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Watch Portfolio: The Oyster Perpetual Date 15000

Jul 15, 2026

Issue 3 of the Watch Portfolio series. The watch that started it all, plus three new financial moves worth knowing about.

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The Orange GMT Hand on the Rolex Explorer II: Why It Matters

Jul 10, 2026

Part 9 of a 14-part series on the Rolex Explorer II 226570. The signature orange hand that ties the modern reference back to the 1655 Freccione.

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Halfway Through 2026. Here's Where Things Actually Stand.

Jul 9, 2026

A novel at 71,000 words, a newsletter that is not yet paying for itself, and a Prius running DoorDash routes in Wasilla to fund a dream car. The honest mid-year version of Own The Watch.

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Why Did We Ever Accept This?

Jul 7, 2026

A guest appearance from something I have been building. Read to the end and tell me what you think.

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Net Worth Report: July 2026

Jul 4, 2026

Net Worth Report: July 2026. The monthly breakdown of where we stand, what moved, and where the trajectory points.

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The Micro Details Most 226570 Owners Miss

Jul 3, 2026

Part 8 of a 14-part series on the Rolex Explorer II 226570. The hidden design details on the dial, hands, case, and bracelet that you only notice after months of wear.

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The Summer Permission Structure-Why July Is the Most Dangerous Month for Intentional Spenders

Jul 2, 2026

73% of Americans plan to do whatever it takes to make a summer vacation happen. The average spend on flights and lodging alone is $3,940. Here's what that number costs the work-optional timeline.

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Why Marriage Might Be the Most Underrated Wealth-Building Strategy There Is

Jun 30, 2026

The data on married couples and net worth is more dramatic than most people realize. Fourteen years in, here's what actually compounds.

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The 16570 Is the Smartest Rolex You Can Buy

Jun 26, 2026

Twenty-two years of production, vintage character without vintage problems, and prices the market hasn't figured out yet.

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Moneymaxxing Is Real. The Industry Built Around It Is the Problem.

Jun 25, 2026

680 million people follow finance influencers online. The creators selling the optimization system are building their work-optional lives. Their audience thinks they are building theirs.

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