Two decades in Startup land…

Mark MacLeod
May 31 · 4 min read

Twenty years ago today, I joined my first startup, Silanis Technology, as their first finance leader. They were a client of the firm I was at. We had helped them raise financing and we were their auditors.

Little did I know that the decision to join a client would have such an impact on my career trajectory.

Timing is a thing. When I look back on all the outcomes, good and bad, that I have had in the last two decades, timing was a big factor in all of them.

The history buffs out there will know that 1999 was near peak dot com madness. Pets.com and others were going public with no fundamentals, yet commanding lofty valuations.

For my part, coming in with no context for the bubble that was happening, I just thought I knew everything about raising capital for startups. Within a few months of joining, I had helped Silanis raise $ 19M. I thought I was unstoppable. Turns out, everyone with a pulse was getting funded.

Some useless trivia: that $19M round included participation from Lehman Brothers. This was their first and only investment in a Canadian company. Lehman, of course, is more, being a victim of the 2008 market crash.

Going back to timing: Silanis, founded in 1996, was a pioneer in the electronic signature market. As Jason M. Lemkin points out, that market is now worth $1B. It was much smaller back then. Timing is a thing!

It’s been a wild ride. In the last twenty years, I spent 14 of them as CFO for a number of startups, including some winners and losers. 3 years as a VC, and now 4+ years running an investment bank. I have been involved in some spectacular successes, like Shopify and FreshBooks, and some big failures, like Mobivox, where we raised $11M, set it ablaze and failed.

Some people like to look back and rewrite history, framing their history as intentional and part of some master plan. I definitely didn’t have one. Looking back, if I had to frame a strategy, it would be this: Be a big fish in a small pond.

For some reason, I have taken this approach from day 1. I am a CPA by training. I instinctually avoided the Big Four firms, and instead worked with smaller firms. As a result, I got to work with founders from day 1. I learned about their businesses. I got far more out of that than I would have as a cog in a giant big 4 wheel.

When I switched to operating and joined Silanis, I joined a small startup as the finance leader. It would have been easier to join a larger company as part of a finance department. I wouldn’t have had to figure things out myself. But that would have been boring.

When I decided to become a VC, I could have joined an established firm as an associate and learned from seasoned partners. VC is an apprentice business. It takes a while to learn. Instead, I became General Partner in a new firm, Real Ventures.

Staying in Canada was also part of this big fish, small pond theme. There are likely 100s of people with my experience in San Francisco as an example. But there are few to none in Canada. That has been to my advantage.

Now, I have defined my pond as SMB software. The goal of SurePath is to be the leading investment bank in SMB software. Period. I feel pretty safe in saying that no investment banker has spent as much time in this space as I have, both on the operating and investing side. This is an unfair advantage.

The other theme in this twenty year span has been to follow my gut. Deep down, I knew I always wanted to be an advisor to CEOs and startups. This came from my very first accounting firm. I worked directly for the founding partner, and saw the deep relationship he had as a trusted advisor to his clients. It was inspiring and guided my career path in a big way.

When the bubble burst in 2001, 2002 I hung out my shingle as an advisor. I even called it SurePath! But I was too young and lacking the experience and relationships to make it work. In some ways, I feel like my time operating and investing was all training to do what I do now.

In some ways, the 20 years has flown by. In others, I can’t remember doing anything else. When I started, SaaS wasn’t a thing (it was ASP — Application Service Provider). Salesforce was just getting going. You needed $3M to buy Oracle databases before you could launch anything. People connected to the internet using AOL dial-up.

Now, technology is everywhere. There is no longer a separation between tech and other industries. Every industry is being effected, or in some cases disrupted, by tech.

I can’t wait to see what the future holds. Not sure there’s another twenty years coming. But I can’t imagine working in any other space.

Mark MacLeod

Founder of SurePath Capital Partners. Reformed VC & seasoned CFO, yogi, F1 & house music addict & DJ

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