The Calculated Contrarian: Extreme Security, Extreme Risk, Extraordinary Returns

The Kevin Rose Show

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Two decades in the investment world have taught me that success lies in both boldness and historical battle-tested financial wisdom. This philosophy guided my journey from a novice index fund investor to an angel investor and, eventually, a General Partner at Google Ventures and True Ventures, helping manage billions in capital. Today, I still serve as General Partner at True Ventures, where we currently invest in early-stage startups — managing 3.5B+ with 350+ companies.

It's been a wild ride. Along the way, I've developed an investment strategy that's weathered bull markets, bear markets, and everything in between. Today, for the first time, I'm pulling back the curtain to share my personal playbook—a carefully crafted approach that balances growth potential with calculated risk-taking. Whether you're a seasoned investor or just starting out, I invite you to explore the investment philosophy that's shaped my financial life for the past 20 years.

Remember, this is my personal playbook. I'm sharing it for information purposes only, not financial advice. You should always consult with a professional financial advisor before making investment decisions.

I've broken this article into several sections

* Timing the Market

* How I think about investing bucket allocations

* Where I Invest

* Index Funds

* Bonds and Cash Management: My Financial Shock Absorbers

* High-risk

* Stock Picking

* Risk Management and the Importance of a Moat

* Angel Investing: The High-Stakes Poker of Investing

* Gold and Bitcoin: Your Financial Apocalypse Insurance

* The Importance of Self-Custody and Physical Redemption

* Retirement Accounts

* When to Buy More

* Conclusion