From Where Success Meets Success, with Ron Kruszewski | WTP with Mikaela Ep. 12 · · Mikaela Shiffrin
“And then there's a cautionary tale too here about my business right now and that is um young people are confusing gambling with investing and I want to caution people about that. You know uh oh I'm investing on whether the Super Bowl coin flip is head or tails and I say that's not investing. That is gambling. And and you need to understand the difference.”
On , Ronald Kruszewski, Chairman & Chief Executive Officer at STIFEL FINANCIAL CORP, spoke about investing during Where Success Meets Success, with Ron Kruszewski | WTP with Mikaela Ep. 12 on Mikaela Shiffrin.
In a May 2026 podcast appearance, Kruszewski discussed his philosophy on retirement, stating that he does what he loves and therefore does not see a reason to retire. He also offered investing advice to young people, emphasizing the difference between compounding and consumption, and cautioned that some young people are confusing gambling with investing. Reflecting on his tenure at Stifel, he said the company grew from a $40 million market cap to $13 billion and from $100 million in revenue to $6 billion. In a June 2025 interview, Kruszewski described Stifel's sponsorship strategy as a form of patronage, comparing it to the Medici family's support of the arts in Florence. He said that associating with athletes and the arts gives Stifel a "backsplash" of being a fun and creative firm, which he noted is not typically associated with financial companies. He also discussed rebranding the U.S. Ski Team as the Stifel U.S. Ski Team, calling it an "unbelievable situation," and expressed support for continued patronage in St. Louis, including for the arts organization COCA.