Building my own on-demand mastermind group of "5".

You are the average of the 5 people you spend the most time with
— Jim Rohn

We've all heard this before. It's one of the most repeated advice/factors mentioned by high performers of various disciplines. The advice comes in different forms like "work with people you admire", "find mentors who are doing what you want to", "choose a life-partner who will challenge you to grow". All focused on surrounding yourself with people that will aid you in your journey of growth. 

It's true, you can't do it alone. No matter how independent or introverted you are, you will need a support network. 

When I first heard this advice I felt I needed to find some amazing people fast. It was stressful. How was I going to find people who would fit criteria like: 1) I could spend a lot of my time with 2) I admired 3) wanted to be mentored by, etc.

I had some pretty high aspirations and I really wasn't going to settle for someone that was "okay".

I stressed about my friends, my girlfriend, my family, my coworkers etc..

They all had various roles they played in my life but I felt they needed to play more than just one role. Time being the finite resource I wanted to find maximum effectiveness and efficiency with the people I hung out with. I took the "5 closest people" way too literally and found myself getting anxious about how selective I should be with my relationships.

In hindsight this was utter stupidity.... naive would be the nice way of putting it. 

This may seem obvious to you, it wasn't to me at the time, but I later learned that various groups of people in your life have different roles to play. Not to mention that I didn't really need to pick "5" in any literal sense. There would not be 5 perfect people. Rather, a varying degree of people who had specific qualities or achievements I admired and would like snippets of. 

Reframing the purpose. 

My family, partner, high school friends, university friends, work friends did not have to all serve the same purpose. They all had a very different purpose to play in my life and they each provided me with something unique that I needed in my life. 

It may not seem like much but it was some "big bang theory" moment for me when I realized I could continuously have a revolving door of different people that I kept close to me to form my "mastermind" group. Some refer to it as their own personal "board of directors" in a company. 

Consider yourself as a business that seeks to be profitable over the years. Your shareholders would be people who have invested their time into building a relationship with you and want to see you succeed (i.e. family). But you as the CEO of the business may need guidance since this is your first time living. The reincarnated may have got this shit figured out already. 

That's where your board of directors come in as mentors and advisors. Companies have directors that guide the CEO and sometimes these directors change based on the needs of the company throughout it's life cycle. 

I was flawed in thinking that I would need to find 5 perfect people because that assumed I would not grow. It assumed that I would be the same person needing guidance in the same areas, with the same goals, same anxieties. The fact is that there is no stagnation. In investing we analyze a company's sustainable competitive advantage; the "moat" as popularly coined by Buffet. The thing with the moat is that it is either growing or shrinking at all times because competitors will either be entering to make goods cheaper/better or leaving because the incumbent has a moat that allows them to make goods cheaper/better. This is the same for us as individuals. I, as a person will either grow or decay. Stagnation in my life would be decay, as the world around me will grow on average. 

Hence, it was foolish for me to assume there would be perfect mentors. Instead, I had to embrace the idea that my board of directors should be an ever changing and revolving door of people who could give me guidance to the me at that specific time and place. Unlike a company, I am a single person so I am capable of much faster growth and directional changes than a 1000, 100 or even 20 person company. This will require a greater fluidity in the people I chose to influence my mind with. 

How do I do that?


I personally prefer speaking with people directly but sometimes it's really hard to get major influencers to meet me at a coffee shop. I've been able to contact a few through email and that get's me super excited for sure. Still, the process of building a personal relationship with various high performers of various social-statuses is an artful process that can't be rushed and should be a joyful process on its own. This leaves podcasts as an invaluable alternative for me.

I assume that I've probably digested information on average 7hrs a week minimum. So, at 52 weeks.... or let's do 49 weeks assuming I take out 3 weeks for vacation from learning (though I'd actually argue I listen to it more on vacation) at 4 years is about 1,372 hours of information I've digested from people I'm interested to learn from. Without a doubt, these hours proved materially more valuable than 4 years of learning accounting...I don't really apply the rules for IFRS 17 or 5 in my life anymore you see...

Picking my 5 people. 

My love for podcasts got me to start my own and a common question I get from friends is what I listen to and how I listen. 

The way I've consumed media has continuously evolved. It's a relatively fluid process but I figured I'd share my strategy here. 

Oddly enough, I don't listen to podcasts per the "top chart". I can't remember the last time I looked up rankings to decide what I should listen to. The way I've found my podcasts are mainly through trial and error. Most of the key podcasts I listened to were sometimes so new that they didn't even have much media coverage or following. 

I used to subscribe to as many as 30 different podcasts but I soon saw an everlasting pile up of episodes that didn't peak my interest and listened to many out of obligation rather than genuine curiosity. Since then I've really cut down my subscription to interviewers I trust to have great guests on a wide ranging selection of disciplines I may be interested in or be forced to learn about to expand my mind. As of September 2018 these are my go-to subscriptions:

  • The Tim Ferriss Show

  • Chase Jarvis Live

  • Invest like the Best

  • Rad Awakenings

  • Capital Allocators

  • Knowledge Project

From here starts my process of the "5 people". I commonly have an area I'm fascinated by or a problem I'm looking to solve at every point in my life. I will usually find a person who I can relate with who has solved that problem or is in a state I aspire to reach. That person may come about in a book, an article, a conversation, or through a podcast I'm subscribed to. After I search for that specific person in the podcast episode directory, I listen to all episodes that person has come on. 

This way, I practically have that person in my ear for about 10 hours. About 80% of the episodes tend to deliver similar content but the magic is in the 20% of different content in each episode as the interviewer has his/her own questions that may fit perfectly with the questions I have. This is a process that allows me to pull out as much as I can from an individual without having actually met them in person. It also allows me to discover other podcasts that may be entirely dedicated to providing me with more people I'd be curious to learn from.

Here is an example of how the discovery happens:

I listen to Invest like the Best and from here, I learn more about Ted Seides. The world of "fund of funds" investing perks my interest so I listen to all Ted Seides interviews and find he has his own podcast. From there I discover Khe Hy of Radreads. Coincidentally, I had a coffee chat with a respected university alum and he recommended I look into Radreads. I listen to every interview Khe has been on to understand his story and turns out he also has his own podcast, Rad Awakenings. It's the perfect podcast for following the story of ex-investors, ex-consultants and other various high performers talking about the raw struggles of entrepreneurship, identity crisis and the journey of self-awareness. It worked wonders in helping me with my own phase of anxiety. This podcast led me to Jerry Colonna's podcast: Reboot, which further helped me on my own journey of self-awareness. 

Find your own channel

That is an example of how a web of relationships may form through immersion into learning about specific people. It's actually my own form of building out a latticework of mental models, per Charlie Munger. Munger is a voracious reader and as much as I aspire to be a "textbook with arms and legs" like him, I've learned reading may not be the best form of learning for me. 

Peter Drucker eludes to the importance of deciphering how you learn best so that you focus on that channel (i.e. listener or reader). I'm definitely a listener. This might actually be why even when I was a fundamentals investor I enjoyed speaking with management so much more than reading annual reports. I would actually try to find YouTube videos that would explain businesses instead of reading the annual reports because I felt it took me much longer than my peers to go through the written material than listening to the oral forms. There is just something very different with learning through conversation that I find so much more powerful. 

This doesn't mean I don't plan on learning from books. On the contrary. I continue to read voraciously and find ways to learn and retain valuable information. I've just accepted that it will take me time to go through books as I'm not a fast reader. So, I reinforce my reading with writing margin notes because it's only when I'm able to combine the two that I can retain the information I've just read. Books are yet another form of defining your own mastermind group. I'll actually expand on the podcast folks I discover by digesting their books after having listened to all their interviews. 

It takes time.

This is how I create my mastermind group. It takes a considerable investment of time and effort to determine if someone will really be the right person I'd like to dig into. Most of the time the simple determinant though is if I really enjoyed hearing the individual speak. It's as simple as that and I start digging from there. Many times I find myself outgrowing the people I add to my mastermind. I feel that I got what I needed from them and I rotate. Though later on when I have a new problem I may come back to them. I may listen some podcast interviews to 10+ times, or I may read the same book 3+ times. That's okay. It's a relationship. It will continue to build over time. 

I hope this may alleviate any anxiety you may have with creating your own mastermind group, or at least give you one additional perspective to help you form your own.