Celebrating Canadian Female Investor & Founder Trailblazers – Part 3: Ups & Downs

The CVCA’s Celebrating Canadian Female Investor & Founder Trailblazers is a five-part series celebrating the success of Canadian Women in business as part of International Women’s Day.

Wednesday was International Women’s Day. A day to celebrate the social, economic, cultural and political achievement of women all over the globe. However, progress has slowed in many places across the world, so global action is needed to accelerate gender parity.

The Canadian federal government, under Prime Minister Justin Trudeau, has made headlines for its approach to gender equality. The government took meaningful steps to support women’s leadership ​“by appointing Canada’s first gender-balanced cabinet and deciding to restore funding for women’s rights advocacy,” in November 2015.

While the government has put an increased focus on gender-based policy analysis and women’s rights in international development, there is still room for improvement.

Female leaders are important for the attitudes and ambitions of young women. According to a 2012 study from MIT, ​“Seeing women in charge persuaded parents and teens that women can run things, and increased their ambitions. Changing perceptions and giving hope can have an impact on reality.”

The theme for International Women’s Day in 2017, is #BeBoldForChange; a call on the masses, or call on yourself, to help forge a better working world and a more inclusive, gender equal world. On ways you can declare bold actions to help progress the gender agenda, visit the International Women’s Day website for a list of resources.

In the spirit of International Women’s Day, the CVCA reached out to successful female investors and entrepreneurs to expand on their career stories, address current roadblocks to success, and to provide some advice on how to combat inequality in 2017.

The CVCA’s Celebrating Canadian Female Investor & Founder Trailblazers continues with the hard decisions trailblazers have made along the journey to where they are today.

What is the best and worst decision you’ve ever made?

Best decision: Taking the one year MBA at Wilfrid Laurier University. An intense program that prepared me for the intensity of the work I do today. The program forces participants to study a breadth of subjects necessary to be a well-rounded business leader. I graduated feeling comfortable in a range of subjects most importantly those I thought were outside my sweet spot. 

Worst Decision: at home highlights…need I say more? – Shirley Speakman, Partner, CYCLE Capital Management

The best decision I have ever made was starting McRock Capital with my co-founder Scott MacDonald. We have worked together for 20 years and had a vision that the Industrial IoT would emerge as an attractive investment area. Today McRock Capital is one of the world’s leading Industrial IIoT funds. 

The worst decision I ever made was investing in a company back when I ran a corporate venture capital fund at a large power company. There is an expression, ​“don’t confuse me with facts, my mind is made up”. I invested in a company because I was enamoured with the other investors at the table. The company ran out of money shortly after we invested and the relationship between investors turned sour. The company is still around today but it was a good lesson to remind myself never to park my brain outside. – Whitney Rockley, Co-Founder & Managing Partner, McRock Capital

The best decision I ever made was investing in a business co-founded by my sister, Urban Flats Toronto. It went against my investment training and general thesis as it is a traditional SME versus a scaling technology company. Many advised about the risks of investing in family or friends, but the outcome has been great – she’s generated the quickest return on investment I have experienced in my investing career and it’s brought us closer as we work through strategy and ways to improve our customer experience and operations. The biggest win; however, has been the realization that I was viewing investment opportunities through the predominantly male lens that created the North American venture capital industry. I am now very conscious of and working hard to shed that bias when meeting with female entrepreneurs and trying to influence my partners to do the same. 

I think the worst career and life decision I made was turning down an opportunity to spend three years in Europe with KPMG early in my career. I had concerns that I would have to commit to remain in public accounting that much longer and was anxious to leave the firm and find a new role at home here in Toronto. Like many Canadian leaders, my career and network are centered in North America. Looking back now, I realize what an advantage expanding my universe would have been with that opportunity. – Kerri Golden, Partner & CFO at Information Venture Partners Inc.

The best decision: Taking a leap of faith and joining a VC firm – I was seconded to the fund by one of the LPs. At the time, I didn’t know that VC or secondment meant, but the role as described seemed to be exactly where my career, my interest and my passion were leading me. I’ve never looked back.

The worst decision has been to override my gut feeling when making investment decisions – good and bad.– Michelle McBane, Director, MaRS Investment Accelerator Fund

The best decision would be a tie between: 

I) quitting a great job as the Global General Manager for Kijiji to stay at home with my four-year-old son for nine months; or

II) joining Real Ventures, an amazing values-based firm, in a role which enables me to spend my days meeting and working with great entrepreneurs and in some small way, helping them realize their dreams. – Janet Bannister, Partner, Real Ventures

The best decision I’ve ever made was to pursue an Engineering degree from Waterloo; it gave me six co-op terms to experiment working in various roles and industries. I graduated with not only six potential employers, but also an exact idea of what interested me. It was a great jump-start to my career.

Worst decision I’ve ever made relates to being risk averse and not pushing myself more outside my comfort zone. For example, I gave up an international work opportunity and a job in sales, due to fear of the unknown. Both opportunities would have highly benefited me today.– Neha Khera, Partner, 500 Startups

Best: To build my company: VarageSale. When my co-founder and husband agreed to build VarageSale with me, it was nothing more than a website we built for myself and the community I lived in. When we noticed that the website was not only growing but that 50% of our users were returning daily, I was faced with a decision: To build on or to continue on my path as a new mother and teacher. To build on meant that I’d be a ​“female founder”, ​“a female leader,” a ​“woman in tech.” These were all titles that intimidated me as a minority and newbie in the space. But I decided to build on, which was the best decision I’ve ever made. I decided to overcome my fears and realize my strengths: I had all the leadership I needed through being an educator as well as it being a trait that I was naturally born with. I built communities in local school districts which gave me the insight to build a marketplace in communities all over the world. VarageSale raised its initial funding mostly from Canadian investors (iNovia, Real Ventures, Version One Ventures, and Floodgate in California), and ended up growing to have millions of users, further raising $34M dollars USD from top-tier Silicon Valley investors: Sequoia Capital and Lightspeed Ventures. I wasn’t sure we’d make it that far when we started, but I’m sure glad I followed my passion and built my company.

Worst: I took a backseat in a lot of business conversations at first. That intimidation I spoke about didn’t end overnight. As a new female founder, I started off by keeping it safe and only commenting and being forceful on the things I knew a lot about. I failed to ask questions in fear of judgement, I failed to give opinions in areas I was unsure of, and all of this held me back. It took a lot of reading, meeting with mentors and soul searching to fully come out of my shell. My biggest regret was not doing it sooner. Once I started to take a seat at the table and ​‘lean in’, I gained the confidence I needed to lead. – Tami Zuckerman, Co-Founder & Chief Customer Officer, VarageSale

Best – Deciding it was time to stop doing what I thought I should be doing and to do something that allowed me to be totally in my element. I left my corporate job to pursue my entrepreneurial desires. I am at place in my life where my job doesn’t feel like a ​“job.” Worst – Spending the first year and a half building my business at an unsustainable pace and becoming burnt out. – Jen Lee Koss, Co-founder and Builder of Business, Brika

Best decision: Deciding to buy Axonify instead of going to work at Google.

Worst decision: Selling a company to someone I didn’t like. – Carol Leaman, President & CEO, Axonify

The best decision I have ever made was to take a job out of University that offered no salary, only commissions, but a chance to travel and really learn cold, hard sales. Knowing how to sell has been critical to the entrepreneurship road, that I am happy I learned it – that hard way – one cold call at a time. The worst decision I ​“almost made” was to invest all of my savings into my MBA. I used those funds to start OMX instead and do I ever feel that I got my MBA worth in real life learnings.– Nicole Verkindt, President, OMX

The best decision I ever made was to leave Quebec at age 18, allowing me to grow into myself. It opened me to new opportunities and allowed me to gain the confidence that I could accomplish anything I put my mind to – including learning English! The worst decisions I have made involved me trying to hang on to people for too long for the wrong reasons. I believe good people come into your life when you can turn the page and allow for space.– Stephany Lapierre, CEO, tealbook

The best decision I ever made was to be an entrepreneur. I think sometimes universities taint the career options you believe you may have for yourself when you graduate, but I am glad I took the opportunity to be an entrepreneur right after I graduated rather than waiting. 

The worst decision I ever made was trying to fit in. I tried to fit myself into all of these different career paths, never feeling like any of them fully resonated with me. I’d spend two years working toward a career path that in retrospect, I was moving backwards and away from my end career goals (becoming an entrepreneur) just because it wasn’t the ​‘norm’. I spent too long trying to fight being different, rather than embracing it– Jaclyn Ling, Director of Partnerships at kik, Co-founder of Blynkstyle

Best, taking the leap of faith and starting my own company.

Worst, to be honest, I don’t think there’s anything I truly regret in my career. Every mistake served up a very valuable lesson.– Marie Chevrier, Founder, Sampler

The best decision; easy – partnering up with my two incredibly talented co-founders who come from completely different backgrounds, but share a vision for growing a leading global company. While maybe not a ​“worst decision” we definitely made mistakes early on around trying to do too much and be everything to everybody rather than focusing on our customers and team. Once we became disciplined about that, everything fell into place.– Lindsey Goodchild, Founder, Nudge Rewards

This article was part three of the CVCA’s Celebrating Canadian Female Investor & Founder Trailblazers. Celebrating Canadian Female Investor & Founder Trailblazers is a five-part series celebrating the success of Canadian women in business as part of International Women’s Day.