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Christopher Karachale

Christopher A. Karachale

(415) 995-5863


Christopher advises individuals and businesses on a range of tax planning and tax controversy matters at the federal, state, local, and international levels. He also serves as outside general counsel to a variety of companies, providing general corporate and related business guidance.

Christopher’s work on federal tax matters ranges from income tax controversies involving individuals and businesses to partnership structuring and corporate mergers and acquisitions. He regularly works with entrepreneurs and start-up companies, and is a nationally recognized expert on qualified small business stock (QSBS) and related section 1202 issues. He has been quoted in the New York Times, Bloomberg, and Business Insider regarding QSBS.

At the state level, in addition to income tax-related matters, Christopher counsels individuals and entities on issues involving California property taxes. In the international context, he has extensive experience with voluntary disclosures and related planning matters, as well as in-bound and out-bound corporate structuring.

Christopher has published extensively, with articles appearing in Tax Notes, the California Business Law Practitioner, and Law360. He also is a frequent speaker on tax issues to audiences in the United States and abroad. Christopher is certified as a legal specialist in taxation law by the California Board of Legal Specialization and is a fellow of the American College of Tax Counsel.


LL.M., Tax New York University School of Law ( 2007 )
J.D. University of San Francisco School of Law ( 2006 )
M.A. Stanford University ( 1998 )
B.A. cum laude Middlebury College ( 1995 )

Admissions and Courts

New York
U.S. Tax Court


Tax Practice Leader

The Tax Adviser, Board Member

American College of Tax Counsel, Fellow

"Tech Millionaires Chase Billionaire Tax Shields With ‘Swap Fund'," Bloomberg Law (April 2024)

"Could QSBS Save You Big in Taxes? How to Decide Whether it's Right for Your Business," They Got Acquired (May 2022)

"A Lavish Tax Dodge for the Ultrawealthy Is Easily Multiplied," New York Times (December 2021)

"A ‘Two Horses’ Strategy to Salvage a Major Tax Break for Investors in Startups," Financial Planning (December 2021)

"Tax Proposal Targeting Silicon Valley," The Financial Executive Podcast (September 2021)

"Big Tax Changes Are Brewing. What You Need to Know," Barron's (September 2021)

"Tech Millionaires Fear Their Favorite Tax Break Will Be Chopped," Bloomberg Wealth (September 2021)

"Plan to Revive I.R.S. ‘Wealth Squad’ Puts the Richest on Notice,The New York Times (June 2021)

"As U.S. Capital Gains Tax Hike Looms, Wealthy Look for Ways to Soften the Blow," Thomson Reuters (April 2021)

"Virtual State Tax Administration Poised to Stick After Pandemic," Bloomberg Law (January 2021)

"Businesses Sue Over Paycheck Protection Program Guidelines," The Daily Journal (May 2020)

"Law Firms May be Able to Apply for Paycheck Protection Loans," The Daily Journal (April 2020)

"There's a Way to Gift Your Family Members Millions When You Sell Your Startup, Tax Free," Business Insider (February 2020)

"Qualified Small Business Stock and The 'Substantially All' Problem," Tax Notes Federal (September 2019)

"How a Tax Loophole Is Helping Silicon Valley Workers Save Millions," New York Times (July 2019)

"Silicon Valley Wins Big With Tax Break Aimed at Small Businesses," Bloomberg (June 2019)

"Experts cast doubt on San Francisco North Bay 'opportunity zones,'" North Bay Business Journal (May 2019)

 "Basis and Allocation Issues Raised in Opportunity Zone," Tax Notes (November 2018)

"IRS Could Replace Offshore Voluntary Disclosure Program," Law360 (April 2018)

"Tax Tips for Family Caregivers," Where you Live Matters (February 2018)

"Tax Benefits of Senior Living," Where you Live Matters (February 2018)

"The Great 2018 Tax Season," Comstock's (February 2018)

"Cooperatives May Provide End Run Around Limitations on 20% Business Deduction," Forbes (January 2018)

"Accountants Hit By Phase-Outs Under New Tax Law," Accounting Today (January 2018)

"IRS Still Vague On Large Business Audit Details," Law360 (May 2017)

"How to Combat Errors on Tax Forms," TheStreet (April 2017)

"Tax Disclosures," Taiwan Business Topics (November 2016)

"That time Democrats created a massive tax break for the rich," Politico (October 2016)

Super Lawyers, Tax; Business & Corporate (2013-2017)