Your Brain vs. Your Portfolio — With Daniel Crosby

What good is an investment strategy if you can’t stick with it? Jared Dillian, editor of The Daily Dirtnap, returns to Boxes & Lines to talk with Ronan Ryan and John Ramsay about his latest book, The Awesome Portfolio, and his case for making investing less stressful. He shares how losing half his net worth after Lehman Brothers collapsed changed his approach to risk and why your paycheck and portfolio may be more connected than you think. Along the way, he explains why gold is the "Dennis Rodman" of asset classes, makes the case for keeping cash handy, and what it's like to DJ with Goldman Sachs’ David Solomon.

Psychologist Daniel Crosby, Chief Behavioral Officer at Orion and author of The Behavioral Investor, joins Ronan and JR to get to the bottom of why smart people sometimes do questionable things with their money. They talk about sports betting culture spilling into investment accounts, the trouble with chasing headlines, and whether AI can improve our judgment or leave us all making the same trades. Daniel also makes the case for Diet Coke as currency. Hear him out.

After more than 50 years in markets, investing legend and billionaire David Booth has learned a thing or two about keeping perspective. The founder of Dimensional Fund Advisors joins Ronan and JR to talk about his new book, Stay Calm, and what decades of data can teach us about uncertainty and the power of public markets. Booth weighs in on the rise of index investing, why he’s a fan of HFT, and why trying to outsmart the market may not be worth the trouble. Plus: what investing can teach us about careers, compounding, and what it really means to be wealthy. 

Nine interns. Two hosts with varying levels of preparation. Our 2026 intern class joins Ronan and JR to talk about what surprised them about working in finance, how they’re actually using AI, what Gen Z wants from work, and what they’ve learned about starting a career. Plus, the interns turn the questions on Ronan and JR, including what they’d do differently if they were starting over at 22. Hit play! 

JR and Ronan sit down with Tom Chippas and Matt Trudeau of Rothera, a new federally regulated prediction and event markets exchange. Drawing on decades of experience across exchanges, trading, and market structure, they discuss how prediction markets work, how they're regulated, and whether they represent a new horizon of financial infrastructure or something else entirely.

Most people know Aaron Burr as the man who killed Alexander Hamilton. But what if that's the least interesting thing about him? In this special Fourth of July B&L re-release celebrating America's 250th birthday, Jayme Abrahamsen (IEX Exchange Business Development) and Andy Kaplan (Greenlight Capital and Freedom's Edge Cider) explore how Aaron Burr became one of history's greatest villains and why his legacy may deserve another look. Original airdate: January, 2023.

What happens when $84 trillion changes hands? In this episode of Boxes and Lines, Ronan and JR talk with Stephanie Luedke, Head of Private Wealth at Neuberger Berman, about the forces reshaping wealth management. Stephanie discusses the massive generational transfer of wealth underway between boomers, Gen X, and millennials, how younger investors are changing expectations around values-based investing, and why trust will always remain at the center of financial advice. She also reflects on her unconventional path from aspiring ballerina to finance, women’s shifting presence in financial services in recent years, and the money advice her dad gave her that’s stuck with her years later. 

Ronan and JR sit down with Ben Carlson, Director of Institutional Asset Management at Ritholtz Wealth Management, co-host of the Animal Spirits podcast, and author of the new investing book Risk and Reward. The book uncovers one of the hardest truths in investing: there’s no secret formula. Ben gets into how investor behavior matters more than stock picking, how volatility and uncertainty shape decision-making, and why long-term discipline still beats chasing the latest market craze. Plus: pushups as currency.

Ronan's boyhood dreams come true when New York Giant Phil McConkey, who was part of the team's 1986 championship win, stops by Boxes and Lines. Phil entered the financial services world after retiring from the NFL in 1989, later joining Academy Securities where he is now vice chairman. Academy Securities is a disabled veteran-owned and operated investment bank, and nearly half of its employees are military veterans. This includes Phil, who served as a Navy officer and helicopter pilot before joining the Giants at the age of 27. Phil joins Ronan and JR for a wide-ranging conversation about the connections between football and finance, leadership and what it means to fail and get back up - even when you still feel like "the skinny kid from Buffalo."  

“Retail investor” used to mean one thing: long-term and passive. Not anymore. In this episode of Boxes and Lines, Ronan and JR unpack how retail trading has grown into a wide spectrum: from traditional hands-off 401(k) investors to 24/7 app-driven traders navigating options, predictions markets, and beyond. Plus: JR goes full “concerned grandfather.” Hit play.