06/04/2026
Last week, Jeff Bezos completed a planned sale of 25 million Amazon shares.
My take away isn’t the size of the sale, it is the process and how it can help you invest like a CEO.
Like many founders and executives, Bezos sells according to a prearranged Rule 10b5-1 plan. These plans are designed to address insider trading concerns, but they also reveal something interesting about how some sophisticated investors think about wealth management:
They don't operate under a "never sell" philosophy
(Something that is occasionally promoted by various corners of the internet)
Instead, many of the world's wealthiest investors systematically diversify over time.
That raises an interesting question:
If billionaires with concentrated stock positions don't rely on permanent deferral, should everyone else?
Answers will vary to each person, but let me offer an opinion to Washington residents.
Washington currently imposes a 7% tax on certain long-term capital gains above the annual exemption amount. ~$278,000 in 2026. Lawmakers have also discussed additional tiers for larger gains.
Rather than delay, delay, delay, until a major life event or purchase forces a sale, we are helping many Washington residents thoughtfully recognize gains each year, below the threshold.
This can potentially reduce, or in some cases avoid, future Washington capital gains tax exposure while preserving diversification and portfolio balance.
If you feel your investments could benefit from a strategic plan that incorporates tax, preservation, growth, and estate planning considerations… it is quite literally one of my favorite topics to discuss.
Shoot me a message and we will get planning!