Selling a business can bring a large capital gains tax bill, and helping owners plan for it is now the focus of Robin Taliaferro's work. A capital gains and estate tax planning executive with more than five decades of experience advising clients in California, he specializes in the Structured Installment Sale, which lets sellers spread out and defer the tax. Before this, Robin Taliaferro was known for helping senior technology executives diversify out of concentrated company stock holdings while minimizing or deferring capital gains tax.

Robin Taliaferro is CEO of his practice, where he now develops tax strategies for the sale of a business. That work centers on the Structured Installment Sale, where a seller is paid over time rather than in a single lump sum. He also leads tax seminars and meets with clients one on one. Starting in 1992, he built a book of high-net-worth corporate officers, giving them tax strategies that allowed them to diversify their holdings while minimizing or deferring capital gains tax. His ongoing work with clients and their CPAs has kept him informed about tax code changes throughout his career.

The senior leaders Robin has advised come from some of Silicon Valley's most high-profile technology companies. Consider his work in San Jose alone. For the chief operating officer and director of Xilinx, he worked on $5 million of company stock. Adobe Systems' vice president of software imaging and publishing, a corporate officer, engaged him on $20 million in Adobe stock and options. For the executive vice president of programmable flash memories at Cypress Semiconductor, it involved $10 million in restricted stock.

Elsewhere in the region, he advised the CEO and director of Plantronics in Santa Cruz on $7 million in restricted stock. Trident Microsystems' chairman and CEO, in Sunnyvale, relied on him to plan the sale of $7 million in Rule 144 restricted stock and options. The $30 million in Rule 144 restricted stock and options held by the chairman and CEO of Atlantis Computing in Mountain View was the subject of another of his tax planning engagements. He worked with Orbit Semiconductor's chief financial officer and director in Sunnyvale on $1 million in Orbit stock. He also worked with two corporate officers at Zilog in Campbell on $10 million in company stock.

Robin Taliaferro considers his Software.com, Inc., engagement in Santa Barbara one of the high points of his career. Ahead of the company's IPO, in 1999 and 2000, he structured tax strategies for a private sale of $100 million of Software.com stock.

He represented interests on both sides. His clients made up the buying group. They bought their shares privately before the IPO, then held them for six months before selling. Charitable remainder trusts were used on both sides, and Robin Taliaferro structured the ones most of the sellers used to minimize or defer capital gains tax.

Robin's education came first. He earned an MBA from the Babson Institute in Wellesley, Massachusetts, in 1968, and in that same year he joined the U.S. Army. He served from 1968 to 1971 in Vietnam, holding the rank of infantry first lieutenant.

His career began in 1971, after his military service ended, with investment advice for clients in Santa Barbara, California. Investment management for those Santa Barbara clients occupied the first two decades of his career. He also became a Certified Financial Planner (CFP) along the way, completing the designation in 1987 through Denver, Colorado's College for Financial Planning. That accomplishment demanded the successful completion of six examinations and more than a year of effort. What came next was three decades of experience working with corporate clients and their CPAs.

Robin Taliaferro changed his focus in 1992. He left investment management for Santa Barbara clients behind and took up tax planning with corporate clients in Silicon Valley, a group that included pre-IPO companies. In short, his career has led 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 including Xilinx, Plantronics, Adobe Systems, and Cypress Semiconductor.

Robin and his wife have been longtime supporters of local historical charitable organizations. For the Santa Barbara Historical Museum, they contributed time and money every year from 2000 to 2010. For the Santa Ynez Valley Historical Museum, they've done the same since 2024. His wife has served on the board at both of these museums.

A competitive long-distance runner, Robin Taliaferro finished second in the 10K among American men ages 60 to 65 at the 2006 U.S. National Championships in Paso Robles, California.

Robin Taliaferro lives in Solvang, California, and it's from his home there that he now structures tax strategies for business owners selling their companies, with the Structured Installment Sale at the center. His perspective rests on more than 30 years of working with technology executives and their CPAs, combined with the investment background he built over two decades in Santa Barbara before that.