Douglas S. Wolgamot

My Approach

I work with entrepreneurs, executives, and multi-generational families who have complex holdings—closely held businesses, real estate portfolios, concentrated stock positions, and unique family dynamics. Together with a strong trust and estates team, I help them develop comprehensive estate and business succession plans that protect what they’ve built and ensure their legacy continues for generations. My work spans a range of sophisticated tax and wealth transfer strategies—dynasty trusts, GRATs, family limited partnerships, and intentionally defective grantor trusts, to name a few. I also help clients with charitable planning (private foundations, charitable lead and remainder trusts) and asset protection structures tailored to their specific needs.

When the time comes, my team and I guide families through the estate and trust administration process with the same care and attention I bring to the planning process. This includes probate proceedings, trust funding and distributions, fiduciary guidance, tax compliance, and resolving the inevitable questions that arise when plans are put into action. We understand that administration often occurs during difficult times, and we work to make the process as clear and manageable as possible for trustees, executors, and beneficiaries alike.

I’m a firm believer in making the complex understandable. Even for the most sophisticated plan, I make sure I can explain it on a single page. My team and I work closely with each client’s professional advisors—family offices, CPAs, investment advisors, insurance advisors, and CFOs—because we all bring something different to the table, and that collaboration leads to better outcomes. For families navigating generational transitions, I facilitate family governance discussions and help establish structures that promote communication and shared decision-making.

As clients have become increasingly mobile, we help them navigate the legal process of changing personal residency when they choose to relocate to other states. We also incorporate planning in jurisdictions with advantageous trust laws, such as South Dakota.

When I’m not working, you’ll find me water skiing on White Bear Lake or paddleboarding, surfing, or e-foiling off the beaches of 30A in Florida.