Stacking Habits with Olympic Gold Medalist Jon Montgomery

RIMScast

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, faster, and more prepared. He had tried to create a better sled.

[15:43] In skeleton racing, your sled needs to be intertwined with every fiber of your being. You have to know how it will react to the smallest impetus. If you haven’t had the time to become one with your sled, you are at a disadvantage. Jon didn’t have the time to perfect his sled.

[16:18] Jon fell just a hair short. It was wildly disappointing. The feeling in the pit of his stomach was palpable. Today, Jon is so glad it happened to him. What he took away from it was that he realized he had pushed people away who could have helped him in his project.

[17:37] Jon had spent a lot of time, money, and effort on this project and he thought people just wanted to be part of it. He pushed against collaboration. He made himself a man on an island in a solo pursuit. He couldn’t reach the necessary expedited rate of development alone.

[18:12] If you want to go quickly, go alone. If you want to go far, you’ve got to go together. Jon applies that lesson to everything he does today as an entrepreneur and in business. He knows he can’t do it singly. The lesson has stood him well since he moved on from the disappointment.

[18:43] As you move away from a failure, if you focus on the lessons you learned through that pursuit, that’s always going to be a win. You’ll either get the victory or the lesson. In either case, it’s a W!

[19:10] Plug Time! RIMS Webinars! On December 5th, we have “Predictive Strategies to Detect Electrical and Machinery Failures”, presented by Global Risk Consultants, a TÜV SÜD company.

[19:25] On Thursday, December 12th, OneTrust returns to deliver “Staying Vigilant: 7 Practical Tips for Ongoing Third-Party Risk Monitoring”.

[19:35] More webinars will be announced soon and added to the RIMS.org/webinars page. Go there to register. Registration is complimentary for RIMS members.

[19:47] RIMS is now accepting nominations for all awards other than Risk Manager of the Year 2025. The submission deadline is Monday, January 6th, 2025. To receive a RIMS award, all winners must be active members and in good standing.

[20:07] These awards are the Diversity, Equity, and Inclusion Chapter Leadership Award, the Harry and Dorothy Goodell Award, the Volunteer of the Year “Heart of RIMS” Award, the Richard W. Bland Memorial Award, the Chapter of the Year Award, the Rising Risk Professional Award, the Risk Management Hall of Fame, and the Cristy Award.

[20:44] You can find more information about the awards through the About Us page of RIMS.org or the link in this interview’s show notes.

[20:52] Nominations are also open for the Donald M. Stuart Award which recognizes excellence in risk management in Canada. Links are in this episode’s show notes.

[21:04] Back to the Interview!

[22:02] As the tip of the iceberg, the visible part of Amazing Race Canada, Jon stands on the shoulders of a juggernaut of a team. When you saw Jon at the Olympics, going down the mountain on the crazy carpet with rails on it, you didn’t see the team behind the athlete.

[22:27] Jon’s team was made up of coaches, trainers, physiotherapists, and team leaders. All of these people feed into a moment.

[22:40] When that moment becomes visible to the masses, the capacity to see the team for the individual isn’t present but everybody who has done something that they can be proud of knows full well what goes into a result.

[23:22] Jon’s public speaking skills developed in tandem with his pursuit of athletics in high school. Jon and a buddy were student council co-presidents. They spoke in front of their peers at student assemblies. There is no more angst-inducing group to speak to than teen peers.

[24:26] Jon became an auctioneer. He shares a sample of his auctioneer chant. He was often asked to MC weddings and events. He learned to be himself on a grand stage. When a beer was thrust in front of him, he was himself. It led him to develop his career, rather than auctioning.

[27:31] Jon has a great deal of anonymity in a bar although some speak of offering him a beer. His favorite beer is wet and free. When offered, he will chug it.

[29:01] Due to misunderstanding an article on training, Jon found himself overtraining in squats, lifting twice what was suggested. It caused him to break down, physically, emotionally, and mentally, spending hours at the gym to get 100 reps done.

[30:17] On day 10, Jon fell short, being unable to do 100 squats with 200 additional pounds on the bar than he had had on day 1. He looked at the workout again and found he had done almost 100% more work than was required. There was no amount of energy he didn’t expend to do it.

[31:11] It dawned on him that he never would have made it that far had he known the truth. He wouldn’t have put forth that amount of work if he hadn't believed it was possible. That belief that others had done it was compelling and propelled him far past his self-imposed limitations.

[31:39] Almost completing the doubled workout made Jon realize that things are only out of our reach if we put them there; if we use self-limiting verbiage like “I can’t,” or “We’re going to fail.” Confidence is the key, whether you think you can or you think you can’t, you’re right.

[31:59] That experience in the gym made Jon realize that if he was going to be good at skeleton racing, he was going to have to continue to develop his legs, his glutes, his quads, and his core, and also his confidence; his capacity to believe that he could be a 2010 national team skeletor.

[32:22] Jon had to believe he had the same opportunity and chance as every other athlete out there to win a medal; to win the gold medal.

[32:31] All he could do was execute and be the best version of himself on the day that mattered and not worry about anybody else. If he did that, he would put himself in the best possible position. Jon was 30, turning 31. His training had made him strong. He peaked at the Games.

[33:12] Jon’s last push on his last run at the Games was his best. He needed that fast start time to compete with the two fastest pushers in the world.

[34:12] Justin and Jon discuss not drinking alcohol on days you train. Jon says how we manage something inherently unhealthy is an individual thing. Your capacity to recover after having alcohol is reduced. Jon calls drinking a balancing act. You have to weigh things.

[36:42] Jon talks about getting deep sleep and REM. He wears an Oura Ring to track his sleep. His metrics are different when he’s had alcohol. Jon cherishes his sleep.

[37:50] Jon says when you stack habits, your capacity to change short-term interests into long-term commitments is so much more bolstered.

[38:33] Jon Montgomery’s secret sauce is curiosity. He has a great deal of gratitude for having a curious mind. It’s hard to teach or coach curiosity. Curiosity can be nurtured when you recognize it in your children and others. Jon’s curiosity leads him to chase best-informed guesses.

[39:37] Jon never holds anything so dear to his heart that he would die on that front. He is open and willing to have his mind changed about stuff. He’s plain about what he knows right now.

[39:49] Jon, it has been such a pleasure to have this one-on-one time with you for RIMScast. This past year, 2024 RIMS Canada had their best lineup of keynotes with you, Kevin Vallely, Jay Kiew, and Jody Wilson-Raybould. You all were fantastic and there was a lot to take away.

[40:14] It resonated with me so I wanted to keep you at RIMS a little longer to get some more of those nuggets of wisdom.

[40:39] Jon invites you to get your submission tapes in for Amazing Race Canada. Casting is still open. Jon will be the host for as long as they will have him! If they can him, he’ll follow them on the road and sneak into shots! They do the show for men’s health awareness. Donate online.

[41:19] Special thanks again to Olympic gold medalist Jon Montgomery for joining us here on RIMScast. If you missed his keynote at the RIMS Canada Conference 2024, be sure to look for him on the road as he delivers several more at other events.

[41:33] Be sure to follow his adventures as the host of Amazing Race Canada, which is gearing up for its 11th season, brought to you by CTV. Learn more about him at JonMontgomery.CA.

[41:47] More RIMS Plugs! The RIMS App is available to RIMS members exclusively. Go to the App Store and download the RIMS App with all sorts of RIMS resources and coverage. It’s different from the RIMS Events App. Everyone loves the RIMS App!

[42:22] You can sponsor a RIMScast episode for this, our weekly show, or a dedicated episode. Links to sponsored episodes are in our show notes. RIMScast has a global audience of risk and insurance professionals, legal professionals, students, business leaders, C-Suite executives, and more. Let’s collaborate and help you reach them! Contact [e-mail] for more information.

[43:07] Become a RIMS member and get access to the tools, thought leadership, and network you need to succeed. Visit RIMS.org/membership or email [e-mail] for more information.

[43:25] Risk Knowledge is the RIMS searchable content library that provides relevant information for today’s risk professionals. Materials include RIMS executive reports, survey findings, contributed articles, industry research, benchmarking data, and more.

[43:42] For the best reporting on the profession of risk management, read Risk Management Magazine at RMMagazine.com. It is written and published by the best minds in risk management.

[43:56] Justin Smulison is the Business Content Manager at RIMS. You can email Justin at [e-mail].

[44:03] Thank you all for your continued support and engagement on social media channels! We appreciate all your kind words. Listen every week! Stay safe!

Mentioned in this Episode:

RIMS DEI Council

RIMS-Certified Risk Management Professional (RIMS-CRMP)

NEW FOR MEMBERS! RIMS Mobile App

RIMS-CRMP Stories — Featuring Valerie Fox!

Nominations open for RIMS 2025 Awards! (Through Jan. 6, 2025)

Nominations for the Donald M. Stuart Award

RIMS Webinars:

“Predictive Strategies to Detect Electrical and Machinery Failures” | Sponsored by TUV SUD GRC | Dec. 5, 2024

“Staying Vigilant: 7 Practical Tips for Ongoing Third-Party Risk Monitoring” | Sponsored by OneTrust | Dec. 12, 2024

RIMS.org/Webinars

Upcoming Virtual Workshops:

RIMS-CRMP Exam Prep (Virtual)Dec. 17‒18, 2024 | 9:00 am‒4:00 pm EST — Register by Dec. 10.

“Managing Data for ERM” | Dec. 12, 2024 & March 12, 2025

“Captives as an Alternate Risk Financing Technique” | Dec. 17‒18

“Fundamentals of Insurance” | Feb. 19‒20, 2025

See the full calendar of RIMS Virtual Workshops”

RIMS-CRMP Prep Workshops

Related RIMScast Episodes:

“Exploring Risk in Extreme Environments with Kevin Vallely”, RIMS Canada Conference 2024 Keynote

“Change Management and Strategy with Jay Kiew, RIMS Canada Conference 2024 Keynote”

“Live From Vancouver! with Maryam Salmasi, Fred H. Bossons Award Winner 2024”

“RIMS 2024 Rising Star Chelsea Andrusiak” (SKRIMS Vice President)

“Supply and Bike Chains with Emily Buckley”

Sponsored RIMScast Episodes:

“Risk Management in a Changing World: A Deep Dive into AXA's 2024 Future Risks Report” | Sponsored by AXA XL (New!)

“How Insurance Builds Resilience Against An Active Assailant Attack” | Sponsored by Merrill Herzog

“Third-Party and Cyber Risk Management Tips” | Sponsored by Alliant

“RMIS Innovation with Archer” | Sponsored by Archer

“Navigating Commercial Property Risks with Captives” | Sponsored by Zurich

“Breaking Down Silos: AXA XL’s New Approach to Casualty Insurance” | Sponsored by AXA XL

“Weathering Today’s Property Claims Management Challenges” | Sponsored by AXA XL

“Storm Prep 2024: The Growing Impact of Convective Storms and Hail” | Sponsored by Global Risk Consultants, a TÜV SÜD Company

“Partnering Against Cyberrisk” | Sponsored by AXA XL

“Harnessing the Power of Data and Analytics for Effective Risk Management” | Sponsored by Marsh

“Accident Prevention — The Winning Formula For Construction and Insurance” | Sponsored by Otoos

“Platinum Protection: Underwriting and Risk Engineering's Role in Protecting Commercial Properties” | Sponsored by AXA XL

“Elevating RMIS — The Archer Way” | Sponsored by Archer

“Alliant’s P&C Outlook For 2024” | Sponsored by Alliant

“Why Subrogation is the New Arbitration” | Sponsored by Fleet Response

“Cyclone Season: Proactive Preparation for Loss Minimization” | Sponsored by Prudent Insurance Brokers Ltd.

“Subrogation and the Competitive Advantage” | Sponsored by Fleet Response

RIMS Publications, Content, and Links:

RIMS Membership — Whether you are a new member or need to transition, be a part of the global risk management community!

RIMS Virtual Workshops

On-Demand Webinars

RIMS-Certified Risk Management Professional (RIMS-CRMP)

RISK PAC | RIMS Advocacy

RIMS Strategic & Enterprise Risk Center

RIMS Events, Education, and Services:

RIMS Risk Maturity Model®

RIMS Events App Apple | Google Play

Sponsor RIMScast: Contact [e-mail] or [e-mail] for more information.

Want to Learn More?

Keep up with the podcast on RIMS.org, and listen on Spotify and Apple Podcasts.

Have a question or suggestion? Email: [e-mail].

Join the Conversation!

Follow @RIMSorg on Facebook, Twitter, and LinkedIn.

About our guest: Jon Montgomery, 2010 Winter Olympics Men’s Skeleton Gold Medal Winner and Host of Amazing Race Canada

Social Shareables (Edited For Social Media Use):

The best part of a gig is the opportunity to connect one-on-one with people in their space, and getting to put 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 share. — Jon Montgomery

I like to assess risk, on what metrics I use, and I love to compete. I love to stack myself against the best, in whatever it is I get to be a part of. — Jon Montgomery

When I saw skeleton for the first time, I was compelled, from a visual standpoint. Having tried it one time, I was hooked. — Jon Montgomery

When the moment of competition becomes visible to the masses, the capacity to see the individual’s team isn’t present but everybody who has done something that they can be proud of knows full well what goes into a result. — Jon Montgomery

That belief that others had done this doubled workout was compelling and propelled me far past my self-imposed limitations. It made me realize that things are only out of our reach if we put them there. — Jon Montgomery

I am a curious dude. It’s led me to chase best-informed guesses for what we know today. I am open and willing to have my mind changed about stuff. Here’s what I know right now. — Jon Montgomery