It’s Not A Straight Line

In this episode, I sat down with Matt Hopkins, Executive Director, People at the Toronto Transit Commission (TTC).We start with an interesting idea: what can business leaders learn from the movie and real-life story of Moneyball? Aside from creating winning baseball teams, how can a similar way of thinking build better teams for our organizations?For Matt, it’s about looking beyond the traditional resume and asking a different question: How do you assemble a team of people whose strengths complement each other? Instead of trying to find ten perfect individual contributors, he looks at the collective skill set of the team, where people can excel, and how a leader can coach them to get the best outcome as a team.We also go behind the scenes of one of the highest-pressure parts of Matt’s job: collective bargaining. In 2024, Matt was the lead negotiator with the TTC’s largest union, managing the interests of employees, union leadership, management, the TTC Board, the City and, ultimately, millions of people who rely on transit in Toronto.One of my favourite parts of the conversation is Matt’s perspective on difficult conversations. He talks about the difference between someone’s position and their underlying interest and why creating enough trust for people to tell you what is really driving them can completely change the conversation.If you lead people, are navigating through difficult conversations, or are thinking about what the next move in your own career should look like, I think you’ll get a lot out of this one.For career opportunities with the TTC, check out the TTC careers board and follow the organization on LinkedIn. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jjwharding.substack.com

In Episode 50 of It’s Not a Straight Line, I sit down with a longtime friend: Whitney Bell, Chief Marketing Officer of the Toronto Tempo — Canada’s first WNBA franchise, tipping off in May 2026.We talk about motherhood, building Canada’s first WNBA team, and why women’s sports is a movement — not just a moment.Whitney takes us behind the scenes of launching a brand-new franchise, including the moment the Tempo name leaked early and the team had to pivot fast to truly “own the narrative.” We explore what it’s like to market a startup sports brand in a world that moves at full speed and how you build real brand love, not just awareness, while staying rooted in values and community.Beyond the job title, Whitney opens up about her career journey through her experiences at Lyft, Unilever, and startups, and how those experiences shaped her resilience and leadership under pressure. She also shares candidly about IVF, miscarriage, postpartum, and the reality of balancing an executive role with two young children while building a “village” in Toronto without family nearby.This conversation is a reminder that careers don’t move in straight lines and neither does life. Whitney is proof that you can chase big ambitions, lead with empathy, and still make space to give back and mentor the next generation.https://tempo.wnba.com/@TorontoTempo on Instagram This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jjwharding.substack.com

Kendra Fisher was on track for Olympic greatness—a standout goaltender with Team Canada’s hockey program who once heard the words every athlete dreams of: You made the Olympic team. But during those tryouts, her mental health had a different plan and her life changed directions.In this episode of It’s Not A Straight Line, Kendra opens up about the five-year stretch that nearly broke her, and the moment she decided to take giving up off the table. From working tirelessly just to survive the day to actively choosing to participate in her mental health, Kendra’s story is about reclaiming power, rewriting identity, and learning how to move forward.Now a professional speaker, podcaster, and mental health coach, Kendra draws from her experience as a firefighter, 3x inline hockey world champion, and her experience with her own mental health journey. She speaks candidly about the courage it takes to show up for ourselves and for each other.If you’ve ever wondered how to keep going when it feels like everything is falling apart, this conversation is a masterclass in vulnerability and redefining success on your own terms.Follow Kendra on Instagram @kfisher30 and learn more at kendrafisher.com. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jjwharding.substack.com

On this episode of It’s Not A Straight Line, I was joined by Michael Downey, a leader who left his mark on Tennis in Canada. His career journey started far from the courts and it is anything but a straight line. He is the former CEO of Tennis Canada and the Lawn Tennis Association (LTA) in Britain, and currently serves as Chair of the Advisory Committee for the greater (a strategy consulting firm) and as a volunteer board director for Canada’s most successful community tennis hub. Michael started his career in Consumer Packaged Goods Marketing and worked for Labatt, MLSE, Skydome, and Molson before a career pivot into tennis that would change the trajectory of the sport in Canada. During his tenure at Tennis Canada, tennis pros like Milos Raonic, Bianca Andreescu, Denis Shapovalov, and Genie Bouchard broke through on the world stage, and there was a significant emphasis from Michael to fostering the grassroots development of the sport, add training facilities across the country, and secure key long-term partnershipsDuring the episode, Michael reflects on the lessons he learned early in his career, the challenges, and the moment when he joined the Toronto Raptors during their inaugural year. We also discuss his cancer diagnosis, when Michael heard the words “you have cancer” twice in one day.You'll hear behind-the-scenes stories from the LTA, including attending Wimbledon management meetings, sitting in the Royal Box, and seeing first-hand the tournament's focus on perfection.This episode is filled with inspiring insights: from navigating career transitions and building resiliency, to Michael’s advice for anyone facing a job loss. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jjwharding.substack.com

On this episode of It’s Not A Straight Line, I’m joined by Clayton Peters, producer, writer, and long-time manager of his brother, global comedy icon Russell Peters. For almost 20 years, Clayton has been at the helm of Russell’s remarkable career, managing one of the longest and most successful runs in comedy, with Russell selling out venues worldwide since 2005.Clayton’s journey into management is rooted in a promise made to his father on his deathbed when he told Clayton to take care of and always look out for his younger brother. After years of working in corporate jobs where he felt like a “square peg in a round hole,” Clayton transitioned into the comedy and entertainment space around the age of 40. From early work in international business and managing other acts alongside his brother like Joe Koy, to focusing fully on Russell’s career, Clayton’s path to manage one of comedy’s stars has been anything but a “straight line”.In this episode, Clayton shares thrilling stories about their successes and challenges—especially navigating the pandemic, while not spending time in person together—and the time they defied critics by filling the Air Canada Centre (now Scotiabank Arena) despite being told they’d fail. Clayton’s insights are inspiring, and his advice to “not take it personally” is a lesson anyone can apply to life and career, and one he has learned in Entertainment.We also discuss his thoughts on what would happen if Russell ever wanted to go with another manager and the life lessons Clayton now passes on to his own son. Recorded in-person in August 2024, this conversation is full of insights, honesty, and candid moments.Plus, don’t miss seeing Russell’s upcoming Canadian and World Tour, Relax It’s Not That Serious, which hits Toronto this December 2024. For tour information, head to https://www.russellpeters.com/ This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jjwharding.substack.com

On Episode 46 of the It’s Not A Straight Line podcast, I had the pleasure of sitting down with Hugh Lawson, a business development expert, Vanier Cup football champion, and leadership advisor. As the Principal at Lawson Leadership Advisory, Hugh is a purpose-driven, people-centric leader who embodies the principles of Ikigai—finding the intersection of what the world needs, what you love, what you're good at, and what you can get paid to do.During our conversation, Hugh shares his journey towards living a life of purpose, emphasizing the importance of making a positive impact while also earning a living. We delve into his experience as a University football player at Laurier, where he won the Vanier Cup, and how his successes have always been achieved through teamwork. We also explore his involvement in socially impactful companies like the grocery buying platform, Tre’dish, and how African proverbs have shaped his leadership philosophy.With over 25 years of experience in business development, enterprise sales, and leadership, Hugh’s insights on resilience, relationship-building, and teamwork are invaluable. Join us as we discuss his pursuit of Ikigai, the wisdom he’s gained from his career, and his commitment to creating positive change in the world. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jjwharding.substack.com

Join us for an inspiring episode as I sit down with Matty and Alex Hill, better known as the Hill Brothers. Matty, Founder and Commissioner of Niagara Youth Flag Football (NYFF), is celebrated as one of Canada's top flag football coaches, having led teams to two World Championships. Meanwhile, Alex, a Sales Representative at RE/MAX Escarpment Realty and renowned for his dynamic career in real estate, shares his journey from High School and University Quarterback to Night Club Promoting before finding his stride and career in Real Estate.Matty's passion for sports and community led him to establish NYFF, now boasting 1200 players per season and fostering championship-winning teams. Learn how Matty's personal challenges, including a shoulder injury, fueled his dedication to youth sports and community building.Alex, recognized as one of RE/MAX Canada's Top 30 under 30, offers insights into his real estate career, including navigating challenges like rising interest rates and debt management. Discover how Alex's diverse experiences in promoting, investing, and running an Airbnb business have enriched his professional journey and client relationships.From coaching triumphs to entrepreneurial pursuits, Matty and Alex embody resilience and leadership in their respective fields. Tune in to uncover their secrets to success and their vision for the future of youth sports and real estate in Niagara, Hamilton and beyond.Follow Matty and NYFF's journey on Instagram @niagarayouthflagfootball and Alex's real estate and personal ventures @AlexHill14. For a glimpse into Alex's Airbnb cottage, visit @kawartha_lakescape. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jjwharding.substack.com

We're thrilled to welcome Wayne Hannah, the mastermind behind "Mindful'Ish" on YouTube and "@goodmorningassholes" on TikTok. Wayne is a humorist, content creator, firefighter, and veteran of the Canadian Armed Forces. After serving 20 years as an artillery soldier, Wayne's journey took him from counteracting Somali pirates to injecting humour into the "dry morning announcements" on a Naval Vessel during one of the longest at-sea deployments since World War II. Wayne's passion for bringing laughter to others has earned him a massive online community of over 230,000 followers on TikTok. As a dedicated mental health advocate, Wayne's iconic "Good Morning A******s" greeting is a reminder that we often treat ourselves more harshly than anyone else. He created this content during the pandemic, realizing the importance of self-compassion as he was his own biggest critic and he was saying hi to himself, referring to himself as an a*****e. Wayne Hannah, CD, holds the Canadian Forces' Decoration, awarded to members of the Canadian Armed Forces who have completed twelve years of service under specific conditions. While Wayne values his military experiences and the leaders he encountered, he also candidly discusses the deep-rooted belief of not being good enough that led to ongoing mental health struggles.Join us as we dive into Wayne's incredible and diverse journey, exploring the challenges and rewards that have shaped his life. Don't miss this inspiring conversation filled with humour, resilience, and valuable insights.Tune in now to It's Not A Straight Line!YouTube - https://www.youtube.com/@Wayne.HannahInstagram - @goodmorningassholesTikTok - @goodmorningassholes This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jjwharding.substack.com

Discover the inspiring journey of Monique Giroux, a former corporate banker turned soulful guide. Once the powerhouse behind sponsorship at a major Canadian bank, Monique's path took a surprising turn after nearly two decades in the corporate world. Now, as the founder of Flourish with Monique, she's dedicated to helping others find peace and purpose in life.Join Monique as she shares her transformational story, from her prestigious role at CIBC to her recent adventures in Thailand, where she became a certified yoga teacher and learn how she embraced the practice of silent meditation in Ontario and the Netherlands. Through her experiences, including profound moments during Vipassana Meditations, Monique discovered a deeper calling to share her insights and wisdom with those struggling with anxiety and mental health challenges.Explore Monique's journey of self-discovery and spiritual growth, including the profound impact of Vipassana meditation and the loving-kindness teachings of her mentor, Dhamma Sukha. Delve into her newly released book, "Lost Intentionally," offering a roadmap for navigating life's twists and turns with intention and grace. The book was officially released on June 11th, and is available on Amazon - Lost Intentionally: The Inner and Outer Journey of a Spiritual Nomad https://a.co/d/3d2RwaGYou can learn more on Dhamma Sukha’s website - https://www.dhammasukha.org/ and the Plum Village Monastery https://plumvillage.org/about/plum-village Monique’s website is https://flourishwithmonique.comInstagram - @flourishwithmonique      LinkedIn - https://www.linkedin.com/in/moniquefgiroux/ This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jjwharding.substack.com

On this episode, I sat down with Chris Reynolds - the Co-Founder and Executive Chair of Investment Planning Counsel (IPC). When Chris co-founded IPC in 1996, he set out on a mission to help entrepreneurial financial advisors build better businesses. Since then, he has remained committed to this mission, which continues to be the focus at IPC, which was acquired by Canada Life in 2023. Chris has spent over 25 years in the Finance and Investment industry, and he believes at the heart of any great business is a remarkable client experience. Chris is a life-long learner who is always learning from the best of the best, from within his industry, as well as outside/new perspectives. Chris Reynolds is the Host of the "Turning The Page" Podcast, a big fan of live music and rock n' roll, and his former radio show on a popular Toronto radio station was syndicated across ten other stations. When asked what gets him "out of bed in the morning", he stated "it is the people that get me most excited!"You'll hear why Chris is a huge advocate for entrepreneurship and why to him, there is no safer way to go.Enjoy the episode! Turning The Page Podcast - Spotify Link Investment Planning Counsel - Website This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jjwharding.substack.com