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Weird Side Bets That Made Founders Millions

Weird Side Bets That Made Founders Millions

Moneywise · Dec 16, 2025

Founders share their riskiest investments: angel deals, real estate, crypto, and buying businesses, all built on a safe financial foundation.

Hyper-Growth in Volatile Assets Like Crypto Can Destabilize Your Portfolio

When a small, speculative investment like crypto appreciates massively, it can unbalance an entire portfolio by becoming an oversized allocation. This 'good problem' forces investors to systematically sell the high-performing asset to manage risk, even as it continues to grow.

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Weird Side Bets That Made Founders Millions

Moneywise·2 months ago

Post-Exit Founders Reinvest by Acquiring Businesses in Their Area of Expertise

Instead of starting from scratch, a common strategy for successful founders is to use their exit capital to acquire existing, profitable businesses. By sticking to industries they already know, they can apply their specific expertise to grow established companies, mimicking Warren Buffett's investment philosophy.

Weird Side Bets That Made Founders Millions thumbnail

Weird Side Bets That Made Founders Millions

Moneywise·2 months ago

Founders Can Leapfrog 10 Years Financially by Relocating to Lower-Cost Countries

Moving to a location with a lower cost of living (geo-arbitrage) is more than a cost-saving tactic; it's a strategic lever to accelerate financial and lifestyle goals by a decade. This allows founders to extend their runway, free up capital for investments, and achieve their desired lifestyle much faster.

Weird Side Bets That Made Founders Millions thumbnail

Weird Side Bets That Made Founders Millions

Moneywise·2 months ago

Successful Angel Investing Requires Active Operational Support, Not Just Writing Checks

The most fulfilling and effective angel investments involve more than capital. Founders benefit most from investors who act as operators, offering hands-on help and staying involved in the business. This approach is more rewarding and can lead to better outcomes than passive check-writing.

Weird Side Bets That Made Founders Millions thumbnail

Weird Side Bets That Made Founders Millions

Moneywise·2 months ago