Recently named a 2026 Top Estate and Wealth Management Lawyer by the Daily Journal, Venable partner and co-chair of the firm's Private Wealth Planning Group Jason Trenton advises clients on sophisticated estate, tax, and succession planning. In this Q&A, Jason discusses the changing tax landscape for wealthy Californians, planning for a new generation of entrepreneurs, and why understanding people is just as important as understanding the tax code.
Q: How did you get into private wealth planning, and how has your Canadian background shaped your practice?
Jason: I studied psychology and social behavior as an undergraduate, so I've always been fascinated by people and human behavior. My father was also a tax auditor for the Ontario government, so when I went to law school, tax was something that came naturally to me. Private wealth planning really brings those two interests together, because you're dealing with tax, but you're also dealing very closely with people and families. When I moved to the United States more than 25 years ago, I naturally started doing a lot of U.S.-Canada cross-border estate planning. From there, my practice expanded into California-based planning and broader international work.
Q: Does working across the U.S. and Canadian systems change the way you approach planning?
Jason: Absolutely. Canada has a whole different language when it comes to trust and estate planning, so you learn to think differently. LLCs, for example, are tax-efficient entities we use all the time in the United States, but not so in Canada. Trusts are also treated very differently.
In the United States, depending on the jurisdiction, assets can potentially remain in certain trusts forever. Canada has a 21-year deemed disposition rule, which generally treats assets in a trust as though they have been sold every 21 years, potentially triggering capital gains tax. So, you have to understand both systems and how they interact. That experience also keeps you open-minded and creative when you're planning for clients who have no connection to Canada.
Q: What tax issues are you seeing among high-net-worth clients in California?
Jason: California is a high-tax environment, so clients are very conscious of how taxes can affect major transactions. You have California income tax, federal capital gains tax, potentially the net investment income tax, and, in Los Angeles, the transfer tax on certain real estate transactions. If someone is preparing to sell a business or another highly appreciated asset, the combined tax impact can be significant.
That makes advance planning increasingly important. We do a lot of sophisticated trust planning, including establishing trusts in jurisdictions outside California. Qualified small business stock planning is another significant area for entrepreneurs and founders. The key is getting involved early enough to understand what clients are trying to accomplish and determine what planning opportunities may be available before a liquidity event occurs.
Q: You told the Daily Journal that clients "no longer have to die to benefit from sophisticated tax strategies." How has that changed the conversations you have with clients?
Jason: A lot of our clients are very young. We work with entrepreneurs and people in technology who may be in their 30s and building companies that could create substantial wealth. Talking to someone at that stage about succession planning can be difficult. They may not be married yet or have children, so planning for what happens after their death can seem very remote.
That shifts the conversation toward what planning can do for them during their lifetime. We can look at structures that may provide income tax benefits now while also creating a long-term framework for their wealth. You can establish a trust that benefits them today but can ultimately be there for their future spouse, children, and more remote generations. That makes the planning much more relevant to where they are in life.
Q: How much of wealth planning is about understanding the people and family dynamics involved, rather than just the tax and legal issues?
Jason: The "human element" is extremely important. No matter how much wealth someone has, people have many of the same day-to-day concerns. They worry about their children, their parents, siblings, their marriage—wealth doesn't make those issues disappear, and very often it adds another complex layer to them.
That's why this practice is about much more than tax. You have to understand the people involved and what they're trying to accomplish. Someone who has managed family wealth for decades may already understand the need to prepare the next generation, while a young entrepreneur who has recently created significant wealth may be encountering these issues for the first time. Part of our job is helping clients anticipate those challenges and guiding them through them.
Q: What kinds of services do high-net-worth clients need beyond traditional estate and tax planning?
Jason: We often start by helping a client with an estate plan, but you learn a lot about their family, their assets, and their concerns in that process. So, you become a trusted advisor, and clients start coming to you with other issues. Then, being part of a large firm means we can connect them with lawyers in areas such as corporate, real estate, intellectual property, and litigation.
Privacy and asset protection have also become increasingly important. We help clients structure ownership of significant assets through privacy trusts, for example. And as wealthy individuals face greater cybersecurity, privacy, and personal security concerns, we can bring in Venable Blue to help assess and address those risks. The goal is to be able to look at the client's needs much more broadly than traditional wealth planning.
Q: As chair of the West Coast Private Wealth Planning Group, how have you seen the practice grow, and what has driven that growth?
Jason: The practice has grown exponentially over the last five or six years. Venable has always had a strong tax foundation, and the firm has really invested in private wealth as a practice. That has helped us attract great people and build out our team.
It also helps that we have this tremendous bench across the firm. We can draw on tax, corporate, litigation, intellectual property, Venable Blue, and other areas, depending on what a client needs. That allows us to provide a very high level of service, which is ultimately what this practice is about. Our clients expect us to be there for them and to give them that experience no matter what. That's our philosophy, and I think it's worked out really well for our group.
Learn more about Venable's Private Wealth Planning and Family Offices practice.