Managing Tech Millions

Family Office CEO Ranks Every Income Investment BEST to WORST (For $1M–$10M Portfolios)

May 12, 2026·16 min
Episode Description from the Publisher

Most first-gen millionaires I meet have a portfolio that looks the way mine did 14 years ago — over-concentrated in growth stocks. That works when markets are ripping. It breaks the moment you actually need the portfolio to pay you.I've spent the last decade building an income portfolio that now generates around $200K per year in tax-efficient income across multiple asset types. Along the way I've evaluated every income vehicle on the menu — and the ones getting pushed hardest on YouTube aren't the ones I'd actually recommend.In this video I rank all 15 income investments S through F for a specific situation: $5M, five years from retirement, growth-stock background, semi-liquid preference. A few of the "obvious" picks land much lower than you'd expect. One vehicle most investors overlook turns out to be the cleanest on-ramp on the entire list.If you're trying to make the shift from money maker to money manager, this is the map.Let's keep building.

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