Gray to Great

Sleep is the secret superpower that most high-performing advisors have access to and very few are actually using. Dr. Melissa Milanak, PhD, has spent decades working with trauma survivors, professional athletes, and corporate executives, and her work keeps pointing to the same conclusion: quality sleep is the foundation everything else is built on, and most high performers are quietly undermining it every single day. 

In this episode of Gray to Great, host Dan Dal Degan sits down with the clinical psychologist, executive consultant, and founder of MIND Impact Consulting for one of the most unexpectedly practical c...

Dan Dal Degan sits down with Greg Cantone, Managing Director of Retirement Solutions at Citizens Private Wealth, for a conversation that is as much about mindset as it is about the business. Greg spent twelve years doing stand-up comedy in New York City while building his career in financial services, and the overlap between those two worlds shapes everything about how he communicates, connects, and advises clients today. 

Greg and Dan explore what it really means to read a room, why listening is the most underutilized skill in the advisory business, and how Greg's experience being part o...

A year ago, Charlotte Hickey of BlackRock and Zachary Rosenoff of Marsh McLennan Agency joined Gray to Great for a conversation about private markets in defined contribution (DC) plans. In this follow-up episode, host Dan Dal Degan reconnects with Charlotte and welcomes a new voice to the conversation: Josh Anderson, AIF®, CEPA®, Vice President, Investments at the Workplace Retirement Group of Raymond James. 

In this follow-up episode, Josh and Charlotte revisit where the conversation stands today, from the initial wave of plan sponsor concern following the August 2025 executive order to the more constructive dialogue that has emerged sin...

In Episode 19 of Gray to Great, Dan Dal Degan sits down with Matt Compton, AIF, CRPC, Partner, Retirement and Wealth Services at Alera Group. Matt spent over eleven years at Principal Financial Group on the record keeping and administrative side before transitioning to plan advising in 2019, and that background shapes everything about how he serves clients today. He and Dan explore what it really means to be a plan advisor, how integrating retirement benefits into the broader employee benefit relationship creates better outcomes, and why day-to-day plan oversight matters as much as the investment process. 

Matt also s...

Many advisory teams are built around a book of business. Bryan Farwell and Jesse Hernandez built theirs around a belief. In Episode 20 of Gray to Great, the partners at Prevail Innovative Wealth Strategies join host Dan Dal Degan for a candid conversation about passion, partnership, and what it takes to serve plan sponsors and participants the way they deserve to be served. Jesse brings over 30 years of experience on the record keeping and wholesaling side of the business, and Bryan brings a deep background in banking, private wealth, and entrepreneurship. Together they make the case that the advisors who...

In this episode, Michaela Scott, Principal and Founder of Strategic Retirement Benefits Group and RPAG Council Member, shares her inspiring journey of becoming a leading and award-winning retirement plan advisor, emphasizing the importance of clarity, client selection, prioritizing your time, and how to build a strong team. Discover her insights on creating impact, fostering a positive culture, and mentoring the next generation.

More About Michaela Scott:
Michaela is the Founder and Principal of the Strategic Retirement Benefits Group, partnering with businesses on the financial portion of their benefits program – specifically their retirement Plans. She has been re...

In this episode, Dan Dal Degan speaks with Andrew Mirolli, co-founder of buyAUM, about the unique challenges and opportunities faced by financial advisors, particularly in the context of succession planning and retirement. Andrew shares his journey from a financial wholesaler to a business owner focused on helping advisors navigate their transitions. The conversation delves into the emotional aspects of selling a business, the importance of planning for life after work and the need for a structured approach to succession. Andrew emphasizes the significance of finding purpose in the next chapter of life and offers advice for business owners looking...

In this episode of Gray to Great, Dan Dal Degan speaks with Mark Forbes of Strategic Retirement Partners about helping participants cross the retirement finish line with confidence. Mark draws on more than 30 years in the industry to explain why intimidation around investing is often the biggest barrier and how small, consistent actions, supported by compounding and automation, can meaningfully improve outcomes.

This conversation explores why retirement is a marathon rather than a sprint and how budgeting decisions connect to allocation and long-term outcomes. It also addresses the emotional side of retirement, including finding purpose beyond the...

In this episode of Gray to Great, Doug Bermudez, Managing Director at Strategic Retirement Partners, joins Dan Dal Degan to discuss the role clear communication plays in improving retirement outcomes for plan sponsors and participants. Doug shares how his background as a bilingual advisor has shaped his approach to participant education. He explains how organizations can simplify complex retirement concepts and communicate in ways that reflect employees’ real-world needs, time constraints, and financial realities.  

Doug explores how advisors can balance brevity with impact, use technology to improve engagement, and apply thoughtful messaging to support better decision-making. He als...

In this episode of Gray to Great, Kristine Meyer of Stiles Financial Services joins Dan Dal Degan to explore what adaptability looks like as workforce demographics continue to shift. She discusses the importance of understanding client needs, communicating effectively, and adjusting to generational differences. Kristine reflects on the realities of Gen Z entering the workforce and how advisors can align with evolving expectations and new plan demographics. She also shares her path into the field, how she builds client relationships, and why adaptability matters as plan demographics shift. Kristine's insights provide valuable takeaways for both plan advisors and participants...

In this episode of Gray to Great, Dan Dal Degan interviews Scott Colangelo, chairman of Prime Capital, discussing his journey from starting at Edward Jones to establishing the first RIA in Kansas. Scott shares insights on building a scalable retirement advisory firm, the convergence of wealth management and retirement advising, and his advocacy efforts in the industry. He emphasizes the importance of finding passion in one's work and the impact of education on participants' financial futures. 

More About Scott Colangelo:
Scott Colangelo is the Chairman of Prime Capital, where he has been instrumental i...

In this episode of "Gray to Great," host Dan Dal Degan and guest Lloyd Engleman, a Managing Director of Alkeme Financial Services of Accelerate Retirement, discuss the intricacies of scaling efficiently as a retirement plan advisor. They explore strategies for success, the importance of building trust with clients, the power of the RPAG platform, and the evolving landscape of retirement planning. Lloyd shares personal stories of growth, mentorship, and the impact of effective communication in the industry. Engleman reflects on the profound impact of his work, emphasizing the life-changing potential of effective retirement planning.

More About...

In this episode of "Gray to Great," Dan Dal Degan speaks with Steven Puckett, Managing Partner of Fiduciary Pension Partners, about the evolving landscape of corporate retirement planning. They discuss the importance of personalized, 1:1 consulting, especially during challenging times like the COVID-19 pandemic, and how proactive communication can lead to business growth. Steve shares his effective lead generation strategies, including the use of webinars and maintaining a human touch in an increasingly automated retirement ecosystem. He emphasizes the significance of client education and storytelling in building trust, as well as the importance of mentorship for young professionals entering the...

In this episode of "Gray to Great," Dan Dal Degan interviews Phil Senderowitz, a 2025 Plan Advisor of the Year in the Covering the Gap category, focusing on the importance of providing retirement solutions for small and mid-size businesses. They discuss the impact of recent legislation, the significance of understanding client needs, and the value of specialization in the retirement planning industry. Phil shares his personal journey into retirement planning, lessons learned from market downturns, and insights on how to effectively engage with clients to ensure their financial well-being.

More About Phil Senderowitz:
Phil is an Investment...

This episode is the second of a two-part special edition of the Gray to Great podcast, dissecting private assets in defined contribution plans with 2 special guests: Zachary Rosenoff, Director of Investments at Marsh McLennan Agency, and Charlotte Hickey, Director of National Accounts at BlackRock.

In this special episode of Gray to Great, host Dan Dal Degan engages in a rich conversation with guests Charlotte Hickey and Zachary Rosenoff about the evolving landscape of retirement planning and investment strategies in relation to the incorporation of private assets in defined contribution plans. They discuss the impact of recent legislation...

This episode is the first of a two-part special edition of the Gray to Great podcast, dissecting private assets in defined contribution plans with 2 special guests: Zachary Rosenoff, Director of Investments at Marsh McLennan Agency, and Charlotte Hickey, Director of National Accounts at BlackRock.

In this special episode of Gray to Great, host Dan Dal Degan engages in a rich conversation with guests Charlotte Hickey and Zachary Rosenoff about the evolving landscape of retirement planning and investment strategies in relation to the incorporation of private assets in defined contribution plans. They discuss the impact of recent legislation...

In this episode of "Gray to Great," host Dan Dal Degan is joined by Rick Unser, a managing director at Creative Retirement Planning Services. They discuss Rick's career journey, focusing on his specialization in private equity retirement plans. Rick shares insights on the importance of curiosity and specialization in career development, emphasizing the value of building relationships and becoming a trusted advisor. The conversation also touches on the complexities of retirement planning, the evolving market, and the significance of understanding both B2B and B2C dynamics. Rick offers advice for younger advisors and highlights the importance of continuous...

In this episode of "Gray to Great," Board Member of the Great Gray Group and host, Dan Dal Degan, is joined by Virginia Ryan, a plan advisor with 401(k) Plan Professionals in the Twin Cities. Virginia shares her unique journey from being a flight attendant to becoming a 401(k) plan advisor. She discusses the challenges and learning experiences she faced while transitioning into the financial world, emphasizing the importance of open conversations and financial education. 

Virginia highlights the role of financial advisors as "financial therapists," helping clients navigate the often intimidating world of retirement plans. She shares s...

Summary  

In this conversation, Dan Dal Degan (Board Member of Great Gray Group) and Holly Knight (Director of Retirement Services at Alera Group) discuss the impact and role of AI in financial services.  

They explore topics around how to use AI to make your daily schedule more efficient, the trade-offs and risks of AI and how to address those concerns, how AI may impact the financial services industry, and how Holly became interested in AI and more specifically the role it plays in the finance industry.  

More About Holly Knight:

My jou...

Summary: In this conversation, Burak Alpaslan and Dan Dal Degan discuss the importance of educating clients and how that builds a trusted relationship. 

They explore topics around the strategy and playbook Burak uses for client retention, how to help and educate clients through storytelling, lessons around identifying and prospecting for clients, and how culture plays a role in Vital Planning Group’s success. The conversation emphasizes the significance of human connection and genuine relationships in any industry, and how that honesty really pushes for great client relationships.

Why You Should Listen: 

Discover the power of authenticity and human connection in sales with Renee Scherzer.

Summary: In this episode of "Gray to Great," host Dan Dal Degan has a value-packed conversation with Renee Scherzer, Senior Vice President at OneDigital Retirement & Wealth, to discuss the importance of being authentic and personable in your network and connections. They delve into topics such as differentiating your sales practice, the significance of branding on LinkedIn, tips for networking with accomplished individuals, and how to create excitement for meetings and calls. The conversation highlights the value of human connection and genuine relationships in sales...

In this episode, Sean Kelly, Vice President at Heffernan Retirement Services, shares practical tips to deepen connections with clients and prospects. Sean reminds us, “Hopes, dreams, fears, and goals in personal life also drive the ways people do business.”

Here’s why you should listen:

·         Human Connection: Master the art of meaningful client relationships.

·         Sales Best Practices: Proven strategies tailored for financial services.

·         Adaptability: Flex your approach to meet clients' unique needs

Summary: In this episode of the Gray to Great podcast, Dan Dal Degan and Sean Kelly discuss the essential sk...