Ian Winer just turned in the lease to his dream car. The hefty monthly payments made sense when, just last month, he was still banking wads of Wall Street cash as the head trader for Wedbush Securities in Los Angeles.
But not anymore.
“Happiness is picking up your last suit from the dry cleaners and keeping it in its plastic cover because it is going into storage,” the 44-year-old Winer tweeted shortly after handing in his resignation.
“Don’t get me wrong, living a life of advantage is great in many ways,” he told MarketWatch. “But it just wasn’t making me happy anymore.”
Before calling it quits, Winer spent his career, which included stints at Goldman Sachs GS, +0.56% , Bank of America BAC, -0.05% and J.P. Morgan JPM, +0.10% , enjoying all the trappings of a high-profile finance gig — fat paychecks, fancy meals, luxury vacations, etc.
He also embraced the media during his two decades in the trading pits. He was a regular guest on Bloomberg TV and CNBC, where you might have seen him interviewed about shorting Apple AAPL, +1.23% , staying underweight tech and loading up on Amazon AMZN, +0.71% .
The call that perhaps made the biggest splash came during the presidential campaign in 2016, when he predicted that a Trump win would be catastrophic for investors. Winer’s had many more wins than losses — otherwise his career wouldn’t have spanned decades. But it’s the bad predictions everybody remembers. And this was a doozy.
“If Trump becomes president of this country, the S&P 500 SPX, +0.33% will go to 1,000,” he said at the time. “People are brushing it off, but there is absolutely no way that this market — and this economy — does not get pounded. Bad for home builders, bad for everybody, but most of all bad for the United States of America.”
When asked if a Trump win would send him running for the border, Winer, a West Point grad, replied, “I would pretty much go anywhere but here.”
Less than two years later, he’s following through on that vow, although it has nothing to do with his epic misfire.
The journey
“What’s next?” is the question traders often ask themselves while getting beaten down by the grind of their daily life. It’s a common fantasy that helps them endure the long hours and cushions the blow of a trade gone sideways. “One day, I’ll live the life I want to live and leave this all behind.” Few have the conviction or wherewithal to make it happen.
Winer doesn’t want to be saddled with regret.
“The way I used to measure success no longer makes sense,” he said. “For me, all the stuff my career allowed me to afford just weren’t doing it for me anymore. Now I’m shedding things each day and embracing the opportunity to really know myself.”
So, after an epiphany years in the making, Winer’s trading in his Bloomberg terminal for a ticket to Indonesia, where his adventure starts with teaching English and volunteering to save sea turtles. Along with his wife, who’s putting her career on hold, as well, he’ll eventually move on to Africa and take up the fight against elephant poachers.
“Truth is, I haven’t really experienced the world,” he said. “Top-shelf vacations to Europe, sure, but that doesn’t show you what’s really going on out there.”
Winer said his co-workers have been very understanding, with many confiding that they wish they could do the same, he said. But, shackled by golden handcuffs, it’s easier said than done.
Gary Wedbush, the newly appointed co-president of Wedbush Securities and son of the company’s founder, said he’s not surprised Winer is making such a bold move.
“He’s always been a big-picture thinker, with unique viewpoints on the markets and the people and institutions that inhabit them,” Wedbush told MarketWatch. “Although I am bummed that Ian is leaving our trading desk, I’m also proud because he exemplifies the type of professional and individual that Wedbush Securities attempts to build its teams with — unique, passionate and skillful.”
‘Finding my identity’
At times, Winer comes off as a twentysomething — fresh out of college, starry-eyed, with lofty, perhaps unrealistic, aspirations. A dreamer. He’s planning to write a book about his experiences, and, like many a searching millennial, his Instagram account is primed to chronicle his travels:
Winer’s not naive, however, about the reality of what lies ahead and what it means to be giving up the security of a steady job that provides a direct, albeit stressful, path to a cushy retirement. He’s got that analytical trader mind-set, and he’s chewed on all the possible outcomes.
“Whatever income I’m leaving on the table is less than the opportunity cost of missing out on my life,” he said. “It’s exciting and terrifying. But it’s time. The idea of sitting at my desk for another 20 years is much scarier than fears over living with less.”
He explained that money was his biggest concern when he and his wife first fantasized about making such a dramatic shift, but, just a few weeks into his new life, it’s already a nonfactor. “I’m more concerned about finding my identity,” he said.
Will the allure of big money ever draw him back to his old way of life?
“I have enough money to last me for a few years — not enough to retire and never work again,” he said. “But it’s unlikely I’ll ever go back to Wall Street.”