Stefan Cheplick

My thoughts on trading & investing

A Quick Reflection on My Career

The other day, someone asked me a simple but loaded question: What projects are you most proud of in your career?

It made me pause.

Since graduating in 2012, I’ve spent seven years at Stocktwits and more than five at TradingView. That’s what I love about my path. I go deep. I build things for the long term.

I remember when Robinhood was a scrappy startup. Meanwhile, we were building content, tools, and products to help people talk about markets and understand them. If you saw the charts and market memes circulating from 2013 to 2015, there’s a good chance you came across something we had a hand in.

At the time, I thought that was escape velocity. In hindsight, it was just the beginning.

My career. A changing industry.

Open a milestone to read more. Career memories alongside changes in the industry; some dates are approximate.

2012 The starting point

My path
I graduated in 2012. The years that followed took me deep into the world of trading, investing, and online communities.

Early years Stocktwits & the social market

My path
Seven years at Stocktwits, building content, tools, and products for retail investors. Charts, conversations, newsletters, and the early market memes were part of our daily work.

Around 2014 Stocktoberfest: the community in person

What I remember
In the early Stocktwits days, Stocktoberfest brought the online trading community into the same room. Traders, founders, and people building tools for investors. It was an early look at the industry taking shape around us.

2014–2015 Our first market memes

What we were making
We were posting our first market memes in 2014 and 2015, as that way of talking about stocks started taking off. Humor became part of the daily market conversation, alongside charts and news.

2014–2015 Watching Robinhood launch

What I saw
I was at Stocktwits watching Robinhood’s early launch. A new generation was getting introduced to trading through its phone. Robinhood’s App Store rollout began in late 2014 and expanded in 2015. Robinhood’s early recap ↗

Mid-2010s The rise of trader chat groups

What I saw
More of the trading day was happening in online groups. People shared charts, watched the same stocks, and reacted to news together. The community itself was becoming part of the trading experience.

2017 Crypto brings a new crowd

The industry around us
Crypto became a much bigger part of the market conversation, bringing new traders, communities, and demand for charting tools. By December 2017, CME was launching Bitcoin futures. CME announcement ↗

2018 Options take up more of the conversation

What I saw
Options were becoming a bigger part of the retail trading conversation. The volume backed it up: OCC cleared a record 5.14 billion options contracts in 2018. OCC’s year-end figures ↗

2019 The commission barrier falls

The industry
Schwab eliminated online commissions for US- and Canadian-listed stocks and ETFs, effective October 7, 2019. The economics of retail trading were changing fast. Source ↗

The next chapter TradingView & a global audience

My path
More than five years at TradingView, working on community and trader education. The audience was global, and so was the opportunity to help people understand and use financial tools.

2021 Online communities move to center stage

The industry
GameStop and the meme-stock surge put retail traders, social platforms, and market structure in the spotlight. SEC report ↗

2022 Charting becomes a shared language

What I saw at TradingView
By 2022, charting felt bigger than a tool for technical traders. Charts were how more people explored markets, explained an idea, and shared their view. Working at TradingView, I saw that shift up close. TradingView’s 2022 Desktop update ↗

2024 Markets settle faster

The industry
On May 28, the US moved most broker-dealer securities transactions to T+1: settlement one business day after the trade. Source ↗

2025 → Merchant Seven

My path
A new chapter working with fintech founders and teams through Merchant Seven. Growth, community, distribution, and the next generation of trading technology. The launch ↗

The work stays out there

One of my favorite things is finding our work scattered around the web. A product. An old chart. A newsletter, video, or piece of education. Something a teammate and I made years ago, still helping someone understand the market.

At TradingView, that feeling grew. We were building for people all over the world. Different markets, different languages, the same curiosity.

It’s a quiet kind of pride. Most people will never know who made those things. But we know.

What comes next

Today, I’m working with founders and teams through Merchant Seven. The industry keeps changing. I still want to be close to the people building it.

My work today → · Selected projects →

Written by , a fintech builder and writer with experience at Stocktwits and TradingView. Background and published work.


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