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TRAILBREAK

Counsel, Ops and Strategic Advice for Frontier Technologists

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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 researcher and DeFi 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:
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  • 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.

Services


Trailbreak is a boutique transactional firm offering sophisticated corporate / regulatory / product / IP counsel, strategic consulting and operational leadership.

‍Evan Zinaman, Esq., Founder & Principal at Trailbreak, has developed a rare combination of skills that builders value most, with particular expertise in the following practice areas:
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OUTSIDE GENERAL COUNSEL SERVICES

Financing rounds / M&A, cap table administration, risk management, governance, terms of service and privacy policies, commercial contracts, etc.

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FRACTIONAL COO / CSO SERVICES

Managing staff and outside service providers, government relations, setting internal processes, automation and other software integrations, etc.

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FINANCIAL REGULATIONS

SEC, CFTC, FinCEN, OFAC, DOC, NYDFS, etc., including proposed federal and state legislation and extranational legal regimes

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CORPORATE STRUCTURING

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

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.
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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 self-sovereign Bitcoin mining and full nodes, and is conversant with Solidity, Python and leading AI models.

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Trailbreak comes from the hiker slang, "to break trail," where one sets out in a lead position through fresh-fallen snow, forging the path for others to follow.

Licensed to practice law in NY (inactive in CA). No attorney-client relationship shall be deemed to exist absent a signed engagement letter. All rights reserved.