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.