Why Shorting Stocks Is Harder Than You Think

Why Shorting Stocks Is Harder Than You Think

Shorting Stocks: A Riskier Gamble Than Going Long

When you think about shorting, remember the classic warning: “You can lose more than you put in.” That’s not just sarcasm; it’s a real possibility. Shorting is essentially taking a bet that a stock will drop, which flips the usual investing equation on its head.

Shorting vs. Going Long – The Simple Math

  • Going long: buy low, sell high – you profit when the price walks up.
  • Shorting: sell high (by borrowing), then buy low – you profit when the price slides down.
  • Risk difference: A long position can lose at most the money you invested. A short position can lose essentially unlimited dollars if the stock surges.

Why Those Numbers Matter

Shorting isn’t just a flip‑flop of the long term; it demands a distinct skill set. You’re looking for a price trigger, but you’re also battling market sentiment, analyst bias, and the mechanics of borrowing and covering your position. It’s a different beast to tame.

Real‑World Examples That Teach Us the Rules

  • Case 1: The “Cinderella” Stock – You shorted a company because it looked weak, but a surprise product launch turned it into a darling. By the time you closed the short, the price had climbed 30% – you had to cough up more than you’d initially invested.
  • Case 2: The “Blind Spot” Stock – Expecting a regulation to choke a firm’s earnings, you shorted the stock. Instead, an unexpected partnership revived its valuation, and the price shot up wildly. Your short became an unbounded loss.

Shorting can feel like riding a roller coaster: you’re screaming while watching the line spin. If you want to juggle that dare, double‑check whether you really have the tools in your toolbox. If not, staying on the long side might be the smarter, more comforting route.

My investment club


  • My Journey Through the Witty World of Kairos Research

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  • What’s Kairos, Anyway?

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  • Kairos Research isn’t your run‑of‑the‑mill investment club – it’s the brainchild of three rockstars: Stanley Lim, Cheong Mun Hong, and Willie Keng. These same guys also launched the Value Invest Asia portal, the go‑to spot for hand‑picked, top‑tier investment wisdom that’s laser‑focused on Asia.


  • Why I’m Still All‑Hearted About It

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  • I’ve been rocking the club for years.
  • I’ve made lifelong friends: brilliant, humble, and a second‑hand alma mater of wit in every sense.
  • The club felt like a bootcamp for the soul – learning to invest and becoming a better human at the same time.

  • The “Intellectual Toll” You Pay

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  • To stay in the club, you only need to contribute one fresh stock‑market idea per year.That’s my membership fee, and I’ve gladly paid it for ages.It’s a tiny price to sweep up growth, both in portfolio and personality. And guess what? I’ll keep paying this fee as long as I’ve got a brain to dream up a new idea.

    Riding all the way up

    Luckin Coffee: A Wild Ride From Boom to Bust

    June 2019 – The ‘Lucky’ Moment

    In June 2019, our club gathered, and one of the most respected investors in the room cracked the whip on Luckin Coffee (NASDAQ: LK). He talked about a company that’s trying to be a coffee‑cue‑Big‑Ip in China, taking the thriving “take‑away” scene by storm.

    From Startup to Superstore Frenzy

    • Founded: Late 2017
    • By next year, 2,000+ stores across China – that’s faster than most tech unicorns can grow.
    • Target: To be the biggest coffee hit next to Starbucks, which views China as its biggest growth playground.

    The Stock Market Rollercoaster

    Back then, the stock’s hovering around $20 ( 28) – pretty close to its IPO close price from May 2019.

    Fast forward to January 2020: our savvy clubmate dumped his shares as the stock screamed its peak at $50. Today, the price pokes around $4.

    Why the Collapse?

    A single day, April 2, 2020, saw the price dive 76% from $26, and the downward spiral kept rolling. NASDAQ even slapped a trading halt on Luckin’s shares to pause the chaos.

    In short, a rapid rise followed by an even quicker fall – a classic case of a startup that grew fast enough to ask the market, “Can I reinvent the coffee grind?”

    Not the first time…

    Luckin Coffee’s “Cash‑Croc” Crisis

    In January 2020, the gossip‑machine Muddy Waters Research dropped a bomb: Luckin Coffee had staged a fraud of its own.
    Luckin, however, was quick to shut the door and deny the claim. The market didn’ explode this time – the stock only yawned a little.

    Gradual Slide & Global Panic

    Later that year, the share price fell, but the whole world margin shrank because of the Covid‑19 storm. It wasn’t the bank’s fault – it was the market’s.

    April 2, 2020 – The Reality Check

    On that day, Luckin announced a real rear‑view mirror – the board started an internal probe into the alleged fraud.

    • Fraud covered 2nd to 4th quarter of 2019.
    • Amount: RMB 2.2 billion (≈ $430 million).
    • Revenue for 12 months – end 30 Sep 2019: $470 million.

    Investors now can’t trust the previous financial statements for the 9 months ending 30 Sep 2019.

    Liu Jian – The Face Behind the Smoke

    The Chief Operating Officer, Liu Jian, was named the main culprit and has been suspended from his role.

    Will There Be More?

    When the bus finally shut down, it didn’t simply stop at that one cobweb. The “cockroach” story isn’t just a one‑foot tale – it’s a whole kitchen if you start looking around.

    As Warren Buffett famously said: “What you find is there’s never just one cockroach in the kitchen when you start looking around.”

    It’s tough being short

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    What Luckin Really Did (The Untold Story)

    “Mooning” from April 2019 to Jan 2020

    • First red‑flag: Muddy Waters rang the alarm in January 2020.
    • Turns out, the real party started in April 2019.
    • Stock? Yo‑yoed up 59 % in that span.
    • And once, it saw a near‑150 % jump—talk about a roller‑coaster.

    Shorting Luckin: A Lesson in Financial Fashion Faux Pas

    Picture this: you’re all set to flip a whole box of Luckin Coffee shares in April 2019 – you’re confident, you’re slick, you think you’ve got the inside scoop that the company is about to reveal some sun‑burnt secrets. But when the market shakes up, you find that you’ve lost more money than you originally staked.

    Why Shorting Can Be a Deal‑breaker

    • Timing is everything: Even if you’ve nailed the fundamentals, a wrong moment can cripple your position.
    • Negative gearing anxiety: Unlike a regular long‑position, the downside is unlimited – you’re not capped at your initial investment.
    • Feel the burn: Luckin’s infamous fraud scandal turned a short pot into a hot, burning mess, turning potential profit into a scalpel‑sharpened loss.

    Shortening the Laughs – How Much You Could Actually Lose

    Shorting isn’t just about a back‑to‑the‑future “who will pull the rug out from under the trader?” It’s about the terrifying possibility that the price dance could push you deeper into the red than your original bet. That’s why a lot of investors dodge the short side unless they’re absolutely sure they can survive the fallout.

    Long‑Term “Ride the Wave” Strategy

    In contrast, playing the long side with no leverage is a far less nerve‑wracking bet. If you’re riding the stock wave for the long haul, a temporary dip is just a blink of an eye. You don’t have to be a time‑teller’s wizard; you just hold, and the market smooths things out over the long run.

    Bottom Line

    • Shorting is a double‑edged sword – you need both crisp fundamentals and perfect timing to avoid turning your trade into a “more loss than you put in” nightmare.
    • Going long stays comfy if you steer clear of leverage, letting the market give you a gentle nudge rather than a hard slap.

    Shorting Luckin Coffee in 2019? A gut‑twisting reminder that the markets can be a brutal referee. Tune in, learn the lesson, and keep your future trades a bit less dramatic.

    Even the legend fails


  • Jim Chanos: Legend of the Lengthy Short‑Squeeze

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  • Who’s this guy?

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  • A wall‑street wizard who built his name out of shorting stocks.
  • Most famous for calling Enron’s collapse a “bad‑boy finale”, whose fallout sent the company crashing and executives getting a no‑excuse‑tour to prison halls.

  • Why His World Holds a Secret

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  • It all started in 1985 when Kynikos Capital Partners launched its flagship, a barefoot‑short partner called Ursus.* The fund’s exotic math:

  • 190 % long & 90 % short—net‑long by design, but the real brainpower goes into short bets.
  • Longs? Think E‑Funds and passive moves, so the heavy lifting is in hunting down bad guys.

  • The “Double‑Down” Strategy (Its Risk‑Double‑Reward Skillset)

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  • Chanos says: “Protect your downside with shorts, and your risk can actually double.”
  • Over 32 years, Kynikos poured its net annualized gain at an impressive 28.6 %—roughly twice the S&P 500’s raking haul.

  • But What About That Little Short Arm, Ursus?

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  • The short side of his vehicle, Ursus, turned out to have been giving its investors a big oops: a –0.7 % yearly loss from 1985 till the end of 2017.
  • Marked for a ghastly 32‑year drizzle of negative returns, the short side proved to be a little tragedy in a saga that’s otherwise a bumper‑car victory.

  • In a Nutshell (Why the Internet Hums)

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  • Jim Chanos, the short‑selling icon, turned his very shorter arm into a disappointment.
  • Yet his whole operation still waltzed past the market, booming at a steady tempo of 28.6 %—proof that a portfolio can outshine its own mis‑steps.
  • Feeling petty? Don’t blame the short side; it just had an off day for 32 years in a whirlwind that turned the good‑derby of your changes into a triumphant one‑liner.

  • Remember:*

  • Stay skeptical, keep your eye on the big picture, and double‑check whether the “short” side is performing or generating a heart‑breaking story.
  • If you’re buying into a fund, consider the full story—even legends may have a short‑sell glitch that’s surprisingly innocent.*
  • My conclusion  

    Why Betting on Weak Stocks is a Bad Idea (and Shorting is Even Worse)

    Shorting a stock is like betting that the company’s house will collapse—high risk, high reward, but you’re playing against the universe’s unlimited appetite for losses.

    Red‑Flag Checklist for “Chilly” Stocks

    • Weak balance sheets – Picture a company that can’t even keep its lights on.
    • No free cash flow – They’re spending more than they’re making, and that’s a recipe for disaster.
    • Rapidly declining industries – If the whole sector is dying, the company is just one grim addition.

    Long positions: The Safer Road

    When you buy a stock (“go long”), your upside is potentially limitless, while your downside is capped at the money you invested. It’s a classic one‑way street: you can only lose what you put in, but the sky’s the limit if the company thrives.

    Why Shorting is a Double‑Edged Sword

    Shorting means betting against a company—your potential loss is theoretically infinite, whereas your maximum gain is capped at 100 %. Plus, if the company surprises the market, you could be stuck in a price roller coaster that’s impossible to unwind.

    Bottom Line

    • Spot weak stocks first, then skip them—avoid the risk of shorting altogether.
    • Shorting is only worth it if you’re okay with unlimited losses.
    • Invest with the mindset that going long is a safer bet with controlled downside.

    Curious about how the pandemic is affecting markets? Check out our latest coronavirus updates on the platform—no links, just fresh info!

    This article was originally posted by The Good Investors.