted to be the largest and most influential industry out there.”

Rampersad is pushing for change in her own ways. She prioritizes women and women of colour when hiring, and she pays her staff at least $15 an hour. She has also started organizing marketplace events where people can purchase products from vendors from marginalized communities and folks who have been affected by the long prohibition on cannabis, such as Rastafarian organizations and Indigenous exhibitors.

“This is how I’m able to work back in my social justice aspect since so many people are being left out of this newly emerging industry,” she says.

Working in the cannabis space isn’t just a political and professional endeavour—it’s also deeply personal. Rampersad has lost a number of family members to the war on drugs and the destructive policies that have negatively impacted marginalized communities. Growing up, she saw her father get accosted by the police for his cannabis use, over and over. What she learned from witnessing this was that the law enforcement could over look some dabbling in recreational use of cannabis before it was legal, but often came down hard on people of colour using the substance. “It’s enraging to see how racist it was in the beginning. It showed me that sometimes the law can be wrong.”

Wanting to right the wrongs of the past, Rampersad joined the Campaign For Cannabis Amnesty as a volunteer coordinator. The group’s main push right now is to convince the federal government to amend and pass Bill C-93 so that it gives expungements rather than pardons to Canadians convicted of simple possession of marijuana. With expungements the government would be admitting it was wrong in the and would permanently delete an individual’s criminal record. Pardons, on the other hand, would merely forgive individuals of their criminal past, but would not protect them from having their convictions reinstated or accidentally disclosed.

As for her High Society Supper Club, Rampersad looks forward to legalization of food and drink this fall but worries whether the legal framework will extend to grassroots companies such as her own.  Cannabis edibles alone could be a $4.1 billion market in Canada and the U.S. by 2022, with large companies vying for the action. It’s only fair that entrepreneurs like her get a taste of that too, she says. “We are the people that helped to build the demand and set certain standards. All we want is for them to include us too.”

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Katelyn Bourgoin’s “aha!” moment happened on a bathroom floor. Last year, she was running a business networking site for women entrepreneurs called Vendeve. Then, in a short period of time, an investor backed out, her co-founder left, and she only had enough cash to keep her company afloat for six weeks. She went out to dinner with a friend to de-stress, which led to a few bottles of wine and, later, throwing up in her bathroom and waking up on the floor crying. “All I was thinking was, ‘My business is failing. I’ve got no money. No one understands me. I’m so alone!’”

In reality, she wasn’t alone. She had a group of friends—tech founders she met at the Propel ICT accelerator program for startups in Atlantic Canada—who would know exactly what she was going through, if only she picked up the phone.

“Why did I stop talking to the people who understood my journey?” she says. “Then I thought about the other women [entrepreneurs] who don’t even have a squad to turn to. How do they deal with this stuff when they feel so alone?”

That’s when Bourgoin came up with Squads, a community that matches whip-smart women entrepreneurs with a small group so they can provide each other with laser-focused feedback on their businesses. Each squad has between ten and 20 people who talk via video conferencing for one hour every week, offering mutual support and objective criticism. Members can also hop on one of three themed calls: Hot Seat (where everyone helps one person problem-solve a specific business issue), Expert Feedback (where you can pick the brain of a subject matter expert), and Coffee Chats (for when you just need to vent).

The entrepreneurs are based all over the world but most reside in Canada, United States and Western Europe. They head businesses as diverse as executive coaching companies, holistic health practices and furniture design.

A standard membership costs $27 a month, which gives access to those three themed calls, while the premium membership of $27 a month plus a $129 one-time fee adds the weekly squad call.

Bourgoin successfully ran a beta version with 200 members last year, and is officially launching Squads this month, with a goal of reaching 300 members in this new cohort.

“It’s not easy for women to get out and network in person as often and they don’t ask for the help they need because they don’t want to impose on people,” she says. “Instead we end up Googling the answer and getting a generic one-size-fits-all solution.”

A Few Turns Lead to the Right Turn

It took several pivots before Bourgoin finally figured out that Squads was what her business networking site should have been all along.

Born in the small port town of Lunenburg, Nova Scotia, Bourgoin, who oozes an infectious energy and charisma, moved to the capital city of Halifax to study public relations at the Nova Scotia Community College and later founded two freelance PR companies. When she struggled to find other freelancers who had the skills she needed to grow her business, she came up with Swapskis, a skill-swapping service that helped entrepreneurs barter skills with one another.

When she presented the idea to men, they would say, “Why wouldn’t you sell your skills instead of swapping them for free?” To Bourgoin, the answer was obvious: Not all entrepreneurs have the money when they’re starting up. It also became clear to her that men and women entrepreneurs operated differently when it came to networking. “Our natural way of building our business is by sharing and creating value for others,” she says. “Women are less calculated in who they choose to help out.”

Bourgoin decided to make Swapskis just for women, then later changed the name to Vendeve. “It wasn’t until I made the conversation ‘women only’ that I realized how powerful that was and that we were tapping into something much bigger.”

That power, however, wasn’t obvious to the venture capitalists and angel investors she met, the majority of whom were men. Some would say she was stupid for excluding men, thereby reducing the size of her audience. Others snidely suggested that if her business fails, she could coach entrepreneurs since her pitch was so great. She even got asked how she was going to attract female investors, a microaggressive way of saying no male investor would be interested. “I get that it’s hard to get excited about a business that is never going to serve you but wow, there’s some pretty blatant sexism here,” says Bourgoin.

Despite the non-believers, Bourgoin managed to raise $350,000—$250,000 from the Nova Scotia venture capital firm Innovacorp and the rest from a handful of angel investors who believed in her passion and were very aware of the fact that women-led companies yield higher returns on investment than male-led ones according to McKinsey & Company, Catalyst, and MSCI ESG Research. “One investor even said to me, ‘Women entrepreneurs is too big a market. You have to go more niche.’ I thought, ‘Thank you! The one man that gets it!’”

A Safe Space For Everyone

Now that Bourgoin has nailed down her business vision, she can now spend more time making sure that her female-centric space is safe and inclusive. When a space is designed for women, the use of gendered language and generalizations can often make trans women and non-binary individuals (who don’t identify as male or female) feel unwelcome or excluded. Bourgoin admits that Squads’ members are overwhelmingly cisgendered women but says her platform maintains strong principles of inclusion. “We don’t want to place any strict rules on gender.”

Jessica Drury, who runs Heartlines Copywriting Studio from her home in Lindsay, Ont., joined Squads last August when she realized she had been working in a silo, with no one to bounce ideas off. When her children are at school or sleeping, she squeezes in Squad calls so she can talk to like-minded women entrepreneurs—who also happen to be her ideal client. “Before, I was in 20 different Facebook groups and I was wasting my time and energy and not getting the interaction or feedback that I really desired,” she says.

Menna Riley, a Halifax-based events manager, was also an early joiner. She says she shaves off months of mistakes every time she talks to her squad. As an example, when she told her squad she wanted to launch an annual online course to teach entrepreneurs how to plan their own events, they told her that holding a once-a-year course was not ideal for people wanting to plan an event right away. “They were right. I almost went in the wrong direction that would’ve cost me a year and a half!” she says. “They gave me straight-up feedback and never made me feel like a dummy.”

That’s exactly what Bourgoin wants Squads to offer to women entrepreneurs: no-nonsense conversations about what it takes to run a business with people who care and get it. She’s currently winding down her skill-swapping network site so she can focus on building Squads. Like any other startup, it’s hit dead ends and missteps. The company is not yet profitable and is being run by just two people, including the founder. Over the holidays, Bourgoin asked herself whether she should just pack it in.

To answer her question, Bourgoin jumped into a Squads Hot Seat herself to get the brutal truth. She asked whether Squads was helpful to the women entrepreneurs, if the price was too high, and what areas of the community could use improvement. She hung up the phone with a few ideas and fire in her belly, determined as ever to keep Squads going. “You always leave these calls feeling lit up and enthusiastic.”

Down the road, she can envision Squads turning into something much larger, perhaps even mix-gendered. But for now, the strength of Squads lies in the fact that it’s providing immense value to a concentrated group of women, including Bourgoin herself.

“There are certain kinds of conversations we can have when it’s just a group of women entrepreneurs. My mom and my husband and his mom have been an amazing support system, but I can’t sit down and talk to them about what’s going on with my email subscription model and what my email subject lines should be. They just don’t have the context for that and I was putting a lot of pressure on them to provide that support for me. Now my squad provides that for me.”

Related Articles

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The Problem with Bro-preneurship: On Display at Montreal’s Startupfest, by Petra Kassun-Mutch

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