Aaron Klein started Riskalyze in his basement in 2011, grew it to 35,000 users, and in 2023 handed the CEO role to someone else. He's candid about why: leading a PE-backed company called for a different skill set, and he wasn't sure he was made for it.

We spend most of the conversation on The Hard Thing About Hard Things, which Aaron read in 2014 while the company was growing tenfold and running short on cash. He shares how he applies Horowitz's idea of hiring for strength rather than lack of weakness, including the interview questions he uses to "convict the candidate of greatness" and an unusual question about a candidate's parents.

We also cover Extreme Ownership, wartime versus peacetime leadership, Choosing to Cheat, and the book he'd put on every RIA leader's shelf, The Sacredness of Secular Work.

If you've ever wondered whether you're still the right person for the seat you're in, this one's for you.

Why do clients agree with the plan and then never act on it? Derek Hagen has spent years on that question, as an advisor, a financial therapist, a life planning trainer for other advisors, and now at Root Financial.

We get into motivational interviewing, including the one-to-ten scale Derek uses to help a client finally act on a concentrated stock position they keep agreeing to sell, and the listening gap that leads advisors to answer the question they assumed the client asked.

We also cover life planning, and why "what are your financial goals" is the start of the conversation rather than the end. Derek shares the questions and exercises he uses to find out what the money is for, drawing on Facilitating Financial Health, Stumbling on Happiness, and The Top Five Regrets of the Dying.

If you've ever had a client agree with your recommendation and then never act on it, this one's for you.

Jerry Cobb read The Odyssey in ninth grade, the same year he lost his father. Decades later, he tracked down the exact 1957 edition he read as a teenager, and opening it again felt like the book finally coming home to him.

Jerry is a Senior Business Management Consultant at Charles Schwab and helps lead the Schwab Executive Leadership Program. We trace the book forward into his own atypical path from journalism into wealth management, and what he only recognized as a through line once I asked him about it directly.

We also get into Grant, Ron Chernow's biography of Ulysses S. Grant, and what it taught Jerry about the loneliness of leading, the reading list behind Schwab's leadership curriculum, and John Kotter's eight-step framework for change.

If you're leading people through decisions that never feel entirely comfortable, and you want a reading list to go with it, this one's for you.

Spenser Segal spent sixteen months and 27 interviews writing the book behind a moonshot he's chased for two decades: closing the gap between the sliver of people who get world-class financial advice today and the far larger group who could, with AI.

He joins me for the first Author Chats episode to unpack his book, The AI-Enabled Future of Wealth Management: why a firm without clean data is building a skyscraper on sand, and what an agentic mesh of specialized AI agents can do to prep an advisor for a Friday meeting before they open a laptop.

But his real argument is that the AI is the easy part: the firms that win will be the ones whose leaders treat this as an organizational capability problem, not a technology decision, starting with the change management most firms underestimate. We get into what that looks like day to day, and the line his whole book builds toward: human-AI synergy at the speed and strength of trust.

In 2001, on vacation, Chip Munn finished The E-Myth at two in the morning and sketched his first org chart on the only paper he had: the back of a paper plate. He kept that plate for twenty years. He joins me to talk about the book that started it, and where twenty-five years of building on it took him: EOS, a hundred-year firm, and a plan to hand it all to the next generation.

Dan Wanous got into wealth management at a New Year's Eve party. He was a junior in college, talking macro econ with a family friend who ran an advisory firm in Sioux Falls, South Dakota, and got hooked interning there the following summer. A decade at Thrivent later, he landed at 49 Financial and helped launch its sister firm, Alongside, where he now leads business development and partner growth.

Dan and I spend most of our time on Strong Ground, Brené Brown's newest, and two ideas he'd already underlined before we hit record: compensatory injuries, the notion that the thing that hurts is rarely the thing that's broken, and pocket presence, the football term for confidence built on preparation instead of fear or arrogance.

We also get into Katharine Graham's Personal History, the story of a woman who inherited the Washington Post after her husband's suicide and built it into the paper that broke Watergate, and Scaling People, Claire Hughes Johnson's field manual for hiring and onboarding that Dan says he's pulled off the shelf mid-crisis more than once.

If you care about staying composed under pressure, reading with intention, and building a team the right way, this one's for you.

Thomas Pargett didn't set out to become a wealth advisor. He spent four years teaching fourth grade in Lincoln, Nebraska before a mentor told him something that stuck: the best advisors are the best teachers. A decade, an MBA, and a CFP later, he's advising clients across the country at Boulay Wealth and he's become one of the most curious readers I know.

To kick off The Advisor Library, Thomas and I get into the books that shaped how he thinks, leads, and advises. We dig into Four Thousand Weeks and what changes when you remind a client they might have five hundred weeks left, not five thousand.

We talk about The Go-Giver and why, for Thomas, the more he gives the better things seem to go. And we get into the human side of the job: reading "like a wolf eats," the last time you pick up your kid without knowing it's the last time, and what keeps advising personal as AI reshapes everything around it.

If you care about reading, leadership, and the craft of advising well, this is a good place to begin.