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Ronald Kruszewski
Chairman & Chief Executive Officer, STIFEL FINANCIAL CORP

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

📅 Jun 03, 2026 Mikaela Shiffrin 44 MIN 2281 VIEWS 100 SEGMENTS · 2 SPEAKERS
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 Sti...

What Ronald Kruszewski said

Written from the verified transcript and checked against it. Every figure links to the moment it was said.

Ronald Kruszewski, chairman and CEO of Stifel Financial, discussed his passion for skiing, his company's sports sponsorships, and his views on investing and retirement. He said he learned to ski at Swiss Valley in southern Michigan, a 264-foot vertical hill, using tube socks as gloves on tow ropes. He explained that Stifel's 'Where Success Meets Success' tagline originated from marketing with the US ski team, and that the ski team sponsorship is Stifel's number one sports sponsorship. Kruszewski said he has no plans to retire, as he loves his work, and he promised to throw a retirement party for Mikaela Shiffrin after the 2034 Salt Lake Olympics. He advised young investors to understand the difference between compounding and consumption, and cautioned against confusing gambling with investing. He also noted Stifel's growth from a $40 million market cap to $13 billion and from $100 million to $6 billion in revenue during his 29-year tenure.

Key takeaways

  1. Kruszewski has no plans to retire, saying he loves his work and would not know what else to do.
  2. He promised to throw a retirement party for Shiffrin after the 2034 Salt Lake Olympics.
  3. Stifel's ski team sponsorship is its number one sports sponsorship, driven by Shiffrin's attributes.
  4. Stifel grew from a $40 million market cap to $13 billion and from $100 million to $6 billion in revenue during his tenure.

Numbers and commitments

FigureWhat it refers toTypeAt
29 years Kruszewski's tenure as CEO of Stifel metric 19:34
$40 million Stifel's market cap at start of his tenure metric 40:39
$13 billion Stifel's current market cap metric 40:39
$100 million Stifel's revenue at start of his tenure metric 40:39
$6 billion Stifel's current revenue metric 40:39
264 feet Vertical drop of Swiss Valley ski hill metric 14:02
10,000 Number of Stifel employees metric 40:39
12 Number of grandchildren Kruszewski has or expects metric 38:24
2034 Year of Salt Lake Olympics for retirement party promise timeline 23:22

Chapters

  1. 0:00Rapid fire ski questions
  2. 11:40Stifel's sports sponsorship and US ski team
  3. 14:02Learning to ski in Michigan
  4. 18:28Origin of 'Where Success Meets Success'
  5. 20:08Retirement plans and philosophy
  6. 25:32Regrets and family balance
  7. 32:01Investing advice for young people
  8. 34:05Education and success principles
  9. 40:39Stifel's growth and legacy

Questions asked in this interview

12
  1. 0:00Apres ski in the US or apres in France?
  2. 3:00Fire. What's your favorite ski destination?
  3. 5:02Apres ski in the US or apres in France or Switzerland?
  4. 6:07What's your go-to apres ski drink?
  5. 9:50And there were other reasons for that, but I was like, man, I wish I could have just gotten a good night's sleep the night after that Olympic slalom, right?
  6. 13:12Do you have a theme yet?
  7. 15:51What drives your interest to invest in and to support skiing?
  8. 18:12Um, well, I was wondering, you know, Stifel, you have this tagline where success meets success. Where did that come from?
  9. 22:03Like I know that I can, my body speaks to me, you know?
  10. 27:17And sometimes I wonder like how does one strike a balance in that way?
  11. 31:18How do I save? How do I invest?
  12. 35:29What would be your top three like educational tools?
Michaela Shiffrin 0:00 ↗
What do you think? Apres ski in the US or apres in France?
Ronald Kruszewski 0:04 ↗
Uh, you know, it's not even close.
Michaela Shiffrin 0:06 ↗
You know, I think about my life sometimes. I think about this parallel life where I wasn't a skier and maybe I did go to college.
Ronald Kruszewski 0:12 ↗
And the way you disagree will define your success. I promise you that.
Michaela Shiffrin 0:17 ↗
Hosting a podcast. Man, it is scary.
Ronald Kruszewski 0:20 ↗
But she had this pole that she would whack me when she would say, 'Get on your toes.'
I get asked this question a lot and then I'll answer it this way. I'll say, 'Why do you retire?'
Michaela Shiffrin 0:32 ↗
Welcome back to What's the Point for our final episode of season 1. For anyone tuning in, I want to thank you for listening and I hope that you've learned something or felt inspired or maybe taken some time for yourself to reflect on the things that drive you and motivate you in your daily life. And there's really no better guest to wrap season 1 of What's the Point than today's very distinguished guest. He's the reason this podcast venture really even happened. And if we do have a season 2, fingers crossed, you can also thank him for that. A large part of the Stifel US ski team success in recent years is truly because of today's guest. Ron Kruszewski is chairman of the board and chief executive officer of Stifel Financial. He's one of the most passionate people I have ever met. He's won several accolades and is on countless awards and invests deeply in several elite sports including hockey, golf, skiing, soccer, and most recently figure skating with the Stars on Ice Tour. Honestly, I can't keep up, so I don't really even try. Speaking of which, Ron is also quite the skier. So, Ron, I can't thank you enough for everything you've done for me throughout my career and for the US ski team. And thank you for joining me today. Welcome to What's the Point?
Ronald Kruszewski 1:52 ↗
Well, Michaela, first of all, I have listened to your podcast and I have been inspired and it's fantastic to be with you today. I was thinking that you must have, you know, for your last episode, you must have run out of interesting guests. So, you called me because you've had some pretty interesting guests on this and we'll see if I can even get close to what some of your other guests have been able to contribute.
Michaela Shiffrin 2:17 ↗
Well, it's been great. We've had great guests, but I think we've had you on the guest list since the beginning. I think this is the first conversation I'm going to have with somebody who's, I mean, you're very involved in the snow sports world. You're very involved with ski racing, obviously. So, it's like one degree removed, but for somebody who has such an incredible background in business and finance, so this is really exciting for me. First things first, we're going to start with a faster always rapid fire segment which is presented by Atomic.
Ronald Kruszewski 2:53 ↗
So, I was just wondering, I have a couple for you. I think you might have a couple rapid fire for me. So, we'll just get into it.
Michaela Shiffrin 3:00 ↗
Fire. What's your favorite ski destination?
Ronald Kruszewski 3:03 ↗
Well, you know, I ski out of Vail and so the back bowls of Vail when there's snow, you know, this Michaela is, I hate to go to the home field advantage, but I love Colorado. But in Europe, obviously Kitzbühel and St. Moritz have their own special things. So, but I'm going to go to my hometown course and tell you that if I'm going to go skiing, I'll meet you in Blue Sky.
Michaela Shiffrin 3:33 ↗
Okay. Blue Sky. I have a lot of fond memories of Blue Sky. That's for sure. What's your favorite World Cup destination?
Ronald Kruszewski 3:42 ↗
Well, that's interesting. I've thought about, let me think about that. Certainly for the event, the men's event in Kitzbühel, which I've made for the last few years, there's nothing like that. I wish more Americans could see the passion of skiing like at Kitzbühel as you know and that weekend is always fun. But also I have fond memories and I love to go to Killington. I go to Killington every year. That's usually where I run into you for the first time and the New Yorkers and the people that run up there and I think that we're going to really get something special in the US with the World Cup finals in Sun Valley. I think that we did a really good job and now we're going to get them again this year.
Michaela Shiffrin 4:29 ↗
It was unbelievable. So that's what we're going to do. And those are my places. St. Moritz. I mean, I can name a lot of them but I like to ski. Yeah. Well, for anyone listening, if you're interested in coming to a World Cup race, Sun Valley is definitely a great one to attend. We'll have Beaver Creek this winter. I believe the men will be in Copper Mountain, maybe. We'll be back in Killington as well, and then Tremblant in Canada. So, there's quite a few in North America that you can attend if you're interested.
Ronald Kruszewski 5:01 ↗
Absolutely.
Michaela Shiffrin 5:02 ↗
Okay. So, Ron, what do you think? Apres ski in the US or apres in France or Switzerland?
Ronald Kruszewski 5:11 ↗
Uh, you know, it's not even close. I remember one of my favorite apres ever was at Maribel and Flo and you and I, your mom and what I'll never forget about it was that when we got done apres-ing, there was that guy with the helicopter that would take people down that couldn't ski for very good reason. If you remember that.
Michaela Shiffrin 5:33 ↗
Of course. I think Eileen towed me down the hill, but there is no like they have. Didn't she start giving you about your pinky toe and like how to carve a turn?
Ronald Kruszewski 5:46 ↗
Well, as I said to her at the bottom, I said if that was even a microcosm of what you did with Michaela, then I understand why she's the greatest in the world because she changed my skiing in about 400 vertical feet or whatever it was. But she had this pole that she would whack me when she would say, 'Get on your toes.' I loved it.
Michaela Shiffrin 6:07 ↗
Oh, that's too funny. What's your go-to apres ski drink?
Ronald Kruszewski 6:12 ↗
Uh, you know what? I'd like to say water, but that'd be lying, so I'll say anything with tequila.
Michaela Shiffrin 6:19 ↗
Fair enough. Fair enough. What's your favorite ski racing discipline to watch live?
Ronald Kruszewski 6:28 ↗
Well, you know, that is a great question and I would answer it by what my favorite to watch live and there's two of them but for different reasons. I love obviously slalom, you know, I've told you Michaela when you're skiing in Europe and I have to get up at 3:00 in the morning and then 5:00 in the morning to watch, which I do. But I like slalom because of the way that it's reverse order in the end and it builds excitement and one of the most exciting moments in my life live was watching you in your second run in Cortina. I also really love watching downhill and the craziness of downhill. We've got to figure out in the sport how we make that a little more something where the racers can somehow be winning at the end, not at the beginning. I think that's a challenge for the sport. But I love actually, I love all of skiing. The thrill of victory and the agony of defeat. There's nothing like it is in World Cup skiing.
Michaela Shiffrin 7:32 ↗
Yeah, I totally agree. It's special. Do you have any rapid fire questions for me?
Ronald Kruszewski 7:39 ↗
You had said something. I do. And you know, well, let's, I could ask you a bunch of ski questions, but if you weren't skiing, what would your dream job be?
Michaela Shiffrin 7:51 ↗
Yeah. Yikes. Rapid fire, Ron. Man, come on. No, I mean, I loved science in school. I loved biology. I loved chemistry, too. I used to think that maybe something in environmental science or maybe mixing that with interior design as well, trying to find like sustainable ways to create beautiful spaces within whether it's company buildings or private homes. But you know, now I think of my life more about what I can do moving forward and I feel like you've actually helped me to get this concept of like, and that's part of the reason for this podcast was thinking like what are ways that I can be impactful beyond the sport. You know, what are questions that I ask myself on a daily basis and where the interests are because I think the life that I would have had if I never skied is just not something that's going to exist.
Ronald Kruszewski 8:55 ↗
Well, I say thank you from the skiing world that you decided to ski. What about your favorite movie? Come on quickly. What's your favorite movie?
Michaela Shiffrin 9:04 ↗
Probably Secretariat.
Ronald Kruszewski 9:06 ↗
Secretariat. Wow, that is a talk. That is very interesting. Yeah, that is interesting. I like Shawshank Redemption, which probably says a lot about me in some stupid way, but I do like the movie. You know what? One of the things I want to ask you, you asked me about my favorite drink. You and I spent a little time after you won the gold in the hotel in Cortina and you jumped up on the wall there and you started talking and someone handed you an espresso martini.
Michaela Shiffrin 9:39 ↗
Yes.
Ronald Kruszewski 9:39 ↗
And I somehow, you were in St. Louis and I saw you, that must be one of your go-to favorite drinks.
Michaela Shiffrin 9:50 ↗
Well, I like it, but in small doses. Portillo was the first time I ever tasted one, and I thought it was delicious for the first few sips, but then I'm like, coffee is the morning thing for me, and you know, alcohol is just an evening thing. And I don't know if I like mixing them as much because I didn't sleep very well last night. And there were other reasons for that, but I was like, man, I wish I could have just gotten a good night's sleep the night after that Olympic slalom, right?
Ronald Kruszewski 10:19 ↗
I hear you. I hear you. All right. The last question kind of personal here. I'm just wondering. I check my mail all the time and I have yet, am I off the invitation list if you ever get married or is that, where's my invitation?
Michaela Shiffrin 10:36 ↗
I have not sent out invitations yet. Don't you worry. You will be on the list. Don't worry about that. Yeah, we've had like very minor conversations about it. This is a great question because people do tend to ask a lot. When are you getting married? Just get married already. It's so, I find it very complicated to know whether we want it small or we want it big. If we want to do multiple in different continents or if we want to do one great celebration somewhere in the middle. But I like the idea of a celebration for Alex and myself to also be a celebration of those who have supported us. And that could get really, really big. So, we're just putting a pin in that one for now. But don't worry, invitations have not.
Ronald Kruszewski 11:26 ↗
All right. Well, go big. Go big or go home. Okay. That's what I'm going to tell you. All right. But if you go small, I still expect an invitation. So, there you go. So those are my questions for you.
Michaela Shiffrin 11:40 ↗
Anyone listening by now, you've probably gathered that Stifel has been so impactful in the support of ski racing and so many sports beyond that for so many years. Most recently, Ron hosted a massive event at the Stifel Theater in St. Louis for the premiere of the final episode of On the Edge, which is a docu-series following this past FIS Alpine racing season. For anyone interested, you can find the show on Disney Plus and ESPN streaming platforms. This event was by far one of the coolest things I've been a part of. There was 18,000 people who attended from the greater St. Louis area and it was so incredible to see that kind of support from an area that's not necessarily known for skiing. So, I want to say thank you yet again to Stifel and to Ron. That was a really cool thing for me to be part of.
Ronald Kruszewski 12:34 ↗
You know, Michaela, for St. Louis to be able to have, you were the draw, but we had Breezy and we had Alex and we had Jaylen that came in and Elliot from Snowboard. It was just a tremendous event and I still get people talking to me about that. So, our fundraiser that we're going to have in September that you have been so kind for 10 years, that's how you and I got to know each other, is already sold out, just so you know. So, boy, it was a big deal. Yeah.
Michaela Shiffrin 13:12 ↗
Do you have a theme yet?
Ronald Kruszewski 13:13 ↗
No. No. We got to have to think about that. But we usually figure that out, right?
Michaela Shiffrin 13:18 ↗
Yeah. No, no stress. No stress on that one. So, not only were this season results incredible, but Stifel stepped it up and invested with several more initiatives, increasing prize money with the On the Edge docu-series, US ski team contract renewal, and so much more. And it all seemingly points towards the buildup of Salt Lake 2034. People do find the connection between St. Louis and skiing and snow sports intriguing, but I've learned over the last 10 years that there are so many ski fans in St. Louis. So, I was wondering where did you actually grow up and how did you learn to ski? How did you get into skiing?
Ronald Kruszewski 14:02 ↗
Oh, you go. I don't know I've ever told you this, Michaela, but I actually learned to ski in southern Michigan at a hill called Swiss Valley that if you look it up, I think the vertical feet is 264 ft, which is about a third of your slalom run, best I can tell, as to what I had to do. But what I remember about it, and this kind of goes to my youth a little bit and how I grew up, but I used to go and they only had one way up the hill, which were tow ropes. All right? And you remember these tow ropes? And I actually really couldn't afford ski gloves. And I don't want to make this woe about me. I can afford ski gloves today, so don't worry about me. But then I couldn't. And so what I used to do was I took two pairs of tube socks. I put them on my hands. Okay? And then I would hold on to the rope until my socks were sprayed away and then I had to quit skiing. They wore through. And that is actually one of my favorite memories of skiing was tube socks and tow ropes on a 260 vertical drop hill in southern Michigan. So I would say it's not your classic Burke Academy, let's say.
Michaela Shiffrin 15:20 ↗
No. And not your classic Colorado either. You know, it's, but those are the stories, you know, that's how my mom learned to ski and my whole, my dad's side of the family, my mom's side of the family, and I have actually ridden several tow ropes in my life. I went back to where my mom grew up skiing and I was like, 'This is crazy. Anybody doing this, why did you even ski?' But it just goes to show how much passion there is and how amazing the sport is, I think.
Ronald Kruszewski 15:49 ↗
Yeah, I agree.
Michaela Shiffrin 15:51 ↗
What drives your interest to invest in and to support skiing?
Ronald Kruszewski 15:57 ↗
Well, first of all, what drives it, and I'm going to give you a compliment back. My involvement with the US ski team, now the Stifel US ski team, as you know, has at its very core our relationship and the beginning of our relationship and getting to know you and then looking at what drives you and your preparation and your dedication and how hard you work to be the best at what you do. And when I thought about it, I said, you know, those are the exact attributes that we or any business, frankly, anything in life that you really want to do. If you apply what you do every day to be the best at your craft, which is being the best skier in the world, well, then that works everywhere. And we just wanted to connect them. And so, our view was that skiing was a sport that we could help, we could help fund, the athletes would know, the athletes would then in turn support Stifel, which they do, and you do. And it's just a nice little flywheel of business. It's the best sports sponsorship that we do. And we do a number of them, but this by far is the number one. And look, Michaela, you and I have talked about this a long time. I wouldn't be sitting here sponsoring the team but for getting to know you 10 plus years ago.
Michaela Shiffrin 17:19 ↗
Well, thank you. I appreciate that, it's a big compliment and it's been an honor for me to be able to sort of help build this relationship between Stifel and ski racing and the US ski team over the last 10 years. Is that what we've said? Yeah. The event, I forgot. I have one other fire question for you now that you bring it up. Okay. So, you said a point to 2034. I mean, I'm actually thinking about 2030, and I'm sure everyone wants to know if you're even considering 2030. And all you have to do is say yes. There's no one on this call. It's not like anyone is going to know but you and I. So, everyone's going to ask. We'll edit this one out. I'll say yes for you.
Ronald Kruszewski 18:03 ↗
I'll say yes for you. It's a good question. Enough said. That's a very good question. Well, I'll play the P.
Michaela Shiffrin 18:12 ↗
You're not gonna edit it out. You're gonna say yes for you and but of course it's four years. Anyway, go ahead. Um, well, I was wondering, you know, Stifel, you have this tagline where success meets success. Where did that come from?

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APA

Kruszewski, R. (2026, June 3). Where Success Meets Success, with Ron Kruszewski | WTP with Mikaela Ep. 12 [Interview transcript]. Mikaela Shiffrin. CEOInterviews.AI. https://ceointerviews.ai/interview/967474/

MLA

Ronald Kruszewski. "Where Success Meets Success, with Ron Kruszewski | WTP with Mikaela Ep. 12." Mikaela Shiffrin, 3 Jun. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/967474/.

BibTeX
@misc{kruszewski2026_967474,
  author       = {Ronald Kruszewski},
  title        = {Where Success Meets Success, with Ron Kruszewski | WTP with Mikaela Ep. 12},
  howpublished = {Interview transcript, Mikaela Shiffrin. CEOInterviews.AI},
  year         = {2026},
  month        = {jun},
  url          = {https://ceointerviews.ai/interview/967474/},
  note         = {Speaker-attributed transcript with timestamps}
}