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Taxes. Tuition. Cryptocurrency trading. Since 2008, Ron Lieber has answered hard-hitting questions about personal finance as the Your Money columnist.

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When Ron Lieber arrived at The Wall Street Journal’s office in 2002 for a job interview, a couple of editors immediately sized him up.

“They said, ‘We know what your beat is: beating the system,’” said Mr. Lieber, who had last worked as a senior writer for Fast Company covering management, design and careers. “And now you’re going to come here and do that for us.”

After cofounding the Personal Journal section of The Wall Street Journal and writing a separate money management column, he was hired by The New York Times in 2008 to take over Your Money, a personal finance column. Sixteen years later, he has gained a reputation for offering readers

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