The Dwayne Kerrigan Podcast

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...

In Part 2 of this powerful conversation, Robyn Benincasa returns to go deeper on one of the most misunderstood elements of leadership: commitment when motivation fades. Drawing from decades of adventure racing, firefighting, and nonprofit leadership, Robyn explains why elite teams don’t wait to feel ready — they move forward anyway.
Together with Dwayne Kerrigan, Robyn unpacks the difference between confidence and ego, why standing still is often more dangerous than moving imperfectly, and how innovation only emerges when teams focus on how to win, not how to avoid losing. Through unforgettable stories involving Steve Gurney, creative rule-bending, and suffering with grace, she illustrates how forward momentum unlocks answers that planning alone never will.
The conversation culminates with a deep dive into Project Athena, the nonprofit Robyn founded to help survivors of medical and traumatic setbacks reclaim identity, confidence, and purpose through team-based endurance adventures. This episode is a masterclass in leadership under pressure, culture design, and why the ability to suffer well — together — is a competitive advantage in business and in life.

EPISODE HIGHLIGHTS:
00:00 – Robyn explains commitment through action, not emotion.
02:00 – Dwayne connects mentorship, influence, and leadership responsibility.
05:00 – Why being willing to be a beginner fuels innovation.
07:30 – Failure, repetition, and learning through action.
10:30 – Why preparation paralysis keeps people stuck.
13:30 – Emotions, discipline, and not letting feelings run your life.
16:00 – “Winning is that way” and the mindset shift that sparks innovation.
18:30 – Steve Gurney stories and thinking inside the rules vs. white space.
22:00 – Team selection, culture fit, and suffering equally.
26:00 – Ego vs. confidence and rotating leadership by strength.
30:00 – Why top-down leadership fails in complex environments.
34:00 – Relinquishing ego to avoid slowing the entire team down.
38:00 – Project Athena’s mission and creating comeback identities.
43:00 – How shared suffering builds lifelong trust and leadership.
48:00 – “Excellent suffering” and using adversity as an advantage.
52:00 – Robyn’s six hip surgeries and redefining resilience.
54:00 – Where to find Robyn, Project Athena, and closing reflections.

KEY TAKEAWAYS:
Commitment is demonstrated by action, not emotion.
Feelings can inform decisions, but they should never rule them.
Forward momentum creates clarity; standing still creates fear.
Innovation comes from operating in the white space.
Helping others is the healthiest outlet for ego.
Identity is shaped by comeback stories, not setbacks.


NOTABLE QUOTES:
“ I show my commitment to my goals by what I do, regardless of how I feel.” - Robyn Benincasa
“ Commitment starts when the fun stops, right? I mean, you're not actually showing your commitment until shit's not fun anymore.” - Robyn Benincasa
“There’s a difference between...

Dwayne Kerrigan sits down with world-class endurance athlete, firefighter, nonprofit founder, and keynote speaker Robyn Benincasa to unpack what truly separates great teams from the rest.
Drawing from decades of extreme adventure racing, Robyn shares how elite teams win not by being the most talented, but by being the most committed to each other. She introduces her powerful TEAMWORK framework, revealing why total commitment, empathy, adversity management, mutual respect, and relinquishing ego are the real competitive advantages—whether you’re racing through jungles or leading a modern organization.
Through unforgettable stories—including hallucinations after days without sleep, tying boats together to beat world champions, and redefining leadership mid-race—Robyn shows how purpose, preparation, creativity, and shared ownership create cultures that don’t just survive pressure… they win because of it.
This episode is a masterclass in leadership, resilience, and building teams that operate as one heart, one mind, especially when the stakes are high and the path forward is uncertain.

EPISODE HIGHLIGHTS:
00:00 – Robyn opens with the defining trait of elite teammates: leaving ego at the start line.
01:00 – Dwayne formally introduces Robyn and outlines her extraordinary background.
03:00 – Robyn shares discovering kayaking after hip surgery and focusing on what she could do.
06:30 – Why progress toward a meaningful goal is what makes humans feel alive.
10:30 – Competing to explore personal limits rather than seeking validation or approval.
14:00 – Why great teams care more about each other than themselves.
18:00 – How Robyn accidentally became a speaker after Fast Company’s “Extreme Teamwork”
21:30 – The importance of leaving ego behind and accepting help to win as a team.
25:30 – The “Steve Gurney Missile” story and choosing to race to win instead of not lose.
30:00 – Creativity, calculated risk, and living in your strengths under pressure.
34:30 – Relinquishing ego, rotating leadership, and leading based on strengths—not titles.
39:00 – Hallucinations, extreme fatigue, and supporting teammates through suffering.
42:00 – Kinetic leadership and adapting leadership styles to what the team needs.
45:30 – Purpose, coaching influence, and how early mentors shaped Robyn’s drive.
50:30 – Innovation, self-awareness, and evolving by leaning into strengths.
56:00 – Finding a greater purpose in business.
KEY TAKEAWAYS:
Winning teams prioritize commitment to each other, not individual performance.
Progress toward a meaningful goal is what makes humans feel alive.
Creativity and innovation emerge when teams operate from trust and purpose.
Leadership should rotate based on strengths, not titles or tenure.
Accepting help is not a weakness, it’s how teams move faster and farther.
Great leaders show people how amazing they are, not how amazing the leader is.


NOTABLE QUOTES:
“ I feel weird when I don't have a goal. I get my juju, I get my energy from...

In Part 2 of this conversation, Michael Grandjean shares the emotional and psychological turning point that allowed him to rebuild his life and career after profound loss. From a raw moment of self-forgiveness in the mountains of Morocco to the daily discipline of “kicking the can,” Michael walks through the mindset shifts, rituals, and relentless patience required to climb out of depression, debt, and despair.
Together with Dwayne Kerrigan, this episode explores the role of brotherhood, leverage, honest self-reflection, and creating a compelling new story when the old one no longer serves you. This is a masterclass in resilience, identity rebuilding, and what it truly takes to come back stronger — with wisdom, humility, and purpose.
Episode Highlights:
00:00 – Michael opens with the realization that self-forgiveness was required to move forward.
01:00 – Episode introduction and framing this as Part 2 of Michael’s comeback story.
02:00 – The Morocco mastermind trip and being forced to confront the truth.
05:00 – Emotional breakthrough on the mountain and the decision to rebuild.
07:30 – Creating the Three Ps: plan, persistence, and patience.
09:00 – “Kick the can” explained and committing to daily forward movement.
12:00 – Brotherhood, accountability, and why we’re not meant to do life alone.
16:00 – Letting go of guilt, disappointment, and the need for self-forgiveness.
20:00 – Depression, isolation, and breaking life down to “just get through today.”
24:00 – Writing the plan on a whiteboard and becoming resourceful again.
30:00 – Changing the internal story to create a compelling future.
36:00 – Writing goals again, paying off debt, and getting back to zero.
42:00 – Daily mantras, rituals, and retraining the mind.
48:00 – Shifting from hourly work to profit-based consulting and rebuilding cash flow.
01:01:00 – Final reflections, where to find Michael, and the podcast disclaimer.
Key Takeaways:
Self-forgiveness is a prerequisite for real forward movement.
Progress is built daily through patience, persistence, and simple actions.
You cannot rebuild alone - community and accountability matter.
Changing your internal story changes your future trajectory.
Rituals, mantras, and physiology are tools for rewiring the mind.

Resources Mentioned:
Checkmate: https://www.facebook.com/reel/1365025640684229
Tony Robbins – Date With Destiny
Mastermind
Personal goal-setting and written planning practices
Daily mantras and meditation rituals
Whiteboard strategic planning

Notable Quotes:
“The past is the past. The past doesn't equal the future.” - Michael Grandjean
“You have to change your story … If you’re living in a shitty story, you’re going to stay in a shitty story.” - Michael...

In this candid and powerful conversation, Michael Grandjean joins Dwayne Kerrigan to share the real story behind his rise, collapse, and rebuilding as an entrepreneur who led with heart—and paid a steep price for it.
From early service as a volunteer firefighter and Navy corpsman to building a $25M remediation company, Michael reflects on the leadership blind spots that quietly dismantled his business: avoiding confrontation, ignoring early warning signs, and letting emotion override structure and accountability.
He opens up about losing everything, the humility required to face hard truths, and the moment that changed his trajectory—the realization that even at checkmate, the king still has one more move. This episode is a raw masterclass in leadership self-awareness, responsibility, and what it truly takes to rebuild when everything falls apart.
Episode Highlights:
01:15 — Dwayne introduces Michael and some of his background
03:00 — Framing the conversation: collapse, comeback, and leadership through adversity
05:00 — Early life experiences that shaped Michael’s instinct to serve and protect others
08:00 — How learning-by-doing in the military built confidence, skill, and leadership
12:00 — The missed Naval Academy opportunity and how a single point changed his life path
16:00 — Discovering the root of his need to “fix everything” through early childhood memory
20:00 — How that identity became both a leadership strength and a business liability
24:00 — From couch-surfing to starting his first company with borrowed money
28:00 — Explosive growth: scaling from zero to $25M and building teams that drove success
35:00 — Hiring high-accountability leaders and why standards matter more than likability
42:00 — The beginning of complacency and losing focus after reaching the “top”
48:00 — Major projects fail, millions lost, and the cost of avoiding confrontation
55:00 — Hard truths: personal blind spots, delayed decisions, and leadership responsibility
01:05:00 — The emotional bottom, rebuilding identity, and the realization that “the king still has one more move”
01:20:00 — Final reflections on honesty, courage, accountability, and choosing to move forward
Key Takeaways:
Leading with heart is powerful, but without boundaries it becomes expensive.
Relationships, not brands, carry small and mid-sized businesses.
SOPs, structure, and accountability protect leaders from their blind spots.
Complacency quietly erodes even successful companies.
Leaders must be honest with themselves before they can fix anything else.
Even at your lowest point, you still have one more move.

Resources Mentioned:
Checkmate: https://www.facebook.com/reel/1365025640684229
Tony Robbins – Date With Destiny
Awaken the Giant Within (Tony Robbins)
Mastermind

Notable Quotes:
“The king still has one more move” - Michael Grandjean