Todd & Maria
From DIY to Delegated — Without Giving Up Control
The Story
Todd has owned a successful dental practice in Duxbury, MA for over 25 years. He and his wife, Maria, live in Hingham, where they raised their four children, now grown. Over the years, Todd took pride in managing their investment portfolio himself—building up a $4 million nest egg across their joint brokerage account and his SEP IRA through disciplined saving and strong market performance.
While confident in his investment decisions, Todd had started thinking more seriously about the long term. He wondered: If something happened to me, would Maria know what to do? Or worse, would she get taken advantage of by an advisor search on her own? His portfolio had become increasingly complex, and he wanted a second opinion, a simpler structure, and reassurance that Maria would be supported if she ever had to manage things on her own.
At the same time, Todd had some hesitation about working with a financial advisor. After managing everything himself for years, he wasn’t sure how the dynamic would work. He had no interest in being handed a cookie-cutter allocation or sitting through a lecture about diversification. He wanted a partner—not a top-down manager—and was unsure whether someone could both respect what he’d built and still bring meaningful value to the table.
How Evergreen Helped
When Todd came to Evergreen Wealth Management, he was looking for a streamlined, professional approach to support what he had already built. He wanted validation of his investment strategy and confidence that his wife would have someone to rely on. What he received went beyond that—delivering not only peace of mind, but new planning opportunities he hadn’t expected.
From the outset, Todd found working with Nick to be a comfortable and collaborative experience. Rather than imposing a new system, Nick took the time to understand the portfolio Todd had constructed—acknowledging its strengths and identifying areas where it could be further optimized. Where changes were appropriate, Nick presented clear trade-offs and allowed Todd to make the final call. That flexibility and mutual respect built immediate trust.
Several of their large, long-term stock holdings—particularly in the joint brokerage account—were retained, as they were high-quality companies with significant unrealized gains that Todd still believed in. These became the foundation for the ongoing plan.
To reduce complexity, Nick recommended selling a handful of smaller, underperforming positions to clean up the portfolio and realize tax losses. This helped declutter their holdings while improving tax efficiency. Every investment transferred seamlessly to Evergreen’s custodian, Charles Schwab, with no sales during the transition—ensuring no capital gains taxes were triggered. Nick also made it clear: no trades would be placed until he and Todd were fully aligned on the strategy. The result was a smoother, stress-free transition.
As part of getting to know the full financial picture, Nick uncovered an overlooked opportunity. During a planning conversation, Todd casually mentioned that he and Maria made annual charitable donations of $2,500–$4,000 to their local hospital—usually writing checks directly from their bank account. This opened the door for a strategy Todd hadn’t considered: establishing a donor-advised fund (DAF).
Nick proposed using appreciated shares from their brokerage
account to fund five years of future giving in one tax year.
The benefits were substantial:
They were able to itemize deductions and surpass the standard deduction threshold in that year.
They avoided capital gains taxes on the donated stock.
They used cash to repurchase the same stock, effectively raising their cost basis while keeping their portfolio aligned.
The DAF now acts as a charitable “piggy bank,” allowing Todd and Maria to continue their normal giving schedule while capturing the full tax benefit upfront—something they’d never considered before.
In addition to simplifying the portfolio, Nick helped address an issue Todd hadn’t fully acknowledged: his investment risk was higher than he was truly comfortable with. Nick introduced FDIC-insured CDs through Schwab’s platform, aligned with their anticipated expenses over the next four years. This reduced their market exposure and provided a reliable source of liquidity—giving Todd confidence that their short-term needs were protected. He was also pleasantly surprised by how flexible and open Schwab’s investment architecture was.
The Outcome
Maria, who had typically stayed hands-off, became more engaged throughout the process. She joined meetings, asked questions about budgeting and Social Security, and began using the Evergreen client portal to track spending and view their financial picture. While she didn’t get into the weeds, she appreciated seeing the tax impact of their new giving strategy clearly modeled in the Holistiplan scenario Nick shared.
Todd came in with specific goals—he wanted clarity, simplicity, and a succession plan that would support Maria. He got all of that—but also gained a deeper understanding of tax strategy, a better approach to charitable giving, and a more resilient portfolio. Most importantly, he was able to work with someone who honored the work he’d done, offered practical improvements, and gave him the freedom to stay in control of the decisions that matter most.
Now, Todd feels confident that not only is Maria protected and the portfolio in good hands, but that any future planning opportunities—whether financial, tax-related, or estate-focused—will be uncovered and thoughtfully addressed. Nothing will fall through the cracks, and he knows Evergreen will continue to bring value well beyond the investment portfolio.