In this series of posts we’re “grilling” the mentors of the Startupify program with the hope of discovering who is best able to answer a standardized set of questions. Points for accuracy and un-originality will be assigned. Actually we’re just trying to learn more about them .. the kind of stuff that doesn’t appear in boilerplate bios.

Let’s get going and welcome our sixth contestant: Brydon Gilliss

What qualifies you to be a Startupify mentor?

Primarily my mistakes and failures. I tend to believe that great coaches are mentors who typically aren’t the superstars. They tend to be people who had some level of success but had to grind it out more rather than rely on raw talent, and ultimately failed. That failure caused great reflection and introspection into why they failed. It’s that reflection on personal failure that often creates master coaches.

What hurdles/failures/lessons have you encountered along your professional journey that early stage entrepreneurs could learn from?

Well hopefully all of them! Individual failures play a massive role in improving ecosystems. Within startups, I don’t believe we talk about our failures in enough detail to really drive that sharing and learning across the ecosystem. Without getting into specific failures, my hope is that Startupify provides an intimate setting for myself and other mentors to share the painful details of our failures with our cohort.

To be more specific, I’ve been involved in projects that haven’t acquired enough customers, that met technical deal breaking hurdles, that haven’t found a first customer, and on and on. I hope that being able to share these details will help our cohort select which projects/ideas should be dealt a swift death. Knowing which ideas to not work on is almost more important of a skill than generating new ideas.

What excites you most about the Startupify program?

That’s tough as I’d like to say all of it. I’d say I’m most excited about the folks in our cohort. I used to be them. I followed the traditional Canadian path. Get a degree, get a good job, make your boss happy, get a promotion, get a raise, get more vacation, etc. No one ever told me there were other options. No one ever pointed to this other exit. I’m excited to see our cohort accelerate through that progression from begin gainfully employed to being a difference maker in an early stage startup business. I’m excited to be a part of creating this so others can move through the stages I went through faster and with more support.

Downstream, I’m excited to see our graduates making real differences in the startups in Ontario, Canada and beyond. Longer term, that will be our real measure of success.

What characteristics have you seen in the startups you’ve mentored in the past that you feel are indicators for success?

Drive. As we talk about in finding and selecting people for our cohort, we need individuals that will shove us over and rush past us if we get in their way. For some reason, something in their past is now driving them to succeed in this. Creating new businesses isn’t complicated but it’s hard, hard work. Without raw drive, your startup won’t last.

Skin in the game. Startups aren’t beauty pageants. I always say ideas don’t matter, tell me what you’re willing to risk for your idea, that matters. Where’s the commitment, what have you risked to be here?

Humility. Startups must have confidence but they can’t be arrogant. Success requires so much ongoing learning, support etc from the wider community that being humble and open to all of it is a requirement.

Hustle. Something in their background where they’ve hustled. Walls they’ve hit and knocked down, went around.

BONUS: Which Startupify mentor are you most excited to collaborate with and why?

Once again I’d like to say all but I’ll go with Michael Litt, mostly because I know Mike the least of our mentors. He spoke at our last DemoCampGuelph and his talk was awesome as it focused on his failures in a very authentic, honest way. As well, Mike’s a guy I’ve heard great things about over recent years from guys like Brett Shellhammer. Both Mike and Zak Homuth are so young, yet have multiple startup attempts already in their rear view mirror.