The Total Mom Inc.

Anna Sinclair is a mother of two young boys. An award winning serial entrepreneur, she is also founder and CEO of Total Mom Inc., an online media brand and powerful platform for mom entrepreneurs. Named one Top 100 Most Powerful Women, she is indeed a force of nature—a business leader who launched one terrific event that is now growing it into something much, much larger.

…what about Mom?
It all started in 2017 when Sinclair gave birth to her first child and was taking a break from a budding pop music career. She attended a baby show and got oodles of free stuff, but then realized it was all for babies. ‘Doesn’t anybody give a crap about the mom?’ she asked herself. ‘Isn’t there a mom show?’ The answer was no, there wasn’t. So she created one: The Total Mom Show. Debuting in 2019, the show was a dream for any Mom. You could walk in and say ‘what do I need to be supported personally and professionally right now?’ Not just another trade show with pop-up tables, The Total Mom Show was a VIP event that brought together influencers, brands, experts, placing the focus squarely on moms. It proved immensely popular and landed a 20-minute segment on CBC’s The National.

From event marketing to pop stardom
The Total Mom Show wasn’t Sinclair’s first success. After high school, she attended Georgian College and Laurentian university but would drive from Barrie to Toronto on the weekends for marketing and promotional jobs in the big city. She was feeding a passion: experiential marketing and events. “I worked for North America’s biggest marketing firms on the side with incredible clients & brands whom I loved and used myself. I was fascinated to learn about how they engaged with their customers.” It was a skillset that would come in handy. At the same time as she worked in the trenches of promotional marketing, Sinclair was a union actress filming, writing music, modeling, singing and becoming a social-media influencer after photographing her favorite brands. Her big music breakthrough came at a low point in her life when, in her 5th year of a 6-year psychology degree, she broke up with her fiancée at the time. Moving back in with her parents, she came to realize that she couldn’t sink any lower, a thought that gave her the courage to simply take the risk and go for what she really wanted in life. “So I dropped psych and went for my music dream,” she laughs. Sinclair was eventually signed by Universal as a pop artist, made it onto the Disney & Family channel and had her album “ Something Inside You” -Anastasia A was considered for a Juno Award. “I found myself on stages of up to 30,000 people, I was working around some of my favourite artists like The Weekend and Taylor Swift, I was on set with Will Smith…and I realized that I had somehow made it happen.”

The Founder of The Total Mom Inc. , Anna Sinclair

From pop star to mompreneur
While Sinclair was finding purpose through her voice, she got into blogging and social media influencing. Very much in the public eye, she was working with different brands, building a marketing-media-event-planning experience for herself. “I was really happy in my career,” Sinclair remembers. “I was about to get signed in the U.S. Very exciting. That’s when my husband and I found out that I was pregnant.” The news put a huge pause on her budding career and Sinclair came home. After the birth of her eldest in 2017, Sinclair was back in her husband’s parents basement, suffering from a baby brain. “I couldn’t think, I had no time, I was constantly nursing,” she says. It struck her that this was her new life—being a mom with many new challenges and barriers to get back to work. So she decided to embrace it.

For a quick breather and to embrace her new found motherhood, Sinclair went to a mom & baby show. The consummate influencer, Sinclair came home with thousands of dollars in products that exhibitors hoped she would review and play up to her social media audience. “Normally I would have been excited,” she notes. “But after the show I felt more alone and depleted and exhausted than ever. I dumped all the items on the ground and it struck me: Holy shit, this is all for the baby. What about the moms?’”

From babies to moms
Sinclair began researching mom-and-baby events and quickly found that the focus was mostly on shopping experiences and mommy and me groups…not moms.
Sinclair decided that Moms were worthy of a show of their own. “I am going to disrupt this whole ‘let’s treat Moms like a consumer situation’ thing” was Sinclair’s driving thought.
“The ideas came thick and fast,” she remembers. “I wrote it all down, about creating this festival, better than a trade show, inspiring and empowering for moms. I wanted it to be something that would help them in all areas of their lives, to help them feel powerful again.” The newly minted Founder and CEO of Total Mom Inc. then spent an entire year and a half while nursing her newborn planning out an elaborate show: two floors, two days, a VIP lounge, a massive stage with over 35 speakers, a beauty lounge, a closed-off activation area for changing and nursing, with unlimited diapers and wipes and everything that moms needed so that they could actually enjoy themselves.

Sinclair’s Eureka moment
Sinclair’s passion sprang from her personal situation at the time. She knew that she wasn’t going to be stuck in a basement with her career on pause. “If I feel like this, there have to be thousands of other moms who feel exactly like me,” she reasoned. Yet Sinclair was under no illusions that building a show from scratch was going to be easy. “It’s going to be hard for a
while and that’s the price you have to pay,” she observes. “There’s a lot of grit and tenacity and strength that is required as an entrepreneur.” Being an entrepreneur was not Sinclair’s only source of grit, however. Born to parents who left the Soviet Union for Israel when she was a tot, Sinclair’s family lived through the Gulf War, then immigrated to Canada. Starting from scratch is nothing new to her. “When we moved to Israel my family couldn’t afford a bedroom for me. I had like one toy in the cupboard, growing up. I’ve had to start over many times and I think I learned from that,” observes Sinclair. “You can sit there and cry about it, or you can get up and do something. And when you do fail, you just learn a little bit more about how to take that next
step forward because you’re not going to do it the same way.”

Anna Sinclair, The Total Mom IncA huge success
Sinclair put together huge sponsorships, including the likes of Pampers® Pure, and blue-chip show sponsors like Scotiabank, Export Development Canada, VISA, UPS and GoDaddy. She pulled in mental health experts, divorce lawyers and many other specialists for educational talks. The 2019 Total Mom Show had everything that modern moms needed to gain knowledge and feel empowered. The 2019 show was a huge success. With write-ups in major media across Canada and a 20-minute interview airing on CBC’s The National, The Total Mom Show got great exposure. “It really drove me to that next level of advocacy,” says Sinclair. “I wanted to disrupt how people view moms by introducing a new concept.” Although The Total Mom Show got lots of press, Sinclair felt that somehow the media was twisting the story. “In featuring the show, they made it seem like we were simply tapping into a big market. What I wanted them to see was that we were focusing on and empowering moms.”

The birth of Total Mom Pitch
This laser beam focus on moms was nowhere more evident than something that took place towards the end of the event: a ‘pitch’ competition that encouraged mompreneurs to get up on stage and pitch their businesses and access funding and resources while juggling motherhood. Moms applied to compete for a grand prize valued at $20,000 ($10,000 in cash and $10,000 in- kind, including mentorship by the judges). The judges reviewed the applications and selected the top 5 finalists to present. The criterion to apply included identifying as a ‘mom’ living in Ontario, owning a Canadian business that was at least one year old, and not making a huge amount of money. The panel of judges included luminaries such as executives at brands like Shopify, DivaCup and c-suite influential women leaders. Sinclair had put her influencer marketing skills to work, collaborating with talent and influencers and well-known brands. Suddenly the media buzz was all about ‘what’s this Pitch show that’s like a shark tank for moms’? Sinclair recalls that the business ideas were amazing and the feedback incredible. It was at the after party for Pitch applicants, friends and family that she first realized she was actually beginning to develop a business community. “It left me wanting to make it even bigger and made me realize that I was not the only mom who wanted to get back out there and run a business of my own,” says Sinclair.

Bumps in the road
Sinclair had brought on a business partner in time for the first Total Mom Show. Once it was over, her partner jumped ship. “That was probably the rockiest time I had ever faced personally and professionally,” she says. The business was in the red after such a grandiose event. Not only did Sinclair have to manage that debt, but she also had to buy her partner out. True to form, Sinclair made lemonade out of lemons. It was the messy breakup of her business partnership that would later feed a passion: helping women to understand how to build a business sustainably and profitably. Things like setting up a proper business structure, protecting intellectual property and putting an exit strategy into place in case a partnership does not work out. To make ends meet during this time, Sinclair and her husband worked at odd jobs, they survived and Sinclair continued to build what is now recognized as Canada’s largest pitch competition for moms and the fastest-growing business community for mom entrepreneurs in Canada with expansion into the US. Not long after moving out of her in-laws’’ house, Sinclair was named one of Forbes’ Top 100 Most Powerful Women. “When that happened, I felt like an awestruck child,” she says. “ I literally had no idea what I was doing and I was just running by the seat of my pants, hoping that I wasn’t going to burn through all of our cash while bootstrapping and trying to figure out what systems and processes I needed in place to run a company.” Sinclair acknowledges that, through everything, her husband Brandon was her rock: her business sounding board, often her source of inspiration, and a great source of emotional support. Together for 11 years now, Brandon was there through the music industry days, the building of Total Mom Inc. and everything that Sinclair has done since. “In 2019 we didn’t have any employees,” laughs Sinclair. “Up until about a year ago, we didn’t even have a payroll!” To this day, Sinclair puts money into her team first, taking home very little as part of a strategy to grow and scale her business.

Total Mom expands
After The Total Mom Show Toronto, Sinclair drew up plans for the Total Mom Show in Simcoe County and the Total Mom Business Summit, among other shows. Then COVID struck. “I remember sitting in my headquarters office in Collingwood and hearing the announcement from Trudeau about the first COVID lockdown. ‘What happens now?’ I wondered.” With four massive events just months away, the Total Mom team had an internal meeting and decided that they would have to cancel. “It was a hard pill to swallow, because I was helping moms and businesses. But I was going to have to ask for my money back from them and that made me sick to my stomach,” says Sinclair. The cancellations went ahead and Total Mom Inc. offered a credit to registrants. Total Mom Inc.’s corporate landlord at 1 First Street in Collingwood, The Clever Office, believed in what they were doing and let them stay on a little longer as they transitioned out of office and back home.

Not long afterwards, inspiration struck. “You’re going to find a way to help businesses right now that need funding resources and support,” is what Sinclair told herself. Since she was in the middle of building one, she knew what power ‘community’ can hold. “I remembered all of those times where I was sleepless and felt hopeless and was always able to find someone in our community to lean on.” Sinclair decided to go ahead with the Pitch Competition and Business Summit—taking them both digital. “We were going to support the moms, help them achieve their dreams despite the situation, and walk with them through this dark period.” And Canada’s Total Mom Pitch was born. In need of sponsorship, Sinclair consulted with her business manager at the Collingwood Scotiabank branch, Zora McGladdery, who jumped right on board with information about programs like CEBA and connections to potential sponsors. With Zora vouching for the team, Sinclair pitched the concept to one of those connections, who became the presenting sponsor. “From a local Toronto or Simcoe County pitch competition, we became a national resource for moms looking to grow a business but not sure where to turn for support,” says Sinclair.

Anna Sinclair, TheTotalMomShow


In 2016, back in Sinclair’s music days, her brother moved to Collingwood. Sinclair and her husband made a couple of short trips from Toronto to visit and soon fell madly fell in love with the place. “The nature and health-and-wellness lifestyle, the trails and the breathtaking waterfront…I realized this was a place I might be able to grow and scale my business career,” she says. Housing was cost-prohibitive for the couple and they struggled to find a rental. Three years later, and after seeing a billboard promoting migrating to Collingwood from Toronto, they found the perfect place and made the big move with their now three-year-old son Hudson and 5 year old Oliver-Bradley. Total Mom Inc. operated out of a big barn on the leased property and six months later Sinclair and Brandon had their second child, Hudson. Brandon was still going back and forth to Toronto where he worked in marketing, but to move Total Mom forward, they both knew that the business needed him full time.

Building a powerful business network in Collingwood
Once settled in Collingwood, Sinclair set out to acquaint herself with the local business community. It was at the Entrepreneur Coffee Hour held by Brandon Houston at the Collingwood Foundry, a collaborative workspace where Collingwood entrepreneurs meet to network, that she first heard about the Collingwood Business Development Center (BDC). There she met Gillian Fairley, General Manager of Community Futures South Georgian Bay (CFSGB). “I told Gillian ‘I’m bursting with all these ideas and we’re going to do a Simcoe County Total MomFestival’ (the 4 shows) and Gillian said ‘whoa Anna, what is your business plan?’”

In Toronto, Sinclair had been moving quickly and flying by the seat of her pants. When Fairley sat her down and said she needed her to put everything down on paper, identify revenue streams and help her to understand the financials, Sinclair thought ‘I like this no-BS lady! I need her in my life and I’m going to keep her as one of my peeps!’ Fairley instantly became Sinclair’s ‘go to business expert’.

Total Mom Pitch goes digital
The pandemic that struck in January 2020 immediately put Total Mom’s plans on hold. But by April 2020—just three months later—The Total Mom Pitch had over 700 applicants, a national audience of 5,400 voting for the top 100 semi-finalists and a reach of 17 million. This was thanks to blistering-fast work on Sinclair and her teams part, including massive promotion on social media that built in cross-promotion through influencers and sponsors. The program included many inspiring and influential speakers, workshops and meet-and-greet events. There was a virtual VIP box sponsored by 10 brands where seats were sold to fund women-led programs. A shop-local vendor market included women-owned businesses, local to wherever they were in Canada, since this was a national program that anyone in the nation could support.

Sinclair used her influence and connections as a singer to procure resources to help entrepreneurs to develop powerful brands that would positively impact their lives, careers and also the communities in which they lived. “Seeing hope restored to these women with small businesses is what keeps me doing what I do,” she says. The funding that Total Mom brought in provided resources such as an Accelerator Program where women entrepreneurs would receive training and mentorship from the likes of Google, Shopify , Visa, EDC and more, at no cost. The program put budding entrepreneurs under the wings of coaches and experts that would ordinarily have cost thousands of dollars to work with.

What’s up next?
More transformation, what else? With Total Mom, Sinclair is planning to take what was originally a support network for women struggling through COVID and build it into a business ecosystem for mompreneurs. Oh, and May 30/31st this year is when the Total Mom Pitch and the Total Mom Business Summit will take place—mark your calendar.

Getting past the pandemic will be big for Sinclair. “I just want women to be able to get back together in the same room, to be able to hug and to be able to feel each other’s energy,” she says. She envisions future Total Mom events as a tour where the team stops off at stadium-sized venues, with powerful, inspirational speakers and performing artists. “What we’re building is a place, online and in person, where entrepreneurial women come to get energized,
excited and empowered,” says Sinclair.

The Total Mom Inc. organization still numbers fewer than 50 employees. That’s likely to change, as Sinclair realizes her plan to build a billion-dollar empire. “I want Total Mom to go global,” states Sinclair. “I really want to make sure that there’s a Total Mom in every country. And that requires a global digital presence.”

Anna Sinclair with the whole family

Total Mom Business Membership
Sinclair realizes that her quest for global reach will require even more of a shift towards ‘media’. While Total Mom events will proliferate in various jurisdictions, rich content will fuel the organization’s reach and influence. “The best way to describe The Total Mom Network is kind of like an Oprah network where you watch content, where it’s fireside chats or interviews with experts sharing profound information and/or experiences,” says Sinclair. Programming will focus on different stages of mompreneurhood, including both the total mom’s business and the total mom’s personal life, such as entrepreneur and continuing-education e-learning programs as well as health and wellness programming—mostly delivered as high-quality video content.
To initiate the transformation, Sinclair is (surprise, surprise!) moving quickly. At time of writing she landed an Emmy-winning producer and TEDX speaker, who as her new CCO ( Chief Community Officer) says “Together we’ll be creating rich video content and experiences in the membership and providing business programs with our partners that women will be able to digest when becoming a member,” says Sinclair.

Looking even further into the future, Sinclair envisions a Total Mom Business Academy, where entrepreneurs can find mentorship, develop and grow…but that’s a tale for another time.
To find out more about Total Mom Inc. or to apply to The Total Mom Pitch, visit www.totalmompitch.ca or the main website.

Photo Credit: Julie Card, MyCollingwood.ca

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