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My Thoughts on Going All In

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Written by Timothy Sykes Reviewed by Jack Kellogg Fact-checked by Ellis Hobbs
Updated 7/31/2026 5 min read
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Let me put this as bluntly as possible…

This is what I think about going all in…

The same goes for using leverage without proper risk management.

What happened last week with Leopold Aschenbrenner’s hedge fund Situational Awareness is sad.

The fund was up 450% YTD in early July, then the AI selloff blew up its 4x-levered book, triggered margin calls, and forced him to sell his entire public stock portfolio to Ken Griffin’s Citadel at a MASSIVE discount.

But there’s also a great lesson in it about mindset and perspective.

Check it out…

Rudyard Kipling Got THIS Wrong

Image created by Google Gemini, young men playing pitch-and-toss
Image created by Google Gemini, young men playing pitch-and-toss

Rudyard Kipling’s famous poem “If” is great. (It has nothing to do with trading, but bear with me.)

There’s no denying that you can learn a lot by reading it and applying its wisdom.

But there’s one stanza that drives me crazy when people quote it out of context.

It goes like this…

If you can make one heap of all your winnings

And risk it on one turn of pitch-and-toss,

And lose, and start again at your beginnings

And never breathe a word about your loss

When it comes to trading?

NEVER Make One Heap and Risk It All

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Sorry, that’s just dumb. That kind of thinking is dangerous.

Image created by Google Gemini
Image created by Google Gemini

It’s a sick, sick financial world right now that encourages people to risk everything.

Sadly, there will be more Leopold’s unless people learn proper risk management.

One of the most important things we can all do is…

Stop Celebrating Going All In

Look, I get it. Everyone wants to win

But going all in is careless (and encouraging it is sick).

The whole WallStreetBets “You Only Live Once” (YOLO) culture is for morons.

Encouraging people to use leverage when they don’t know what they’re doing is also disgusting.

I’m not trying to discourage anyone from following your dreams.

Be obsessed with trading and studying the markets (or whatever you want to do).

But NEVER think that means you have to risk everything on one trade.

Don’t get caught up in the all-in culture (or think that you have to use leverage).

It won’t end well (it never does).

You CAN achieve your dreams and reach your trading goals WITHOUT taking unnecessary risks.

It starts like this…

Millionaire Moves

None of my most successful students got where they are by going all in or using leverage.

Instead, they learned the 7-Step Framework and focused on being more selective.

It really boils down to a few simple concepts.

  • Be selective about the stocks you trade
  • Cut losses quickly
  • Take gains into strength
  • Manage your risk (by having a trading plan and sticking to it)
  • NEVER force trades.

Also, open your mind to the possibilities in this market…

The Night Tape

For the past few months, the biggest moves of the day happen in after-hours trading.

Right now, after-hours is my favorite time to trade.

SO many people have asked about it that I’ve been working on a special project with my team…

Get my after-hours watchlist free, every trading day

Be sure to go through the included guide, “The Second Session” so you understand how after-hours trading works.

On My Radar

It’s official…

We’ve now opened 134 schools, including 67 in Bali.

Our goal is 1,000 schools worldwide. Like trading, we’ll take it one at a time and get there.

Key Takeaway

There is so much opportunity in this market. But it drives me CRAZY when I see otherwise smart people take huge risks for no reason.

What happened with Leopold Aschenbrenner didn’t have to happen.

I can only guess, but the fact that he was so leveraged (rumors of up to 400% on some positions) means people who DO know the risks were willing to fund it.

He got married over the weekend.

If you have a bad day this week, just remember it could always be worse.

You could be Leo, who was on top of the world a month ago.

Now he’s lost billions and had to put on a happy face for his wedding.

Aye, aye, aye…

Cheers,

– Tim Sykes

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Timothy Sykes

Tim Sykes is a penny stock trader and teacher who became a self-made millionaire by the age of 22 by trading $12,415 of bar mitzvah money. After becoming disenchanted with the hedge fund world, he established the Tim Sykes Trading Challenge to teach aspiring traders how to follow his trading strategies. He’s been featured in a variety of media outlets including CNN, Larry King, Steve Harvey, Forbes, Men’s Journal, and more. He’s also an active philanthropist and environmental activist, a co-founder of Karmagawa, and has donated millions of dollars to charity.
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* Results are not typical and will vary from person to person. Making money trading stocks takes time, dedication, and hard work. There are inherent risks involved with investing in the stock market, including the loss of your investment. Past performance in the market is not indicative of future results. Any investment is at your own risk. See Terms of Service here

The available research on day trading suggests that most active traders lose money. Fees and overtrading are major contributors to these losses.

A 2000 study called “Trading is Hazardous to Your Wealth: The Common Stock Investment Performance of Individual Investors” evaluated 66,465 U.S. households that held stocks from 1991 to 1996. The households that traded most averaged an 11.4% annual return during a period where the overall market gained 17.9%. These lower returns were attributed to overconfidence.

A 2014 paper (revised 2019) titled “Learning Fast or Slow?” analyzed the complete transaction history of the Taiwan Stock Exchange between 1992 and 2006. It looked at the ongoing performance of day traders in this sample, and found that 97% of day traders can expect to lose money from trading, and more than 90% of all day trading volume can be traced to investors who predictably lose money. Additionally, it tied the behavior of gamblers and drivers who get more speeding tickets to overtrading, and cited studies showing that legalized gambling has an inverse effect on trading volume.

A 2019 research study (revised 2020) called “Day Trading for a Living?” observed 19,646 Brazilian futures contract traders who started day trading from 2013 to 2015, and recorded two years of their trading activity. The study authors found that 97% of traders with more than 300 days actively trading lost money, and only 1.1% earned more than the Brazilian minimum wage ($16 USD per day). They hypothesized that the greater returns shown in previous studies did not differentiate between frequent day traders and those who traded rarely, and that more frequent trading activity decreases the chance of profitability.

These studies show the wide variance of the available data on day trading profitability. One thing that seems clear from the research is that most day traders lose money .

Millionaire Media 66 W Flagler St. Ste. 900 Miami, FL 33130 United States (888) 878-3621 This is for information purposes only as Millionaire Media LLC nor Timothy Sykes is registered as a securities broker-dealer or an investment adviser. No information herein is intended as securities brokerage, investment, tax, accounting or legal advice, as an offer or solicitation of an offer to sell or buy, or as an endorsement, recommendation or sponsorship of any company, security or fund. Millionaire Media LLC and Timothy Sykes cannot and does not assess, verify or guarantee the adequacy, accuracy or completeness of any information, the suitability or profitability of any particular investment, or the potential value of any investment or informational source. The reader bears responsibility for his/her own investment research and decisions, should seek the advice of a qualified securities professional before making any investment, and investigate and fully understand any and all risks before investing. Millionaire Media LLC and Timothy Sykes in no way warrants the solvency, financial condition, or investment advisability of any of the securities mentioned in communications or websites. In addition, Millionaire Media LLC and Timothy Sykes accepts no liability whatsoever for any direct or consequential loss arising from any use of this information. This information is not intended to be used as the sole basis of any investment decision, nor should it be construed as advice designed to meet the investment needs of any particular investor. Past performance is not necessarily indicative of future returns.

Citations for Disclaimer

Barber, Brad M. and Odean, Terrance, Trading is Hazardous to Your Wealth: The Common Stock Investment Performance of Individual Investors. Available at SSRN: “Day Trading for a Living?”

Barber, Brad M. and Lee, Yi-Tsung and Liu, Yu-Jane and Odean, Terrance and Zhang, Ke, Learning Fast or Slow? (May 28, 2019). Forthcoming: Review of Asset Pricing Studies, Available at SSRN: “https://ssrn.com/abstract=2535636”

Chague, Fernando and De-Losso, Rodrigo and Giovannetti, Bruno, Day Trading for a Living? (June 11, 2020). Available at SSRN: “https://ssrn.com/abstract=3423101”