Bloomberg Tax Insights & Commentary is featuring a recurring questionnaire of prominent tax professionals who are willing to share their thoughts about their work and the practice of tax these days. Today we feature tax attorney Brian Organ, a project finance and public finance partner at Nixon Peabody in San Francisco.
What is the biggest challenge that tax practitioners are facing in 2026?
Technology, particularly AI, is accelerating the pace of tax practice. The challenge isn’t simply adopting new technology responsibly; it’s also understanding its benefits and shortcomings. Our clients want us to deliver practical, accurate advice in a timely manner, and we need to understand that AI, when used appropriately, can assist in meeting our clients’ needs.
What’s the biggest lesson you learned in your early years of practice?
Ask questions early and often. Ask senior colleagues, deal team members in other practice areas, and, importantly, the client. Early in my career, it was easy to focus on a specific tax issue in front of me. Over time, I learned that the better answer often depends on understanding the full transaction, the client’s broader objectives, and the practical outcome they are trying to achieve.
I recall one instance when I was discussing a transaction that involved several proposals. I believed one of the proposals would likely require some restructuring due to tax concerns. Through kicking the structure around with a colleague, I learned more about the type of analysis that the client wanted with each proposal. We presented the client with our analysis, outlining the risks associated with the proposed structure and alternative options. The client was happy with our assessment and ultimately elected to move forward with the alternate approach, given the tax considerations in the initial proposal.
That outcome underscored why asking questions beyond the immediate tax issue is so important. While the technical answer matters, it is only part of the analysis. You also have to understand the financing structure, the timing, the client’s risk tolerance, and how the tax analysis fits into the overall deal.
What is one section of the tax code that you’d like to change?
I would revisit Section 145(b). It’s a provision that was partially repealed in 1997, but the remaining aspects of the rule can still complicate transactions and can create structuring challenges.
In public finance, we often work within a highly technical framework, and many of those rules serve important policy purposes. But over time, remnants of older rules can become traps for otherwise sound transactions and, in the case of Section 145(b), there are other rules that address similar concerns.
I would favor a more streamlined approach that preserves the policy objectives of the tax-exempt bond rules while reducing unnecessary complexity in public finance deals.
What’s the most memorable case you’ve worked on?
One of the things I enjoy about working as a public finance tax attorney is that the projects are often tangible. At the end of the transaction, there may be a hospital building, a museum, a school, sewer and water infrastructure, or another public project that serves a community.
One matter that stands out involves a museum in San Francisco, where I’m based. We helped finance its relocation to a temporary facility and later its new permanent facility. Now, I go back there with my kids and see the result of the work. I didn’t physically build it, of course, but I helped with the financing that made it possible.
That is one of the most rewarding parts of this practice. You can point to something real in the community and say, “we helped make that happen.”
What was the last thing you believed beyond a reasonable doubt?
That no two clients are the same. Even when clients are dealing with similar tax issues, they come to us with different levels of sophistication, different business objectives, different timing pressures, and different approaches to risk.
Part of being an effective adviser is recognizing those differences. The answer can’t be purely technical. It must be tailored to the client, the transaction, and the outcome the client is trying to achieve. In public finance, that judgment is often just as important as the tax law itself.
This article does not necessarily reflect the opinion of Bloomberg Industry Group Inc., the publisher of Bloomberg Law, Bloomberg Tax, and Bloomberg Government, or its owners.
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