Interview: How Timothy Sykes Made Two Million From His Dorm Room

by / ⠀Entrepreneur Interviews / March 8, 2010

Timothy Sykes

Photo via Gawker

First things first, how the hell did you make $2million from your college dorm room?

I traded thousands of hyped up penny stocks, discovering several chart patterns that were predictable 90% of the time, taking small gains nearly every day and those gains added up over time. My first million was made through buying these stocks as they hit new highs, but my second million was from short selling, or betting against, that same pattern on the way down–it’s just really pattern recognition…like a pendulum. I’ve never dealt in the corruption part of penny stocks, but I’ve learned a ton about it over the years so now I teach others how to identify and profit from it. You can read one cool story about how I made $123,000 in one weekend during my Freshman year

For more details see my FAQ page and my book “An American Hedge Fund: How I Made $2 Million…”

So, you are in college and you have a hedgefund–honestly now, how many times did you use that line out at the bar? Do freshman girls even know what a hedge fund is?

Ha, nobody in college had the slightest clue what a hedge fund was, when I said the word hedge fund, people asked me if I was in landscaping. You have to remember I went to Tulane down in New Orleans so I worked all day and then went out at night–by the time I was chatting with anybody, we were all pretty drunk so it didn’t matter. I can’t stress how important it is to let loose every now and then, whether you’re into drinking, fine dining or even something like fishing…especially if you work 16 hour days like I have always done. Mind you half my days are spent working, the other half are for reading/researching so it’s important.

Your Twitter profile @TimothySykes says “Stock guru to the little people”. Obviously you’ve never lacked confidence.  Tell us how this came to bite you back…

I haven’t always known my strategy would be so crucial for others to learn, but after trading for over a decade and now teaching for the past two years, I have a fairly solid grasp on the curriculum and the problems most people have (90-95% of traders lose money), but yes my confidence does get me in trouble. Because I know what I’m doing is helpful and real (as compared to the industry full of cowards and frauds), I don’t take crap from anybody as my brutally honesty and transparency makes me the friggin messiah of the finance industry. This makes it partnering rather difficult because I can only ever be a one man brand…like Martha Stewart, without the perjury.

Your fund lost 1/3 of its value at one point; how did you bounce back to earn the trust of so many people who take your advice?

As I detail in my book “An American Hedge Fund”, the loss was due to my getting away from my core trading strategy, so it wizened me up which has made me an infinitely better teacher. I would never recommend learning from anyone who hasn’t experienced firsthand such important scarring.

But this isn’t an easy concept to preach so I went back to my core trading strategy and my $12,415 Bar Mitzvah gift money roots to repeat my feat of turning it into $2 million with the goal of detailing every step of the way. Two years and 2,300 blog posts later, I’ve become the #1 ranked trader out of 45,000 on Covestor (a website that verifies all trades and performance) by growing that $12,415 into $115,000….nearly 10x all through the same strategies I employed the first time around…with slight adjustments in order to adapt to current market conditions.

Most people think you are just a trader, but you also operate an internet empire teaching people what you know.   How did you bridge the gap between being an investor and internet marketer?

There isn’t much of a gap at all because my books, DVDs and websites illustrate what I know about finance and trading…they are extensions of the research I normally do except I’m also educating my readers daily…I highly encourage everyone to create businesses around their passion and explore multiple channels of income.

You’ve been quoted by saying “These are the July results of a hardworking internet entrepreneur, think 16-20 hours days, including weekends…it’s all about how bad you want it, f$%^ the 4-hour work week you fat lazy American slobs, working hard, and honestly, is the path to righteousness and fulfillment…” Is money and influence really what fulfills you? If so, give us your most outrageous purchase.

Money and influence are byproducts of success and hard work but they mean relatively little to me. That said, I do love fine dining and have been known to drop a few thousand dollars on dinners at great restaurants worldwide. All starting when I made that $123,000 over the weekend in college and I took my entire dorm out to dinner at Boston’s awesome Fire & Ice. Now some of my favorite restaurants are Sushi Yasuda & Corton in NYC, L’Arpege in Paris, Sukiyabashi Jiro in Tokyo.

Let’s talk about controversy; you write blog posts like: Suck On This John Chow, My Blog Made $45,000 Last Month!, Gawker titled you as “Capital Schmuck”, and you aren’t afraid to speak your mind.  How does this infamy help your personal brand and why aren’t you afraid of it?

I call this strategy “hate marketing” since I know my trading strategy is real, proven and unique, I can say just about anything to get people to remember me and be curious enough to want to learn more about why I am so confident. I wish I could just go about teaching and being normal, but people are dubious of those teaching others to make money so I have to go to extremes to show that I am real. Think about it, my exposure strategy differentiates me quite nicely because all the true frauds can never risk annoying anyone or making so many enemies and risk being exposed. I have ZERO fear because I have nothing to hide and great things to teach. In fact, many of my initial “haters” go on to become my best students–take Michael Goode of who I first learned about when he wrote a blog post entitled “Timothy Sykes Is Full Of BS” but now has bought all my instructional DVDs, has profited over $125,000 from my strategy and is my #1 affiliate.

So do you really suggest short-selling penny stocks from your dorm room? What happened to the buy and hold strategy that is so often preached?

Short selling penny stocks when they are manipulated/pumped up is actually one of the safer strategies around because I’m literally betting for frauds and schemes to collapse. Imagine being able to make money off Madoff–that’s essentially what I’m doing Buy and hold was so 1990s…in these dangerous economic times, it’s probably the single riskiest strategy around and it’s sad that so many financial neophytes believe it to be safe. I put all the blame on entertainment-masquerading-as-responsible-financial-advisor outlets like CNBC and Motley Fool.

How can our Under30CEOs get started with their investing empire?

Start learning from all the top rated investment books on my brand new site Investimonials which is gonna be the TripAdvisor/Yelp for the finance world, already with 3,000+ user reviews in the first 2 months since we launched.

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About The Author


Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.

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