Read this before you join (or start) a mastermind

What I learned from 5+ years of running masterminds

By the time this email lands in your inbox, I’ll be in São Miguel in the Azores. 

Depending on what time you open it, I’m either taking a surf lesson with a dark and handsome surf instructor named Constantine, canyoning down a waterfall, or spinning up dust on an ATV, burning down dirt trails in Sete Cidades, a massive volcanic crater in the middle of the island.

Officially, I’m in Portugal on business. 

Our retreat coordinator Zya is already in Lisbon getting ready, restocking the emergency supplies bag (the same one we’ve been using for four retreats now), buying gifts for our guests and coordinating with the caterers. 

I decided to take my vacation first, and then do the work part, which also feels a bit like vacation because I’ve grown close with the members of my mastermind. I’m facilitating so it’s definitely work, but it’s the kind of work that makes all the hard parts of entrepreneurship worthwhile.

This is my fifth time running a mastermind and they’ve each been different. 

The first couple of times I wasn’t very skilled at leadership. People signed up so they could learn email from me and this was the only offer available. I still wonder where I found the chutzpah, honestly. Ten thousand dollars to work with someone that green? 2025 Tarzan would never!

But those programs were well-reviewed and launched many careers that are still going today. In the past I’ve been much too hard on myself about charging what I charged when I didn’t have a long track record in business. Past participants occasionally write to me to share what an impact those programs had on their lives, and to encourage me to chill out with the constant self-criticism.

I’ve met so many incredible humans from running masterminds. I still remember all of their names and their stories, even the ones who aren’t in business and don’t write newsletters anymore. 

They taught me so much, and still do. Sometimes I forget which internet people were once my mentees because so many of them are now my peers. It’s an incredible feeling when someone whose work you admire reminds you that you are the person they learned it from. 

A couple months back I was at a business dinner and the man sitting next to me said, “Tarzan, you gave me my career,” and proceeded to explain all the small and impactful ways I’d helped him launch his business, the introductions I made, the ways I encouraged him, even work I hired him for. 

My cup runneth’d over

Apparently I knew what I was doing, even when I didn’t know what I was doing. Note to self to go easy on Tarzan.

But this mastermind, Power, has been a whole other level of mastermind, and, without a doubt, some of the work I am most proud of in my career. From the beginning I said, “Power is a circle, not a pyramid,” but it took time to actually get it there because none of my programs have ever been run that way.

This year I was finally able to bring together a group that could truly lead each other. Instead of looking to me for answers, they looked to each other, and their collective wisdom was far more than anything I could’ve come up with on my own. Watching the ways they support each other has been an unexpected gift. 

I’ve found my stride as a leader.

We’ve laughed together and cried together, coached each other through the inevitable low seasons, and shared each other’s triumphs in the high seasons. 

We shared our stories and our gifts. 

We sat around campfires and dreamed the future into being. 

I’m proud of myself for bringing together this incredible group of humans. I care for them all so much. Their losses are my losses. Their wins are my wins. I know they feel the same about each other. None of us want it to end, but here we are, braving the red eye and flying across oceans to gather one final time in this configuration. I feel so, so lucky. 

Power members doing a “Kendrick Lamar walk” 8 months before the Superbowl—how did they know??

I’ll be promoting Power again in April or May, not sure yet. I need time to breathe and regroup, to dream the next iteration into existence. 

It takes a certain amount of curating to put together a group like this, and a certain amount of courage just to apply. Most masterminds will accept anyone who has the money but I prioritize the coherence of the group. This isn’t the most lucrative way to run a mastermind, but it’s made for the most meaningful experience for both the members and me—and that’s more important to me than making the most money possible. If you’re interested and looking for a group like that, you can reply to this post. 

I’m curious to read your questions about this email, and reflections on your experiences with masterminds. 

What did you love? What did you wish was different? If you’ve never done a mastermind before, what’s holding you back? 

You won’t be tagged or marked as interested if you reply. This is just research for me. I’ve set aside time to read and thoughtfully reply to your emails myself. Please be generous with me about response time. I’m away this week. 

Thanks for helping me dream my next mastermind into being. 

See you next week

Tarzan

Tarzan Kalryzian [she/they]
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