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
A few months ago I gave a talk at a local high school here in Moncton. I shared my journey, went deep in the challenges I overcame, and gave my ALL to help inspire these kids live a bigger life. But during the Q&A, the tables got turned. And it was this kid in the front row. Someone I’ve never met before. Who with ONE question, hit me right at my core.
"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.
Do you know what it takes to buy a private jet? Have you thought about why you would want a private jet? These are questions that pop in the minds of a lot of business owners and for good reason, because they symbolize a form and level of success. Not only that... the private jet allows you to buy back time.
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!
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
As a high-performing founder, you’re confronted with TWO seemingly opposing forces. You need to travel (a lot) Your health and fitness are a vital part of your capacity to show up and do your best work So how do you reconcile this? How do you stay razor sharp (and fit) while sitting long hours on planes and scavenging for food in a place you’ve never been before?
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
No matter how great your product is, at some point the success of your SaaS company is gonna be DIRECTLY linked to your personal productivity as a founder. Talk about pressure, right? I can totally relate. I built clarity.fm during an insane 11 month stretch where Renee was starting an agency of her own AND we brought two little humans into the world.
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