3 investment mistakes that cost me a lot of money, involving: ·...
Investing visuals@InvestingVisual
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Oct 16, 2025
~2 min read
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1
3 investment mistakes that cost me a lot of money, involving:
· $UPST
· $BABA
· $TSLA
I figured it’s time to share more about my personal investment journey. So let’s start with my biggest mistakes.
Let’s dive in!🧵👇
· $UPST
· $BABA
· $TSLA
I figured it’s time to share more about my personal investment journey. So let’s start with my biggest mistakes.
Let’s dive in!🧵👇
2
$UPST - Main mistake: not knowing what I owned
I bought $UPST in 2022, a few months after it got hyped as the next big FinTech and nearly touched ~$400.
I did some due diligence, but not nearly enough in hindsight. Truth is, I didn’t fully understand what they were doing (and didn't truly care either) – yet I invested at an average price of ~$90.
In the months after, a string of disappointing quarters sent the stock crashing. Instead of cutting my losses, I held on, hoping it would bounce back. That was my second mistake. By the time I sold, I was down -75%. Yikes...
Lesson 💡
Know what I own, don’t chase hype, ‘hope’ is not a strategy.
I bought $UPST in 2022, a few months after it got hyped as the next big FinTech and nearly touched ~$400.
I did some due diligence, but not nearly enough in hindsight. Truth is, I didn’t fully understand what they were doing (and didn't truly care either) – yet I invested at an average price of ~$90.
In the months after, a string of disappointing quarters sent the stock crashing. Instead of cutting my losses, I held on, hoping it would bounce back. That was my second mistake. By the time I sold, I was down -75%. Yikes...
Lesson 💡
Know what I own, don’t chase hype, ‘hope’ is not a strategy.
3
$BABA - Overestimation and dismissing risks
I initially bought $BABA in 2021 for its cloud business and what I thought was a “cheap” valuation. My average buy price was ~$197 – I basically bought and averaged up on the worst possible moment. The founder stepped down (or rather, went missing), the cloud business stagnated, and I was left holding the bag.
Worse, I dismissed the political risks. The CCP can make or break a business at will. That’s why the stock looked cheap, it was already discounted for that risk.
I eventually sold at a 50% loss, and it had even been my top position at one point. Painful...
Lesson 💡
A low valuation ≠ a good investment and don’t dismiss major risks.
I initially bought $BABA in 2021 for its cloud business and what I thought was a “cheap” valuation. My average buy price was ~$197 – I basically bought and averaged up on the worst possible moment. The founder stepped down (or rather, went missing), the cloud business stagnated, and I was left holding the bag.
Worse, I dismissed the political risks. The CCP can make or break a business at will. That’s why the stock looked cheap, it was already discounted for that risk.
I eventually sold at a 50% loss, and it had even been my top position at one point. Painful...
Lesson 💡
A low valuation ≠ a good investment and don’t dismiss major risks.
4
$TSLA – Selling too early
$TSLA will always have a special place in my investor’s heart. It was the first stock I bought when I shifted from ETFs to individual stocks. In 2019, I picked up a single share at a split-adjusted price of ~$17.
I had actually written a research paper on Tesla back in college, which first put it on my radar. But here’s the painful part: in early 2020, I sold that share for a 327% gain, thinking I was a genius. That single stock would now be up 2400% (24-bagger) and worth ~$4,416.
Lesson💡
Don’t sell too early, locking in a (minor) gain while a business still has much more room to grow, missing out on a potential 10+ bagger.
$TSLA will always have a special place in my investor’s heart. It was the first stock I bought when I shifted from ETFs to individual stocks. In 2019, I picked up a single share at a split-adjusted price of ~$17.
I had actually written a research paper on Tesla back in college, which first put it on my radar. But here’s the painful part: in early 2020, I sold that share for a 327% gain, thinking I was a genius. That single stock would now be up 2400% (24-bagger) and worth ~$4,416.
Lesson💡
Don’t sell too early, locking in a (minor) gain while a business still has much more room to grow, missing out on a potential 10+ bagger.
5
Final words
My mindset is that I’m either successful or I learn. That’s also true for every business I have in my portfolio.
It’s either a successful position, or I learn why it wasn’t. Win-Win! It’s this mindset that really helps me embrace my mistakes because they make a better investors.
Knowledge compounds over time, just as stocks do!
Cheers to the weekend!🍻
My mindset is that I’m either successful or I learn. That’s also true for every business I have in my portfolio.
It’s either a successful position, or I learn why it wasn’t. Win-Win! It’s this mindset that really helps me embrace my mistakes because they make a better investors.
Knowledge compounds over time, just as stocks do!
Cheers to the weekend!🍻