12 Investing Mistakes You’ll Keep Making
🪤 Even When You Swear You’ve Learned
It’s Sunday night, you put the book on the table to take a break: you’ve spent the weekend reading about discipline, process, edge. And you tell yourself: this time, I won’t fall for the same traps.
But guess what happened three months later?
You’re staring at your screen like a guy waking up after a bad night out, trying to piece together what happened. Down 30%. Out of conviction. Or fear. Or even pride.
Who knows anymore?
Here’s the sad truth about our own human condition: we all make the same mistakes. Over. And over again. Even the ones writing newsletters about them (aka me). But don’t loose faith, one day you’ll learn. Until we reach this point, I want to highlight to you these 12 mistakes you’ll keep making — and the real companies that show what they look like when they blow up in the wild.
1. You think it’s just “one red flag”
In 2018, Wirecard had some “weird stuff” going on. An office in Singapore that didn’t exist… Funds in the Philippines that nobody could confirm…
But hey — one-off issues happen, right?
No.
Anomalies aren’t bugs. They’re smoke. In investing, no smoke and mirrors.
And when there’s smoke… you’ll find the mirror broken into pieces (your portfolio).
2. You confuse hype with momentum
Peloton was everywhere.
The product was slick, the branding worked, the narrative was viral. It was cool as hell.
But the stock wasn’t climbing because people loved spin class: it was funds chasing liquid COVID darlings. And so when the hype cooled and the comps turned south, the valuation imploded.
Hype is about stories. Momentum is about money. Know which one you’re riding… Don’t fall for the same traps
3. You cling to your original thesis like a security blanket
Teladoc overpaid for Livongo by billions.
The synergy was wishful and the narrative tired. However you held on, because you remembered the COVID bull run and told yourself: “Telehealth is the future.”
Maybe it is, we can agree on that — (Look at Hims And Hers ($HIMS), that company is crazy) — but that doesn’t mean this business is.
4. You think the market gives a damn about your cost basis
ARKK holders doubled down on Roku, Zoom, Teladoc — anything that was down 40%.
Then 60%. Then 80%. “I’ve lowered my average,” they said.
Ahahahaha Cool. But guess what genius, Mister Market still doesn’t care. Your portfolio isn’t a redemption arc. Is this a game to you?
5. You think illiquidity means opportunity
In 2020, Grenke (I wrote about it btw) — a sleepy German leasing firm — got slammed by a short report: accusations of fake cash, shady acquisitions. Anyway, nasty sh*t.
The stock tanked. But worse? You couldn’t exit. No bids, no liquidity….
Microcaps feel like secrets and your next good idea until they feel like traps. And it’s you inside. That’s what you should always be careful with micro caps.
6. You think you can time earnings
Remember Meta in late 2022? Let me summarise the situation: everyone thought they were genius and thought the pain was priced in. « Zuck was gonna pivot. Focus. Cut spending. »
Instead? Reality check: he doubled down on the metaverse and dropped another $13 billion into the void and the stock lost 20% overnight.
If you think you can time the market and even earnings…you’re playing earnings for the bounce… you’re not investing. You just try guessing. Go play Poker Star ⭐️ instead.
7. You confuse long-term conviction with denial
Intel still had fabs, patents, government love and meanwhile, AMD was eating their lunch and TSMC out-executing every quarter… Every QUARTER.
But hey — “undervalued long-term compounder,” right? Right? Huh? ?
Sometimes, so called “long-term investor” is just code for “too scared to cut.”
8. You think doing more work makes you more right
(Very personal take here)
→ Alibaba bulls read every report.
→ Built models, mapped VIE structures, tracked spin-offs.
Wow congratulations for the homework John, but the stock didn’t care. Because what mattered wasn’t their spreadsheet — it was Beijing’s mood. Real life.
More homework =/= more alpha. Sometimes it’s just more pain.
9. You ignore insider selling
You think you are more than this?
After Beyond Meat’s IPO, insiders dumped shares en masse. It wasn’t subtle but the story — vegan revolution, health, ESG vibes — was too strong to ignore.
You tell yourself: « they’re just diversifying » but when insiders bail hard and early, take the hint.
10. You don’t read between the lines
Deliveroo would issue updates like:
“We remain confident in our positioning amidst macro uncertainty.”
Sounds okay but there were no numbers. No conviction at all: just vague vibes. So If a company is only using adjectives, you should probably sell the noun…
11. You hold because it once made you money
NIO made you feel like a genius in 2020.
+1,000%. Clean tech, EV hype, China dream.
Now?
The cash burn’s real, competition’s brutal, and your gain has vanished.
But you still hold — not out of belief, but out of memory.
Let go.
Your portfolio isn’t a scrapbook.
12. You assume others know better
When GameStop and AMC blew up in 2021, most people froze.
“I’m out — this is irrational.” But then you saw hedge funds chasing retail. Funds chasing each other nobody had the script anymore. You stayed out. Or jumped in late. Either way, you deferred to the herd and the herd was scared shitless too.
You’ll make these mistakes. Again. But don’t worry, me too. Cause the market’s not a checklist. It’s a pressure cooker. You’ll panic-sell winners. You’ll double-down on losers… You’ll fall in love with your model, your thesis, your cost basis…
The trick isn’t to be perfect.
It’s to get quicker at realizing when you’ve slipped so maybe next time, you’ll spot the pattern early. And maybe you’ll catch your hand on the stove before it burns.
And maybe — just maybe — you’ll scratch the ticket, see “LOSER,” and smile, because this time… you knew it was coming. 😌
This analysis is for informational purposes only and does not constitute financial advice or investment recommendations. Investing in financial markets involves risks, including the risk of loss of capital. Always do your own research or speak with a qualified advisor.
Good points, and great writing. Funny.