130: Leadership, Ownership & Winning the Cup with Brad May
In this powerful episode, Brad May returns for Part 2 of a raw and honest conversation about leadership, resilience, identity, and what it truly takes to win at the highest level.
Brad reflects on being traded multiple times during his NHL career, adapting to new teams, and learning how to integrate into different locker rooms without disrupting culture. He shares the emotional journey of winning the Stanley Cup with the Anaheim Ducks — and why celebrating that moment with his family meant more than the trophy itself.
The conversation expands beyond hockey into business leadership. Brad breaks down why coaches are “salesmen,” why clarity of vision is essential, and why delegation without interference builds trust. He unpacks the difference between playing not to lose versus playing to win — and why excuses quietly erode culture.
At its core, this episode is about ownership. Ownership of performance. Ownership of mistakes. Ownership of mindset.
As Brad says, there is no “try.” You either do or you don’t.
Episode Highlights:
0:00 - Mindset over body: eliminating "try" and taking ownership
0:34 - Welcome and introduction to part two of the episode
1:31 - Adapting to seven different NHL teams and building new relationships
6:00 - Winning the 2007 Stanley Cup with Anaheim after 16-year career
7:50 - Scott Niedermeyer's perspective on being lucky to share the Cup with family
11:04 - What makes a good coach: selling a system and getting buy-in
13:49 - Comparing coaching styles: Mark Crawford vs Ted Nolan vs Randy Carlisle
15:30 - Ted Nolan's simple advice: "Just play left wing" analogy
17:31 - Randy Carlisle's relentless work ethic and pursuit of excellence
21:28 - Why some players leave the game bitter and unfulfilled
25:08 - Identity after hockey: from "I used to be" to "I am a hockey player"
30:28 - Eliminating excuses: "You either do or you don't"
33:28 - Leadership lesson from Brian Burke: delegating responsibility to coaches
55:38 - Playing to win vs playing not to lose: the power of identifying your goal
58:38 - The bar speech that united the team and families to win together
Key Takeaways:
- Leaders must communicate crystal-clear goals (short, medium, and long term).
- Identity loss can derail high performers after retirement or career shifts.
- Playing to “not lose” creates hesitation; playing to win creates momentum.
- Ownership beats excuses — every time.
- Leaders must reflect on whether failure was execution or lack of resources.
- Energy, clarity, and consistency win over time.
- You must declare what you want — silence guarantees nothing.
Resources Mentioned:
- The Secret (law of attraction concept)
- Tony Robbins – mindset principle referenced
- NIL (Name, Image, Likeness) era in NCAA athletics
- Cold plunge discipline practice
- Billions (TV show reference for executive coaching concept)
Notable Quotes:
- “Your mind is in charge. Doesn’t matter what your body feels, just do it.” - Brad May
- “It’s okay if you’re not successful, but own it and learn from it and let’s go. Let’s keep moving.” - Brad May
- “The moment that a coach compromises his values, he's not the same guy and he's probably not as good.” - Brad May
- “A coach is just a salesman. He needs 25 guys to buy in.” - Brad May
- “You gotta enjoy the small wins.” - Dwayne Kerrigan
- “There's just some people, some leaders, who are just not having the hard enough conversations.” - Dwayne Kerrigan
- “You also have to have people around you that are willing to say - hey, you're being either too easy or too hard. Like you just, you have to have a team around you to help you identify as a leader.” - Dwayne Kerrigan
Guest Bio:
Brad May is a former NHL forward whose 19-year career spanned more than 1,000 regular-season games across the league. He is a Stanley Cup champion, winning with the Anaheim Ducks in 2007, and remains a recognizable figure in hockey history for his 1993 overtime playoff goal against Boston, remembered by fans as the iconic “May Day” moment.
Following his retirement from professional hockey in 2010, May transitioned into broadcasting, working as an NHL analyst with CBC, Rogers Sportsnet, and AT&T SportsNet, where his candid, player-first perspective made him a natural presence on air. In 2024, May entered a new chapter off the ice, joining NFP as a Client Executive, where he works with businesses and individuals on insurance and risk management.
Guest Social Links:
Instagram: www.instagram.com/maydayhockey
LinkedIn: ca.linkedin.com/in/brad-may-24228662
Connect with Dwayne Kerrigan:
Disclaimer: The views, information, or opinions expressed by guests during The Dwayne Kerrigan Podcast are solely those of the individuals involved and do not necessarily represent those of Dwayne Kerrigan and his affiliates. Dwayne Kerrigan or The Dwayne Kerrigan Podcast is not responsible for and does not verify the accuracy of any of the information contained in the podcast series. The primary purpose of this podcast is to educate and inform. Listeners are advised to consult with a qualified professional or specialist before making any decisions based on the content of this podcast.