A Rite of Passage

December / 2020
Author: Glenn Cowan – CANSOF, Venture Capitalist

The parallels between venture investing and a life in special operations are uncanny and it starts right at the beginning; from the time you throw your hat in the arena.  

As I pounded the pavement raising capital, the comments were always the same:  “you’re great, your story is so compelling and in a crowded space of Series A SaaS funds, your thesis is different and unique.  We love it, but we don’t invest in first time fund managers.” 

Wasn’t everybody a first time fund manager at some point? I would think to myself as I left feeling dejected.  A similar feeling, I experienced many times as I would self-critique my performance on some assessed activity in selection for Canada’s National Mission Unit in Special Operations. 

For the next 14 months, I continued to tell myself that as a newbie to the venture game, raising a first time fund was ‘selection’ and a critical rite of passage for those that come out the other end with the badge of honour that only those who have done it can appreciate.  The feeling of success and accomplishment compounded by overcoming the obstacle. 

As Ryan Holliday points out “the obstacle is the way”.  I was so fixated on raising Fund 1, that at times I lost sight of the value of the lessons being taught to me along the way.  I was gaining access to some of the most sophisticated investors, funds and ultra-high net worth individuals in the county and in each meeting, I was being imbued with gems of advice, lessons learned and considerations for how to think about my business.  

Each one of these investors were staunch supporters of the military and special operations, and I was seeing a side of Canadians that I didn’t expect.  They almost all believed in me and my vision but were so disciplined in their own thesis that wouldn’t deviate from their plan to chase something new and shiny.  Again, a lesson that I’d learned many times conducting combat operations in Afghanistan.  Stick to the plan. 

Walking out of a few meetings, feeling defeated, I would have doubt about my choice to enter this business; a tough business.  A vivid memory entered my head.  It was 2003, I was standing outside in a freezing cold October rain, my oversized coveralls drenched.  I was standing facing a wall.  My nose 6 inches from the cold, rusty corrugated metal siding of a building.  “what the f*ck and I am doing?” I thought to myself.  It was probably around day 4 of a 10 day process… at that point, I’d lost track of days. Out of the corner of my eye, I caught some glimpse of movement, two operators walked by casually with carbine rifles slung over their shoulders.  Neither said a word, but their faces said it all as they bore a slight grin and walked with a calm, confident step and an overall air of contentment.  

Probably not too long ago, they’d been standing where I was, and I knew in an instant, I’d get there too. 

Glenn founded One 9 Investments while serving as an Assaulter Officer in Canadian Special Operations Forces; Joint Task Force 2. As a Squadron Commander, Glenn specialized in leadership, command, and strategic planning and successfully translated these skills with the creation of a venture capital fund that invests utilizing the principles of special operations planning, risk mitigation, and execution.