Shelagh Cummins, founder of The Road to Seven™, believes in the power, strength, brilliance and resilience of women entrepreneurs. Recognizing that only 12 per cent of women bring their companies to over six figures — and a mere 2 per cent to over seven figures — she knows that their potential to succeed requires some support. This is where The Road to Seven comes in.
Time flexibility and financial freedom: The forces that drive the entrepreneurial journey
As the story goes with many entrepreneurs, Cummins’s business was born out of a need. A teacher for 13 years, she experienced a lightbulb moment when pregnant with her daughter. The realization was this: No matter how much better she might get at teaching, she was not going to grow her salary in any material way. “I was teaching at a girls’ school, and it dawned on me that I wouldn’t necessarily be able to afford to put my daughter into one of the chairs at that school,” she shares.
Cummins needed to contribute to her family in a more meaningful way while also being the primary caregiver for her children. After trying a few different paths — from tutoring to writing a parenting blog — an emcee gig at a women’s entrepreneur event proved to be the catalyst she needed. A business owner in the audience, impressed with Cummins’ insights, wanted to hire her to increase her sales.
Eighteen years later, Cummins has built The Road to Seven into a multi-platform company that helps women grow and scale their businesses — which often originated from a similar starting point as hers. “The women I work with are very happy to work hard because they love what they do, but they’d like to have flexibility about when they work. Time flexibility and financial freedom are the two main drivers of their entrepreneurial journeys, followed by a very close third, which is impact,” says Cummins.
Nurturing the drivers of success to overcome barriers
While these factors are strong motivators to start a business, Cummins reveals the characteristics that help turn inspiration into action — and ultimately into success. “Above and beyond anything else, it’s vision and need,” says Cummins. What I mean by that is that a successful entrepreneur will have a really clear vision of the impact they want to make, the problems they want to solve and the solutions they will provide. That’s number one.”
Number two, she reveals, is the willingness to take the risk, followed by grit and resilience. “The journey is not going to be smooth, because you’re out there every day searching for your next paycheque — you’re operating without the safety net of a company that’s going to pay you every two weeks and cover your benefits. That’s a lot of pressure.”
The women who work with Cummins possess this spirit – along with extraordinary work ethic, commitment and talent. Yet they also face common challenges that hold them back on their the path to growing six- or seven-figure businesses. The Road to Seven programming addresses these challenges through Cummins’ proprietary curriculum, called the Scale Roadmap™.
The ‘C’s of scaling a business
The Content offered by Cummins delivers actionable insights that may have a tangible impact on an entrepreneur’s current and future success. “We only know what we know,” says Cummins, who emphasizes the importance of an ongoing commitment to learning. “Sometimes the content we provide enables a business owner to look at something differently, or it helps them put the pieces of a puzzle together they couldn’t before.”
Community is another benefit women entrepreneurs may benefit from. “One of the ways our programming has the most impact is through the community,” explains Cummins. “Being surrounded by other women who are experiencing similar challenges, frustrations and successes leads to confidence and comfort.”
In a recent podcast, Cummins identified 10 ‘C’s that can help women entrepreneurs successfully scale in 2025. While Content and Community are pivotal, she says perhaps the most influential of all the ‘C’s is Capital.
“When you’re scaling, there is going to come a point where time and energy alone are not going to cut it,” says Cummins. “You have to make a financial investment that will allow the company to be more efficient.”
Unfortunately, access to capital has historically been one of the greatest barriers faced by women entrepreneurs.
“A lot of women have been bootstrapping the growth of their business and putting anything extra back into the company. While that’s needed, it means they don’t look great on paper as an investment.” Other societal factors may influence women entrepreneurs accessing capital. Cummins says that many women look at debt as a negative, while men may be quicker to leverage. “Women say they can’t take on debt, while men are happy to leverage collateral to make something happen.”
So, in addition to coaching, training and community, The Road to Seven offers support and funding opportunities for entrepreneurs facing time and financial constraints, as well as advice on how to access capital through traditional lending sources, helping them make strategic investments to grow their companies.
“When I rise, the women I work with rise as well”
When it comes growing and scaling her business, Cummins follows her own advice. “I’m always learning too — I’m growing and evolving every single day,” she says, explaining she has her own coaches and training programs designed for women at her level. “This allows me to be a stronger leader – one of the visions I have is that when I rise, the women I work with will rise as well.”
Women’s business ownership is growing — the latest data shows that 18.4% of all businesses are majority-owned by women in Canada. Shelagh Cummins wants to see not only more women-owned businesses, but more women owned businesses that land above the seven-figure threshold – enabling them to run businesses that provide them with the time, money and freedom they desire.
