Betting On People

We're all born, by default, betting our mother won't stab us. Newborns might be robust against accidental drops, but most people chuckle at dead baby jokes. Killing defenseless children revolts us due to the obvious moral absurdity.

Another default is our country of birth. This is a bet our parents make for us, some more proactively than others. I disagree with Warren at times on McDonalds and Coca-cola, but we undeniably both won the Ovarian Lottery.

Most of us don't have much choice in the school systems we attend. But once we start making money in a job, assuming we don't have debt, we can usually choose what we want to do with that money. Do I buy a toaster or an air fryer?

If we're lucky enough to think beyond our basic needs and into the realms of vegetable toastability, we can start making bets on the future. Do I put my extra $5 under my mattress, into a bank account, or store it with Vlad? In the latter case on Robinhood, should I choose the S&P500 or Bitcoin?

Most of us grow up shackled by bets we didn't make. We're only taught fragments of how the world really works, mostly by people who don't know enough themselves. We're never coached in autonomy. Only if we're lucky, we'll eventually run into some agentic people and learn from their examples.

Universities supposedly teach us to think critically about the world, but my major life learnings came from a variety of other sources. Listening to an audiobook like The Richest Man in Babylon and reading Rich Dad Poor Dad advanced me further toward personal wealth creation than almost any Econ 101 class would. Thankfully, the internet sets us free.

I graduated 2 semesters early to save $60k, and even then got lucky my $200,000 MIT degree ended up being worth it for the overall experience. I'm not sure if I would do it again, and I'd encourage the vast majority of smart kids today to try a gap year or study elsewhere.

The terms "betting" and "investing" are loaded and often misunderstood—it's not about money. In the most general sense, we're doubling down on our choices every day. Where we live is a bet. Who we hang out with is a bet. What we work on is a bet too, and hopefully we get a good ROI from our time spent doing that work.

Experience is the truest teacher. The lessons from your own life—processed by introspection and reflection—are the ones that will stick with you. This is why every human has interesting stories to tell. And why I strongly recommend blogging to accelerate and force your personal self-learning process.

Developing any skill—from chess to empathetic listening—starts with exposure and improves by practice. I've made a lot of seemingly bad bets that helped me slowly build up my intuition and conviction. For example:

• a $5M bet on myself and my career misconceptions over my job and future stock options at Scale AI.
• a $100k bet on land in Ecuador that ended up being pretty useless after the first rainy season took out the main road in a landslide. Sold the property for less than half of what I put in, around $45k, at end of 2023.
• a couple bets on restaurants in Ecuador that ultimately shut down, probably costing me around $25k or more.
• selling my 3 bitcoin at $2,000 (betting they peaked in value, up from $80 each in 2013) and also splurging on fish instead of holding on (each btc is worth $116k today, or ~$300k+ in total missed gains for me).
• my first company Senseg, for which I raised $280k and lost $140k, also spending 20 months of my life to do it.
• playing poker for a large portion of this year after winning $15k at a tournament in January. I already knew hold'em is a bad bet for me and have since lost all the prize money and more.

The best bets are the ones where you literally cannot lose. In the above list, bitcoin and poker most squarely fall into some kind of "needlessly silly bets" category. But I see the other ones as important life experiences that taught me valuable lessons about myself and the world. Those lessons just happened to be a bit expensive.

On the other hand, one of my least expensive bets with the highest upside was befriending Lucas Kasle in 5th grade. Having moved school districts from Oriole Lane in Mequon to Maple Dale in Glendale Wisconsin, I wanted to be besties with him so so badly. Other kids were fun, but Lucas was somehow extra special.

At the time, I wasn't thinking in terms of bets at all. I can't remember the particularities of my man-friend-crush. But my default family had exploded, the people we lived with were incompetent caretakers to the point of malice, and Lucas became a brother to me. I not only accomplished my friendship mission, but his family ended up adopting me. They have all my junk in their attic, to this day.

In addition to the good people around me, I'm compelled to bet on myself. These two bets have never steered me wrong. I've discovered my deep passion for people and instigation always outlives any particular interest in a product or project.

I've never spent over $3,000 in a single poker session. But now I'm willing to lose an order of magnitude more than that, betting on certain things that I believe create more value than I can possibly lose. I think I'm well-calibrated to the risks of my decisions, and I knowingly embrace that I could be wrong.

I started with $50,000 allocated to helping Phu in alignment with &U. I recently found a second person and wired them $39,000 last Wednesday. In total, I've put $150k into my new company's account and have around $25k left.

In addition to rent, new office furniture, and living expenses, there were a few big ticket items like the All-in Summit and Abundance House retreat. I have another $100k in personal savings that haven't yet been liquidated and sent into the company bank account.

I believe in the power of stories. My bet is that blasting off $125k in a few months—nearly half of my available resources—will result in profitable and strategic storytelling rather than reckless lunacy.

It remains to be seen if this arc in the story of my life is worth more than those dollars in the long run. I suspect the counterfactual portfolio of Nvidia, Tesla, and bitcoin will give me a serious run for my money...

But I'm not sure if omniscient baby Andy could have done any better in setting up the perfect preconditions: I've elected to get a PhD in life, I've reaffirmed my country after years away, and I continue to curate the people around me with each new day.

Now more than ever, I don't think I can lose.