Robin Taliaferro CEO - Capital Gains & Estate Tax Planning Robin Taliaferro is a capital gains and estate tax planning executive with more than five decades of experience advising clients in California. As CEO of his practice, Robin now specializes in tax strategies for the sale of a business. He uses the Structured Installment Sale to help business owners spread out and defer the capital gains tax on a sale. Earlier in his career, he was known for helping senior technology executives diversify out of concentrated holdings in their own company stock. His career has taken him from the U.S. Army in Vietnam to handling investment accounts in Santa Barbara and, since 1992, to tax planning with corporate executives at companies such as Xilinx, Plantronics, Adobe Systems, and Cypress Semiconductor. He also conducts tax seminars and personal meetings with clients.
Education and Military Service Robin Taliaferro earned his MBA from the Babson Institute in Wellesley, Massachusetts, in 1968. That same year, he joined the U.S. Army, where he served as an infantry first lieutenant in Vietnam from 1968 to 1971.
Early Career in Santa Barbara
After his military service, Robin began his career in 1971 by giving investment advice to clients in Santa Barbara, California. He focused on investment management for these Santa Barbara clients for the first two decades of his career. In 1987, he earned the Certified Financial Planner (CFP) designation from the College for Financial Planning in Denver, Colorado. This required the successful completion of six examinations and took more than a year to complete. This was followed by three decades of experience working with corporate clients and their CPAs.
Tax Planning for Silicon Valley Executives In 1992, Robin Taliaferro changed the focus of his business. He moved from investment management for Santa Barbara clients to tax planning with corporate clients in Silicon Valley, including pre-IPO companies. Over the following decades, he built a book of high-net-worth corporate officers. Many of them shared a common challenge: too much of their wealth was concentrated in their own company's stock. He structured tax strategies that allowed these executives to diversify their holdings while minimizing or deferring capital gains tax. His work with clients and their CPAs has kept him current with changes in the tax code throughout his career. His corporate clients have included senior leaders at some of Silicon Valley's most high-profile technology companies. At Xilinx in San Jose, he worked with the chief operating officer and director on $5 million of company stock. At Plantronics in Santa Cruz, he advised the CEO and director on $7 million in restricted stock. At Adobe Systems in San Jose, he worked with a corporate officer, the vice president of software imaging and publishing, on $20 million in Adobe stock and options. At Cypress Semiconductor in San Jose, his client was the executive vice president of programmable flash memories, who held $10 million in restricted stock. His client list also includes the chairman and CEO of Trident Microsystems in Sunnyvale, for whom he planned the sale of $7 million in Rule 144 restricted stock and options. He provided tax planning to the chairman and CEO of Atlantis Computing in Mountain View on $30 million in Rule 144 restricted stock and options. He also worked with the chief financial officer and director of Orbit Semiconductor in Sunnyvale on $1 million in Orbit stock, and with two corporate officers at Zilog in Campbell on $10 million in company stock.
A Career Highlight: Software.com Robin Taliaferro counts his work with Software.com, Inc., in Santa Barbara among the high points of his career. In 1999 and 2000, ahead of the company's IPO, he structured tax strategies around a private sale of $100 million of Software.com stock.
He worked on both sides of the transaction. His clients were the buyers, who purchased their shares privately before the IPO and held them for six months before selling. Both the buyers and most of the sellers used charitable remainder trusts, and Robin Taliaferro structured the sellers' trusts to help minimize or defer capital gains tax.
Community Involvement Robin Taliaferro and his wife have a long record of supporting local historical charitable organizations. From 2000 to 2010, they contributed time and money each year to the Santa Barbara Historical Museum. Since 2024, they've done the same for the Santa Ynez Valley Historical Museum. His wife has served on the board of both museums.
Personal Interests Outside of his work, Robin Taliaferro is a competitive long-distance runner. At the 2006 U.S. National Championships in Paso Robles, California, he finished second in the 10K among American men ages 60 to 65. He lives in Solvang, California. Today, from his home in Solvang, Robin Taliaferro focuses on tax strategies for the sale of a business, centered on the Structured Installment Sale. The approach lets business owners receive payments over time instead of one lump sum, spreading out the capital gains tax that comes with a sale. He brings more than 30 years of experience working with technology executives and their CPAs, along with the investment background he built in Santa Barbara over the two decades before that.
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