Leading Leaders

One of the best compliments I ever received was when a friend told me that I was a leader of leaders. He was also a leader, so it meant a lot coming from him. I’ve had this topic on my “to write” list for years now, but every time I attempt to write it I’m worried that it will come off as conceited. So first, a disclaimer.

This post does not mean that I think I am THE leader of my friends. I think that most or all of my friends are leaders and that we all take turns leading or lead simultaneously in different ways. So this post is just as much from the perspective of leading friends as it is from the perspective of being led by friends.

When I talk about leading, I am mostly talking about serving. I’ve led my friends on many trips around the world, I’ve orchestrated a lot of group property purchases, and I’ve gotten many of my friends into things like tea, living in RVs, crypto, my style of personal finance, etc. I like to go off and figure something out that can benefit everyone, and then bring it back to the group and guide them through it. And, of course, my friends have also done the same for me countless times. My friend Nick got me into art, it was my friend Todd’s idea to travel minimally (I wanted to get a huge backpack at first!), and my friend Jesse led me to love tea.

The biggest difference in leading leaders is that they don’t need you. If you do a poor job leading or lead them astray, they’ll just go off on their own and figure it out. For this reason, trust is the most important factor. A leader will not follow someone that they don’t trust. For example, what’s the point of friends following me on a 1 week trip around Japan if they think I might waste their time and they could have just gone and done their own trip? If I tell them that I’ve discovered a better way to manage finances, but they don’t trust that I’ve actually done enough research, they’d be better off figuring out it out themselves.

The two primary ways to foster trust in this context are to build a track record and to provide context.

At this point I have such a good track record buying properties for friends that I literally had a friend buy hare of the last one without knowing what country it was in. Two properties ago he said, “I’ll be in for any property you do, so for the next one just tell me how much money to send you and I’ll find out where it is once it’s all done.” It was mostly just for fun, but illustrates the level of trust. Your process track record is even more important than the results, though. If people see that I research everything thoroughly, then even if I said, “Hey guys you should buy this random gadget”, they would probably buy it because they know how thoroughly I research this things.

Of course, a track record can’t magically appear, so there has to be another way. That other way is by providing the context that can allow someone to simulate their own research. For example, when I wanted to convince a friend to manage his money like a billionaire, I explained why each step was important and what the point of it was. I mentioned other things I had learned along the way. Someone who is a leader is used to doing this sort of process by himself, maybe in a different field, so he can relate and see that I recognized all of the factors that were important in making the decision.

Incidentally, I’ve found that in some ways it’s actually easier to lead leaders. It may take longer or more effort to earn their trust, but they tend to ask fewer questions and procrastinate less because they recognize the process and also know that they won’t be totally stuck if it turns out I’m wrong. Someone who isn’t comfortable leading may ask a lot of questions out of fear and worry that if I’m wrong they’ll be in a position that they won’t know how to get out of.

Allow other leaders to lead too. A good balance for most people is leading when they’re most suited to doing so, and allowing someone else to lead at other times. Only an insecure leader tries to lead everything. Leaders usually feel most valuable when they can lead others, and it doesn’t make sense to have a relationship where you aren’t allowing someone else to feel valuable. Plus that’s really the best sort of friendship anyway, one where you each specialize in different areas and bring that expertise and experience to each other.


Photo is from a hike I did in Oahu last week. I laid over there for just long enough to visit the Honolulu Museum of Art, which is one of my favorite museums in the world.

Tomorrow (Sunday 3/14) I’m doing my first YouTube Livestream! Please join as we talk about buying properties with friends, the island, and anything else people ask about. If people show up and enjoy it I will do more of them and maybe more YouTube.





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