440 | Jakob Graham | Why You Don’t Need to Be Ready to Start Leading

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.

🔗 LinkedIn | Website | Facebook

Resources & Links Mentioned

• Ego Is the Enemy by Ryan Holiday
• The Coaching Habit by Michael Bungay Stanier
• Gary Vaynerchuk on failure and time
• Alex Hormozi on focus and execution

Important Links

• Connect with Chris: Website | LinkedIn
• Learn more about the