125: Financial Literacy, Education Gaps, and Reinventing Yourself with Sarah Jeanneault
Wed Feb 04 2026
In this wide-ranging conversation, Sarah Jeanneault shares her unconventional journey from struggling with math in school to becoming a respected leader in fintech, trading education, and enterprise knowledge management. She and Dwayne Kerrigan explore the deep gaps in financial literacy, why traditional education often fails to prepare people for real-world decision-making, and how learning truly begins after formal schooling ends.
Sarah explains how she applied adult learning theory to teach herself trading, why psychology matters more than numbers in the markets, and how curiosity, pattern recognition, and humility shaped her success. The discussion expands into the future of education, AI’s role in learning, entrepreneurship, identity shifts after business exits, and the emotional reality of leadership transitions. This episode is a thoughtful examination of growth, risk, and why continuous learning is the most valuable skill anyone can develop.
Episode Highlights:
00:00 – Sarah opens by naming the gap in real-world financial literacy.
02:00 – Dwayne introduces Sarah and frames the episode around learning and reinvention.
05:00 – Sarah shares struggling with math and early assumptions about intelligence.
09:00 – Losing her best friend and questioning the direction of her life.
14:00 – Discovering trading and applying adult learning theory to self-education.
18:00 – Why financial literacy is rarely taught despite its life-long impact.
23:00 – Breaking down trading basics and removing unnecessary complexity.
28:00 – Psychology, emotion, and why ego derails good financial decisions.
33:00 – Risk, uncertainty, and learning to sit with discomfort.
38:00 – Podcasts, curiosity, and self-directed learning as modern education.
44:00 – Continuous learning as the foundation of entrepreneurship and leadership.
49:00 – Gamifying learning to build confidence and consistency over time.
54:00 – Building community through transparency and shared learning.
59:00 – Scaling education-driven businesses and teaching at scale.
64:00 – Identity shifts after acquisitions and redefining success.
69:00 – Leadership, disagreement, and creating psychologically safe teams.
74:00 – AI, critical thinking, and the future of learning.
79:00 – Personal growth, reinvention, and staying curious long-term.
84:00 – Reflections on learning, humility, and what truly creates confidence.
88:00 – Closing thoughts, gratitude, and setting up Part 2.
Key Takeaways:
Financial literacy is rarely taught, yet deeply shapes life decisions.Learning accelerates when curiosity replaces fear of being “bad at math.”Real education often begins after formal schooling ends.Trading and business are driven as much by psychology as by data.Growth comes from pattern recognition, experimentation, and reflection.Entrepreneurship requires comfort with uncertainty and identity shifts.AI will amplify learning — but only if critical thinking is prioritized.Strong leaders create environments where disagreement is encouraged.Sustainable success comes from continuous learning and reinvention.
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In this wide-ranging conversation, Sarah Jeanneault shares her unconventional journey from struggling with math in school to becoming a respected leader in fintech, trading education, and enterprise knowledge management. She and Dwayne Kerrigan explore the deep gaps in financial literacy, why traditional education often fails to prepare people for real-world decision-making, and how learning truly begins after formal schooling ends. Sarah explains how she applied adult learning theory to teach herself trading, why psychology matters more than numbers in the markets, and how curiosity, pattern recognition, and humility shaped her success. The discussion expands into the future of education, AI’s role in learning, entrepreneurship, identity shifts after business exits, and the emotional reality of leadership transitions. This episode is a thoughtful examination of growth, risk, and why continuous learning is the most valuable skill anyone can develop. Episode Highlights: 00:00 – Sarah opens by naming the gap in real-world financial literacy. 02:00 – Dwayne introduces Sarah and frames the episode around learning and reinvention. 05:00 – Sarah shares struggling with math and early assumptions about intelligence. 09:00 – Losing her best friend and questioning the direction of her life. 14:00 – Discovering trading and applying adult learning theory to self-education. 18:00 – Why financial literacy is rarely taught despite its life-long impact. 23:00 – Breaking down trading basics and removing unnecessary complexity. 28:00 – Psychology, emotion, and why ego derails good financial decisions. 33:00 – Risk, uncertainty, and learning to sit with discomfort. 38:00 – Podcasts, curiosity, and self-directed learning as modern education. 44:00 – Continuous learning as the foundation of entrepreneurship and leadership. 49:00 – Gamifying learning to build confidence and consistency over time. 54:00 – Building community through transparency and shared learning. 59:00 – Scaling education-driven businesses and teaching at scale. 64:00 – Identity shifts after acquisitions and redefining success. 69:00 – Leadership, disagreement, and creating psychologically safe teams. 74:00 – AI, critical thinking, and the future of learning. 79:00 – Personal growth, reinvention, and staying curious long-term. 84:00 – Reflections on learning, humility, and what truly creates confidence. 88:00 – Closing thoughts, gratitude, and setting up Part 2. Key Takeaways: Financial literacy is rarely taught, yet deeply shapes life decisions.Learning accelerates when curiosity replaces fear of being “bad at math.”Real education often begins after formal schooling ends.Trading and business are driven as much by psychology as by data.Growth comes from pattern recognition, experimentation, and reflection.Entrepreneurship requires comfort with uncertainty and identity shifts.AI will amplify learning — but only if critical thinking is prioritized.Strong leaders create environments where disagreement is encouraged.Sustainable success comes from continuous learning and reinvention. Resources...