Prosper Street Curators

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Perspectives on
the market.

Fine Watches/September 2026

How to Buy Your First Luxury Watch

Which watch you buy is the last decision, not the first. How much to spend, the three questions that narrow the field, whether it should be a Rolex, and what separates an authorized dealer from the grey market and pre-owned.

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Fine Art/September 2026

When a Blue Chip Artist Dies, What Happens to the Price?

Yayoi Kusama died in August at 97, ten weeks after David Hockney. The instinct is that the work just got more valuable. What the research actually finds, and why for a prolific artist death does not make the work scarcer.

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Fine Watches/August 2026

Where to Buy a Used Luxury Watch Online (and Which Sites Are Legit)

Working out which watch you want is the easy part. Choosing which specific one to buy is where it falls apart, because every listing leaves out something different and the gaps are where the money goes.

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Collecting/August 2026

How to Insure Art and Watches, and What Your Current Policy Might Be Missing

Your renters or homeowners policy probably caps art and jewelry at a couple thousand dollars. What the caps really are, what it means to schedule a piece, and what I pay to insure my own collection.

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Fine Art/August 2026

Are Art Advisors Only for the Wealthy? What an Art Advisor Actually Does

What an art advisor actually does, whether they really have exclusive access or inventory, how they charge, and when hiring one is worth it, even on a modest budget.

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Fine Watches/July 2026

The Dealership Tax: Why Cash Can’t Buy You a Rolex Submariner

Authorized dealers won’t sell you a stainless steel Rolex at list price without a purchase history. Here’s what that actually means, and how to decide between waiting and paying the premium.

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Auctions/July 2026

How to Read an Auction Estimate

An estimate isn’t a price, and the hammer isn’t your total. How to read an estimate, factor in the buyer’s premium, and judge condition, with real results from Phillips, Koller, and SBI.

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Fine Art/July 2026

The Museum Fallacy: You Don’t Need an Original to Own Great Art

The assumption that museum-quality art is unaffordable is one of the biggest fallacies in the art world. Here’s what the market for lithographs and signed prints actually looks like.

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Fine Art/July 2026

Comprehensive Guide to Fine Art Prints

Lithograph, screenprint, etching, linocut, giclée: what each technique is, how it’s made, and whether it holds value. Plus the one thing that actually determines what a print is worth.

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