Jon Montgomery

When you step outside your comfort zone, you truly find life.

Host of The Amazing Race Canada and Olympic Gold Medalist

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Jon Montgomery | Host of The Amazing Race Canada and Olympic Gold Medalist

Jon Montgomery delighted Canadians by winning Gold in Men’s Skeleton at the Vancouver 2010 Olympics. Now, as host of The Amazing Race Canada, he is a charming ambassador for our country’s most beautiful sights. In his talks, Montgomery shares his Olympic journey and important lessons on teamwork, leadership, and dreaming big. Whether he’s in snowy Nunavut, on a lentil farm in Saskatchewan, or on stage presenting a keynote speech, Montgomery is genuinely funny and always inspiring. 

Proudly Canadian, Jon Montgomery says that being the host of The Amazing Race Canada has given him an even greater appreciation for the country. “I already had a profound sense I was a lucky man to be Canadian, but doing this show, you get to meet other Canadians, you get to see how they interact with the racers and a sense of commonality amongst the people.” For his work on the show, Montgomery received a Canadian Screen Award for Best Host in a Variety, Lifestyle, Reality/Competition, or Talk Program or Series.

In February 2009, Montgomery won the Whistler World Cup, which served as the test event for the Vancouver Olympics. At that time, he called the victory the highlight of his career, adding that it was especially meaningful to win at home in front of family and friends. But what he really yearned for was Olympic gold. At the 2010 Olympics, he defended his home track once more, but this time, he did it in front of the world. The now infamous video of Montgomery drinking a pitcher of beer while walking through the streets of Whistler surrounded by screaming fans is sure to go down in Canadian lore.


It was Montgomery’s natural curiosity that launched his Skeleton career. Wandering through Calgary Olympic Park years ago, he saw a Skeleton racer whip by at top speed. Fearing it was a Luge accident, he inquired as to what the sport was all about at the visitor's centre. He immediately signed up for a “discover session” and began his long journey to Olympic gold. He won his first World Cup event in January 2008, and also won a silver medal at the World Championships that same year, finishing the season ranked second overall on the World Cup. Some called it quick success, but Montgomery sees things differently. He’s been sliding since 2002, but didn’t experience his first win until the 2007/2008 World Cup tour. As he says, “I had my butt handed to me on countless occasions when I first started.”   


Montgomery and his wife Darla are also committed and passionate about giving back. They are affiliated with WaterAid, which works with the poorest and most marginalized communities in sub-Saharan Africa, Asia, the Pacific region and Central America, and Right to Play, which uses the power of play to educate and empower children to be guardians of their own health and active participants in their communities.


“It was such a pleasure to have Jon Montgomery host our Guys’ Night Out event at Hudson’s Bay Vancouver. He was enthusiastic and genuine with all of our guests, and his charisma was felt throughout the room. He took the time to shake everyone’s hand, take pictures with fans, and even let guests give his gold medal a try. He was approachable, great to work with, and made sure that everyone had a good time.”

Hudson’s Bay Company

“Jon Montgomery was a featured speaker at the Alberta Sport and Recreation Leadership Summit Olympic Athlete Panel Presentation. Jon’s passion and inspiration along with his charismatic personality had everyone’s attention. He is an outstanding spokesperson who is engaging and compelling. His ability to share his journey of what has transpired throughout his career on his path to an Olympic gold medal was absolutely brilliant.”

Alberta Sport, Recreation, Parks, and Wildlife Foundation

“Jon had a lot of energy and relatable experience. His delivery was humble and at the same time proud of his accomplishments. His story was very relevant to a Canadian audience and his participation with our audience was gracious. He took time to meet and greet many of the attendees at the conclusion of the event, signing autographs, providing his gold medal to anyone and everyone to touch and share in the experience. He is a true Canadian in every sense of the word!”

Vancouver Tourism Awards

“It was a pleasure to have Jon Montgomery speak at our Gatorade sales rally this past January. He was engaging, inspiring, and incredibly authentic in his delivery. There wasn't a single person in the room who didn't feel intimately connected to Jon's talk and at the end, he took time to shake hands, take pictures, and sign autographs for each and every one of us.”


“Jon was the keynote speaker at our National Firm Retreat this past June. He was an absolute pleasure to work with and was very accommodating to our schedule and needs. Jon has a very down to earth, Canadian style about him that allowed him to easily connect with everyone in the room. He was able to tie his messages of taking ownership of your future and working collaboratively with others directly to the central themes of our retreat using humour and real-life anecdotes. Jon helped to get our retreat off to an energetic start and I would highly recommend him to anyone.”

Borden Ladner Gervais LLP

“Jon did such a great job speaking at our conference; the delegates loved him and were so pleased to have opportunities to have photos with him before and after his talk. Yes that’s right, he was gracious enough to take photos before his talk while the AV was being set up. We have had nothing but positive feedback on his talk, and that he was the highlight of the conference!”

Pharmacy Technicians Society of Alberta

“Jon delivered a truly inspirational message at our national leader conference earlier this year. His message was right on the mark…inspiring leaders to take responsibility for challenging goals in the face of an uncertain path and really demonstrating how to take ownership for developing your full potential and that of your team. Jon is skilled at communicating his message in a way that resonates across a diverse audience with just the right blend of humour and candour. Jon Montgomery was the perfect keynote speaker for setting the stage at our national conference.”

Great-West Life

“Thank you for helping give the Parks and Recreation Ontario Forum such a spectacular finish! You wove your understanding of our sector just beautifully into your story. People laughed, were inspired, felt emphatic, and celebrated your success. And, because you presented your story in such a genuine way, the delegates could see a little bit of themselves come to life. Lastly, you really made the day of everyone who waited to get a picture with you and the gold medal. For a moment, each of them was on top of that mountain, and the podium, with you. Stellar, Jon, just stellar!”

Parks and Recreation Ontario

“Jon Montgomery gave a first class professional presentation at the Winnipeg Convention Centre to an audience of independent retailers, hardware vendors, and TruServ Canada staff at the TruServ Canada Spring Market. His presentation was very well received and cited by audience members as the best pre-market function ever. Jon is friendly, unpretentious and a captivating speaker with a great Canadian story. He connects with his audience and is a real crowd-pleaser. I highly recommend Jon as a motivational speaker in any context.”

Truserv Canada

“Jon was a wonderfully energetic and infectiously enthusiastic speaker. He spoke from the heart, and very naturally, about his journey to his Olympic dream, and kept our group captivated and entertained the entire time. He is a true Canadian spirit.”

Canadian Security Traders Association, Inc.

Speech Topics

Dreaming Big Living Bigger

While Jon Montgomery always wanted to be a Canadian National Team athlete, he didn’t know which sport it would be in. Keeping his eyes wide open, living outside his comfort zone, trying new things, and accepting the challenges that presented themselves enabled him to find his passion and his opportunity to realize his dreams. Montgomery’s story inspires others to go after what they’re looking for, no matter how daunting the task may at first seem.

Jon Montgomery’s Olympic Journey

The story of Jon Montgomery’s Olympic journey: how a small-town boy from Manitoba, who grew up playing hockey and idolizing his home town hero, Theo Fleury (the smallest guy to ever play in the NHL), was inspired to become an Olympic champion.

The Importance of Teamwork
In an individual sport like skeleton, one’s success as an athlete is directly tied to an ability to work collaboratively with the team behind the front lines. Jon Montgomery explains the importance of teamwork in our families, workplaces, and communities.