It was around 10 a.m. on a sun-drenched summer morning, and James Altucher, perhaps the world’s least likely success guru, was packing his worldly possessions, about 15 items, into a small canvas carry-on bag.
"If I were to die, my kids get this bag," Mr. Altucher said sardonically as he packed away his laptop, iPad, three sets of chinos, three T-shirts and a Ziploc bag filled with $4,000 worth of $2 bills ("People always remember you if you tip with $2 bills," he said), and departed a friend's loft on East 20th Street.
A few months ago, the boyish 48-year-old let the lease expire on his Cold Spring, N.Y., apartment, and dumped or donated virtually everything he owned, more than 40 garbage bags of sheets, dishes, clothes, books, his college diploma, even childhood photo albums. Since then, he's been bouncing among friends' apartments and Airbnb rentals.
It is not that he is down on his luck. Several of the 16 books he has written, including his 2013 personal-empowerment manifesto, "Choose Yourself," continue to sell briskly. His weekly podcasts, "The James Altucher Show," featuring interviews with notables as diverse as Ron Paul and Luther Campbell of 2 Live Crew, and "Question of the Day," with Stephen Dubner, are downloaded about two million times a month.
Mr. Altucher is simply practicing what he preaches. Over the last half-decade, this former tech entrepreneur, venture capitalist and financial pundit has reinvented himself as a gimlet-eyed self-help guru, preaching survival in an era when the American Dream — the gold-embossed college diploma, the corner office, the three-bedroom home — seems like a sham. So one by one, he has shed all of them.
"I have ambition," he said, "to have no ambition."
"In the past 25 years, income has gone down for the 18-to-35-year-olds, student loan debt is at an all-time high," Mr. Altucher said over a lunch of zucchini pancakes at a Russian restaurant in the Flatiron district. "We had $3 trillion in bailout money, and income inequality got higher than ever. People feel like they were scammed."
Mr. Altucher's diagnosis will come as no surprise to the anxious middle class, the downsized and the dispossessed who have propelled the angry populism of Bernie Sanders and Donald J. Trump.
But while there is no shortage of anger and confusion about the supposed waning of the American Dream, what makes Mr. Altucher stand out are his Cassandra-like conclusions.
College, he says, is a waste of money. Although he graduated from Cornell, Mr. Altucher argues that the college degree has become a costly luxury in a world where millennials feel like debt serfs and entry-level professional jobs are scarce.
In a 2012 self-published book, "40 Alternatives to College," he argued that young adults could travel the world, educate themselves online and start a business with the same $200,000 they may spend on college.
"Choose Yourself," which Mr. Altucher, 48, self-published on Amazon, sold more than a half-million copies, he said, and made The Wall Street Journal's best-seller list.
Investing the money with even a 5 percent return would offer greater financial benefit over the course of a lifetime, he wrote in a blog post.
Similarly, he believes homeownership is a rip-off foisted upon unwitting citizens by a $14 trillion mortgage industry.
"It's a total scam," he said in an online interview. "Nobody should put more than 5 to 10 percent of their portfolio, their assets, in any one investment. But when people buy a home, they go crazy. They put like 50, 60, 70 percent of their net worth into this one investment. It's illiquid, so when times are hard, you can't sell it."
And he think stocks are a racket. It's a fierce worldview that is rooted in Mr. Altucher's own roller-coaster life.
In the 1990s, as a young Silicon Alley start-up whiz, Mr. Altucher made millions with a web-design company, Reset Inc., that counted Sony and Miramax as clients.
Soon, he and his wife at the time, Anne (they divorced in 2010), were living in a 5,000-square-foot loft in TriBeCa that he bought for $1.8 million and spent another $1 million renovating. He felt flush enough to take a helicopter to Atlantic City on weekends to play poker.
The lavish lifestyle did not fill his emotional void. "Nobody should feel sorry for me," he said. "I was really stupid, but I thought I was dirt poor. I felt like I needed $100 million to be happy. So I just started investing in all these other companies, and they were just stupid companies. Zero of these investments worked out."
As his fortunes collapsed, he was forced to sell his apartment for a $1 million loss (it was after the attacks of Sept. 11, 2001).
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To reclaim his wealth, he set his sights on the stock market. He read more than a hundred books on investing, and eventually wrangled a job writing for James Cramer's site, TheStreet, and later The Financial Times. Before long, his trademark hairdo, which looks like carnival cotton candy spun from steel wool, was a familiar sight on CNBC.
But his fortunes crumbled once again during the financial crisis that began in 2008. The hedge fund he started ran out of gas, various start-ups withered, writing gigs dried up. With few options open, he decided to chronicle his failures on a personal blog, which he named Altucher Confidential.
"I just said, 'I've made every mistake in the book: Here's what they are,'" Mr. Altucher said. To Wall Street friends, he seemed like Howard Beale, the anchorman in "Network" who had a meltdown on-air.