Our story begins on a fateful, frigid Bostonian evening. On December 2nd, 2015, my good friend Chris Denaro invited Charlie (then Charles) Johnson and I to meet at the famous Aeronaut Brewery in Cambridge to discuss the idea of a "mastermind." He mentioned the search for wild success and The Junto - Benjamin Franklin's advisory and accountability group. Details were scarce, but I was intrigued. Little did I know, I was about to make one of the most positively impactful decisions of my life.
*Excitement after a successful first meeting.*
Needless to say, after getting to spend some more time with Charlie and spitball ideas about starting our own mastermind, I was hooked. We spent a few weeks talking about how we would organize our accountability, what our values would be, and when we would meet. We researched other famous masterminds and talked to our mentors about the groups they had successfully participated in. (Thank you, Cort!) Shortly thereafter, we had our first draft of the format, and began crafting our goals and holding weekly accountability calls.
*The invitation to the first sheet.*
What ensued was over three years of the most productive and supported work I've ever done in my life. The mastermind has given me hope in my hardest times, kept me on track when feeling overwhelmed by my workload, and gotten me to think critically about how to best spend my time to get what I want out of life, both professionally and personally. I credit my good health (putting on 15lbs of muscle and healing my relationship to food), my good habits (exercising, logging food, and meditation), and my resilience in entrepreneurship (recovering after my first company failure) all to the support I have from our mastermind.
Given the impact the mastermind has had on me, I am inspired to share how we run it so that other people can achieve the same benefits without having to start from scratch. Over the last three years, we've gone through dozens of iterations on the format and the way we use technology to support the process. We've tested out incentives and punishments, goal setting methodologies, and a variety of accountability sheets.
*One of the earliest versions of the sheet.*
The following article is an attempt to explain what we've learned over the last three years, so you can kick off your own mastermind group! We'll go into the philosophy and ethos of how we run our mastermind, the process and format we use, and the technology we leverage to bring it all together. So, without further ado:
We strongly believe that the only way to become wildly successful is A) to prioritize how you spend your time effectively, B) get increasingly good at (A), and C) get brutally honest feedback from people that you trust. For us, the mastermind provides all three of these.
Accountability is built on brutal honesty. We made a commitment to each other that we would be honest even when it was difficult or we thought it might be hard for the other person to hear, because that is what we were all looking for, and because that is what would help us all the most.
Unsurprisingly, the people make the mastermind. There has to be strong motivational alignment, similarity of investment, and I hypothesize that similarity of interests or focus area is important too (we are all entrepreneurs, though it didn't start that way). I like this idea of looking for "co-insipirators" - when someone inspires you and you have a burning want to learn from them and get on their level, and they simultaneously feel the same way about you.
The darker side of the people point is that weakest link will set the standard. If people are showing up without having really thought through their goals or tasks, or if they aren't present on the call and engaging with the other members to ask deep and challenging questions, the mastermind will suffer doubly. First, because that will be missing, and second, because others' engagement will decrease to the lowest level. The antidote to this is to have high accountability from the beginning and build good habits. This even includes accountability on the accountability (showing up on time, coming prepared with sheet filled out, responding to group reminders).
Since we added the Habits Tab, we've been thinking about habit formation as a habit. Intentionally creating new habits that will help us be healthy and more productive has become a core part of the mastermind. At its most structured, these exist as 30 Day Challenges (thanks to Mike and Andrew for the idea!) We wrote about this here: