Mark MacLeod is one of Canada’s leading startup finance experts. Mark spent twelve years as CFO for a number of highly successful venture-backed startups including Shopify and Tungle. He then spent three years as a General Partner at Real Ventures, Canada’s largest and most active seed venture fund, where he remains a Venture Partner. Mark now leads finance, business and corporate development for FreshBooks, the #1 cloud accounting specialist for small business.

Mark is a frequent blogger on funding, growing and exiting startups at startupcfo.ca.

1) Tell us about your early beginnings, how did you get your start? 

I began my career in public accounting. Spent over 8 years advising entrepreneurs on financial matters before going into industry myself. My first industry gig was in a chain of skateboard and snowboard stores. Since 1999 I have been in the software startup World as an executive and venture capitalist.

2) Can you share with us your latest project? 

Today, I am responsible for finance, business development and strategy at FreshBooks - the #1 cloud accounting service designed for small business owners. We have a ton of freelancers and solo entrepreneurs using our service and have a simple vision that we are trying to enable: a World where entrepreneurs can successfully build their businesses without having to know accounting.

3) What do you think is the biggest challenge our industry faces right now? 

The biggest challenge is that the pool of freelancers is expected to increase dramatically in the next few years. oDesk predicts that in a few years more people will work for themselves vs working for "the man". This will force people to differentiate their brand and offerings so as not to be commoditized or forced to find work on spec sites / job boards.

4) Do you have any future projects lined up, and can you share them with us? 

Planning on spending a LONG time at FreshBooks.

5) For those new to the industry, how do you recommend they break in?

The best source of new business is existing customers. This is true in any service-based business. That often creates a chicken and egg problem - how do you get those first few customers? Don't cold call. Do work your existing relationships. Don't do spec work on public sites like 99 Designs. Do, however, consider free or cheap work with a key client who will actively give you references after. Do have a specialty. Let the World know what you stand for and what you are great at!

6) Favourite music to work to? Any specific artists?

7) If you weren't doing what you are now, what would we find you up to? 

I love advising entrepreneurs so I would probably be a coach for CEOs. On the more crazy end, I'd probably own a yoga studio. And if I had thought of it when I was 7, I'd be a Formula 1 driver. Though I'm probably too tall (and likely afraid of the speeds they drive at).

8) If there was one person dead or alive you could have dinner with, who would it be and why?

Ghandi. A truly wise man. As a dedicated yogi it would have been a true gift to be in his presence.

Thanks for taking the time with us! 

Mark will be covering all the finance basics you need to know like invoicing, getting paid, collecting and remitting sales taxes, and more at his presentation Finance for Freelancers at Spotlight: Freelance September 28!