Dennis Kelleher on Deregulation and Financial Bull(…)

When the government shuts down, what happens to Wall Street? In this “Boxes and Lines Light” episode, Ronan and JR get into how a shutdown grinds key market functions to a halt. Drawing on JR's experience at the SEC, they unpack what “essential” really means when 90% of staff are furloughed and explore the ripple effects through Wall Street.  

Ronan and JR sit down with David Gardner — co-founder of investor education juggernaut The Motley Fool, host of podcast Rule Breaker Investing, and author of a new book by the same title, Rule Breaker Investing: How to Pick the Best Stocks of the Future and Build Lasting Wealth. From getting booed on The View for making a dud stock pick (that later went 30x). to breaking the mold of buttoned-up Wall Street, David shares why optimism and long-term thinking can go far.

In this special episode of Boxes and Lines, Ronan and JR sit down with members of IEX’s 2025 summer intern class, mostly incoming seniors in engineering, marketing, finance, and cybersecurity, for a conversation that spans Gen Z in the workplace, what they’ve learned at IEX, and their hopes (and hot takes) on the future of work, tech, and life. Two intern panels, one insightful summer, and at least one spreadsheet created in 5th grade. The kids are alright. 

On the latest episode of Boxes and Lines, Ronan and JR welcome back Mett Kinak, Head of Global Trading at T. Rowe Price, for some real talk about market fragmentation, private rooms, and more. Mett also dispels his biggest pet peeve market structure myths, shares his skepticism about tokenizing equities, and pitches two new financial holidays—we'll raise a Bloody Mary to that. 

Subdollar stocks —those priced under $1—now make up nearly half of all share volume in U.S. markets, while contributing a fraction of the notional value (the actual dollar amount being traded). In this episode of Boxes and Lines Lite, Ronan and JR get into why this trend deserves more attention than it’s getting. From wild one-day volume spikes in penny stocks to distorted exchange market share and rebate incentives, they chat about how a handful of ultra-low-priced names are reshaping the trading landscape, and why it’s not just noise. 

We’re re-airing one of our most surprising and most popular episodes for you this week -- a deep dive into Aaron Burr from January 2023. This episode is guest-hosted by IEX’s Jayme Abrahamsen and features Andy Kaplan (former Greenlight Capital partner, now CEO of Freedom’s Edge Cider). In a previous episode, they broke down the mythology of Hamilton. This time, they turn the spotlight on his adversary, Aaron Burr. Vice President. Revolutionary War hero. Romance novel star. Duelist. Exile. They explore how Burr’s legacy was rewritten by enemies like Hamilton and Jefferson, how he became a political cautionary tale, and what it says about who we choose to put on our currency and why.

Tokenization. You’ve been hearing about it since 2017. So have we. In this short episode of Boxes and Lines, Ronan and JR unpack the hype around tokenizing stocks — what it actually means, what it changes, and what ends up left out of the conversation. They get into the post-trade plumbing, investor protections and regulatory realities. Hit play! 

IEX is often labeled a "3% market share" venue, but what does that number really reflect? In this Boxes and Lines Lite, Ronan and JR chat with IEX’s Matt Weinberg (Head of Business Development) and Sam Stevens (Head of Business Analytics) to unpack a cleaner way to think about institutional-accessible liquidity. They break down why total market share can be a misleading benchmark for routing, how "Institutional Market Share" better reflects where orders can actually interact, and what firms might be missing by benchmarking to the wrong number.

In this special FILMED episode of Boxes and Lines (watch here!), Ronan and JR welcome John Palmer and Ivan Brown, who are leading IEX’s charge into the options market. They get into what makes options different from equities, explain the rise of 0DTE (zero-day-to-expiration) contracts, and talk about the unique risks market makers face in a quote-driven ecosystem. We share why now is the right time for IEX to launch an options exchange, how IEX’s Signal is designed to detect when the market is shifting and help protect against adverse selection, and what makes this effort more than just a me-too market. Plus: JR's love for lazy rivers, 40 types of jelly, and Ronan’s lunchtime cocktail. Whether you're deep in the weeds or just options-curious, this episode peels back the layers of what’s going on in the market today.

Dennis Kelleher, co-founder and CEO of Better Markets, joins Boxes and Lines for a no-holds-barred conversation on the state of financial regulation. By the end, Ronan may or may not have entered a mild fugue state.