Ben Simpson reflects on the emotional difficulty of crypto investing, emphasizing that losses feel far worse than gains. He recounts a painful 2017–2018 altcoin mistake (Haven → synthetics) where he sold at a large loss and later missed outsized gains, and explains that mitigating downside risk and removing emotion (e.g., using a performance coach, rotating underperforming coins into more liquid assets) improved his results.
Chapters
No one told me this would be the hardest part of crypto and that is that losses feel so much worse than the upside feeling of gains. Now a lot of you are probably feeling this when you're in crypto. You buy something goes down. That pain, that feeling, that guilt, that shame that comes with losing money is so real. The worst trade I made was back in 2017, 2018. I got into an early stage altcoin and I was impatient. I didn't know what was going on with the project. It was, it was called Haven back then, flipped into synthetics and I sold 100% of it at a loss, huge loss. And in the, in the coming weeks and months, that project did a phenomenal run. You know, probably worth in the millions that I would have made and said I made absolutely nothing. I lost money. And that feeling of like shame and guilt and watching that coin run up and losing it, a loss was so painful. And if you compare that to where I made life changing amounts of Money back in 2021, where I made a lot of money until profits, it was nowhere near the same. In fact, it felt so much worse in the pain. And that has stuck by me this entire time of any crypto. It's the reason I got a performance coach to help with the mindset side of things. Because crypto is so painful. You can never win. You feel as though you can never win. Even if you make money, you don't make enough. And when you lose, you lost too much and you could have made more. So for me, what I realize now is being able to mitigate my downside risk and understand the losses feel more painful and I take the emotion out of it. Especially when your portfolio is down and your old coins are not performing. That pain of selling at a loss is so great, but it is where I made my best trades in the last 12 and 24 months. I sold a lot of my coins that were down back at the start of the year that I shared with our members that was gaming AI rwas that just weren't performing. I rotated those coins into hyper liquid. Hyper liquid's gone up 150, 140% since then. Those coins that I sold were down 25% and now down close to 60% since then. So the pain I felt when I sold was, yes, great. But what I would have felt now if I continue holding was so much greater. So that is why you've got to take the emotion out of it, realize it's going to be painful, but you've got to make the tough choice in crypto. And that is why crypto is so hard to make money, although everyone thinks it's easy.
