The Sea Captain Leadership Podcast

Phil Bender
  • 5.0 (12)
  • Entrepreneurship
  • Updated Biweekly

Ahoy! Welcome to the Sea Captain Way podcast with Phil Bender, where we help listeners navigate the uncharted waters of personal and professional growth. The Sea Captain Way is about energizing top performers to take on risks and push beyond their comfort zone to pursue life-changing goals and achieve peak performance. We’re going to help you build your vision by showing you how to break free of the boundaries that are holding you back.

  1. Feb 5

    Track That Advisor Data Analytics

    In this episode of the Sea Captain Leadership Podcast, Phil Bender sits down with Molly Pierce of Track That Advisor — a marketing analytics and benchmarking platform built specifically for financial advisors. Many advisors are collecting data but still unsure what it actually means. This conversation focuses on bringing clarity, structure, and accountability to marketing decisions. In this episode, we discuss: What Track That Advisor does — and how to explain it in simple termsThe biggest gaps in how advisors approach marketing analytics todayWhy benchmarking against industry norms mattersThe difference between dashboards and true insightWhen DIY tracking systems start to break downThe first quantitative and qualitative wins advisors noticeHow analytics and coaching together drive sustainable growthWhy the Sea Captain Performance + Track That Advisor partnership creates stronger alignment between strategy and execution If you’ve ever wondered whether your marketing is actually working — or how your efforts compare to your peers — this episode offers a practical roadmap for turning data into informed decisions. Connect with Phil Bender LinkedIn Sea Captain Performance Website Connect with Molly Pierce: Email: Molly@TrackThatAdvisor.com Track That Advisor Website LinkedIn

    Track That Advisor Data Analytics

  2. Jan 22

    Social Security Myths & Truths

    Social Security is one of the most important — and most misunderstood — components of retirement planning. In this episode, host Phil Bender is joined by Thomas Drapala, Registered Director of Strategic Partnerships at Social Security Analysts (RSSA), to unpack the myths, misconceptions, and costly assumptions that lead many Americans to leave meaningful benefits unclaimed. Phil and Tom discuss why Social Security decisions are often mishandled, why the benefit still matters for affluent and high-net-worth clients, and how advisors can use clarity in this area to build trust and confidence. They also cut through fear-based headlines to explain the realities surrounding Social Security’s long-term outlook and what advisors should understand before guiding clients through claiming decisions. This conversation is a must-listen for advisors who want to deepen planning value, serve as stronger advocates, and lead with confidence in one of retirement’s most impactful decisions. Episode Highlights Common Social Security myths and why they persistCostly assumptions clients and advisors often makeWhy Social Security matters even for high-net-worth householdsSeparating headlines from reality on Social Security’s futureHow RSSA certification strengthens advisor leadership and trust Connect with us SeaCaptainPerformance.com Instagram link FB link Connect with Phil LinkedIn Connect with RSSA RSSA Certification Program Connect with Thomas LinkedIn Now Available! The Sea Captain Way for Financial Advisors The Voyage: The Adventure of Your Lifetime

    Social Security Myths & Truths

  3. Jan 8

    My Virtual COO with Devon Volker and Jennifer Goldman

    On this episode of the Sea Captain Leadership Podcast, host Phil Bender is joined by Devon Volker and Jennifer Goldman, the dynamic leaders behind My Virtual COO and new Affiliate Partners of Sea Captain Performance. My Virtual COO helps businesses stop struggling and start improving by transforming operations into a true growth engine. Through a powerful blend of coaching, consulting, and fractional COO services, Devon and Jennifer help leaders gain traction, build accountability, and scale sustainably—especially in today’s fast-moving environment shaped by technology and AI. In this conversation, Phil, Devon, and Jennifer explore how operational clarity, human-centered leadership, and adaptive systems are redefining what it means to lead well. Key Topics Covered:The My Virtual COO MissionHow My Virtual COO was founded in 2005 and how its mission—“Stop Struggling, Start Improving, Reach Your Vision”—has evolved alongside modern leadership challenges.The Trifecta of Growth: Coaching, Consulting, and SaaSWhy true transformation happens when leadership coaching, strategic consulting, and the right technology work together—and where clients see the biggest breakthroughs.The Human Side of OperationsHow culture, communication, and trust must evolve alongside systems and processes to create lasting operational change.AI, Technology, and Fluid RecalibrationJennifer introduces the concept of “fluidity around recalibration” and explains how leaders can responsibly integrate AI while staying aligned with their values and people.The Three P’s FrameworkA foundational model for sustainable growth—and how leaders can quickly identify which area is out of alignment inside their business.Aligning People, Processes, and ProvidersMy Virtual COO’s approach to sequencing outsourcing partners, technology platforms, and workflows to drive growth without chaos or burnout.Partnering with Sea Captain PerformanceWhy this affiliate partnership expands what’s possible for advisors and leaders—and how leadership coaching and operational strategy together create a powerful competitive advantage. About Our GuestsDevon Volker and Jennifer Goldman are the founders of My Virtual COO, where they serve as trusted operational advisors, coaches, and strategists to growing organizations. Their work helps leaders move from friction to flow, turning complexity into clarity and vision into execution. About the PodcastThe Sea Captain Leadership Podcast is hosted by Phil Bender, CEO of Sea Captain Performance, where we help leaders chart a clear course for growth, culture, and impact. Connect with us SeaCaptainCoaching.com
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    My Virtual COO with Devon Volker and Jennifer Goldman

  4. 12/18/2025

    Unlocking Purpose & Meaning with Danny Kenny

    On this episode of The Sea Captain Leadership Podcast, host Phil Bender sits down with Danny Kenny—leadership and performance coach, behavioral scientist, former college soccer player, and facilitator with organizations such as Inspirecore and the McChrystal Group. Danny’s story is one of identity, resilience, and meaning. After years of defining himself through athletic performance, the end of his playing career sparked a profound personal transition. That journey led him into the world of behavioral science, human performance, and leadership development—ultimately shaping a mission to help others “unlock their lives” and pursue aligned, purposeful success. Together, Phil and Danny explore how performance is built, how identity evolves, and how leaders can move from striving to living with intention, authenticity, and clarity. What We DiscussThe Making of a CoachHow Danny’s early experiences in sports shaped his view of teamwork, discipline, and leadership—and how those lessons became the foundation of his coaching approach. Behavioral Science Meets Human PotentialDanny shares why he pursued a PhD to understand why people act the way they do—and how research-based insight informs real, human-centered development. Learning Design as Leadership WorkA look at Danny’s approach to designing learning experiences—from intentional agendas to behavioral systems—and why structure matters in real change. Identity After SportsWhen the cheering stops, many athletes face a loss of direction. Danny opens up about his own transition and how that experience now fuels his work helping others navigate major life and career shifts. Unlocking Meaning & PurposeWe discuss the shift from high performance to aligned performance—where success is not just measured, but felt. Danny shares how he helps individuals reconnect to meaning, values, and self-leadership. The Work AheadDanny reflects on the projects that inspire him today—from coaching leadership teams to writing his Seeking Wisdom newsletter—and shares his vision for helping people make work more human, fulfilling, and alive. Key TakeawaysPerformance isn’t just skill—it’s identity, purpose, and environment.True growth happens when we ask who we are becoming, not just what we’re achieving.Learning design shapes behavior change; change doesn’t happen by accident.Transitions are invitations—opportunities to redefine what matters most.Leadership begins with self-awareness and expands outward through intentional influence. Connect with us SeaCaptainCoaching.com
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    Unlocking Purpose & Meaning with Danny Kenny

  5. 12/04/2025

    AI for Visionary Leaders with Eric Doherty

    On this episode of The Sea Captain Leadership Podcast, Phil Bender sits down with Eric Doherty, President & CEO of DPE International, a global AI and healthcare consulting firm. Eric’s career has spanned pharmaceutical leadership, medical device commercialization, global business development, and now the rapidly evolving landscape of artificial intelligence. Rooted in a childhood surrounded by science and medicine — with a pharmacist father and microbiologist mother — Eric has dedicated his work to helping organizations harness data, technology, and innovation to drive better decisions and improve lives. This conversation explores how AI is reshaping entire industries, what leaders must understand about navigating disruption, and the mindset shifts required to move from reaction to vision. What We Discuss From Healthcare Foundations to Global Strategy Eric shares how his upbringing and early career in healthcare shaped his understanding of how systems function — and why change often requires rethinking those systems from the ground up. Founding DPE International Eric explains the problem his firm set out to solve: helping organizations not just adopt technology, but integrate it strategically. The role of AI has dramatically expanded in that mission. AI as a Catalyst — Not a Replacement We explore how AI is currently impacting healthcare, pharmaceuticals, and digital health — including which applications matter now and which are still emerging. Leadership in an Era of Disruption Industries are shifting fast. Jobs are changing. Efficiency is increasing — sometimes painfully. Eric and Phil discuss: Why adaptability is now the defining leadership skillHow transparency and communication shape trust during changeHow to ensure transformation is human-centered, not just cost-driven Navigating Change Without Losing Culture From COVID diagnostic systems to AI-enabled workflow design, Eric reflects on lessons in resilience, clarity, and guiding organizations through uncertainty. Preparing for the Next Decade Eric offers grounded, strategic guidance for leaders who want to remain relevant: Stay curiousInvest in systems, not just toolsLead from values, not fear Key Insights AI is not about replacing people — it’s about elevating human intelligence with better data and better systems.Leadership during disruption requires clarity of mission, not just efficiency.The organizations that thrive are the ones willing to rethink how they work — not just what they do. About The Sea Captain Leadership Podcast Hosted by Phil Bender, Founder & CEO of Sea Captain Coaching, this podcast explores the systems, habits, and decisions that empower leaders to build alignment, grow intentionally, and create lasting impact. SeaCaptainCoaching.com Instagram link FB link Connect with Phil LinkedIn Connect with Eric a href="https://www.linkedin.com/in/ericdohertygloballeader/" rel="noopener noreferrer"...

    AI for Visionary Leaders with Eric Doherty

  6. 11/20/2025

    Everything Recruiting with REKROOT

    The Origin StoryKim and Morgan first met in high school and stayed connected through early career chapters in financial services.Rekroot began as a coaching and consulting firm before evolving into its signature recruiting and recruiter development model. The Four Components of Rekroot’s Work Today:CoachingConsultingRecruitingRecruiter Development & Placement Support Their model is intentionally integrated—designed to help firms not just hire, but hire well and sustainably. A Recruiting Program That Actually WorksRekroot’s placement fee includes a year-long training program after the recruiter has been hired.This long-term development model is designed to build confidence, skill, and clarity around the recruiting function.The result: average recruiter retention of ~3 years, compared to the industry norm of about one year. Why Contract Recruiting MattersRekroot pioneered contract recruiting for financial services firms before it became common.The goal: allow firms to scale responsibly while testing and developing recruiting capacity before committing to full-time roles. The Power of TransparencyOne of Rekroot’s core business principles is direct and real feedback.Transparency accelerates alignment between leadership expectations and recruiter performance.It also builds trust and strengthens long-term partnerships with client firms. Leadership & MentorshipKim and Morgan share the mentors and leaders who shaped them—and how modeling confidence, clarity, and empowerment has defined their firm’s culture.Their work is rooted in helping others see who they can become, not just who they are today. About The Sea Captain Leadership PodcastHosted by Phil Bender, CEO of Sea Captain Coaching, this podcast explores leadership, growth, culture, and the systems that bring vision into reality—especially within entrepreneurial financial services. SeaCaptainCoaching.com Instagram link FB link Connect with Phil LinkedIn Connect with rekrootWebsite: https://rekrootpartner.com LinkedIn  Now Available! The Sea Captain Way for Financial Advisors The Voyage: The Adventure of Your Lifetime

    Everything Recruiting with REKROOT

  7. 11/06/2025

    Flawless Not Perfection with Boo Boucousis

    This podcast features Christian “Boo” Boucousis, a former Australian fighter pilot who’s turned his elite aviation mindset into a framework for high performance and leadership. Boo is now the CEO of Afterburner, and his journey is one of transformation — from being diagnosed with ADHD and a debilitating auto-immune disorder, to becoming a human behavior specialist, strategist, and sought-after keynote speaker. He’s proof that excellence isn’t born — it’s built. Key points: Boo is neurodiverse and grew up with ADHD, and Phil and Boo talk about why these experiences with adversity gave Boo an edge as a leader.Phil and Boo dive in to the unlikely transition from the precision and discipline of being a fighter pilot and moving to the complexity of running a business and advising global leaders.The Get It Done (GID) Mindset is one that Boo embraces.The Flawless Leadership model is a framework that emphasizes speed, alignment, and adaptability. SeaCaptainCoaching.com Instagram link FB link Connect with Phil LinkedIn Connect with Christian “Boo” Boucousis LinkedIn Website: https://callmeboo.com AI Agent (Ask Boo’s book questions): https://ai.afterburner.com Now Available! The Sea Captain Way for Financial Advisors The Voyage: The Adventure of Your Lifetime

    Flawless Not Perfection with Boo Boucousis

  8. 10/23/2025

    Bold Moves & Brilliant Outcomes with Jevon Wooden

    This podcast features Jevon Wooden of Bright Minds Consulting.  Jevon is an Bronze Star–awarded Army veteran turned leadership advisor, keynote speaker, and coach. He partners with organizations and entrepreneurs to increase retention, strengthen leadership, and build cultures that drive growth. And now, Jevon is inspired to live a life leading others to be their best version of themselves.  Key points: Jevon inspires others to accelerate their growth by leading with empathy. Jevon served in Afghanistan, where he worked in the technology field. He didn’t want to continue with a career in the technology sector, so he looked elsewhere, and coaching is what caught his eye. He became ICF-certified, and then took advantage of professional coaches himself to overcame his own depression and help manage his PTSD. Listen in and hear Jevon and Phil discuss Vulnerability as a Super Power and Mistakes as Growth in Disguise.  SeaCaptainCoaching.com Instagram link FB link Connect with Phil LinkedIn Connect with Jevon Wooden LinkedIn https://brightmindconsultinggroup.com Now Available! The Sea Captain Way for Financial Advisors The Voyage: The Adventure of Your Lifetime

    Bold Moves & Brilliant Outcomes with Jevon Wooden
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Ratings & Reviews

5
out of 5
12 Ratings

About

Ahoy! Welcome to the Sea Captain Way podcast with Phil Bender, where we help listeners navigate the uncharted waters of personal and professional growth. The Sea Captain Way is about energizing top performers to take on risks and push beyond their comfort zone to pursue life-changing goals and achieve peak performance. We’re going to help you build your vision by showing you how to break free of the boundaries that are holding you back.

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