2001. The tech bubble burst, and suddenly my expertise seemed worthless. But here's what I learned: legal frameworks don't disappear—they just find new applications. The contract structures we built for software licensing? They became SaaS agreements. The IP assignment clauses? Open-source licenses. The escrow mechanisms? Smart contracts, decades later. I didn't know I was building pattern libraries for the future.

Real Estate (2015)

The $50M Comma

A $50M deal that almost died over a comma. Three jurisdictions (Delaware, Cayman, Israel), one term sheet. The client wanted tax consolidation, the lender wanted structural subordination, and the tax authorities in each country had different definitions of what 'substance' actually means. The breakthrough wasn't legal gymnastics—it was realizing we needed three separate truthful narratives for the same economic reality. The deal closed because I stopped trying to make one story fit three audiences.

Digital Assets (2019)

One Model, Three Regulators, Three Truths

A client had a stablecoin-backed lending product. The SEC saw it as a security. FinCEN saw it as money transmission. CFTC thought it might be a derivative. They weren't wrong—they were each seeing a different facet of the same thing. The 'aha' moment: we weren't looking at three problems. We needed three truthful regulatory narratives for one business model. That's when I realized digital assets weren't a legal specialty—they were a stress test for every framework I'd learned in 25 years. And a reminder that clarity beats cleverness every time.

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