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 of one of the largest bank failures in US history taught him the most important lesson of his career: detach from the outcome and focus on what you put out.

This is an episode about the communication skills, mental resilience, and sense of purpose that define the best retirement plan advisors. Worth the listen for advisors at any stage of their career.

More About Greg Cantone:

Greg Cantone, CPFA®, CRPS®, AAMS®, CRPC®, is Managing Director of Retirement Solutions at Citizens Private Wealth, where he focuses on helping mid-sized businesses navigate the complexities of employer-sponsored retirement plans. With a career that began at Merrill Lynch and spans some of the most challenging chapters in recent financial history, Greg brings a perspective on client service, communication, and resilience that is difficult to replicate.

Before building his reputation in retirement plan advising, Greg spent twelve years doing stand-up comedy in New York City. That experience did not just make him a better presenter. It made him a better listener, a sharper communicator, and someone who understands instinctively how to make complex information land with any audience. Greg's approach to the business has always centered on one idea: the most effective way to help the most amount of people is through the retirement plan.

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 since. They cover the DOL's proposed safe harbor framework for fiduciaries, the practical difference between 3(21) and 3(38) arrangements and how each affects adoption pace, why target date funds remain the most thoughtful entry point for most plans, and what advisors should be doing right now to stay ahead of this landscape. Charlotte's advice is direct: you do not have to be an expert in private markets, but your partners do.

More About Our Guests:

Charlotte Hickey is a Director of Defined Contribution National Accounts at BlackRock, based in Boston. With experience spanning roles at PIMCO and BlackRock, she brings deep expertise in DC plan strategy and the evolving conversation around private markets in retirement portfolios.

Josh Anderson, AIF®, CEPA®, is a Vice President, Investments and partner of the Workplace Retirement Group at Raymond James, based in Newtown, Pennsylvania. With over two decades of experience in retirement plan consulting, Josh guides companies through the full spectrum of plan strategy including governance, plan design, fiduciary responsibility, and service provider evaluation.

Chapters:
00:00 - Introducing Charlotte Hickey and Josh Anderson

01:40 - The Regulatory Climate Around Private Investments

05:31 - Balancing Risk and Opportunity as a Plan Advisor

09:08 - Understanding Private Market Allocations

12:29 - The Advisor's Role in an Evolving Landscape

14:52 - Communicating Complex Concepts to Plan Sponsors

17:36 - Career Reflections and Advice

Disclosures:

Great Gray® and Great Gray Trust Company are service marks used in connection with various fiduciary and non-fiduciary services offered by Great Gray Trust Company, LLC.

The opinions and thoughts expressed here are those of Charlotte Hickey of BlackRock and Josh Anderson of Raymond James, based on their professional and personal experience, and do not represent the views or opinions of BlackRock, Raymond James, Great Gray Trust Company, or any of their parent companies or affiliated entities.

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 shares what COVID taught him about building a service model, how his team develops talent, and the advice he would give his younger self. This episode is worth the listen for advisors at any stage of their career.

More About Matt:

Matt Compton, AIF, CRPC, is a Partner, Retirement and Wealth Services at Alera Group. Before joining Alera Group in October 2023, Matt spent over six years at Brio Benefit Consulting, an Alera Group company, serving as Director of Retirement Services and later Partner, Retirement Solutions. Prior to that, he spent over eleven years at Principal Financial Group, building deep expertise in record keeping and plan administration across defined contribution, defined benefit, and nonqualified deferred compensation plans.

That provider-side foundation shapes everything about how Matt approaches plan advising today. Since transitioning to the advisory side in 2019, he and his team have grown their retirement practice from approximately $70 million to over $1.4 billion in assets under advisement. Matt has been recognized as a PLANADVISER Top Retirement Plan Adviser, and his team has earned national accolades including Plan Adviser of the Year and the Excellence in Operations Award.

Chapters for Podcast:

00:00 – Introduction to Matt Compton

02:29 – The Importance of Record Keeping Retirement Plans

07:02 – Transitioning from Record Keeping to Advisory Services

11:19 – Building a Holistic Approach to Employee Benefits

15:29 – Navigating Complexity in Retirement Planning

19:56 – Advice for Young Professionals in the Industry

Disclosures:

Matthew Compton and Alera Group, Inc., are not affiliated with or endorsed by, Great Gray Trust Company, LLC.

Great Gray® and Great Gray Trust Company are service marks used in connection with various fiduciary and non-fiduciary services offered by Great Gray Trust Company, LLC.

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 show up the same way for every client are the ones who build something that lasts.

Bryan and Jesse don’t just talk about their philosophy. They demonstrate it. The way they speak about their clients, their team, and each other makes it clear that their partnership is the differentiator. At Prevail, the team is not a supporting structure behind the service. It is the service. For advisors at any stage of their career who are wondering what it looks like to build a practice that actually reflects their values, this conversation is worth the listen.

More About Jesse Hernandez:

Jesse Hernandez spent 30 years on the road as a wholesaler before making the decision to cross over to the advisory side as a fiduciary consultant at Prevail Innovative Wealth Strategies. His career spans roles at American Century Investments, Marshall & Ilsley Trust Services, and two decades as Regional Vice President of Retirement Plans at Voya, giving him a firsthand understanding of what separates plans that work from plans that fall short. At Prevail, Jesse focuses on plan design, fiduciary oversight, participant education, and financial wellness, bringing the same hands-on commitment to every client relationship that he has carried throughout his career. Outside of work, Jesse is a devoted family man and lifelong coach and mentor in wrestling, football, judo, and jiu-jitsu.

More About Bryan Farwell:

Bryan Farwell leads Prevail's Corporate Retirement Division with more than two decades of experience across private banking, investment management, and financial services. His background includes serving as CEO and Principal of his own investment management firm, Director of Private Banking at a regional bank, and Chairman of the Board of a local children's hospital, a range of experiences that shaped a leadership style built equally around strategic thinking and genuine care for the people he serves. At Prevail, Bryan brings that same energy to every client relationship, pairing deep fiduciary expertise with a belief that great service is not a differentiator but a baseline. He and his wife Emily have been married 19 years and are the proud parents of four children.

Chapters:

00:00 – Introduction to Prevail Innovative Wealth Strategies

02:33 – Jesse and Bryan's Journey in Financial Services

07:22 – The Importance of Team Dynamics and Culture

10:42 – Passion and Energy in Client Relationships

12:54 – The Philosophy Behind Prevail’s Approach

18:14 – Engaging Plan Participants Effectively

26:39 – Advice to Their Younger Selves

Disclosures:

Bryan Farwell, Jesse Hernandez, and Prevail Wealth Management, LLC are not affiliated with or endorsed by, Great Gray Trust Company, LLC.

Great Gray® and Great Gray Trust Company are service marks used in connection with various fiduciary and non-fiduciary services offered by Great Gray Trust Company, LLC.

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 recognized as the Top Women Advisors Rising Star and Top Plan Advisors under 40, and their team has earned Top DC Advisory Team.

Michaela earned her Master of Science in Financial Services with a concentration in Retirement Planning from the American College of Financial Services, where she serves as the incoming President of the Advisory Committee. She was awarded their Millennial Advisor of the Year award.

She is a Certified Financial Planner™, Accredited Investment Fiduciary, Retirement Income Certified Professional®, Charted Financial Consultant, and Certified Health Savings Advisor. Michaela earned her Certified 401(k) Professional Designation administered by the Retirement Advisor University in collaboration with UCLA Anderson School of Management Executive Education. She serves at The Plan Sponsor University as an adjunct professor.

She holds an honors Bachelor of Arts in Politics from Saint Anselm College and is the immediate past President of the St. A’s Alumni Association and current Advisory Council Co-Chair for the Department of Business and Economics. Michaela was selected to serve on the Retirement Plan Advisory Council (RPAC) for Osaic. Osaic is one of the largest networks of independent advisor firms in the country, overseeing approximately $500 billion in assets. RPAC comprises a select group of advisors who specialize in retirement plans, are innovative, and can lead by example with best practices for servicing clients and delivering results for participants.

Chapters
00:00 Introduction to Gray to Great and Michaela Scott
02:07 Michaela's Origin Story and Career Path
06:44 The Importance of Client Outcomes
08:58 Building a Strong Team
12:45 Clarity as a Differentiator
17:22 Selecting Ideal Clients
21:35 The Role of Mentorship
26:34 Advice to a Younger Self
29:22 Outro to Gray to Great

Disclosures:
Michaela Scott and The Strategic Retirement Benefits Group, LLC are not affiliated with or endorsed by, Great Gray Trust Company, LLC.

Great Gray® and Great Gray Trust Company are service marks used in connection with various fiduciary and non-fiduciary services offered by Great Gray Trust Company, LLC.

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 to prepare for their future.

More About Andrew Mirolli:

Andrew Mirolli, CEPA®, is Co-Founder and Head of Client Services at buyAUM.com, where he partners with Registered Investment Advisors to grow through acquisition and navigate succession planning with confidence. He works with both buyers and sellers to structure transitions that protect enterprise value, preserve client relationships, and honor the legacy that advisors have built.

Prior to buyAUM.com, Andrew worked directly with advisors in roles across wholesaling, capital markets, and advisory consulting. Early in his career, he worked closely with RIAs and independent advisors, building relationships across the industry and gaining a foundation for how advisory practices are built, scaled, and eventually transitioned.

Andrew is a Certified Exit Planning Advisor (CEPA®) and he holds his Series 63 license. His practical focus is on helping advisors think beyond discretionary revenue to the structural and relational elements that drive valuation and continuity. He graduated from the University of Georgia with a degree in Real Estate Development and currently resides outside Atlanta.

Follow Great Gray on LinkedIn

Chapters
00:00 Introduction
01:03 Introduction and Andrew's Journey with BuyAUM
04:29 The Importance of Succession Planning
06:36 Finding Purpose After Retirement
07:38 Creating a Third Act Business Plan
13:02 The Emotional Transition of Selling a Business
15:18 Timing the Transition: When to Start Planning
18:07 Understanding Buyer Perspectives
21:06 The Role of Advisors in Personal Planning
23:57 Advice for Young Entrepreneurs

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 also shares his perspective on collective investment trusts, fiduciary responsibility, and the lessons from his career that continue to shape how he serves plan sponsors, participants, and advisory teams.

Connect with Us on LinkedIn

More About Doug Bermudez:

Doug and his team work with both organizations and professionals, along with their families, to help work towards their life dreams through establishing long-term, trusting relationships and delivering comprehensive financial services. He works with each client to create customized wealth management solutions and provides ongoing services through a complete range of financial resources.

Doug’s team provides advisory consulting services to organizations for pursuing retirement plan success through best practices that provide plan design and administration, fiduciary responsibility, and employee retirement readiness. When working with individuals and families, his team provides clients with comprehensive advice that seeks to build, manage, preserve, and transition wealth.

Doug recognized early in his career that providing comprehensive financial advice was his true passion. He helps achieve this by understanding his or her current financial situation through investment, liability management, risk management, and legacy planning needs. By working one-on-one with his clients, Doug defines his success when his clients can achieve a dignified retirement. Doug also has developed an extensive knowledge of employer-sponsored benefit programs, such as 401(k), 403(b) plans, and 457 deferred compensation plans. He works directly with decision makers in designing, administering, and servicing their retirement plans.

Doug began his career in the financial services industry in 1994 with Empower Retirement. He later joined ABD Insurance & Financial Services, a predecessor firm of Wells Fargo Insurance Services. In 2007, he joined Wells Fargo Advisors and formed the Bermudez/Hall Retirement Group with his associate, Erin Hall. They provide high-level service to both corporations and individuals through comprehensive financial advice. Doug and Erin joined SRP in June of 2019, opening the Los Angeles area office. In 2005 and 2012, respectively, Doug earned the Certified Fund Specialist® and Certified 401(k) Professional certifications after completing approved educational programs, passing rigorous examinations, and meeting stringent experience requirements

Doug is dedicated to the ongoing development of the financial services industry—recently participating as a member of the NAPA Next Generation committee and the NAPA DC Fly-In Forum steering committee. He is also devoted to the betterment of his community with his participation in Leadership Manhattan Beach (LMB) and the Kiwanis Club of Manhattan Beach. Above all, Doug values his time with his wife, Nuria (an accountant), and his three children—Emma, Alissa, and DJ. Doug also enjoys a good round of golf with friends and is an avid cyclist.