Category: Entrepreneurship

13 min read

Many years ago, I used to write annual birthday essays sharing the most important lessons I’ve learned over time. They were an annual tradition I…

12 min read

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…

14 min read

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…

20 min read

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…

Three figures are lost in fog as they hike over a crest of loose boulders
5 min read

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…

6 min read

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…

10 min read

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…

8 min read

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…

8 min read

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…

9 min read

“So, what do you do?” – Random person at a friendly gathering. “I run LivingforMonday.com where we do coaching and training for young professionals.” –…