The Right Leader for Each Chapter: The Books Behind Riskalyze and Its Founder, with Aaron Klein
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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.