The U.S. has built the most dynamic financial system in the world—a trend that shows no sign of slowing. The banking sector is undergoing major changes as new firms rise and crypto unlocks novel investment opportunities. Americans, arguably more investment-savvy than most, already enjoy access to a wide range of low-cost investment apps and services.

Back in 2012, working as an early engineer at startups and surrounded by investment opportunities, I began thinking about how to value both experience and ownership—across stocks, debt, fiat, crypto, and more. Recently, I revisited the ownership side by evaluating my portfolio along two axes: return and risk. I estimated the annualized return (CAGR, real or projected) and risk (coefficient of variation, or CV) per year over the 2014–2024 period. While I can't share the raw data or methodology, the high-level view below reflects my best attempt. I had to make several assumptions, and there's a wide margin of error—but it still paints a relatively fair picture. One outcome, in particular, surprised me.

I'm a self-taught, mostly passive investor—never focused deeply on any one asset class and typically spending only a few hours a month. My returns have been good enough for me, though likely well below what a dedicated investor would achieve.

Some investments fell within what I call the "classical" frontier—regulated products accessible via platforms like Robinhood or ThinkOrSwim. Crypto dramatically expanded that frontier, offering both high-return/low-risk opportunities and high-volatility/negative-return assets like meme coins. (I treated those more as entertainment than investment, but included them in the graph for completeness.)

Early crypto markets, though unregulated, offered compelling returns as the space matured. The surprisingly low risk score for Bitcoin in my analysis is largely because CV doesn't account for tail risk. For those who picked assets with economic value or strong teams in 2014 and held through 2024, the CV can appear low. In my view, many people missed the crypto opportunity by focusing on noise—scams, hype, and regulatory uncertainty—rather than the core innovation: programmable, decentralized money. With regulation now arriving, the "crypto frontier" is converging with the traditional one.

One surprising result came from my startup equity. I've always believed in buying my vested stock—only working at a startup if I was confident I'd want to exercise. Except for one clearly overvalued company, I bought stock every time I left. While I had to make big assumptions to model outcomes, my startup equity CAGR came out to ~22%, driven by two standout results, with acceptable risk. Founder selection—and being based in San Francisco with a strong network—was key.

Finally, I agree with The Economist[0] that the American financial system faces serious structural risks—unproven fintech entrants, soaring deficits, and unchecked monetary expansion. The next decade will not resemble the last. I increasingly feel unprepared for what's coming. The era of the unfocused investor may be over.

[0] American finance, always unique, is now uniquely dangerous, The Economist, May 29th 2025.

The U.S. has built the most dynamic financial system in the world—a trend that shows no sign of slowing. The banking sector is undergoing major changes as new firms rise and crypto unlocks novel investment opportunities. Americans, arguably more investment-savvy than most, already enjoy access to a wide range of low-cost investment apps and services.

Back in 2012, working as an early engineer at startups and surrounded by investment opportunities, I began thinking about how to value both experience and ownership—across stocks, debt, fiat, crypto, and more. Recently, I revisited the ownership side by evaluating my portfolio along two axes: return and risk. I estimated the annualized return (CAGR, real or projected) and risk (coefficient of variation, or CV) per year over the 2014–2024 period. While I can't share the raw data or methodology, the high-level view below reflects my best attempt. I had to make several assumptions, and there's a wide margin of error—but it still paints a relatively fair picture. One outcome, in particular, surprised me.

I'm a self-taught, mostly passive investor—never focused deeply on any one asset class and typically spending only a few hours a month. My returns have been good enough for me, though likely well below what a dedicated investor would achieve.

Some investments fell within what I call the "classical" frontier—regulated products accessible via platforms like Robinhood or ThinkOrSwim. Crypto dramatically expanded that frontier, offering both high-return/low-risk opportunities and high-volatility/negative-return assets like meme coins. (I treated those more as entertainment than investment, but included them in the graph for completeness.)

Early crypto markets, though unregulated, offered compelling returns as the space matured. The surprisingly low risk score for Bitcoin in my analysis is largely because CV doesn't account for tail risk. For those who picked assets with economic value or strong teams in 2014 and held through 2024, the CV can appear low. In my view, many people missed the crypto opportunity by focusing on noise—scams, hype, and regulatory uncertainty—rather than the core innovation: programmable, decentralized money. With regulation now arriving, the "crypto frontier" is converging with the traditional one.

One surprising result came from my startup equity. I've always believed in buying my vested stock—only working at a startup if I was confident I'd want to exercise. Except for one clearly overvalued company, I bought stock every time I left. While I had to make big assumptions to model outcomes, my startup equity CAGR came out to ~22%, driven by two standout results, with acceptable risk. Founder selection—and being based in San Francisco with a strong network—was key.

Finally, I agree with The Economist[0] that the American financial system faces serious structural risks—unproven fintech entrants, soaring deficits, and unchecked monetary expansion. The next decade will not resemble the last. I increasingly feel unprepared for what's coming. The era of the unfocused investor may be over.

[0] American finance, always unique, is now uniquely dangerous, The Economist, May 29th 2025.