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: Molly@TrackThatAdvisor.com

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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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