When Tom Steyer was running a hedge fund in 2000, he wrote a letter telling some wealthy investors their money would soon flow through an offshore company that would shield their gains from U.S. taxes.
It was routine in finance, but could prove toxic in politics.
Now that the San Francisco billionaire has joined the crowd of Democrats running for president, much of what he did to build his personal fortune, including a stint at Goldman Sachs in the 1980s, could turn off voters. His fund's investments in coal mining and private prisons are two of the biggest hazards.
Part of Steyer's challenge is timing. Wall Street's reputation is in tatters in the aftermath of the Great Recession. Many Democrats are upset about growing income inequality. And billionaires -- President Donald Trump first among them -- are routinely demonized by the party's left wing.
Steyer is the founder of Farallon Capital Management, one of America's largest hedge funds, the high-risk investment pools for big investors. He left Farallon in 2012 after running the San Francisco firm for 26 years.
He did not mention his experience there when asked by the Los Angeles Times what qualified him to serve as president. He focused instead on his work fighting climate change and big corporations over the last decade.
Attacks by Steyer's opponents have been mild so far, but that will change if he starts gaining support.
"He will have to answer for his involvement in anti-climate-control activities, his relationship to the coal industry, and his relationship to Wall Street, which young people particularly find abhorrent," said Democratic ad maker Hank Sheinkopf, who is unaligned in the presidential race.
"In a political campaign, there is no past tense and there is no future tense. Everything in your life you've ever done, thought of and said is in present tense."
In written responses to questions sent by email, Steyer expressed remorse over some of Farallon's investments.