FreshBooks CFO Mark MacLeod steps down to launch SurePath Capital Partners

Mark MacLeod SurePath Capital Partners

The Canadian startup ecosystem is about to get a lot more exit and fundraising advice from Mark MacLeod, the now former FreshBooks CFO, who is stepping down to launch new advisory firm, SurePath Capital Partners.

“I’d be even less interested in being a CFO of a public company.”

MacLeod has years of experience on both sides of that table: as a CFO for leading companies such as FreshBooks and Shopify, and as a partner at Real Ventures, leading investments in Unbounce, VarageSale, and Frank & Oak. And it’s hard to find a startup founder not following MacLeod’s prolific startup CFO blog.

It couldn’t have been an easy decision to leave FreshBooks behind, but MacLeod indicated that it was the right decision for him personally.

“The next big challenge for me would’ve been to prepare us for a company that could go public,” MacLeod told BetaKit. “It’s non-trivial to prepare for that. I’ve observed Shopify, and what I’ve seen confirmed to me that I’m not that person, and I’d have to completely change my stripes to be that person who would be preparing companies to go public. I’d be even less interested in being a CFO of a public company.”

“FreshBooks is going to be a truly remarkable company, and I’m fully aware that I’m walking away from something very valuable,” MacLeod continued. “FreshBooks has not started the process to go public, because it takes years to set things up in order to build a business that can choose to go public. We raised the round, executing against a good plan, and I’m leaving now, while everything is working very well, so FreshBooks can get the right person to lead the company through the next phase.

MacLeod has mentored and advised countless founders for over a decade, and now that hobby – as far as startup CFO hobbies go – turned into SurePath Capital Partners.

“I had to be honest with myself. Ironically, for a finance guy, I had to follow my heart. I wanted to leverage my love for being an advisor, my passion for early-stage startups, love for complex financial transactions, and establish a relationship with clients as a trusted advisor.”

Mark MacLeod SurePath Capital Partners

With SurePath, MacLeod aims to address two key pain points he says he sees startups face most often: fundraising and exit.

“Most startups don’t actually have an exit strategy.”

On a fundraising front, MacLeod says that it’s relatively easy to raise early-stage capital, as investors are willing to take a leap of faith, but the growth round takes serious preparation: the management team needs to be in place, user economics validated, and everything has to work.

“The companies just don’t realize the bar they need to hit,” MacLeod said. “In preparing FreshBooks to raise $30M, I met many people who control that kind of capital, and I know now what that bar looks like.”

On the exit front, when startups are raising capital, investors often ask about the strategy, and MacLeod thinks it’s an important question. “Most startups don’t actually have an exit strategy. They’re working on product roadmaps and marketing plans, but the truth is those exit outcomes don’t just happen, and when they do, you may or may not have the sophistication internally to deal with the finance and legal departments descending upon you.”

With nightmare exit stories like the recent Get Satisfaction fiasco, startups need trusted advisors on their side. SurePath aims to be that trusted advisor and resource to fill fundraising and exit gaps. “SurePath is not an investment bank,” MacLeod said. “While we help our clients with fundraising and exits our model is fundamentally different. Our engagements can start as simple as coaching agreements. And unlike banks, we are looking to build long-term relationships with our clients, not just collect a fee and move on.”

MacLeod plans to grow SurePath slowly, deliberately, and bring in horsepower overtime. For now, he is staring his new adventure in the face: starting his first week at SurePath’s brand new office in Liberty Village in Toronto, hiring a Graphic Designer and a strong Analyst to join the firm, and working with new clients. A CFO, VC, mentor and advisor, MacLeod has had a real and deep impact on the Canadian ecosystem over the past several years. It seems he is just getting started.


Elena Yunusov

Elena Yunusov works at the intersection of digital communications and experience design. She is known in Toronto’s startup community as a HoHoTO & Toronto Maker Faire co-organizer. She likes coffee, robots, and wearable tech.

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