Editor’s Note: This is the first essay in a series on what I learned as COO of ConvertKit as we grew from $3M to $30M ARR and 20 to 75 teammates while being bootstrapped and fully remote (before it was cool). ConvertKit is a creator economy software startup on a mission to help creators earn […]
Coaching Questions to Help You Make Breakthroughs at Work and in Life
I get a version of this question regularly: “What are the 3-4 coaching questions or exercises most likely to produce breakthroughs?” I get where it comes from. What if you could boil coaching down to powerful questions anyone can ask themselves anytime they’re looking for a breakthrough? Coaching doesn’t work like that. Coaching is a […]
How to Reinvent Yourself: Lessons Learned from My Career Transition and How to Find Your Next Great Thing
In August 2021, I resigned from my role as COO at ConvertKit. I sold most of my stock and set aside funds for a sabbatical of undetermined length. In the 18 months following my departure, I transitioned industries; pursued three six-month career experiments; experienced deep anxiety and depression; and came out the other side, more […]
I am nothing: On the loss of identity in times of transition
1,868 days. That’s the number of days I spent on the ConvertKit team. 12,408 days. That’s the number of days since I was born. I’ve spent 15% of my life at one company. 32% of my adult life. Nearly 47% of my working life. 10,000 hours of deliberate practice is the mark of an expert. […]
Define Your Flywheel to Fuel Faster Business Growth
In his classic management book, Good to Great, Jim Collins shares an idea called a flywheel. That concept can help you and your company define what drives growth and then do more of those things over time. It’s a powerful tool for strategic clarity. Collins recently expanded on the concept in a recent manifesto called […]
How to Plan and Host a Mastermind Group Retreat
If you haven’t heard of the concept of a mastermind group before, it might be best to start with this post on starting and maintaining a mastermind group. I gave Nathan and Caleb big hugs as they loaded their bags into the back of my dad’s F-150. After grabbing dinner with my fiancé and picking […]
10 Questions to Ask Yourself Before Raising Money to Fund Your New Business
It was April 2014, halfway through a two-year investment deal. I was pitching my investor on why we needed to double the funds we were receiving every month and shorten our runway to 6 months (a fancy term for how long we have until we need to be self-sustaining). His answer was “No” and he […]
College Students: How to Get an Education Without Ever Going to Class
So often people ask me what inspired me to start my own business just one year after graduating college and what coursework was important in giving me the foundation for an entrepreneurial career. Those same people are often taken aback when I tell them that most of the skills and knowledge I put to use […]
How to Build a Sustainable Business Coaching Practice (And Double Your Rates in the Process)
“So, what do you do?” – Random person at a friendly gathering. “I run LivingforMonday.com where we do coaching and training for young professionals.” – Me “Oh, so you must be in pretty good shape, huh?” – Same random person in complete confusion. “Dammit.” – Me knowing that was coming. That’s my typical conversation at […]
Case Study: How to Sell a $5,000 Consulting Project in Less Than a Week
I woke up just before Christmas with an invoice in my inbox for $2,447… And no money to pay it. That’s jumping ahead a bit, so let’s rewind for a bit of the back story. Just before Christmas at the end of 2012 we were getting finishing up the design of the new LivingforMonday.com. Our […]