330 · Steve Quirk - From Chicago Pit Trader to Robinhood Exec

Steve Quirk began his career in 1987 on the fast-paced trading floors of Chicago, surviving the historic market crash that wiped out $1.7 trillion worldwide.
From navigating open-outcry pits where a trader's word was their bond, Steve transitioned into market technology, helping build landmark tools at thinkorswim and leading trading strategy initiatives at TD Ameritrade. Today, as Chief Brokerage Officer at Robinhood, he sits at the intersection of retail investing, market structure, and financial innovation, shaping products for millions of retail investors.
In this conversation, Steve shares key lessons from decades in the markets, the evolution of retail trading technology, and how removing friction like the Pattern Day Trader rule is unlocking the next era of retail investing.

In this episode, we explore:
• Steve’s early days in the Chicago trading pits in 1987
• Why decisive decision-making and accepting being wrong 50% of the time is crucial
• The transition from floor trading to building technology at thinkorswim
• How Robinhood levels the playing field for retail investors and opens up global access
• Managing risks: framing the absolute worst-case scenario before taking a trade
• The impact of removing the Pattern Day Trader (PDT) rule for retail traders

About Steve Quirk:
Steve Quirk is Chief Brokerage Officer at Robinhood Markets. With over 35 years of financial markets experience, he previously led trading strategy at TD Ameritrade, developed innovative trading tools for thinkorswim®, and created the TD Ameritrade U program. Steve started his career in 1987 in the Chicago open-outcry pits across the CME and CBOE, and is a frequent market commentator featured on CNBC, Fox Business, and The Wall Street Journal.

Links + Resources:
LinkedIn: https://www.linkedin.com/in/steve-quirk-56148a22/
X (Twitter): https://x.com/SteveQuirk_

Sponsor of Chat With Traders Podcast:
Trade The Pool: http://www.tradethepool.com

Time Stamps:
Please note: Exact times will vary depending on current ads.
00:00 From Chicago Pit Trader to Robinhood Exec

02:57 What Pulled You to the Market?

07:17 Trading Pits Are More Organized Than They Appear

11:51 Transitioning to Creating Technology for Retail Trading

19:01 Leveling the Playing Field for Retail Traders

21:10 Giving People What They Want

24:45 Did You Fall in Love with Scaling Robinhood Like You Did with Trading?

29:48 What Robinhood Is Doing to Teach

32:12 Early Mistakes in Trading

34:31 Advice to People from Robinhood CBO

36:44 What's Your Next Product Going to Be?

40:24 What Is the PDT Rule?

43:23 What Is a Memory That Came to Mind in Your Trading Career?

45:16 Is There Anything in Your Life That Changed Your Line of Thinking?

46:22 Your Piece of Advice to Your Younger Self

46:57 Where Can Traders Find You?

Trading Disclaimer:
Trading in the financial markets involves a risk of loss. Podcast episodes and other content produced by Chat With Traders are for informational or educational purposes only and do not constitute trading or investment recommendations or advice.

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