BLOG POST: How I Invest My Money

Episode Summary

Executive Summary: The episode is a blog-post-style personal investing disclosure centered on the idea that actions matter more than opinions. The speaker explains an investing approach dominated by automation in stocks, supplemented by speculative alternative assets and a small stock-picking “play” account, while emphasizing discipline, diversification, and a willingness to risk only what can be lost.

Main Topics: Investing behavior vs. investing opinions (Priority: 5/5): The core theme is that real portfolios reveal more than market commentary or public opinions; the speaker frames the episode around showing actual money decisions rather than abstract views. Automated stock investing as the foundation (Priority: 5/5): Most capital is invested automatically across retirement and taxable accounts, with a strong bias toward regular buying of diversified stock funds regardless of market direction. Selective stock picking for enjoyment (Priority: 4/5): A separate play account is used for building positions in individual stocks, but only as a hobby and not as a serious attempt to beat the market. Diversification into alternative assets (Priority: 5/5): Because the speaker’s financial future is heavily tied to the stock market, he adds exposure to private markets, real estate, art, income-share agreements, and Bitcoin as speculative diversifiers. Risk tolerance and speculative boundaries (Priority: 4/5): The speaker repeatedly stresses that alternative investments are small, non-essential allocations and that losses would not materially affect financial security. Interest rates and the search for yield (Priority: 3/5): Very low cash yields are presented as a key reason for moving money out of savings accounts and into higher-risk or less correlated assets.

Key Arguments: Investment opinions are less useful than seeing how someone actually allocates capital. Automation helps prevent emotional decision-making and keeps contributions consistent through up and down markets. A portfolio should reflect personal context; the speaker’s largest asset is his ownership stake in his business, so he seeks diversification beyond stocks. Alternative assets can offer exposure to returns and risks that differ from public equities, but they should be treated as speculative. Bitcoin is justified not by a precise price target but by the fact that many highly capable investors are bullish on it. Low savings yields make holding excess cash less attractive, though a liquidity reserve is still maintained for emergencies.

Data Points: 401(k) contribution frequency: Every other week - Stocks are purchased automatically in the speaker’s 401(k) on a biweekly schedule. 401(k) asset mix: Domestic, international, and emerging market funds - The retirement account uses broad diversified equity funds similar to those recommended to clients. Liftoff account contribution frequency: Once a month - A taxable account powered by Betterment receives monthly automated investing. Titan contribution frequency: Once a month - An automated asset manager focused on individual stocks receives monthly investments. Allocation ratio: For every $10 in 401(k), $6 into Liftoff and $3 into Titan - The speaker gives a relative breakdown of how money is distributed across accounts. Bitcoin first purchase date: June 2, 2020 - The speaker states the date of the initial Bitcoin buy. High-yield savings rate: 0.6% - Low cash yields are cited as a reason to seek other investment options. Liquidity reserve: Some money kept in savings - Cash is retained for absolute emergencies even though most excess money is invested elsewhere.

Pivotal Quotes: "Don't tell me what you think. Tell me what you have in your portfolio." — Nassim Taleb: Used to frame the episode’s argument that actual allocations matter more than market commentary. "What would you do if this is your house?" — Speaker: A recurring question from the opening anecdote that symbolizes wanting practical advice rather than theory. "If stocks are going up, I buy. If stocks are going down, I buy more." — Speaker: Describes the speaker’s automated, disciplined approach to long-term investing.

Implications: Listeners are encouraged to focus on process, automation, and risk limits rather than predictions. The episode also highlights how low-rate environments can push investors toward broader diversification and small speculative positions.