Leaders Of Tomorrow Podcast

In this end-of-year solo episode, Chris Thomson reflects on one of the most transformational chapters in the history of Student Works. From smashing revenue records to reinventing the company’s systems, 2025 marked massive progress for the team and set the stage for an even stronger 2026.

Chris walks through the company’s growth, the evolution of the Leaders of Tomorrow podcast, breakthroughs in technology (including the full rebuild of SIMON), increases in operator success metrics, and the continued expansion of fundraising efforts for MS.

He also shares a personal milestone: becoming a grandfather and redefining his vision for the future.

If you want a snapshot of what makes this community powerful…and what’s coming next…this is the episode to hear.

Timestamped Highlights

[00:00:00] – The power of a competitive and cooperative culture

[00:01:10] – Why recognizing progress is a leadership best practice

[00:02:00] – From $10M to $43M: how Student Works accelerated after the pandemic

[00:03:15] – Seven years, 70,000 downloads: the evolution of the podcast

[00:03:40] – Shoutout to Podcast Your Brand for bringing the show to life

[00:04:45] – “I’m a proud grandfather”: welcoming Ella Rae Manje

[00:05:20] – New record averages in both painting and window cleaning

[00:06:30] – Eight million-dollar painting operators…and the first million-dollar window cleaner

[00:07:00] – $2.3M raised for MS: a legacy of impact

[00:08:00] – Five years of system building…and now a full-scale cleanup

[00:09:00] – Introducing SIMON 3.0: a complete rebuild of the company CRM

[00:12:50] – New estimating module + automated profitability safeguards

[00:14:13] – Daily production plans generated instantly inside SIMON

[00:14:50] – Major upgrades to safety, compliance, and team training

[00:18:00] – Final recruitment window: why December is the deadline

[00:19:35] – A call to future leaders: this is your moment to get on the bus

Resources & Links Mentioned

• SIMON CRM – Student Works Information Management Organizational Network

Important Links

This week, we’re sharing the first part of a recast of Chris Thomson’s powerful conversation on Paper Napkin Wisdom with host Govindh Jayaraman.

In this second part of “Cancer Is a Journey,” Chris opens up about the next chapter of his cancer experience, from jaundice and hospitalization to finally receiving a confirmed diagnosis and beginning chemotherapy.

What unfolds is a story not just of treatment, but of mindset, gratitude, and the expansion of purpose. Chris reflects on reframing chemo as healing, finding meaning in mortality, and discovering an even greater reason to live: to be present for his family, his team, and now his first grandchild.

Timestamped Highlights

[00:00:00] – Picking up where Part 1 left off: from feeling great to noticing symptoms

[00:01:43] – Turning yellow: the first signs of jaundice and the rush to the hospital

[00:03:00] – Emergency biopsy, stent surgery, and the fear of what’s next

[00:05:26] – Finally, a diagnosis: follicular lymphoma — and why Chris calls it “fantastic news”

[00:06:40] – The entrepreneur’s instinct: “Tell me what I need to do. Put me in, coach.”

[00:07:32] – Overcoming fear of chemo and reframing it as a healing process

[00:08:46] – “Chemo made me feel better.” How mindset and gratitude shaped recovery

[00:10:42] – Seeing chemo not as poison, but as partnership with medicine

[00:11:23] – Gratitude for Canada’s healthcare and perspective from others’ stories

[00:12:30] – The day of the banquet: from biopsy to public speaking in one day

[00:13:38] – What’s changed: health, priorities, and becoming a grandfather

[00:14:49] – “I want to have with my grandkids what I have with my kids.”

[00:16:41] – Turning lemons into lemonade — how cancer expanded his mission

[00:17:46] – Living beyond the physical: how loved ones continue through legacy

[00:19:59] – Staying in the moment and letting go of unrealistic expectations

[00:21:00] – A powerful goodbye: honoring his late friend Wendy Porter

[00:23:21] – Facing death daily — a Stoic approach to living fully

[00:26:29] – The ROI of a life of contribution: “Profit follows purpose.”

[00:27:46] – Climbing new mountains — redefining success after survival

[00:30:00] – Reaching out and finding connection: “We’re better together.”

[00:32:00] – Closing reflections: remembering who you are and being there for others

Resources Mentioned

What happens when success meets humility and life throws you the ultimate curveball?

In this deeply personal conversation, Chris Thomson sits down with Jakob Graham, a three-year veteran of the Student Works Management Program and incoming coach, to unpack how entrepreneurship, ego, and family challenges shaped him into a grounded, mature leader.

Jakob shares his journey from being a confident 21-year-old who thought he had it all figured out to facing a family health crisis that changed everything. Through heartbreak, hard lessons, and real growth, he learned the value of integrity, vulnerability, and showing up even when life feels uncertain.

Listen now because if you’ve ever wondered what true leadership looks like beyond the numbers, this episode will remind you that success starts with who you become when things get hard.

Timestamped Highlights

• [00:03:36] – Jakob’s early years in painting and his first taste of entrepreneurship
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• [00:07:12] – The harsh truth about “luck” and the myth of overnight success
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• [00:10:34] – How Student Works improved his time management, focus, and grades
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• [00:12:02] – The ego check that changed how he handled conflict and coaching
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• [00:15:03] – Building systems and auditing his business for long-term growth
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• [00:17:38] – How self-awareness and vulnerability became his superpowers
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• [00:22:48] – The life-changing family crisis that reshaped his priorities
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• [00:30:33] – Rebuilding a $260K business with a “we not me” mindset
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• [00:34:00] – Why integrity and consistency separate the top performers
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• [00:39:20] – Becoming a mini coach: why you’ll never feel fully ready—and that’s okay
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• [00:42:37] – Advice for new entrepreneurs: fail fast, ask for help, and keep swinging
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About the Guest

Jakob Graham is a three-year Student Works Management Program veteran and an incoming coach for the 2026 season. A graduate of the University of Guelph, Jakob has grown his business to over $260K while building a reputation for consistency, humility, and servant leadership. After stepping away from his business to support his family through a major health challenge, Jakob returned stronger—with a renewed sense of purpose and a focus on developing others.

This week, we’re sharing a recast of Chris Thomson’s feature on Canadians Leading With Impact, where he sat down with Troy Treleaven and Kevin Robert Crone from Dale Carnegie Canada to talk about leadership, mindset, and building Canada’s next generation of entrepreneurs.

Chris shares how he’s spent over three decades developing thousands of young Canadian entrepreneurs, turning ambitious students into confident leaders capable of running six-figure businesses before graduation.

From the fundamentals of accountability and time freedom to the psychology of stress and the discipline behind leadership, Chris breaks down what it really takes to lead with integrity, contribute value, and create lasting impact in both business and life.

Timestamped Highlights

[00:00:00] – Troy and Kevin introduce Chris Thomson and the Student Works legacy

[00:01:00] – Chris on betting on young entrepreneurs and the three freedoms: economic, decision, and time

[00:05:30] – Why mindset and stress management are critical to leadership success (“No pressure, no diamonds”)

[00:07:10] – Troy recalls door-to-door lessons and finding flow through challenge

[00:08:20] – Chris explains why knocking on doors builds sales mastery and confidence

[00:12:50] – Turning mistakes into “miss-takes”: why failure is the best teacher

[00:14:50] – Chris shares his entrepreneurial roots, from university athlete to Student Works leader

[00:18:20] – The 1,000-Millionaire Vision: teaching students to build wealth through leadership

[00:20:15] – Why contribution comes before profit

[00:21:45] – Alumni success stories: from Student Works to Wall Street and corporate leadership

[00:26:30] – The truth about generational differences and why each wave of leaders must evolve

[00:30:00] – Managing social media, FOMO, and the discipline of focus in the digital age

[00:35:00] – The Four Referability Habits (Dan Sullivan’s framework) and restoring integrity

[00:41:20] – Coaching accountability: helping young leaders see the real cost of inaction

[00:43:30] – The concept of willingness and the habits of elite performers

[00:46:00] – Chris on what Canadians need to raise the bar: high standards, high support

[00:51:10] – How Dale Carnegie’s teachings shaped Chris’s coaching philosophy

[00:53:40] – Are we missing positive psychology today? Chris on modern motivation and lifelong learning

[00:54:43] – Closing reflections: leadership, contribution, and becoming your best self

Resources Mentioned