Dennis Kelleher on Deregulation and Financial Bull(…)

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.

Barry Ritholtz, founder and CIO of Ritholtz Wealth Management and host of the hit Bloomberg podcast Masters in Business, returns to Boxes and Lines to talk about his new book, How Not to Invest. Rather than presenting a traditional “how-to” manual, the book emphasizes what investors should not do, covering bad ideas, bad numbers, and bad behaviors. He joins Ronan and JR to break down everything from sketchy media advice to the famous bad trades of industry pros, why he believes market forecasts should be taken with a grain of salt, and why doing less might actually make you a better investor. 

In Part 2 of our conversation with Diana B. Henriques, the Wizard of Lies author and veteran New York Times financial journalist takes us even deeper into the world of Bernie Madoff. She shares what it was like to sit across from him in prison, unraveling the psychology behind his massive Ponzi scheme and the ways he manipulated not just his victims but everyone around him. Diana’s book became the basis for the HBO film Wizard of Lies, starring Robert De Niro as Madoff. And in an unusual twist, she played herself in the movie. What was it like to act opposite De Niro, a method actor who studied Madoff’s mannerisms with almost obsessive precision? And did stepping into Hollywood change the way she saw the man she had investigated for years? Give it a listen! 

Bernie Madoff was a market structure pioneer, a former NASDAQ chairman, and one of the most trusted names on Wall Street—bona fides that allowed him to architect the largest known Ponzi scheme in history under the noses of regulators. In this first episode of our two-part look at Madoff, Ronan and JR sit down with New York Times journalist Diana Henriques, author of The Wizard of Lies, which also inspired the HBO movie starring Robert De Niro. Diana, who was the first journalist to interview him in prison and played herself in the film, discusses Madoff’s early rise in electronic trading, the mechanics of his $65 billion Ponzi scheme, and how he kept finance’s biggest players on the hook for decades.

It’s Boxes and Lines Lite, where we break down the biggest market stories in just 10–15 minutes. This time, we’re tackling the DeepSeek disruption—the surprise AI breakthrough out of China that sent Nvidia’s stock plunging, erased $600 billion in market value, and wiped nearly $100 billion from tech billionaires’ fortunes. Ronan and JR break down why markets reacted so dramatically, how DeepSeek’s low-cost, high-performance AI models are shaking up the industry, and whether this is just another dot-com-style overreaction or a real shift in the AI arms race.