Failure drove my father's success.

Just weeks before he died on February 16, he finished writing his last book. It's a history of the Bonus Army—the military veterans who demanded cash payment of the benefits promised to them for their service in the First World War. They were brutally dispersed by troops and tanks commanded by Gen. Douglas MacArthur, who was honing the skills he'd apply to more deserving targets in the Pacific later in his career.

I doubt my old man would have been motivated to labor on that book, through complications associated with multiple myeloma, if he'd earlier achieved his goal of writing a major bestseller.

His writing career started with politics: magazine articles, newspaper op-eds, and the books—Radical Libertarianism (1970) and It Usually Begins With Ayn Rand (1971)—that made his name. But politics damn near broke him. He didn't expect his 1974 run as the Libertarian candidate for governor of New York to end in electoral victory, but he hoped his candidacy would win enough votes to gain permanent ballot status for the party. He failed in that goal, then put on a suit and snagged a meeting with a Merrill Lynch branch manager by implying he was a potential big-money client. That he had, instead, a big need for money and had bluffed his way in the door impressed the guy and landed him a job.

He went on to write not just about money but about people good at accumulating the stuff, like Rupert Murdoch, Barry Diller, and the Hunt family of Texas.

This was a fortunate turn. If disappointment in politics hadn't spurred him to move on to biographies, his name wouldn't have featured in news coverage across the country and around the world 30 years later, when a shady real estate tycoon who had threatened him repeatedly as he wrote an unauthorized biography of the man made a run that ended at the White House.

He struggled to reconcile himself to the idea of making a living as anything other than an author. Even the lucrative brokerage business was supposed to be a stepping stone until the books he wrote sold enough copies to live off.

That dream failed too. But he made his peace with it and entered what he later admitted was the most rewarding period of his life. He landed a financial writing job at T. Rowe Price that suited his temperament and gave him time to produce some of his best work. He wrote more biographies, including a treatment of Alan Greenspan that brought him back in contact with the Objectivism that had launched his interest in libertarian ideas.

The Greenspan book wasn't the only time his continuing interest in individualism and personal liberty resurfaced in seemingly unrelated projects. Inside the Underground Economy (1982) was a middle finger to regulators and the IRS in the guise of an investment book. Gallo Be Thy Name (2009) examined how the famous wine-making family wrung new opportunities out of Prohibition. And The Roughest Riders (2015) explored the African-American soldiers who saved then–Col. Teddy Roosevelt's bacon at San Juan Hill in 1898.

How could these ideas not recur again and again to the grandson of a speakeasy operator? Many of the relatives with whom he'd grown up specialized in making sure that whatever goods or services had been blacklisted at any given moment remained available to consumers. He'd repeatedly seen control freaks' dreams fail and fuel their opponents' profit lines.

In his later years, my father and I spent a lot of time together on our patios, sipping whiskey, smoking cigars, and solving the world's problems—or at least savaging the people we held responsible for them. When he visited me for Thanksgiving in 2016, we continued our tradition, not knowing it was for the last time.

At the end of the night, when he tried to get up, he couldn't quite make it. The cancer rotting his innards had stolen away a little more of his capacity for good booze than he had realized.

So I threw his arm over my shoulder and lifted him off the outdoor sofa. We walked into the house, both of us laughing at the situation like two buddies exiting their favorite bar after one drink too many.

The evening, like his life, was a success.