Welcome to RIMScast. Your host is Justin Smulison, Business Content Manager at RIMS, the Risk and Insurance Management Society.

As the 2010 Winter Olympics gold medalist in men’s skeleton, Jonathan “Jon” Montgomery became a national icon, renowned for his spontaneous and exuberant celebration. Since 2013, Jon has hosted The Amazing Race Canada, captivating audiences nationwide. His career highlights include winning his first World Cup race in 2008 and earning two silver medals at the 2008 FIBT World Championships. Inducted into the Manitoba Sports Hall of Fame in 2019, Jon continues to inspire through his passion for sport and community.

Jon recently keynoted the RIMS Canada Conference 2024 in Vancouver, where he took the audience along on his journey to Olympic history. RIMScast Host Justin Smulison was in the audience and was inspired by Montgomery’s story, which revealed the parallels between risk management and sports and competition.

To help close out 2024 and usher in the winter, Montgomery joined RIMScast to discuss his risk philosophies, highlighted by the ups and downs of training and competition. Justin and Jon discuss Jon’s victory at the 2010 Olympics followed by his failure to qualify for the 2014 Olympics. Jon reveals where he fell short and how he turned this failure into a life-changing habit of learning lessons from every setback. Jon comments on the differences between individual risk-taking, and risk professionals applying more risk-aware thinking. Jon talks about journaling his wins and losses in life. Jon credits his team for everything he achieves, from the Olympics to Amazing Race Canada. Jon shares how a misunderstood training program challenged him to his limit but built him up for the 2010 Olympics. Jon’s secret sauce is his curiosity and his desire to chase the best-informed guesses. Jon recommends stacking habits to make short-term goals become long-term commitments.

Listen in to hear Jon’s take on the RIMS Canada Conference 2024 and what he experienced there.

Key Takeaways:

[:01] About RIMS.

[:14] Member registration for RISKWORLD 2025 is now open! General registration opens on December 4th. Visit RIMS.org/RISKWORLD.

[:25] About this episode, coming to you from RIMS headquarters in New York. We will be joined by Olympic Gold Medalist, Host of The Amazing Race Canada, and recent RIMS Canada Keynote, Jon Montgomery!

[:49] The next RIMS-CRMP Exam Prep Virtual Workshop will be held on December 17th and 18th. The next RIMS-CRMP-FED Exam Course will be held from February 4th through the 6th, 2025.

[1:08] Links to these courses can be found on the Certification page of RIMS.org and through this episode’s show notes.

[1:15] RIMS Virtual Workshops! Elise Farnham of Illumine Consulting recently joined us here on RIMScast. On December 17th and 18th, she will host “Captives as an Alternate Risk Financing Technique”.

[1:30] Gail Kiyomura of The ART of Risk Consulting, will host the “Fundamentals of Insurance” virtual workshop on February 19th and 20th, 2025.

[1:41] This is the last week to sign up for “Managing Data for ERM”, hosted by Pat Saporito on December 12th. Registration closes on December 11th.

[1:52] A link to the full schedule of virtual workshops can be found through RIMS.org/education/online-learning pages. A link is also in this episode’s show notes.

[2:08] Interview! My guest today is one of my favorite RIMS Keynotes from 2024, the 2010 Winter Olympics Gold Medalist for Men’s Skeleton, Jon Montgomery. He’s an icon in Canada. He’s known since 2013 as the host of The Amazing Race Canada, captivating audiences.

[2:27] He’s an all-around great guy. His keynote at the RIMS Canada Conference 2024 inspired me. We are catching up now to close out 2024 with a little extra inspirado! We will discuss his risk philosophies and how our listeners can apply these philosophies to their lives.

[2:58] Jon Montgomery, welcome to RIMScast!

[3:09] Jon Montgomery is an Olympic Gold Medalist. You may also know him as the recent host of the RIMS Canada Conference 2024. Jon is calling into the interview from his home office. Justin found Jon to be very personable after his keynote address at the conference.

[3:49] Jon says his experience was awesome. The best part was connecting one-on-one with people, and putting a medal around folks’ necks. Not everybody is going to remember what you say but everybody will remember how you made them feel and a moment you shared.

[4:27] Jon gets a charge out of meeting folks and finding out who they might know in common. He says in Canada if it’s more than a couple degrees of separation, one of them has been living under a rock.

[5:13] Jon saw that folks at the conference were genuinely engaged and happy. The level of positivity was the connecting element from person to person. He could feel the energy. It felt like folks looked forward to these opportunities. People were familiar with one another, like family.

[5:36] Jon saw that people look forward to these conferences to be among friends, as well as to learn and network. The level of familiarity was tangible.

[6:26] Jon likes to assess risk, by whatever metrics he uses, and he loves to compete against the best, whatever he gets to be a part of.

[6:51] Jon talks about measuring the risks of skeleton against the potential rewards. Whatever the perceived risks were, he pushed them to the side for the opportunity to represent my country, which carried much greater weight. He downplayed the risk in pursuit of that reward.

[7:27] In hindsight, we might lie to ourselves on occasion about risky endeavors because of that proverbial dangling carrot. Jon would have played any sport that would have him. Skeleton had a shorter bench than the national team in hockey, or even speedskating, or downhill skiing.

[7:55] When Jon first saw skeleton, he was compelled. Having tried it one time, he was hooked. He loved the experience of being on the sled. He didn’t think too much about what would happen to him but it seemed safer than hockey with all its variables, which he grew up playing.

[8:33] In skeleton racing, you go down a frozen chute. There are no right angles and everything is pretty smooth. It just has a great deal of speed. Once Jon got his brain wrapped around that, he was comfortable in that arena.

[8:55] Jon learned that the sport places incredible pressure on the brain. That was glossed over in the pursuit of representing Canada. Some of the athletes got concussions and had to work through them. Jon’s wife was profoundly affected by participation in skeleton racing.

[9:18] Jon says they are where they are today because of that row to hoe and the dark days that followed after she left the sport and Jon retired four years later.

[9:40] Could risk professionals push some risks to the side with a similar outcome or is there a different approach to apply in their roles? Jon suggests risk professionals not turn a blind eye to the outcomes. As an individual chasing a dream, there has to be some of that.

[10:05] Jon says if he focuses solely on the risk, it might detract from his capacity to react and take advantage of a situation and opportunity. If you’re dwelling on what could go wrong, you’re missing things right in front of you that might swing the pendulum in the other direction.

[10:32] As a risk professional, you work to mitigate that negative outcome. For what’s at stake as a risk professional, Jon would not advise turning a blind eye to outcomes. For the public, dwelling on what can go wrong will lead to some of those outcomes. What we focus on grows.

[10:57] If you perpetually focus on the negative and what could go wrong, you will attract it. Focus instead on what you want to have happen. Justin and Jon discuss the law of attraction where thoughts become things. Justin watched it on streaming instead of reading the book.

[12:40] Jon keeps track of his hits and misses, but he doesn’t do as much journaling as he thinks he should. When he does journal, he is proud that he wrote of his successes to be reminded of them later. He finds journaling to be a great tool to be leveraged.

[13:32] Jon says nobody should expect not to experience disappointments. As a parent, Jon has had to realize that his reactions are natural, even if he would have preferred to react a different way.

[13:58] The conversations that are had afterward are humanizing, when he admits not having had the patience the situation warranted. Jon talks of building conversation around expectations, realities, and disappointments, moving forward with purpose.

[14:22] One of Jon’s most disappointing experiences was falling short of making the 2014 Olympic team. As the defending Olympic champion, he failed to qualify for the 2014 Games although he was stronger...

Stacking Habits with Olympic Gold Medalist Jon Montgomery