What I Would Do if I Were Gen Z

I read a really good article the other day about why the younger generations are so into sports betting and prediction markets. The general thesis is that now through social media people see many levels of wealth higher than they used to, and the only path they see to reach that level is gambling. In the past they’d only see a couple rungs higher on the socioeconomic ladder, and if they just went to school and worked hard they could reach those rungs.

The author is correct and the despair that generation feels hit me in the gut. But I think there’s more to the story.

Even though I’m 45, I’d argue I lived through the exact same scenario, so I am better equipped than most to give advice.

I found it impossible to work hard and do well at school. These days I’d probably be diagnosed with ADHD, but my experience was that learning in a classroom was too slow and boring and I had zero interest in what it was leading up to. I can’t remember exactly how I came to this conclusion, but even in middle school I knew there was no chance I would have a normal career. It’s hard to articulate thinking from 30+ years ago, but you’ll have to trust me when I say that I never once considered having a normal job long term.

At the same time, I was exposed to levels of wealth above that of my own family. My parents were middle class, but they prioritized education. I went to a private school for middle school and then one of the best public schools for high school. My middle school had families representing a range of wealth levels, but the top was quite high. A friend took me to Taiwan where we stayed in his family’s seven story house, and I remember going to a pool party on a classmate’s family complex that had an indoor pool.

In high school a friend was obsessed with Robb report, which made me obsessed with Robb report. I’ll never forget an advertisement for a private island in the back, which probably at least indirectly led to me getting one with my friends.

And besides all that, I’ve always just loved life and been so curious about what’s out there. I want to see and experience everything, from the low end to the high end.

On the surface, you might argue that I prove the author’s point. I was actually a professional gambler for many years, a good portion of my success has come through crypto, and the rest has come through being an entrepreneur and investing. I think there are some bigger factors at play though, and those same factors would be very useful to someone who finds themselves in the same dilemma.

One persistent factor is that everyone’s view on life is far too narrow. People limit their thoughts and actions to roughly what their peers do. I think it’s true that up until the 1980s if you just did what your peers were doing (go to school, get a job, etc.) you would achieve a greater level of success than your parents. I can skip making the argument that this is true, because I think everyone innately understands this at this point. 

It’s always so strange to me when people complain about housing prices. Yes, they are much higher than before, especially compared to incomes. But… there are so many places that have inexpensive real estate. Everyone is looking at the same ten real estate markets, panicking because they can’t buy a house there. Why not go somewhere that’s not so in demand? You can buy a livable two bedroom in Vegas for $120k. Chicago real estate is extremely cheap. Go rural or to a less glamorous city and I bet you can find even better deals. And who cares if the jobs aren’t there? There’s never in history been a better time for remote jobs or being an entrepreneur.

If you don’t want to follow the beaten path, and you shouldn’t, you have to learn to be creative. There are so many incredible ways you can combine the resources available in this world, especially these days. Broaden your view and consider everything. Move somewhere weird, start a niche business, learn things other people don’t learn, be an interesting individual and create and incredible network of friends.

The higher levels of wealth, at least the parts of them that matter, have also never been more accessible. Physical luxury goods may be expensive, but they’re also so pointless that I don’t really care if people can’t get them. On the other hand, international travel is so cheap now that it’s not that difficult to get yourself into a position where you can truly see the world. Through the internet and AI, quality education is completely free and can be delivered at your own pace in your own time. You can connect with just about anyone in the world if you have a good enough pitch. 

This world is changing so fast that it requires creativity and resourcefulness most of all. Those are skills that you can develop on your own for free. Another skill, one that’s harder than ever to develop, is focus and attention span. That’s a tall order these days.

In addition to the given reasons for why younger people are turning towards gambling, I’d argue that our short attention span requires immediate gains rather than long term gains. No one cares about earning 8-10% a year, even though that growth will lead to wealth. I’ve been trying to get my siblings to invest money for years, and they only finally did it once I made a spreadsheet that showed that those modest gains coupled with meaningful monthly contributions will lead to them becoming millionaires. They had no idea.

The one aspect of gambling that can be positive, and one that I’ve harnessed for my entire life, is understanding risk and expected value, and harnessing asymmetric risks. Betting on a sports game is dumb— you have no advantage there. But spending a month testing out an idea that could lead to a successful startup? That’s worth trying. 

The guaranteed path to success used to be go to school, follow the rules, get a job, buy a house. That worked for most people who did it. That path is gone now. 

Now there are a lot of paths, but here’s the one I’d prescribe because it will always work. Live below your means as long as you can, including going to a low cost of living area. Don’t live where people who made it are living, live where YOU can make it. You can move wherever you want later. Start a business, work remotely, or both. Don’t indulge in dopamine hits like video games, feeds, the news, reels, etc. Build habits that will serve you for life like a long attention span. Find other people who are on a similar path and help each other. Don’t follow what other people are doing. By the time they’re crowing about it, it’s already too late.

Contrary to what the news says, I think there’s actually no better time to be trying to make your fortune and find your place in this world. The resources available to everyone are better than ever, and leverage through AI is unprecedented. The standard American path is dead, but we don’t have to mourn that. Let’s just move on to better things.

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Photo is the Colorado river just below the Hoover dam. There’s an amazing place you can hike to down there to camp and bathe in amazing hot springs!