How Instagram's penny stock king became a self-employed multimillionaire

Tim timothy sykes penny stock instagramInstagram/Timothy SykesSykes with his fiancée, Bianca Alexa, in Santorini.

Timothy Sykes is a controversial financier who flaunts his flashy lifestyle on Instagram. Each photo of him working remotely in Bora Bora or sunning himself in the Maldives garners thousands of likes from his 396,000 followers.

He’s not just a trader, but also a teacher. Sykes claims to have made $US4.3 million trading stocks, but the bulk of his income — “roughly triple that amount,” he says — comes from teaching his acolytes how to get rich off of penny stocks, at tuition rates of $US50 to $US247 per month. He says his students at online trading school aren’t required to report their profits, but he knows some who “have profited in excess of $US25 million.”

He’s a controversial figure within the finance community for his endorsement of high-risk penny stock trading. He once received a cease-and-desist letter from Shaquille O’Neal.

But his Instagram feed is one of the most loved on the platform, showing him lounging around as he telecommutes from the most beautiful beaches and boats in the world. Like a less wild Dan Bilzerian, he appears to live a life that most guys dream of.

After discovering his enviable feed, we got the scoop from Sykes about what it’s like to be Instagram’s favourite finance bro, with a travel schedule that would make anyone jealous. Here’s what he has to say about being an travel-friendly entrepreneur.

It only took one summer of working a typical job in high school for Sykes to decide he wanted to be his own boss.

Sykes helped manage the inventory of his mother’s retail store in North Haven, Connecticut, as a teen.

“It was then that I decided I would never work for anyone else,” he told Tech Insider. “It was a typical 9-5 back office job, managing inventory at a basic retail operation which is just a tough, tough way to live day in and day out.”

He seems to love the adrenaline rush that comes along with being your own boss and relying on no one but yourself for a paycheck.

“I love the daily hunt for profits where you only get paid based on your dedication and if you’re right, otherwise you go home empty-handed,” he said. “Being an entrepreneur is so much more exciting, especially when you fail and fail again only to succeed eventually and see your early work pay off.”

Now that most of his cash flows from, he trades with “a small amount in order to teach,” he said, “usually starting the year at $100,000 and growing it trade-by-trade so that my students can see. Last year I had a trading profit year of roughly $1 million.”

Freedom is more important to Sykes than a bigger paycheck.

“If I went to work for a big firm, I might get paid decently or even very handsomely, but I wouldn’t have time for anything else,” Sykes said. “Many people in finance make decent to good to even great money, but they’re slaves to their jobs for years, sometimes even decades, before they can come up and enjoy their wealth.”< Snagging a job with a big firm can also mean years of pricey schooling, he points out. “You waste your youth just trying to get into this field, then you waste another decade trying to make enough money to be free,” he said. “It’s like a lifetime of financial slavery as you spend your days building someone else’s dreams, not your own.”

He doesn’t hold any graduate degrees in business or finance. Instead, he finds self-education incredibly important.

“Learn to trade yourself,” he said, “whether it’s stocks, forex, whatever. Understand that the failure rate is high for traders so you must work your butt off studying and testing various strategies if you want to be one of the few who consistently profit.”

His study abroad experience actually motivated him to spend his life traveling — and made him a millionaire.

Plenty of people study abroad in college thinking it will set them up as lifelong travelers, but few actually stick to it. Sykes is an exception to this. He spent a semester at sea in 2002 at age 21 and officially became a millionaire on that trip, he said. He did this by skipping out on class to trade online. His satellite internet bill was “in the thousands,” he said, but it was worth it.

“That trip was so important sine it proved I could indulge my travel addiction and still profit as even with the expensive and slow satellite Internet aboard the cruise ship, I still pocketed $200,000 within three months,” he said. “I’ve been traveling, trading and profiting rather consistently ever since, recently passing 100 countries visited, definitely hurting my overall income potential due to my travel addiction, but living the life I’ve always dreamed of.”

For a traveling trader, timezones matter.

Sykes always trades on New York time. For that reason, he loves traveling to Europe.

“I wake up around noon, go for a nice lunch with my fiancée, head back to whatever hotel suite or villa we’re renting and trade stocks from 3 to 5 p.m., then maybe visit a museum or sightsee until 7 to 8 p.m., then trade another two hours before the US stock market closes at 10 p.m.,” he said.

Sounds like a great workday for everyone, but that’s not even all.

“Then it’s time for a great dinner with my fiancée and usually some new local friends we’ve made, along with some drinking or dancing until 1 or 2 a.m., then sleep till noon the next day and do it all over again,” he said. “It’s not a bad life.”

When he’s in Asia, though, time works against him. He could end up trading well into the middle of the night. Still, Sykes insists on “treat[ing] travel like a job,” so he adjusts his sleep schedule to be there for the market open or market close.

His international business has translated into having friends everywhere he goes.

Sykes has students from all over the world, and this comes in handy when he’s traveling. Students have shown him around in various countries, he said.

“It’s key to have that kind of relationship with my customers,” he said. “For example, last weekend I attended the wedding of one of my top students, Mark Croock, who has made $400,000 with my strategy and that money allowed him to leave his cubicle job in Texas and meet the love of his life in Miami.”

Sykes spends about half of each month traveling and some of his favorite locales are Greece, Spain, Bora Bora, Turks and Caicos, Japan, Italy, Beverly Hills and the Maldives.

“Some people think I’m crazy for traveling so much, but I truly love exploring the world, meeting and talking with people from various cultures, trading and teaching my strategies to students in now over 70 countries,” he said.

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