Case Studies

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A long-time employee had accumulated a significant portion of their net worth in employer stock through years of equity compensation — creating outsized exposure to a single company's performance. Selling outright would have triggered a substantial capital gains tax bill in a single year.

We designed a multi-year diversification plan that paired systematic selling with tax-loss harvesting elsewhere in the portfolio, spreading the tax impact over several years while steadily reducing concentration risk. The client retained meaningful upside in the stock they believed in, while building a more resilient, diversified portfolio around it.

A prospective client came to us with a portfolio that had performed well during a strong bull market, managed through a model built around a small number of high-growth themes. On the surface, returns looked excellent — but the underlying construction carried significant concentration and drawdown risk that hadn't been tested against a downturn.

Using scenario and stress-test modeling, we showed the client how that same portfolio would likely behave in a meaningful market correction. That analysis became the basis for rebuilding the allocation around the client's actual risk tolerance and time horizon, rather than recent performance alone.

A successful business owner had a financial advisor for personal investments and a separate CPA for business and tax matters — the two rarely spoke, and major decisions were made without full visibility into the other side.

By bringing investment management and tax planning under one advisor, we identified opportunities that had been missed for years: aligning the timing of business income recognition with personal investment decisions, coordinating retirement plan contributions with cash flow from the business, and reducing the client's combined effective tax rate — all while keeping the personal portfolio aligned with long-term goals.

A business owner in their peak earning years wanted to accelerate retirement savings well beyond what a 401(k) alone allowed and needed a strategy that also worked for the business's other employees.

We designed and helped implement a cash balance plan layered on top of the existing 401(k), significantly increasing the owner's annual tax-deferred contribution capacity while structuring the plan to remain cost-effective for the business as a whole.

Important Disclosure Regarding Case Studies

The case studies presented above are hypothetical and composite in nature. They do not represent any specific past or current client of Di Bello Financial, and any resemblance to an actual client is coincidental. 

These examples are provided solely for illustrative and educational purposes to describe the types of planning strategies we may use, and do not represent an actual client experience or specific investment or planning results.

These examples should not be construed as a guarantee that similar results will be achieved for any particular client, as individual circumstances, objectives, risk tolerance, and market conditions vary. Nothing in these case studies constitutes investment, tax, or legal advice, and should not be relied upon in making any financial decision. Please consult with a qualified professional regarding your own specific situation.