Interview with Matthew Rappaport

Kathryn Meyer discusses her career in tax, beginning with her discovery of an interest in tax law in law school and her nearly two-decade career with the IRS Office of Chief Counsel. She describes gaining extensive courtroom experience, moving into management and executive roles, overseeing litigation and national tax issues such as the research credit, and later serving as counsel to the National Taxpayer Advocate. After leaving government, Meyer discusses the challenges and rewards of running her own tax practice, including navigating IRS service issues from the taxpayer side. She closes by emphasizing that tax is constantly evolving and expressing particular interest in improving IRS support for caregivers who handle tax matters for aging parents.

Adam Abrahams discusses his unconventional transition into tax law, including earning a tax LL.M. at Georgetown, building a solo practice, and eventually joining his current firm. He emphasizes the importance of mentorship, professional relationships, writing, and involvement in the ABA Tax Section, while also sharing his view that attorneys should embrace AI as a tool but carefully verify its output. Looking ahead, he expects technology to transform tax practice while human judgment, relationships, and adapting to constantly changing tax law will remain essential.

Host Alexander Powell interviews Bob Probasco, senior lecturer at Texas A&M and director of its Tax Dispute Resolution Clinic, about his path from accounting and business into tax law. Bob discusses how his earlier career shaped his teaching, the balance he strikes between giving clinic students autonomy and reining in overconfidence, and how working with low-income taxpayers builds empathy by showing students that small disputes matter as much to clients as large ones. He also touches on his unconventional path to law school at 45, what drew him to tax specifically, and closes with advice on volunteering for bar association work and building networks not for career gain, but to help others.

Host Crist Malekyan and Ken Wang discuss Ken's career path in tax, including his moves between private practice and in-house roles in the energy and technology sectors. He emphasizes the value of mentorship, maintaining work-life balance, and gaining an in-house perspective, while also discussing how AI may make tax work more efficient but could change how junior attorneys develop expertise.

Larry Campagna reflects on his early career path, starting with a summer job in a small law firm's mailroom that taught him the ins and outs of Houston's legal community. He shares his views on the current state of criminal tax enforcement, and touches on emerging trends in tax controversy and sentencing guidelines. He closes with the case he's proudest of, Johnson v. Sawyer, a fifteen-year fight over an unlawful IRS press release that changed how the agency handles disclosures in criminal cases.

Lisa Sperow discusses her path from a reluctant tax lawyer to president of a college of law, tracing her journey through a clerkship, DOJ Civil Division litigation, and fourteen years directing a low-income taxpayer clinic. She reflects on the human stories behind tax cases, mentoring students through their first client interactions, expanding access to legal education for working adults, and her leadership within the ABA Tax Section's Pro Bono and Tax Clinics Committee.

Brandon King discusses his path from a reluctant 1L to a nationally recognized renewable energy tax attorney, tracing his journey through a US Tax Court clerkship, cross-border controversy work, and a pivot to transactional practice during the Inflation Reduction Act. He reflects on the mission-driven nature of renewable energy tax work, the industry's resilience amid policy shifts, AI as a complement rather than a replacement for junior talent, and his decade of leadership within the ABA Tax Section, including founding the LGBTQ+ Lawyers in Tax Forum.

Chuck Levin discusses his journey from aspiring lawyer and CPA to a nationally recognized tax attorney, educator, and co-creator of the Tax Planning Forum. He emphasizes making complex tax concepts practical and engaging, mentoring younger professionals, building strong relationships, and using AI as a helpful starting point rather than a replacement for professional judgment.

Matthew Rappaport discusses his career as a tax attorney focused on real estate, emphasizing the value of being a versatile practitioner who combines deep technical tax knowledge with practical business judgment. He also shares lessons from building his own law firm, stressing that successful tax lawyers should think like entrepreneurs, communicate complex issues in plain language, and help clients understand and weigh risk rather than simply avoid it.

In this episode, host Crist and Andrew discuss staying curious, SALT, and getting involved in the Tax Section. From renewable energy to tribal clinics, to affordable housing, examine Andrew's extensive background and passion for tax.