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Ronald Kruszewski on retirement

From Where Success Meets Success, with Ron Kruszewski | WTP with Mikaela Ep. 12 · · Mikaela Shiffrin

“I get asked this question a lot and then I'll answer it this way. I'll say, 'What do you why do you retire?' If you really ask yourself, why do you retire? And many people will say, 'Well, because I want to do something that I love.' All right? And well, whatever that might be, you you want to do what you love. Well, it might be in some ways weird to be able to say this, but I do what I love. I love uh being able to uh lead. I love being able to get to know you, get the ski team. All of the things that I do day-to-day in my life, I love. So, as long as I have my wits about me and my partners don't want to kick me out, I have no plans to retire because what would I do?”

Ronald Kruszewski
Chairman & Chief Executive Officer, STIFEL FINANCIAL CORP
retirementcareerpassion

On , Ronald Kruszewski, Chairman & Chief Executive Officer at STIFEL FINANCIAL CORP, spoke about retirement during Where Success Meets Success, with Ron Kruszewski | WTP with Mikaela Ep. 12 on Mikaela Shiffrin.

Where Success Meets Success, with Ron Kruszewski | WTP with Mikaela Ep. 12
Watch on YouTube at 20:08
Where Success Meets Success, with Ron Kruszewski | WTP with Mikaela Ep. 12
Mikaela Shiffrin
Watch on YouTube at 20:08
Join Mikaela and Ron Kruszewski, Chairman and CEO of Stifel Financial, for a wide-ranging conversation about skiing, business, and the pursuit of balance in the Season 1 finale of “What’s the Point.” In this episode, Ron shares stories of humble beginnings on the mighty hills of Michigan, his passion for supporting athletes, and the philosophy behind Stifel’s “Where Success Meets Success” tagline. They also touch on Ron’s approach to investing, reflections on legacy and regret, and advice for young listeners on financial independence. Plus, hear stories from World Cup races, the impact of Stifel’s sponsorship on the Stifel U.S. Ski Team and Mikaela personally, and what motivates both Mikaela and Ron to achieve greatness both personally and professionally. Presented by STIFEL . . . Follow What's the Point with Mikaela Shiffrin on social media for all the best moments from the show:   / wtpwithmikaela   Download the Full Podcast: Spotify: https://open.spotify.com/episode/4rGf... Apple: https://podcasts.apple.com/us/podcast... More about STIFEL:   / stifelfinancial   Show Notes: Watch On the Edge on Disney+ or ESPN: https://www.disneyplus.com/browse/ent... Chapters: 0:00 Opening Remarks 1:50 STIFEL Thank You & Ron Kruszewski’s Intro 2:17 “Faster.Always” Rapid Fire, Presented by ATOMIC 7:40 Ron to Mikaela: Reverse Rapid Fire Questions 9:46 Wedding and Personal Life Discussion 11:40 Stifel's Impact and On the Edge Advanced Screening in St. Louis 13:23 Stifel's Increased Investment and Salt Lake 2034 14:02 Ron's Skiing Origins Story on the Mighty Hills of Michigan 15:57 Investment Philosophy in Skiing 17:41 Mikaela + 2030 Olympics Speculation 18:28 "Where Success Meets Success" Tagline Origin 19:30 Leadership Tenure and Retirement Philosophy 23:22 Retirement and Motivation Discussion 24:31 Parallel Lives and Regrets 27:20 Work-Life Balance Challenges 28:37 Investment in Creative People Across Industries 30:15 Passion for Financial Industry 32:01 Investment Advice for Young People 34:05 Education and Success Factors 36:07 Ron Gives Career Advice to Mikaela 38:24 Teaching Financial Independence to Children 40:39 Life Reflections, Family, and Stifel’s Growth 42:20 Ron Commits to Sponsor Season 2 of WTP 43:52 Closing Remarks and Ron’s Thoughts on Mikaela’s Olympic Performance in Cortina #MikaelaShiffrin #RonKruszewski  #skiing #investing #investment #banking #ski #whatsthepoint #podcast
Ronald Kruszewski

About Ronald Kruszewski

Chairman & Chief Executive Officer · STIFEL FINANCIAL CORP

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.

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