The 7 Questions Interview Series: Angels and Venture Capitalists

The 7 Question Interview Series is an investigative content series where I seek out key leaders in a specific industry and/or subject matter expertise area and ask them 7 key questions that “enquiring minds want to know”. There is a twist however to these questions. I provide the interviewee with a hypothesis for each question to help frame and set context for their answer. This specific series of interviews is ideal for startup founders.

Series Objective

The objective of this series is to establish direct connections with VCs and Angel Investors across the globe and ask them the same set of 7 questions regarding investing in technology startups. I’d also like to know what their appetite is for investing in Canadian startups and why they do or don’t.

Interview with Mark Skapinker, co-founder of Brightspark Ventures

Here’s my fifth interview with Mark Skapinker who is the co-founder of Brightspark Ventures. Brightspark Ventures is a next-generation venture capital firm based in Canada, with locations in Toronto and Montreal, that invests to build and grow early stage software companies.

When would it be appropriate for a startup to seek investment from you?

It depends… From my perspective, it is a “marathon” and not a “sprint”, so getting to know the entrepreneur and the concept and the potential takes time. My focus is mainly on repeat entrepreneurs, and/or founders who have proven themselves somehow. We usually are first “institutional money” but also sometimes participate earlier in the process. We like “big” ideas.

What’s more important: the idea, the team or both?

Both. The team is critical because every startup will have major challenges and need to be able to change and adapt to the reality of their market – only a team with the right leadership and corporate culture can do that. At the same time, the idea needs to be able to create something unique, something that can create a huge amount of value and be significant enough to warrant outside investment.

What are you looking for in a startup team? What does a winning team look like?

We look for experience – founders that have proven themselves. Passion, focus on winning, and a strong domain expertise in what they are taking on. Maturity and corporate culture are critical.

What are you looking for in an idea? What does a winning idea look like?

An idea is something that can create significant value. It may be a better way of doing something, it may be capitalizing on new technology or markets. It needs to be something that is in a “space” where focus and money are bing spent now; it needs to have some barriers to entry (even if that is timing); it needs to be something that is a “need”, and not a “nice to have”.

Does a startup really have only one shot?

I do not think this is true. Startups are constantly evolving and pivoting. The right team and focus will get the market’s attention – they may need further proof points or validation, but persistence is more important than a one-shot try.

Can you describe your due diligence and investment process?  What’s important for a startup to know about it?

We need to know if it is an idea/team that we can support. We prefer a quick NO than a long MAYBE. Our diligence is our network, our contacts and a deep dig at the right time. Schedule depends on the company and our access to investment dollars.

In your view, is Canada a fertile ground for tech startups?  If so why and in what ways is Canada unique and competitive in this regard? Are you investing in Canadian startups? If so, why? If not, how come?

Canada is as unique as anywhere else outside of Silicon Valley (which is unique). The right team and company can succeed here. We focus on Canada because we attract entrepreneurs looking for institutional monies from investors that have been entrepreneurs – we have been there, we have started our own companies and have succeeded and failed doing so. We are entrepreneurs investing entrepreneurs – that makes us unique in Canada and we attract the best repeat entrepreneurs. Canada has excellent talent, amazing entrepreneurs but has major challenges in financing and experienced support team members.

About Mark Skapinker

Mark Skapinker is a veteran with more than 25 years experience in software and technology. Mark has a unique vision and understanding of how to zig and zag in an ever changing, and sometimes unforgiving, market place. For entrepreneurs, Mark offers an insider’s view to the scope and magnitude of what it takes to create and build a company from an idea through to a thriving company. The proof of Mark’s expertise is detailed in his track record: in 1988, Mark co-founded Delrina Corporation and successfully grew Delrina to annual revenues topping $150 million.

Mark was President of Delrina from its initial incorporation through its public stock offering and listings on both the Toronto Stock Exchange and NASDAQ — until Delrina was acquired by Symantec in 1995.In 1997, when the technology market place was yet to recognize the tremendous growth of the Internet, Mark founded Balisoft Technologies Inc. – a company focused on intelligent customer interaction software.

Later, in the spring of 1999, Balisoft merged with Boston-based Servicesoft Technologies.Servicesoft became the first major vendor of comprehensive Internet customer service solutions. In September 2000, Servicesoft Technologies was acquired by Broadbase Software Inc. (NASDAQ:BBSW).

In 2008, Mark co-founded iStopOver.com, a Toronto based Internet business focused on peer to peer travel with online ecommerce.  In 2010, Skapinker co-founded GaggleUp, an Internet business focused on Internet marketing, group buying and ecommerce with a focus on enterprise companies.In 2000, Mark co-founded Brightspark Ventures. Mark is a Managing Partner at Brightspark and is based in Brightspark’s Toronto office.

Social Outposts: Twitter | LinkedIn | AngelList

Chris HerbertChris Herbert is the founder of Mi6. Mi6 is a B2B (Business to Business) marketing and business development agency dedicated to helping companies build their brands and develop commercial relationships. He is the founder of ProductCamp Toronto and the Hi-tech community Silicon Halton. He tweets under the handle @B2Bspecialist.

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