Gray to Great

About Gray to Great

Rewrite your practice growth playbook. Hosted by Dan dal Degan—known to many as Triple D—this bi-monthly podcast pulls back the curtain on what it takes to thrive as a corporate retirement plan advisor in an increasingly tech-centric business world. As a former powerhouse sales leader at Salesforce and Oracle, now sitting on the board of Great Gray Trust’s holding company, Dan’s sales experience and curiosity provoke compelling conversations with top advisors. Each episode of ‘Gray to Great’ focuses on the crucial parts of the business that often get overlooked: prospecting, referral business, challenger selling, client service, tech adoption, and cutting-edge marketing tactics. This is where the playbook is rewritten, offering listeners sharp, actionable insights that go beyond investing to fuel lasting growth and success. Tune in to learn the strategies that separate the leaders from the pack—because in sales, there are no gray areas.

Publisher

Great Gray Trust Company

Category

business · business

Language

en

Explicit

No

First episode

6 Feb 2025

Latest episode

6 Oct 2026

Latest episodes

21 episodes in the feed.

1. 

   6 Oct 2026

   21. Detaching from the Outcome: Greg Cantone on Resilience, Communication, and What Really Drives Success

   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.

2. 

   13 Sept 2026

   20. Private Markets, A Year Later: Charlotte Hickey and Josh Anderson on What Has Changed and What Hasn’t

   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.

3. 

   27 Aug 2026

   19. How Matt Compton’s Record Keeping Roots Made Him a Stronger Plan Advisor | Matt Compton

   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.

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

5 ratings

Spotify

5.0 / 5

5 ratings

Podcast Authority Score: 31 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

49

Social presence

0

YouTube

0

Engagement

32

Contact Gray to Great

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.