Introduction

Before co-founding my own business, I was talking to a recruiter who wanted me to be a founding engineer at a startup. I wasn’t confident with the direction of the company, so I told them “I’m not interested at this time” - to which they replied “it’s ok, I guess you’re not a risk taker”.

Risk doesn’t always mean “dive in and hope for the best with no forethought”. I consider that recklessness rather than calculated risk.

Story 1: Moving abroad

I lived in Switzerland for a year, and the US for 2 years. It was scary moving at first, especially to Switzerland where I didn’t know their native language. But I don’t regret taking that risk at all.

I learned how it feels to not understand everyone around me. It was a great experience, but one thing I took away for life is sympathy towards people who move to my home country without knowing English or French natively. I know how it feels to speak like a 5 year old as an adult 😅

Story 2: Leaving a job I liked for a job that’s better on paper

I really liked working at Amazon - they gave me a ton of ownership and let me run free with ideas. On paper, Dropbox was a better bet. Higher salary, better benefits, people on Blind say it’s a better place to work, etc.

But the culture at Dropbox was different. I was told multiple times that I’m “not allowed” to work on certain projects because I wasn’t at level X yet. I NEVER heard that at Amazon, and it really demotivated me. I had some qualms about Amazon culture as well, but overall I liked it more.

I’m still glad I made the switch. It helped me learn more about what motivates me!

Story 3: Gambling! Or: How I Learned to Stop Worrying and Trade Options

Casino gambling is a complete scam. Your expected return is necessarily less than 0, so there’s no good reason to gamble there unless you just like the adrenaline rush.

But gambling on stocks is very different. Under an efficient market, your expected return is still less than 0 due to brokerage fees, but by comparison to a casino your brokerage fees are negligible.

In Eliezer Yudkowsky’s Magnum Opus “Rationality: From AI to Zombies”, he writes about betting on your beliefs to gauge your own confidence.

With the recent DeepSeek news & NVDA stock tank, I bought a small amount of stock call stock options. Trading isn’t my day job, so I did this more for fun than to make massive profits. After all, I need to spare my savings to spend on my startup! And I wasn’t confident enough to risk too much of my savings.

Buying a call option essentially means you have the right to buy the stock at a given price before a set deadline. You have the risk of losing everything if the stock price goes down, but a much higher reward if you’re right.

For those not in the know, there were basically two types of people a couple weeks ago:

1. Those who said “DeepSeek is going to destroy NVDA”
2. Those who said “The DeepSeek hype is irrationally tanking NVDA valuation”

I agreed with #2 off the bat. If I was wrong, I’d learn that my reasoning was incorrect and I could course-correct my decision making about current world events. If I was right, I’d make money 😀

I ended up cashing in my options today since enough news about DeepSeek has come out for the NVDA stock to mostly bounce back. I’m no longer confident that I know better than the market, so I’m out. Deciding when to sell really made me gauge my own confidence in my beliefs as more news came out.

Story 4: Co-founding a startup

This is the biggest monetary risk I’ve ever taken. It’s been a rollercoaster but I’ve learned a ton. Honestly I don’t even know what to write in this section, there are so many risks and tradeoffs you need to make when “doing the startup thing”, and plenty of people have already written about it.

Story 5: Expressing my gender identity

At some point I’d like to post a blog explaining my thoughts on gender ideology - another day!

TL;DR: I agree that it’s a social construct and people get too defensive about others expressing themselves in gender non-conforming ways. I don’t care to argue about it in this post, so if you disagree, just consider me an eccentric male if that makes you more comfortable. And watch this TED Talk if you want to get your gears turning about gender theory.

I consider myself non-binary. After therapy and doing meditation practices from the book No Bad Parts, I realized there are parts of me that want to express both feminine and masculine.

Knowing that myself is different than expressing it publicly! But I want to live in line with my identity, and if people don’t like it.. that’s unfortunate.

I knew that coming out would have all sorts of responses from people. But I had to get comfortable with that, and feel more relaxed in my mind-body connection now that I’ve done so.

Conclusion

Go take some risks! It makes life more fun 😀

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