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.