Editor vs. Author: 5 Strategic Leadership Skills Your Startup Needs For The Long Game

A few years back I had the privilege of hanging out with Jack Dorsey, the founder of Twitter and Square, while we were on a speaking tour in Canada. This guy is a machine. He’s running 2 x Billion dollar businesses with a combined employee count of over 5000… at the same time. So I figured a guy with a net worth of $5.7 Billion (yes… billion) might know a thing or two about leadership for scaling businesses. ...I was

“Why are you here? … What are you doing in this place?” – Keynote @ Portage Atlantic

"Why are you here? … What are you doing here?" Those are the 2 questions Brian asked me. … Brian. Brian was one of the guards in the Saint John Regional Correctional Facility where I was doing an eleven-month sentence for the severity of my crimes. I was 16… And Brian was the guard who got me out of the room where I spent 3 days in solitary confinement (aka The Hole), because of a fight.

The Power of CEO Peer Groups & Why Joining One Might Be Your Most Important Business Move

Imagine you're 27, you've read 100 business books and just want to move on to the next step in your career… what do you do? Well, when I was 27, I was lucky enough to participate in a 3-year CEO program with my brother. He spent $35K on a coaching program because he was determined to invest in his development as an entrepreneur. And the best part, I got to join him as his +1!

8 Lessons For Entrepreneurs Learned Rally Car Racing That You Can Apply To Your Business Today

Okay. Here we go. Focus. Speed. SaaS is Racing. I remember a couple of years ago I watched “Cars” the movie with my two boys. What struck me most about the story was that the main character, Lightning McQueen, didn't learn to be the best on the race track; he learned it on the training dirt track. So today's update comes from the DirtFish Rally School just outside of Seattle. The more time I spent here hucking, hoping and trying

4 Mind-Altering Ways To Become A Confident SaaS Founder Even If You’re Full of Self Doubt

I’ve spoken a lot about my 3 most recent SaaS exits (Clarity.fm, Flowtown, Spheric)... But rarely do I talk about how EASILY I could’ve given up on each. I mean… … Spheric got sued 15 months in. … Flowtown got shut down by Facebook and had to be rebuilt from near-scratch. … Clarity.fm launched to crickets (despite renting out a 300-seat theatre).   As you’d imagine, each had me swallowing a confidence-killing cocktail of fear and frustration. Few would’ve blamed

5 Ways to Teach Kids to Have a Growth Mindset

Six years ago, Renée and I were living in San Francisco. I had just closed a round of funding for Clarity.fm while Renée had just co-founded a new marketing agency of her own. Things were crazy. But they were about to get crazier ;-) Turns out Renée was pregnant with our first son, Max… and it took a whole 3-months after Max was born for Noah to sneak into the picture. Add it all up and our two boys are