Stefan Cheplick

Trading & Investing Insights

  • You Heard It Once and Now You’re Fooled

    I think anyone who works in markets gets more jaded and more skeptical at a faster rate than those who don’t. Like old man jaded. A get-off-my-lawn-grandpa kind of way. Lately, I’ve taken a new approach to all the things people say in markets. The adages and phrases that have been passed down for generation…

  • You Thought The World Was Ending, You Thought Wrong

    The other day a friend and I were talking. We were walking outside Bryant Park in New York City. The humidity was high. Imagine stretching your hand out and grabbing warm lake water out of thin air. That’s what it felt like. While talking with my friend, a cool dude with artist style vibes and…

  • It’s Newer Than We Think But It’s Happened Before

    The iPhone was released 12 years ago. Social media is only 15 years old. Virtual reality in its retail form is 7 years old. Or less. Autonomous driving on a mass appeal is barely 5. It’s easy to lose sight of how young these products really are. We see emerging tech daily in the news…

  • The Greatest Hoax of All-Time

    “You have to be so smart to understand that.” “I could never do that, I’m not smart enough.” The greatest hoax of all-time is certain industries, professions or fields of work telling everyone else they’re not smart enough to do what they do. The greatest hoax is making certain professions or fields of work appear…

  • Then and Now

    Change is hard. It’s a grind. No one changes in a day. Or a week. Or a month. I think there’s nothing more important than perspective. Perspective is how you learn to embrace the long grind of change. Who you were a month ago and who you are today are not very different. Who you…

  • Swinging For The Fences In Markets and Life

    I’ve now spent 10 years in the stock market. And I’ve spent seven working directly with the people who make it what it is at StockTwits. There have been ups. There have been downs. But that is true with anything. You will never find a perfect “thing” that has no ups or downs. What you’ll…

  • Slowing Down While Everyone Taps More

    I am reminded of how easy it is to do something online. You can write, reply, like, report, and follow in a second or less. Tap the button, and mission completed. Action, feedback, reward. We’ve all been taught about Pavlov’s dogs. Or most of us have at least heard of them. Ironically, that’s what we’re…

  • Smart People Don’t Do Dumb Things In Seven Seconds

    It’s said we judge the people around us within the first seven seconds of meeting them.I think something similar happens online. I don’t know what the scientific word is for this, but one image, video, or headline from a Twitter account can push us from 0 to 100 (real quick). The speed from the time…

  • You Are Always Going Up Against Something

    “They’re not gonna give it to you? So what? You’re gonna take it. You’re gonna do whatever it takes. Do you hear me? You’re gonna go your own way. You’re gonna do what they won’t do. You’re gonna be smart. You are gonna cut corners, and you are gonna win. They’re on the 35th floor?…

  • The Importance Of Cash

    A group of Maryland students sat waiting in a classroom on campus. It was 2013. And then, Warren Buffett walked through the door. I don’t know how he came to be there or the purpose of his visit. But, the professor of that class, David Kass, took notes as his students searched for guidance and…

  • What I Learned About The Stock Market In 2018

    I took abnormal risk. I had abnormal gains. I had abnormal losses. That’s what happens. But it happens to everyone. In his thirties, Ray Dalio lost everything. He had to sell his car and borrow $4,000 from his dad to get back on his feet.

  • Taking The Other Side

    A lot of people have been telling me I’m crazy. This is not the market you want to be buying dips in, they say. Don’t do it. Run away. Everyone has done stupid things. I have done many throughout my life. But when I reflect on them, I realize most of the worst decisions share…