California woman admits to stealing nearly $18M from her VC boss — to fund Rolex watches, handbags and private jet travel

The Attorney’s Office explained that Sherman, “an executive assistant to a retired Bay Area venture capitalist,” was responsible for paying her boss’ credit cards and, thus, had access to their bank account.

The press release noted that she “abused this access” and used the money she stole to buy luxury items like Louis Vuitton handbags and Rolex watches, fly on private jets, take vacations, pay for vehicles and home improvements, and buy designer products to resell online.

In the case of the latter, authorities say she made more than $450,000 in nine months re-selling designer items online and that, when they searched her home last December, they found “more than 1,500 luxury items, most in mint condition with original packaging and tags intact,” including Christian Louboutin boots, expensive wines and “handbags made of exotic furs.”

When trust becomes a costly business risk

The U.S. Attorney’s Office told Moneywise that “the origin of the investigation is not part of the public record” and, thus, couldn’t reveal how the scheme was discovered. And while Sherman’s plea agreement leaves her “subject to forfeiture and restitution to her employer of nearly $18 million,” the Attorney’s Office added that “accurate details of the forfeiture and restitution will be available at sentencing” — which is scheduled for March 2027.

It did, however, share the court complaint with Moneywise, which alleges Sherman exploited the victim’s trust and used the stolen funds to pay for her unauthorized purchases as well as her own credit cards, “folding those payments into what appeared to be Victim A’s routine financial activity.”

That exploitation of a victim’s trust, meanwhile, is central to many reports of employees stealing from small businesses or employers.

In September, a Wyoming bookkeeper received a jail sentence for stealing $1.48 million from her family business employer over six years. In 2025, a South Carolina woman was convicted of embezzling $1.7 million over seven years from the family business she worked for while, and in 2022, a Maine man pleaded guilty to a “15-year embezzlement scheme” that stole $1.8 million from his small business employer.

“Smaller businesses or employers typically do not have as many resources to invest in anti-fraud controls, which makes detection more challenging,” Mason Wilder, a certified fraud examiner, told Moneywise. “Additionally, a common cultural feature in small organizations is trust in employees, especially those who have been with the company a long time.”

To that, he added, “We regularly say that trust is not a control.”

In fact, a 2026 report by the Association of Certified Fraud Examiners (ACFE) — which Wilder oversaw — looked at occupational fraud across 143 countries and found that the median scheme lasted 12 months, but noted that some related to billing, expense reimbursements and financial statement fraud could go on for between 14 and 24 months before they’re discovered.

The report estimates the average company loses 5% of revenue to fraud each year, while businesses with fewer than 100 employees experienced the highest median fraud loss amount per organization, at $126,000.

The report classifies the U.S. and Canada together as one region with a median occupational fraud loss of $110,000. It added that only 15% of companies recovered their losses.

Wilder said that key red flags of employee embezzlement in small organizations “include an employee living beyond their means, control issues or unwillingness to share duties, refusal to take vacations, and personal issues such as financial difficulties, divorce, family problems or addiction problems.”

And with a survey from Public Private Strategies Institute finding that 72% of U.S. small businesses suffered billions in losses to external fraud in 2025, the last thing they need is someone skimming from the inside.