TRAILBREAK

Legal Counsel and Strategic Advice for Frontier Technologists

Fluent in Both the Law and the Tech

Trailbreak is a boutique transactional firm, offering sophisticated corporate / regulatory / product / IP counsel and strategic consulting on issues affecting blockchains, AI and beyond.

Evan Zinaman, Esq., Founder and Principal at Trailbreak, has developed a rare combination of skills that builders value most.

He is widely recognized as a crypto-native legal engineer, MEV / DeFi researcher and Ethereum power user. He specializes in understanding the intricate details of the technologies he advises upon, where the trickiest legal issues and the subtle design distinctions to address them lie.

Clients benefit from Evan's decade of top-tier advisory experience, extensive legal, technical and investment network, and passion for frontier technology from long before gamers were celebrities.

Evan is a valuable resource, whether you’re:

  • a pioneering technologist anticipating, navigating and/or making use of your first big capital raise;
  • an established player in need of creative analysis within a dynamic and often-opaque regulatory landscape; or
  • a venture capitalist seeking a unique value-add in your pitch for the most in-demand deal flow.

Clients save time (and money) with a lawyer that doesn't need to be taught the basics of how their products work under the hood. Evan's counsel ensures they stay on top of the fast-evolving legal, technological and market developments arising throughout the space.

Industry-Wide Coverage


Evan has built a multi-faceted practice that has touched all corners of the corporate, tech and media sectors—all directly and increasingly relevant to the issues that his clients face each day. He continually updates and expands his knowledge of relevant law, regulations and best practices, acting as clients' "legal quarterback" as they pursue their most ambitious objectives.

Evan has particular expertise in the following practice areas:

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FINANCIAL REGULATIONS

SEC, CFTC, FinCEN, OFAC, DOC, NYDFS, etc., including proposed federal and state legislation and extranational regimes (e.g., MiCA, GDPR)

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CORPORATE STRUCTURING

Cross-jurisdictional guidance for development companies, token distributors, DAO foundations and trusts, BORGs, investment funds, etc.

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OUTSIDE-GC SERVICES

Financing rounds, cap table management, terms of service and privacy policies, HR and employment matters, commercial contracts, etc.

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INTELLECTUAL PROPERTY

Copyright and trademark licensing and management, including open-sourcing and issues affecting NFTs and AI (e.g., fair use, music rights)

A Dual History

Careerlong Dedication to Builders
Lifelong Dedication to the Tech


Evan began his career at Simpson Thacher & Bartlett LLP in NYC, regularly representing some of the world’s largest funds and financial institutions on complex ten-figure deals. Ever since, he has focused on providing actionable advice to a range of startups, including years as special crypto counsel to clients of Reed Smith LLP, where he advised on cutting-edge issues for an industry-spanning, global blockchain group that he helped found.

Evan’s clients have included all manner of digital-asset projects, infrastructure firms, staking and mining operations, exchanges, investment funds, institutional service providers, Fortune 50 companies and various other entrepreneurs.

Evan's training includes the CIPP/US and CIPP/E data-privacy curricula from IAPP, and the CAMS, CGSS and CCAS AML / sanctions curricula from ACAMS.

Evan is an early adopter and true user of emerging technologies, not a tourist.

His exposure to Bitcoin began in 2012, and he has been deeply engaged with the bleeding edges of the Internet since childhood—designing custom computers, participating in peer-to-peer networks and chatting pseudonymously on mIRC—all which helps him understand his clients’ perspectives today.

Evan runs Bitcoin and Ethereum nodes, and is conversant with Solidity, Python and leading AI models. He prefers his fungible tokens, but owns a few NFTs "for the art."