Interview with Kelly Hoey, entrepreneur, angel investor and CEWiT's Second Anniversary Keynote Speaker

By Sophie Babcock

Tuesday, October 6, 2015

Kelly Hoey, a speaker, strategist and investor wears many hats and holds many titles. Most recently, she has been named CEWiT’s Second Anniversary Keynote Speaker for the celebration event on Oct. 28.  Recognized for her commitment to the startup and tech industries, Forbes named Hoey 1 of 5 Women Changing the World of Venture Capital/Entrepreneurship, and Fast Company identifies her as one of 25 Smartest Women on Twitter. We caught up with Hoey to hear her perspective on women in technology and entrepreneurship, as well as the inspirations, setbacks and mentorship she felt throughout her own career path.

How do you answer, “What do you do for a living?”

Hoey: With great difficulty. My career story is one of transitions and once again, I’m in another transition. I also come from the era of get a college degree and a J.O.B. – changing careers frequently, freelancing, working from home (or coffee shops) were not career paths or options which were touted or valued during my college years.

So what do I do for a living? I’m an angel investor and a Limited Partner (L.P.) in a fund. I’m writing a book on networking. I write for Inc.com. I’m a keynote speaker. I’m an advisor to the New Zealand Trade and Enterprise (NZTE) and Canadian Tech Accelerator startup initiatives.

You are recognized in the startup community for your leadership in the promotion of women in technology, when did you realize you were passionate about this?

Hoey: 2011/2012 when I started angel investing and recognized the opportunity to invest in female-founded startups. I also co-founded the first startup accelerator that invested in mobile tech startups with gender diverse founding teams. The impending tech talent shortage combined with my personal experiences as a lawyer (I practiced corporate law for 11 years) and in law firm management (creating professional development curriculums and structuring global women’s initiative programming) have also fueled my advocacy for inclusion in technology.

Where did you grow up? Did you feel encouraged to pursue a career in entrepreneurship and technology at an early age?

Hoey: I grew up in Victoria, British Columbia in the pre-internet world of rotary phones, where ignorance of technology was still a viable career advancement strategy. I was encouraged to study, to excel in my expertise and to work hard  - in order to ensure career options. Curiosity, expertise and a strong work ethic are attributes that transcend economic eras.

Have you had any inspiring mentors or sponsors who influenced your career path most?

Hoey: I’m fortunate, I’ve had many mentors. A number have been difficult individuals who have pushed me to dig deeper and reach higher. Mentors who more importantly told me how things worked so I could advance professionally.

Let me give you one example.

As a young attorney, I worked a big bankruptcy case in Toronto. The partner noticed my work commitment and that I had a bit of enthusiasm for the practice area. He took me out to dinner and asked what seemed like a simple question: 'Do you like this practice area?' "Yes, actually, I do." was my response. "Do you notice anything Kelly?" – was his response to me.

Well, it wasn't hard to notice - this case regularly involved trips to court where 200+ lawyers and advisors would show up. All the important clients and prominent lawyers were men in the 50+ range (I was 25 or 26 at the time). They also all knew each other. It was the old boys club. I looked at the partner and said, "Yes, Ward. Everyone looks like you." He said, "yes, and we all golf… Do you golf?"

Do I golf...gulp. I replied - "I guess the answer to that question is I'm going to learn."

Good Answer. The partner continued - "I want you to be in the room where the decisions are made. I don't care if you just play three holes. I just want you there [with the decision makers] for the full 18 holes."

The key for me was the partner recognized that I needed to play golf if I was going to advance in the profession, if I was going to be successful as a bankruptcy attorney in that particular legal market. I recognized I had a choice: I could be the outsider, the one who showed up every once in awhile, or I could head to the driving range every Sunday - and be the one getting the good cases.

I’ve had great mentors, but I’d add that I was a good mentee too.

You have had many opportunities to invest in and advise emerging tech companies, what is the most notable thing you see happening today with female entrepreneurs and young startups?

Hoey: More women are pursuing entrepreneurship and not waiting for someone else to define their career options for them.

What do you love most about working with women in technology?

Hoey: Having a chance to shift the balance of power (or perhaps equalize it) and redefine the status quo.

Why is it important for more women to be entrepreneurs? What do you think holds them back from doing so in the first place?

Hoey: Economic uncertainty and stereotypes are big challenges to take on. Being an entrepreneur is not a career path for everyone, although I’d argue that everyone should be entrepreneurial and I’d suggest taking a job with a startup as one of your first jobs or internships as it would be an incredible learning / professional growth experience. Recognize however, that your entrepreneurial ambition may not kick in when you’re in college – for me, it happened unexpectedly when I’d had years of experience, had built a network of professional contacts and had a savings account.

Have you ever had any setbacks or disappointments professionally that discouraged you from continuing in your field? If so, what did you take away from those experiences?

Hoey: Absolutely. Setbacks are a chance to reassess and plan your future course of action. What could I differently? Do I enjoy what I’m doing? Am I in the right work environment? Was the setback caused by factors within my control? Asking these types of questions when your career hits a bump in the road, can help you gain clarity in order to move forward more deliberately. Grab hold of opportunities to gain self-awareness about your professional strengths plus the type of work environment in which you function most productively. Know your worth in the employment market. Equipped with this information you can make wiser career decisions.

What are the most critical problems faced by women in STEM fields? How do you think these problems should be handled?

Hoey: Too many to list, so let me say this: no one should be happy with the challenges women and minorities presently face in STEM and everyone should be taking on the challenge of solving these problems.

What are you most proud of professionally?

Hoey: Being a mentor and seeing others succeed.

What is the best piece of advice you have for young women interested in pursuing tech careers?

Hoey: To quote Nike: Just. Do. It.

There are too many opportunities in technology to have an impact, to change lives and to design your own future. Seize the opportunity to create and define the future.

Technology is our economic foundation. Don’t relegate yourself to the sidelines of opportunity.

Is there anything else you’d like us to know about your experiences advancing women in technology?

Hoey: Ask me when I’m on campus in October.

Don’t miss CEWiT’s second anniversary celebration on Oct. 28 to have a chance to hear from Hoey.