Degenerate Risk-Taking
I recently had a long flight and decided to go old school and buy a real book that I could hold with my hands. I didn’t want to watch a bunch of dumb movies. The funny thing is that once I got the book I ordered, it was way too big for my backpack. Nobody wants a heavy, bulky backpack when they travel. My newly bought book was almost five hundred pages long. I clearly didn’t look at the page length, and now my trip included a homework assignment to finish the book. Spoiler: I did finish the book. At least I finished 95% of it on my trip and the last 5% at home the next day.
The book was On the Edge: The Art of Risking Everything by Nate Silver. Now, this was a bit of a random read for me. I follow Nate on X but had never read anything from him outside of lightly scanning his Substack. I just loved the book's title, so I quickly bought it on Amazon. To my surprise, I didn’t realize it was about poker players, venture capitalists, crypto maxi, and other risk-takers. So much of the book is based in Las Vegas, and as someone whose church doesn’t allow me to gamble as part of my staff covenant, I found it funny that I was reading it. I started to worry that I was breaking my covenant by buying it.
The core of his book is about thinking like “The River” versus “The Village.” River people take calculated risks with big rewards. Yes, they lose sometimes, but losing is part of winning big. The river name refers to the final card in poker. River people are more libertarian in their thinking, have a bold vision of the future, and are willing to put it all on the line to make it happen. Village people are comprised of government, media, and academia types. Village people are more liberal and slow in their thinking. No, this isn’t a reference to the YMCA song. The village name refers to all of them thinking the same, like agents in The Matrix. They are like politicians who blame norms, rules, and loopholes for why things don’t get done. The Village is always blaming someone else and not just hustling to make it happen.
Visual of all the types of people Nate Sliver unpacks in his book
Of course, Nate advocates for the River way in the book, but he is honest that it isn’t for everyone. I don’t think I’m a River thinker fully, but I took some things from the book that will make me a better leader and pastor and maybe even push for a better future at my church. I can’t summarize the whole book, but three things stood out while reading it:
I loved how he leaned into this degenerate theme of how Vegas is and the type of people who desire to live their lives in such a place. It was funny that degenerate was such a negative thing to say, but it was also an honest way to talk about some of these places where The River people exist. The irony is that we are all degenerate, as Scripture teaches. The point of the Gospel is we aren’t good enough. We need saving. I’m a degenerate and need to know it. I felt like Nate sometimes said it like it's only a River person thing, but I saw it as a truth of Scripture for everyone. The Village people aren’t better just because they pretend they aren’t degenerates. We all are sinners. I wanted to shout “Preach Preacher” a few times when he was describing what being a degenerate is all about. I think I will use the word degenerate a bit more moving forward to describe what a sinner is.
How the River people think about the odds of situations or moments was eye-opening. I’m a pretty conservative risk-taker most of the time. Some of my crypto bets might counter this statement, but I often think about money like I endured the Great Depression. A River person is trying to find the edge, and the closer the odds are, the worse the bet. If there's a widespread, there might be an opportunity to make a buck. For example, betting on who will win the election may be near 50/50, and the idea is that risk to reward is too close. Like flipping a coin, why take that bet if it's up to chance and the return is so little? But let's say the odds of winning are more like 60/40, and the return is so high that it may be worth it. They aren’t looking for even splits but more risk with a ton of upside. River people are very risk-tolerant and think analytically about the risk. It’s a numbers game and not an emotional decision. They see the opportunity and lean into the moment. They are open to losing many times in a row because the coming return will most likely cover the previous losses. I for sure don’t think this way. I might only want an Index Fund type of return, which means I’m playing the 30-year game while a River person is playing the meme coin game. I’m not summarizing it entirely, but it made me realize how conservative I am in my risk-taking at times. I sometimes miss out on opportunities because I’m more of a Village thinker in moments, and I need to be more River-like in my thinking in the future. Short-term losses shouldn’t scare me so easily moving forward. Maybe one of those losses will turn into a big win in the next round.
Lastly, River people can decouple the decision from a feeling in a decisive moment. The pressure of the situation doesn’t cloud their decision-making skills. They can still think critically and abstractly and not easily fold. Also, they are great at playing the devil’s advocate position pretty quickly in real time. River people are constantly processing different options and angles and putting themselves in the shoes of everyone at the table. Skills like these allow you to make better decisions when the fire is turned up. I’ve generally been good at this in my roles, and early trauma in my life caused me to be more emotionless when an important decision is needed. I grew up being the peacemaker in my family. I easily see what my boss or a team member might think. I usually, but not always, try to see things from others' perspectives. It's a great skill for improving ideas, refining plans, and working with others. I’ve feared that the more “successful” I get, the more I could discount others' feedback around me. Nate talks about the FTX collapse and how Sam Bankman-Fried crashed in such a fiery Eron way, and a big part of his downfall was just thinking it would all work out in the end. To be fair, if Sam hadn’t been caught moving funds between businesses, with Bitcoin over 100k, as I am writing this, his plan would have worked out. I know I’m not SBF, but I can see how successful people start to believe that they are always right and lose touch with reality. I think this is just pride, and if everything moons around you, it's natural to stop listening to those voices. It happened to Moses, David, and Solomon and can happen to us. I need people in my life who will call me out, and I need to lean toward listening to those trusted voices. This is especially true the more successful I get.
It was a fun book. It’s not for everyone, but try to embrace a bit of the degenerate risk-taking approach in your role this week. It might do you some good to broaden your thinking and maybe even produce a better outcome in your future. Please don’t go full degenerate on me by betting it all and blaming it on this post.
