“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.

5 Piercing Questions You Need To Ask Yourself If You’re Considering Selling Your Startup

Should I exit or should I stay the course? It’s THE single biggest question that nearly every successful founder will eventually be met with. And after taking my coaching clients for a private sit down with Chris Savage at Wistia… … it got us all thinking about the best ways to evaluate whether or not it’s time to exit and start fresh... or buckle in and continue down the path.

[Escape Velocity] – Episode 2 – Todd Herman & The Alter Ego Effect

One small step for a startup founder... one giant leap for his business… As a SaaS entrepreneur you deal with tons of doubts, fears and worries. And sometimes you feel like YOU are just not capable of doing it all. How do you overcome the struggle? Well… you become the Alter Ego who can take on these challenges. And how does that work exactly? Basically, it all boils down to a little game we all played as kids. So... as

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

Fire an Employee With Compassion and Class: 5 Steps To Follow

In over 20 years in business, I’ve never met a single founder who hasn’t had to fire at least one employee. While the thought may create knots in your stomach, letting an employee go is actually a super valuable skill with further reaching implications than you might think. Because done wrong, It could crush team morale, compromise data, and even cost you valuable customer accounts. Breaking up isn’t fun… but it’s a skill that as a founder you need to