Meet four women who have suffered major setbacks and triumphed. Deadly illness. Life-changing injury. Extreme money trouble. They each faced their personal demons while doing business, often while also balancing the needs of their families.

Esteem Lingerie owner Angela O’Brien, whose store is in West Kelowna, says sometimes you have to open your arms to the universe and say, “Bring it on.” 

She’s embraced her title of ‘chief boob- oligist.’ 

The family business has come a long way over the past two decades. O’Brien’s mother, Florenda Pickett, initially conceived of Esteem Custom Foundations almost 20 years ago. As the world changed, so did the name, which evolved into Esteem Lingerie. While in her early 50s, Florenda left the corporate world and sought a new venture. Initially planning to open a fabric and sewing store, she discovered a demand for custom-made bras after discussing specialty supplies for outdoor wear and bra making.

“She very quickly realized she could not keep up with the demand,” says daughter Angela.  

Yet, Florenda knew she still wasn’t quite getting at the heart of the problem: women needed a store where they could be properly fit and educated about how to get the right bra. There was also a need for a wide range of quality products.

Meanwhile, Angela was working in insurance in Toronto, transitioning into training and development. But she was disenchanted with the big city.

“I was done with Toronto,” she says. “I had served my sentence out there.”

She moved to West Kelowna, and they built the store from scratch together. It doubled in size over the next 17 years. 

Angela says she’s proud to help women raise their self-esteem, develop healthy body images and challenge the status quo in the lingerie industry in marketing and mindset.

One of the ways they help women is through their work around breast cancer, which affects about one in eight women.

Esteem has transformed into a haven for women in post-mastectomy recovery, offering proper fitting services and valuable support.

“Our goal is to help women understand that when they’re going through these challenges, there are resources,” says Angela. “As my mom likes to say, ‘become a cancer thriver.’”

Starting and growing a business was especially difficult for female entrepreneurs at the time. Angela recalls the gender bias they encountered, including biases in expansion funding. 

“It became very apparent to us that even lending and loan programs were still skewed towards the men’s world. If I heard it once, I heard it a dozen times from bankers: ‘Oh, isn’t that a cute hobby.’”

At one point, she was asked to have her husband co-sign for her loan.

“In my mom’s generation, they put on their Super Woman capes, and they started trying to break down the glass ceilings,” says Angela, who adds, “I’m generation X.” 

As more women entered influential positions, the landscape began to change. The breakthrough for the mother-daughter team at Esteem came when they found a female commercial lines manager at their bank who took the time to understand their business. 

“That allowed us to move to the next level,” Angela says. “As we grew our business, we did it the hard way. We did it on personal lines of credit and credit cards, which is a very expensive way to grow a business.”

Three weeks after they opened their doors, Angela discovered she was pregnant with her first child. She was in the bathroom with her mom reading the pregnancy test. Her mom half-quipped, “As a grandmother, I’m thrilled; as your business partner, this is very bad timing!”

There’s no maternity leave as an entrepreneur, so babies came to work, she says. 

“I have two girls, and they were literally raised in a bra shop.”

Angela says her husband was very supportive. He took paternity leave and looked after the kids.

Then she took a terrible fall. While on vacation in 2017, she slipped on a rug and hit her head on a solid wood bed frame. She lost the ability to speak and read and had to learn how to do things over again during rehab. There are no safety nets as an entrepreneur, she adds. It took three years to reach ‘new normal,’ which differs from who she was before the head injury.

It has brought them closer. They simplified their life and took care of each other.

“I’m not going to pretend like there weren’t a lot of dark days. However, now on the other side of it, we joke about it being the incredible gift wrapped in shitty wrapping paper,” she says.

They’ve recently launched a new facet of the business, an online Bra Fitting Business Academy, to spread the word globally about how to properly fit a woman for a bra.

Tech law to the grapevine

Serendipity Winery owner Judy Kingston was a trailblazing tech lawyer in Toronto before moving to the South Okanagan. A young bachelor of science student in computing, she saw how the then-current law surrounding computer development  —or the lack thereof  —was hindering technology’s progress. 

“The judges just didn’t get it,” she says.

So Kingston decided to pursue law in that sector, but there were no courses specifically on the subject. While pursuing her law degree, she gave a lecture in Montreal about the emerging need for high-tech lawyers; she was recruited after her graduation by a leading law firm that had attended the lecture.

While high-tech law flourished, Judy’s decades-long law career abruptly ended. A car crash resulted in a severe head injury; her doctors advised her to avoid learning new things — to not tax her mentally  — and warned of participation in sports and physically demanding activities. 

Afraid of a future confined to a bed or couch, she found solace in an unlikely source: food.

Judy’s daily ritual of eating presented intense challenges but eventually led to a life-changing breakthrough. She had to drastically alter her diet so that her broken body could digest her meals. For years, she tried to make enjoyable dishes from unfamiliar foods, including agar seaweed and adzuki beans. “It was a very restricted diet. I had to learn a whole new way of cooking food so that it tasted good.” 

Learning to make palatable dishes with unknown ingredients helped her see she could try new things. 

In 2005, Judy and her husband went on vacation to Osoyoos, BC They had a few hours to explore on the way back to the airport for the flight home. Trying to reach the airport via the east side of Okanagan Lake, they ended up in Naramata, driving along Lower Debeck Road. 

Judy knew she’d found her place. “We saw an apple cherry orchard for sale. We stopped the car, and I walked around, and something just happened to my soul. We put the offer in, and by the time the plane landed in Toronto, I was the proud owner of an apple-cherry orchard,” she says. “That’s why the name is Serendipity.”

Judy planted the grapes with help from her son, daughter, and neighbours in the community. “I tapped them down, gave them their first water, and watched them grow. It’s very fun going out and picking them and bringing them in. It’s a very exciting time.”

The work is paying off, as Serendipity Winery is now recognized for their distinct wine style. 

Rising in Resilience from Revolutionary Iran

Okanagan-author and refugee Mehrnaz Massoudi has been through an uprising. She documented her experiences during the Iranian revolution in her biography, Never Without Love.

The Islamic Revolution, a revolt led by the Muslim majority, toppled the authoritarian government led by the Shah of Iran in February of 1979, transforming the country’s cultural landscape from a more Western-like society to the establishment of an Islamic republic.

Massoudi grew up in Iran before the revolution, attended university in Tehran, and left in 1983 as a young adult. She reminisces about the country she once knew. “It was magnificent for me,” she says, adding she was fortunate to be in an upper-class family and able to take advantage of all the beauty Iran had to offer at the time — including freedom for women. However, witnessing the growing poverty gap between economic classes during her university years and the subsequent revolution shattered that idyllic image.

In university, she became active in trying to change the system for the better. But the revolution brought gender apartheid, she says, with an Islamic regime that invades people’s homes and privacy. It also brought war. In 1983, she had to run from her home during the ensuing Iran-Iraq conflict. “My life was at risk; I was forced to flee for my safety,” says Mehrnaz, who sought refuge in Canada. 

Arriving in Ontario as a refugee, she attended the University of Guelph to study science, specializing in the cutting-edge field of DNA cloning research. However, her priorities shifted after relocating to Vancouver and starting a family. When her second daughter was born, she made the heartfelt decision to become a stay-at-home mom, realizing that the demanding nature of her scientific career and the time she needed to put in at her lab didn’t align with the needs of parenthood.

In 2000, Mehrnaz faced a health crisis when she was diagnosed with breast cancer. Her daughters were six and nine at the time. She had a double mastectomy followed by ten years of treatment.

“It was through that time that slowly there was a shift in my life,” she says. “I was a person with a scientific background, and I was doing everything to prevent cancer. I was very active, athletic, and eating healthy.” 

She started searching for healing. She practiced meditation and yoga and tried to live in the moment. “It was a huge shift — a very gradual turn; it didn’t happen overnight. I didn’t know where it was taking me. I surrendered to that shift.”

For Mehrnaz, there is no clear path to come to an awakening; rather there are many. One thing that has come clear to her over the years is that she has suppressed her own voice and lost her identity to become the woman society pressed her to be. “That woman was not me,” she says.

After a cancer diagnosis, anxiety can be a literal killer, she says. “Every suffering, every illness, becomes a battlefield. You hear when someone loses their life to cancer that she fought a hard battle and finally, she lost.”

Yet even after defeating the disease, Mehrnaz questioned whether she had ‘won the battle’ because inside she was frozen with anxiety —something nobody could tell from the outside.

She searched for peace by finding what she calls her “essence,” getting there through mindful practices like paddle-boarding, nature walks and meditation.

“Cancer was not in my essence,” she says. “Cancer was in my body and then it was in my mind because of the anxiety about it. It was never in my essence.”

In her memoir, she recalls her childhood, including an accident at age four where she suffered third-degree burns to her chest, arms, and neck that left her struggling with body image. After the trauma of losing her home and network of loved ones, she felt she needed to write it all down. Adding to the already daunting task, she chose to write in English, her second language.

She didn’t have formal training in writing or a helpful network. She didn’t know anything about query letters. On top of that, many publishers were closing their doors due to industry struggles. 

“I was passionate about writing my memoir, but I was faced with whether it would ever be published in this market,” she says. 

“I submitted to every publishing company, to every agency in Canada, to every single one of them. And they don’t respond for more than six months.”

Once she did start getting responses, she says the first few rejection emails hurt. But eventually, she got used to the letdowns. 

After many tries, she got an email from a woman at a Toronto publishing company, who suggested she contact Inanna Publications , a Canadian independent feminist press. She did, and within the same day they emailed her back asking her to send a hard copy.

Mehrnaz says she blended into Canadian culture quickly and within two years was in a long-term relationship with a Canadian man. 

“I was blinded to racism in Canada,” she says. “Unconsciously, I hid behind his identity.”

When others faced racism, Mehrnaz says she blamed them for not integrating into society well enough. As time passed, her perspective changed. She saw how her children were treated differently due to their foreign names. Then systemic racism impacted her personally while she tried to find a publisher, with one rejecting her solely based on her name. “They said, ‘sorry, we don’t accept submissions from non-Canadian authors.’”

She shared the experience on social media, eventually receiving an apology over the incident.

Massoudi has a second book coming out in the fall, a collection of short stories about women who have suffered from the loss of identity called The Namaste Way.

Startup Struggles to Software Success

Amanda Findlay-Shirras and her husband Grant started up a successful software company called Parkbench, targeting realtors in Toronto ten years ago. But it didn’t grow without a lot of hustle.

Recently, they moved to Kelowna for the lifestyle and quickly became involved in helping the local startup ecosystem grow, launching a local Start Up Grind networking event.

It all began when Amanda, a former real estate agent, and Grant, a personal trainer, moved to a Toronto community called Liberty Village and sought a unique route to promote themselves.

Recognizing the importance of relationships in the real estate industry, they built a community-centric website that listed local events, deals, and news. They offered local businesses the opportunity to showcase their profiles on the site for free.

 “We knew relationships were the heart of real estate,” says Amanda. “We went door to door and introduced the website to them. I got to meet them all, the hairdressers, the bar owners, and the coffee shop owners. And they got to know me.”

They quickly had almost every local business in the neighbourhood on the community website.

That caught the interest of other agents. So, Amanda cold-called realtors in Toronto’s Danforth, Queen West, different small communities, and pitched each their own micro site. Within a month, she’d sold 10 websites. Their business took off from there, eventually working with about 10,000 clients throughout the last decade, mainly in the U.S.

“There are so many ups and downs that have happened,” she says.

As a bootstrapped startup, Parkbench didn’t receive any investment. For the first couple of years, Amanda and Grant handled all the sales themselves, living out of motels across Canada as they sold their services to realtors. They converted their condo into an office for staff, packed their car with their belongings, and hit the road, starting from Vancouver and driving east.

Paying their staff sometimes came down to making a sale at the last minute.

“That lasted for years,” she says. “Basically, we had to live paycheque to paycheque. We knew that if we had people to pay, we’d make sales that day. Grant and I would argue more when the money was tight. As soon as you’re making sales, you’re not fighting about the little things. 

“We’d always say money cures all, sales cures all. That’s our mantra. Sometimes you get so stressed out that everything seems like the biggest mountain.”

Their pivotal opportunity came when they were invited to a three-month-long Silicon Valley incubator in 2019. They learned how to build a closing sales team, acquired a proper office in Toronto, and spent a $100,000 grant on advertising.

When the pandemic forced businesses worldwide to close, it unexpectedly became a blessing in disguise for Parkbench due to the availability of federal government wage subsidies. That support enabled them to hire more salespeople and provide employment opportunities for those laid off. At one point, they had 50 people working in their office.

Amanda says working alongside her husband presents its challenges, but she wouldn’t want it any other way.

“We started the company together; we work on it together,” she says. “With a startup, you have to go all in. We merged our entire life into our business. Because we’re together, we could do that. If you want a successful company, it has to be your whole world.”  

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Wine Issue 2023 Trends Magazine

Wine Issue 2023: Top wines in BC+ award-winning craft beer. Pet trends, design trends and dining trends