Plenty of founders will tell you about the company they built. Fewer will talk candidly about the moment they stopped being the right person to run it. Aaron Klein started Riskalyze in his basement in 2011, grew it to 35,000 users and about 200 employees, brought in Hg as majority owner in 2021, and in December 2023 passed the CEO role to his successor. His read on that decision is refreshingly honest: leading under private equity ownership called for a different skill set, and he wasn't sure he was made for that piece. After a year off, he's building again with Contio, an AI company designed to amplify client relationships rather than replace them, starting with wealth management and benefits brokers.
We spend much of our time on The Hard Thing About Hard Things, which landed in Aaron's hands in 2014, the year Riskalyze grew roughly tenfold during a stretch when the company nearly died at least four times. He had been searching business books for answers and coming up empty (as he puts it, he couldn't deposit culture in the bank and have it make payroll). Horowitz gave him a playbook instead. The idea he still uses is hiring for strength rather than for lack of weakness, and he walks through exactly how he applies it: three to five non-negotiable requirements, interview questions designed to "convict the candidate of greatness," and an unusual question about a candidate's parents that I suspect a few listeners will borrow.
We also get into the credenza stacked with copies of Extreme Ownership, the wartime and peacetime CEO, and Choosing to Cheat, the book he credits with changing how he showed up at home. He closes with what he's reading now, 1873, a history of the railroad financing boom that he sees echoed in today's AI build-out, and the book he'd put on every RIA leader's shelf, The Sacredness of Secular Work.
In this episode
Riskalyze's arc from a basement in 2011 to 35,000 users, the Hg deal, the Nitrogen rebrand, and the "wife-mandated" year off before starting Contio
Why being CEO turned out to be four different jobs, and how Extreme Ownership's "prioritize and execute" and "cover and move" showed up at Riskalyze
The credenza with ten copies of Extreme Ownership, and how one book spread from the leadership team to an all-hands
Rebuilding the leadership team every few years, the COO he nicknamed the "101st Airborne," and why Aaron eventually stepped down as CEO
The Hard Thing About Hard Things: three months of cash, why culture can't make payroll, and hiring for strength rather than lack of weakness
Wartime versus peacetime CEO, including the 2020 plan he tore up and still finished at 104%
How Aaron hires: three to five requirements, the four types of people he won't hire, and the parents question
Choosing to Cheat, the third-tier Friday meeting he started skipping to be home for dinner, and how he picks what to read next
Books mentioned
Extreme Ownership: How U.S. Navy SEALs Lead and Win — Jocko Willink and Leif Babin
Choosing to Cheat — Andy Stanley (later reissued as When Work and Family Collide)
1873 — Liaquat Ahamed (currently reading)
Notable quotes
"I can't seem to deposit culture in the bank and have it make payroll for me." — Aaron Klein, on why most business books didn't help during Riskalyze's toughest years
"...ask open-ended questions that are going to gather the evidence with which you can convict the candidate of greatness." — Aaron Klein, on how he designs interview questions
"Think about how much nonprofit giving gets unlocked, like life-changing, world-changing nonprofit giving gets unlocked in a multiplied effect by the work that a financial advisor does with their clients." — Aaron Klein, on why he'd put The Sacredness of Secular Work on every RIA leader's shelf
Chapters
(00:00) Intro
(00:35) Welcome
(00:56) Aaron's story: Riskalyze, the Hg deal, a year off, and Contio
(04:45) Evolving as a leader, and Extreme Ownership
(07:31) Ten copies on the credenza
(08:28) How one book spread through the company
(10:10) From founder to enterprise leader: leading through people
(12:54) Rebuilding the leadership team, and the "101st Airborne"
(14:31) Stepping down as CEO, and "Earth Two"
(16:27) The Hard Thing About Hard Things, and nearly dying four times
(18:51) Tough years, and why culture can't make payroll
(20:45) Hire for strength, not lack of weakness
(23:13) Wartime versus peacetime CEO
(26:04) How Aaron hires: convicting a candidate of greatness
(28:52) The parents question
(31:41) Choosing to Cheat
(36:26) How Aaron picks his next book: 1873 and presidential biographies
(38:26) Lightning round
(39:40) The one book for every RIA leader
(40:59) Where to find Aaron
About the guest
Aaron Klein is the founder of Contio, which builds AI for relationship-driven businesses, with a focus on wealth management and benefits brokers. In 2011 he co-founded Riskalyze, now Nitrogen, and served as its founding CEO for more than 12 years, growing it to serve 35,000 users in the advisor space. He handed the CEO role to Dan Zitting at the end of 2023 and remains on Nitrogen's board. He was named CEO of the Year at the 2023 WealthManagement.com Industry Awards and to InvestmentNews' 40 Under 40, and he writes about leadership at aaronklein.com.
