Mikaela Shiffrin has taken a closer look at the person behind one of the most significant corporate partnerships in American ski racing, sitting down with Stifel Chairman and CEO Ron Kruszewski for an in-depth conversation about skiing, business, ambition and the future.
The conversation featured in Shiffrin’s podcast What’s the Point with Mikaela Shiffrin, where Kruszewski discussed his personal connection to skiing and how that passion has influenced Stifel’s involvement in the sport. The episode was released as the Season 1 finale in June 2026.
From Michigan slopes to Wall Street
Kruszewski explained that his relationship with skiing goes back to his childhood, when he learned to ski on the relatively modest hills of Michigan. That early experience became an important part of his connection with the sport.
Although his professional career developed in finance, his enthusiasm for skiing remained. As chairman and CEO of Stifel Financial, Kruszewski has subsequently played a prominent role in the company’s growing support of American snow sports.
That connection is particularly visible through Stifel’s title partnership with U.S. Ski & Snowboard. The organisation and Stifel have extended their partnership through 2034, with the company supporting athletes across multiple disciplines.
A partnership beyond sponsorship
For Shiffrin, Stifel’s involvement has become more than simply placing a company’s name alongside the U.S. Ski Team.
The American star has previously credited Kruszewski and Stifel with investing in athletes and helping promote the growth of skiing. When the partnership was extended, Shiffrin said the company’s support had contributed to greater success on the mountain while also helping tell the stories of the athletes.
Stifel’s commitment has also included initiatives aimed at improving the financial side of ski racing. In 2023, the company helped increase prize money at domestic Alpine World Cup events in the United States by 30 per cent compared with the previous season.
Looking beyond the podium
The discussion between Shiffrin and Kruszewski also moved beyond competition. They explored ideas around success, balance, legacy and what motivates people to continue pursuing ambitious goals.
For Kruszewski, the philosophy behind Stifel’s “Where Success Meets Success” message connects naturally with elite sport. His approach is centred on supporting people who are working towards reaching their potential, while Shiffrin offered the perspective of an athlete who has spent much of her life competing at the highest level.
The conversation also touched on investing, financial independence and lessons for younger people, giving the episode a broader focus than skiing alone.
Building for the future
Stifel’s continued relationship with U.S. Ski & Snowboard suggests that Kruszewski sees the sport as a long-term investment rather than a short-term marketing opportunity.
The company’s support has included prize-money initiatives, athlete awards and its wider title partnership. In June 2026, Stifel again recognised athletes and staff through its annual Stifel Awards, which included categories such as Athlete of the Year, Best Comeback and Most Improved.
For Shiffrin, whose career has made her one of the defining figures in alpine skiing, the relationship provides an opportunity to discuss not only winning races but also how the sport can continue developing for future generations.
The conversation between the Olympic champion and the finance executive therefore offered two different perspectives on the same pursuit: Shiffrin’s experience of chasing excellence on snow and Kruszewski’s view of how investment, leadership and long-term support can help create opportunities away from the starting gate.
Together, their discussion highlighted a shared interest in sustaining skiing’s growth while supporting the athletes who remain at the centre of the sport.
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