Investments

Bitcoin is an alternative asset. And when it comes to alternative assets, my rule since leaving Wall Street in 2012 has been simple: no more than 20% of investable capital. Venture capital, venture debt, private equity, private real estate, collectibles, precious metals, and yes, Bitcoin all fight for space inside that 20%. The problem I […]

As a FIRE parents raising two children in San Francisco, we rely heavily on our investments to remain free. If we significantly misjudge returns, we increase the probability of having to go back to work. Going back to work is not the end of the world. Ideally, however, we would like to avoid it until

I’ve been aggressively buying the dip since March 2020, when I wrote How To Predict A Stock Market Bottom Like Nostradamus. My daughter was born four months earlier, and something inside me clicked, pushing me to invest aggressively for her future in an increasingly difficult world. Since then, I’ve continued to buy virtually every meaningful dip

Beyond expensive valuations, with the S&P 500 trading at roughly 22 times estimated forward earnings, another concern for the stock market is quietly flashing red: U.S. households now have more net worth in stocks than in real estate. On the surface, this might not sound alarming. After all, the stock market has been ripping higher

I’m in a cash crunch, and it doesn’t feel good. After buying my house in 2023 and living paycheck to paycheck for six months, I promised myself I would never return to this state. Yet here I am. Part of it is just bad luck, but part of it comes down to poor planning on

During my free financial review of my investments, I was feeling pretty good about how far it had come. Back when I retired from finance in April 2012, I had about $300,000 in my 401(k). After leaving, I rolled it into an IRA and invested in index ETFs and individual stocks. Since then, it has

It’s a raging bull market, and I’ll confess, I’m a little annoyed I don’t have a large paycheck anymore to take advantage of more investment opportunities. Every day, I see people with steady W-2 income are funneling thousands into stocks, real estate, and private deals. Meanwhile, I’m sitting here, asset rich but cash flow constrained.

1999 is back, and I’ve missed it. Ever since then, I’ve been chasing that next 50-bagger, the kind of life-changing winner that helped me come up with the down payment for my first property. But he’s been elusive. I still remember sitting on the international trading floor at Goldman Sachs at 1 New York Plaza,

It’s been several months since we returned from Hawaii, and surprisingly, my FOMO about the AI tech boom has faded. Sure, I still don’t have a job paying me gobs of money as AI CapEx surges higher, but that’s OK. Instead, I’ve allocated enough money to AI investments to where I no longer feel the

Two decades ago, I learned an important lesson: if you can’t beat them, join them. And if you can’t find a job with the monopolies, then you might as well invest in them! Take what happened on September 1, 2025. I got an email from Apple saying my Apple TV+ monthly subscription was going up from