Broker Check

Case Studies

Successful investor considering retirement.

John Ley came to Red Hook as a successful real estate investor and corporate executive in his mid-60’s looking to evaluate and analyze his assets. Like many successful people with wide-ranging assets, John showed up at our office wielding a well-worn yellow legal pad full of handwritten notes on his assets. Over the years, John had received excellent advice from his attorney and accountant on structuring trusts and family partnerships. His $25 million of net worth comprised a broad complement of taxable and nontaxable assets, including private real estate, startup companies, and restricted stock in a few REITs.

At Red Hook, we developed a strategy to evaluate John’s overall asset allocation, which became the basis for a long-term financial plan. Every quarter, we reported and discussed asset movement, taxes, exposure, and opportunities. Following our advice, John began to move his assets out of concentrated positions and into diversified stocks and bonds as he got more comfortable with a long-term investment strategy. He converted some of his tax-deferred assets into Roth IRAs for his wife and him. He also created a gifting program to fund education for his grandchildren and a Donor Advised Fund in a year when he had excessive income

Young entrepreneur with children anticipating a liquidity event.

A hard-working and successful business builder, Steve was in his late 30s with three children when he came to Red Hook. He and his partner had built a technology business that was headed for a sale in the next few years, and Steve’s share was worth tens of millions of dollars. Steve had some assets in the form of IRAs and Roths for his wife and him, but 99% of his family’s net worth was in the illiquid shares of his private company. We worked with Steve to understand his and his wife’s goals, and then together with the help of a trusted attorney, we rewrote a will and created a family trust, which Steve funded with gifts of undervalued stock. Three years later, when the liquidity event began, we worked with him to minimize taxes with the creation of a Donor Advised Fund, and we invested his assets in a diversified portfolio based on an investment plan. Thanks to his planning before the sale of his business, Steve and his family are now fully reaping the benefits of his hard work. Today our conversations are about preserving his family’s wealth and spending his hard earned money in ways to improve their quality of life. As Steve is learning to relax and appreciate his more secure life status, he is taking better care of his health and wellness. As he figures out what he is going to do next, he and his wife bought a new home and are installing some special amenities. Steve credits Red Hook with helping him through this transition adjusting to his new wealth and opportunities.

Hard-charging mobile executive who doesn’t want to retire.

In his mid-50s and married with no children, Frank was a wealthy executive who had worked for multiple public companies and had a legacy of assets and life insurance policies that needed to be evaluated. Frank was still working and continued to add to his net worth, sometimes through complicated stock options or incentives with venture-backed companies. Red Hook organized Frank’s invested assets in a diversified portfolio. Then, after a complete insurance review, we also evaluated and improved his various insurance policies. Finally, we helped rewrite his will to benefit his wife as well as his alma mater, which he credits with much of his early success. Frank continues to work hard, but he can now spend less time concerned with his money and legacy.

Widow who lives an alternative lifestyle.

In her 50s, Wendy lives in a rural community with her three stepchildren. During her marriage, she began to ride and care for horses, and ultimately she decided to work full-time at the family farm. A few years after losing her husband, Wendy came to Red Hook. She had been unhappy with the investment advisors she inherited from her husband. In her estimation, they were inattentive, and their investment strategies seemed spotty. We were able to maneuver her accounts into an investment strategy sensitive to taxes while helping Wendy think through the operating expenses at her farm. With our help, Wendy was able to lower expenses and feel good about some capital improvements, making her activities more efficient and ultimately less expensive. Finally, we helped her rewrite her will to accommodate her late husband’s wishes while not prejudicing her heirs. Now, Red Hook is more than just an investment advisor to Wendy—she relies on us for general advice, too! On everything from operating her farm to buying a car.


For all case studies, please refer to our Regulatory Disclosure.