Bringing Military Strategy to the Investment World

November 18, 2020 | Colleen O’ Connell-Campbell


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This week’s guest on “I’m a Millionaire. So Now What?” got me thinking about arguably one of the best known, and most read, books on military strategy: The Art of War.

Most of you will know this book, but for those who don’t, it’s an ancient military treatise dated to around the 5th or 6th century B.C. and attributed to the ancient Chinese military strategist Sun Tzu. Its 13 chapters are each devoted to a singular aspect of warfare, and its strategies and tactics.

Not surprisingly, over the millennia, it has influenced not only Eastern and Western military thinking, but also business tactics, legal strategy, and so on.

My guest this week tells a fascinating story himself: about his life, and his career in the military. But what I found most interesting is what he did as he transitioned from the Canadian Forces Special Operations Forces back into civilian life.

He brought The Art of War, to the world of venture capitalism.

Military Strategy Meets Venture Capitalism

A retired Squadron Commander in the Canadian Special Operations Forces, Glenn Cowan specialized in leadership command, and strategic planning. He grew up in an entrepreneurial family, caught the investing bug early, and incorporated his company, ONE9 Investments (named after his Special Ops radio call sign, 1-9) while he was still in active duty.

Today he’s a venture capitalist moving the needle on investing, using principles of Special Ops planning and risk mitigation. As he puts it, “A special forces organization is probably the best incubator and accelerator for identifying, validating and proving new technologies.”

A graduate of McGill University, The Army Operations Course, The Special Operations Assaulter Course, Canadian Securities Course, and Ivey's Executive Leadership programme, his education, along with extensive military experience, affords Glenn an unconventional perspective and application to the investment battlefield.

The Entrepreneurial A-HA! Moment

Like all good entrepreneurs, Glenn had an A-HA! moment, where he realized there’s an underserved market in the venture and private equity space. He believes there’s great opportunity not only for growth, innovation, and accelerating key Canadian technologies, but also providing the ability to push technologies faster to the end users, specifically in the security, intelligence, and defense community.

As he puts it, “We can circumvent some of the bureaucracy on the private side, but at the same time, move at the speed that allows us, as a nation, to maintain the right technological overmatch that we enjoy as a wealthy G7. This is a growing trend that we're starting to see, highlighted and showcased by companies like SpaceX, private rocket launches, private deployment of satellites. This is coming, this is coming on very quickly. And it's exciting to watch some of the technological evolutions that are happening in that space.”

I love this marriage of “Special Ops” and venture capital – as you well know, my goal is to double the number of Canadian millionaires and create a more self-reliant country at the same time!

Here’s a bit of what we spoke about.

The Y Combinator on Steroids

“Special forces soldiers are the best problem solvers in the world. I believe that wholeheartedly. And a special forces organization is probably the best incubator and accelerator for identifying, validating, and proving new technologies. I call it a Y Combinator on steroids. It has all the characteristics of a tech incubator, tech accelerator, with no real requirement for commercializing what they're doing, other than just solving really serious problems that are impacting the world. When you watch any sort of entrepreneur TV show, Shark Tank or Dragons Den, the first question anyone asks is, ‘Well, what problem are you solving?’ and the Special Operations community are solving problems that the rest of us don't even know are problems yet. And, in some cases, they're using pretty innovative technologies to do that. So, I created ONE9 to source and validate the indicators and warnings of future trends. And then look at the different opportunities where the private sector can help the Defense (and predominantly Special Operations) community.”

Dual Use Technology Can Scale to Other Markets

“I look for dual use technologies that solve early problems, but have an ability to scale in other markets, outside of the defense sector. And the military writ large, it’s no surprise to anyone that the military is a great innovator for identifying early technologies. I mean, some of the biggest technologies that we take for granted now - GPS, right? GPS used to be five pounds and they were all secure, talking to the satellites. And now we get our coffee using our phone, all tied to GPS. That is a great example of a technology that has changed our lives. Same with the internet and computers. But some other ones that have sort of migrated in, since 911 - in the post 911 world - our robotics, drones, different payloads, and different camera suites and sensor systems that are on those drones. And now we're really seeing this convergence of AI machine visioning edge analytics, to provide even more technologically savvy solutions to some of these problems. And certainly, in Canada, there wasn't really a private sector investor or fund that was focused exclusively on this area. Really just giving the best possible technology, because I remain a patriot, and want Canada to have the best technology for our security and intelligence professionals. And the traditional systems of government innovation are bureaucratically slow, and moves at the pace molasses!”

The Modern-Day Art of War

“If you don't understand the requirements of the end users, you might be sort of fishing in the wrong spot of the lake. We have to also see the indicators and warning signs, on the problems that are faced by society. So, I did invest in a respirator company in 2018. I saw global respiratory issues, through certain indicators and warnings, and invested in a respirator company. That's been a pretty exciting journey. What we've seen since then, with the presence and onset of COVID is an opportunity in the investment space, to actually find technologies that are accelerated by COVID. COVID-19 has exposed certain weaknesses that are forcing societies to be significantly more self-reliant, whether it's on supply chain, PPE, individual preparation on their financial planning. And there's an increased overlap between sort of some of the national security aspects and critical infrastructure and just the way society functions. And so COVID has really shone a light on some of these, I'll call them weaknesses. But I mean, in essence, Western governments got caught with their pants down. And they're scrambling to strengthen supply chain on everything from PPE, to filter material, to vaccines to pharma, to biotech, to strengthening some of the more digital capabilities that protect critical infrastructure.

[Plus], we have been somewhat sidetracked in the last 20 years, because we've been focused on a global war on terror and fighting Middle Eastern wars in Afghanistan, or Iraq, in the Middle East, from an allied perspective. But what we're seeing now is the trend in conflict shifting, and we are seeing more near-peer adversaries. And that's going to change the nature of conflict. And it's going to require a different type of mindset, technology kit and equipment. I think a lot of those are going to be on a tech side, whether it's data privacy, AI, cybersecurity, threat intelligence reporting. I mean, you name it, integrated IoT. And I'm totally ready. Totally.”

Like most of you in the Self Made Nation, Glenn also gives back. He is an active mentor in Operation Entrepreneur, a program of Prince's Trust Canada that provides veterans and transitioning members of the military community with the tools they need to start and grow successful businesses.

Have a listen to the entire episode. It’s really fascinating stuff.

If you’re an entrepreneur looking to exit, or you’re at the helm of a thriving business or startup, I would love to talk with you about your stories! You can drop me a line here.

Plus, if you are craving like-minded conversation with growth-oriented business owners, consider joining me and eight other business owners, investors and entrepreneurs for our next two editions of Elevated Conversations - watch this space for more details!