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Andrew Leahey, Esq.

Philadelphia, PA
📞 (215) 895-2544
📧 Andrew.Leahey@drexel.edu
🌐 andrew.legal
GitHub: github.com/ajleahey
Mastodon: @andrew@esq.social
Bluesky: bsky.app/profile/esq.social

Professional Summary

Legal scholar and practitioner specializing in tax law, administrative law, and the regulation of technology. Assistant Teaching Professor of Law at Drexel Kline School of Law with extensive experience teaching public law, tax policy, and law–technology intersections at the undergraduate and graduate levels. Regular columnist for Bloomberg Tax and contributor to Forbes and other national outlets.

In addition to scholarly and journalistic writing, I design and build computational research tools that translate legal and regulatory expertise into durable analytical systems for teaching, policy analysis, and institutional research.

Research Tools & Technical Projects

TOSTracker

Founder & Developer | 2025–Present

  • Designed and built a web-based research system that ingests, versions, and analyzes corporate Terms of Service and Privacy Policies over time.
  • Implemented automated change-tracking and similarity analysis to surface substantive shifts in private governance and platform regulation.
  • Used as a teaching and research tool in courses on law, technology, and regulation.

Federal Regulatory Tracker (FRTracker)

Founder & Developer | 2025–Present

  • Built an analytical platform that ingests Federal Register data and normalizes regulatory text into discrete legal obligations.
  • Developed tools to track agency activity, regulatory churn, and changes in compliance burdens across time and agencies.
  • Created plain-English summaries and analytical views for administrative law instruction and policy research.

Pivot (Daily Puzzle Game)

Creator & Developer | 2025

  • Designed and launched a daily word-based logic puzzle with leaderboard and scoring mechanics.
  • Built full front-end game logic and deployment independently; released publicly and iterated based on user behavior.

Academic Experience

Assistant Teaching Professor of Law | 2025–Present

Drexel Kline School of Law, Undergraduate Program — Philadelphia, PA

  • Courses: Public Law: Legislation and Regulation; Law, Technology, and Regulation
  • Committee Service: Senate Committee on Academic Affairs (2025–Present)

Adjunct / Practice Professor | 2023–2025

Drexel Kline School of Law, Undergraduate Program — Philadelphia, PA

  • Courses: Tax Policy and Theory; Legal Systems in Action; American Legal Systems

Graduate Tax Teaching Assistant | 2019–2021

Boston University School of Law — Boston, MA

  • Courses: Tax, Technology, and Fraud; VAT; Tax Writing Seminar

Research Assistant | 2018–2019

Professor Richard T. Ainsworth, NYU School of Law — New York, NY

Writing & Commentary

Columnist | 2022–Present

Bloomberg Tax

  • Creator and author of the weekly column Technically Speaking, covering tax policy, technology, and regulatory design.

Contributor | 2024–Present

Forbes

  • Regular contributor focusing on law, policy, technology, energy, and economic justice.

Contributor | 2022–Present

Baseball Prospectus

  • Author of a recurring series on baseball and the law.

Contributor | 2019–2022

Tax Notes, State Tax Notes, Tax Notes International

Practical Legal Experience

Attorney & Technology Lead | 2019–Present

Sales Tax Suppression Consultants

Tax and Technology Attorney | 2017–Present

Andrew Leahey, Esq.

Associate Attorney – Public Finance | 2016–2017

Parker McCay, P.A. — Mt. Laurel, NJ

Policy & Consulting Experience

  • Cryptocurrency: Advised on tax treatment of digital assets domestically and internationally; EU classification issues.
  • VoIP Industry: Consulted on allegations of high-tech tax fraud involving VoIP systems.
  • Sales Suppression: Investigated alleged sales suppression schemes; forensic review of POS systems and transactional data.
  • Dividend Stripping (Cum-Ex / Cum-Cum): Consultant to German nonprofit investigative journalism group examining EU tax fraud schemes.
  • Digital Economy: Cited by the World Bank (2021) on tax administration challenges in the digital economy.

Digital Infrastructure & Public Scholarship

  • esq.social: Founder and administrator of the largest Mastodon instance dedicated to legal and legal-adjacent professionals.
  • Minimum Competence: Co-creator and co-host of a daily legal news podcast.
  • LSAT Logic Applied: Co-host of a weekly legal test-prep podcast.

Education

New York University School of Law

LL.M. in Taxation, 2020

Thesis: Distributive Justice, Indirect Tax, and Emerging Technologies: Problems and Solutions

Rutgers University School of Law

J.D., 2016

  • Dean’s Highest Academic Excellence Scholarship
  • Executive Committee, Journal of Public Policy
  • Note: Internet Keyword Advertising and Trademark Use

University of Pennsylvania

B.A. in Political Science, 2013

  • Phi Beta Kappa; Summa Cum Laude; Distinction in the Major
  • Published Honors Thesis: GMOs and Southern African Food Policy

Guest Lectures

  • NYU School of Law, Graduate Tax Program (2022): Tax, Fraud, and Technology
  • Boston University School of Law, Graduate Tax Program (2020): Tax Writing Seminar

Selected Publications

(Full list available upon request; shorter-form columns excluded)

  • Tax Policy Belongs in a Liberal Arts Education. Inside Higher Ed, July 16, 2025.
  • Limited E-Invoicing Does Not Stop VAT Fraud, Parts I–III. Tax Notes International, 2022.
  • The MLB Competitive Balance Tax Reimagined. Bloomberg Tax, 2022.
  • Infrastructure Bill May Limit Cryptocurrency Loss Deductions. Law360, 2021.
  • Additional publications in Tax Notes, State Tax Notes, Tax Notes International, SSRN, and CUREJ.

Technical Skills

  • Data analysis: pandas, NumPy, IDEA, Tableau
  • Programming: Python, SQL, Visual Basic (basic–intermediate)
  • Web & cloud development: AWS, web stacks, OSS
  • Media production: Adobe Creative Suite

Bar & Professional Memberships

  • New Jersey Bar
  • Pennsylvania Bar (inactive)