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 terms
• The biggest gaps in how advisors approach marketing analytics today
• Why benchmarking against industry norms matters
• The difference between dashboards and true insight
• When DIY tracking systems start to break down
• The first quantitative and qualitative wins advisors notice
• How analytics and coaching together drive sustainable growth
• Why 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.

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Email: [email protected]

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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

1. Common Social Security myths and why they persist
2. Costly assumptions clients and advisors often make
3. Why Social Security matters even for high-net-worth households
4. Separating headlines from reality on Social Security’s future
5. How RSSA certification strengthens advisor leadership and trust

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The Sea Captain Way for Financial Advisors

The Voyage: The Adventure of Your Lifetime

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.

• The My Virtual COO Mission
• How 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 SaaS
• Why 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 Operations
• How culture, communication, and trust must evolve alongside systems and processes to create lasting operational change.
• AI, Technology, and Fluid Recalibration
• Jennifer 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 Framework
• A foundational model for sustainable growth—and how leaders can quickly identify which area is out of alignment inside their business.
• Aligning People, Processes, and Providers
• My Virtual COO’s approach to sequencing outsourcing partners, technology platforms, and workflows to drive growth without chaos or burnout.
• Partnering with Sea Captain Performance
• Why this affiliate partnership expands what’s possible for advisors and leaders—and how leadership coaching and operational strategy together create a powerful competitive advantage.

Devon 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.

The 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.

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The Sea Captain Way for Financial Advisors

The Voyage: The Adventure of Your Lifetime

My Virtual COO

Website:  https://myvirtualcoo.com/

Company LinkedIn: https://www.linkedin.com/company/myvirtualcoo/

YouTube: https://www.youtube.com/c/Myvirtualcoo

Jen LinkedIn: https://www.linkedin.com/in/jennifergoldman/

Devon LinkedIn: https://www.linkedin.com/in/devon-volker/

https://free.myvirtualcoo.com/roles_and_responsibilities

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.

How 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.

Danny 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.

A look at Danny’s approach to designing learning experiences—from intentional agendas to behavioral systems—and why structure matters in real change.

When 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.

We 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.

Danny 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.

• Performance 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.

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The Sea Captain Way for Financial Advisors

The Voyage: The Adventure of Your Lifetime

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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 skill
• How transparency and communication shape trust during change
• How 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 curious
• Invest in systems, not just tools
• Lead 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.

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The Sea Captain Way for Financial Advisors

The Voyage: The Adventure of Your Lifetime

• Kim 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.

1. Coaching
2. 
   
3. Consulting
4. 
   
5. Recruiting
6. 
   
7. Recruiter Development & Placement Support

Their model is intentionally integrated—designed to help firms not just hire, but hire well and sustainably.

• Rekroot’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.

• Rekroot 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.

• One 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.

• Kim 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.

Hosted 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.

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The Sea Captain Way for Financial Advisors

The Voyage: The Adventure of Your Lifetime

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.

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The Sea Captain Way for Financial Advisors

The Voyage: The Adventure of Your Lifetime

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. 

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The Sea Captain Way for Financial Advisors

The Voyage: The Adventure of Your Lifetime

This podcast features Kim and Joe Koenig, who have been married for more than 30 years and have three sons and two grandchildren. 

Joe is president of World Wide Technology in St. Louis. He joined the company in 1993 when it was a startup. Today the company is a global technology solutions provider with more than $20 billion in revenue. 

Kim holds a Masters in Public Administration and after a career in Community Development and serving as CEO of their home, she now serves as Director of Strategic Initiatives of St. Louis’ Jesuit High School, De Smet.

Along with having successful careers, a strong marriage and raising a family, they have battled possibly their biggest challenge of all: Joe’s cancer diagnosis. He was diagnosed with head and neck cancer in 2017 and given a 50 percent chance to live beyond five years.

Key points:

• This is a truly inspirational story you won’t want to miss.
• 
  
• Joe and Kim took this adversity, overcame it, and are transforming it into good. Not only did they beat the cancer, but they are helping others who are walking a similar path. 
• 
  
• Joe and Kim now share their story and are living testimony proof that resilience, perseverance and positivity serve as a backbone for building a foundation for going toe-to-toe with serious health challenges and overcoming adversity in general. 

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The Sea Captain Way for Financial Advisors

The Voyage: The Adventure of Your Lifetime

This podcast features Gray Rudd, who along with Josie Secola, spearhead NORA Partners.  

Nora Partners is an Operations Consulting Firm that helps financial services firms bridge the gap between where they are and where they want to go. 

Key points:

• The Consulting group works with financial services ensembles and partnerships to refine operations, optimize client experience, and focus teams to help them scale their practice and prepare for exponential growth.
• Phil and Gray talk about “Scale” and how to recognize the need for Ensembles and Partnerships to develop it.
• Nora not only works on Scale with its clients but also Leadership of their firms, which includes Vision, Values and Designing Training. FA’s can be really great at selling and managing clients, but NOT running a business.

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The Sea Captain Way for Financial Advisors

The Voyage: The Adventure of Your Lifetime