Gray to Great

Great Gray Trust Company
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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.

  1. 13. What Advisors Need to Know as Gen Z Becomes the Newest Plan Participants | Kristine Meyer

    12/16/2025

    13. What Advisors Need to Know as Gen Z Becomes the Newest Plan Participants | Kristine Meyer

    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 looking to better understand their financial futures. More About Kristine Meyer: Kristine Meyer is a Retirement Plan Specialist at Stiles Financial Services, where she has delivered tailored guidance to employers and participants for more than six years. She began her career at a small trust company as a Trust Operations Specialist and later became Operations Supervisor as the firm expanded. Her work has focused on high-quality service and helping plan sponsors maintain compliant, well-designed plans that support both organizations and employees.  Kristine is known for building strong client relationships and her dedication to improving financial literacy through participant education. Beyond her client work, she serves as Chair of the Minneapolis Pension Council and leads a study group for industry professionals that encourages collaboration and shared learning across ERISA attorneys, actuaries, accountants, and advisors. Kristine has always called the Twin Cities home and enjoys spending time outdoors, exploring new recipes and restaurants, and spending quality time with her husband and daughter.

    25 min
  2. 12. How Wealth and Retirement are Converging from an RIA Trailblazer | Scott Colangelo

    11/20/2025

    12. How Wealth and Retirement are Converging from an RIA Trailblazer | Scott Colangelo

    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 in pioneering fee-based asset management and establishing the first Registered Investment Advisor (RIA) in Kansas. With a career spanning over two decades, Scott has been a trailblazer in the convergence of wealth management and retirement advising. He began his career at Edward Jones, where he was recognized as a top producer, and later co-founded Prime Capital with Tim Hakes.   Scott's innovative approach includes managing risk-based portfolios and advocating for participant education and wellness in retirement plans. He has been actively involved in legislative advocacy, focusing on issues like collective trusts for 403(b) plans. Scott resides in Kansas, where he is committed to giving back to the community that has supported his career and family.

    24 min
  3. 11. The 2 Secrets to Scale Efficiently as a Retirement Plan Advisor | Lloyd Engleman

    11/06/2025

    11. The 2 Secrets to Scale Efficiently as a Retirement Plan Advisor | Lloyd Engleman

    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 Lloyd Engleman: Lloyd Engleman has worked in the Financial Services sector for 18 years. As a Retirement Plan Specialist, Lloyd serves clients throughout the western United States and was awarded as Plan Adviser of the Year by Plan Sponsor Magazine. Based on nominations from industry peers and quantitative factors, including number of plans and dollar value of plan assets under advisement. Prior to joining Accelerate Retirement, Lloyd worked as a Registered Representative/401K plan consultant for Total Retirement Solutions. Additionally, he worked at Investor Solutions, Inc., also serving the western region. Prior to entering the Financial Services field in 2000, Lloyd worked in hardware technology resales, as the owner of Surcom Technology. Lloyd holds his Series 6, 63, and 65 licenses. Interests Lloyd is a board member of Moreno Valley Optimist Foundation and volunteers on their fund raisers. Lloyd is well-known for his love of golf. He also considers himself an RV enthusiast. Lloyd currently resides in Riverside with his family. Disclosures:Retirement Plan Advisory Group, LLC (“RPAG”) provides technology, solutions and services for a fee to its customers, who are primarily retirement plan advisors and associated institutions. The services include ratings of various third-party investment vehicles based on RPAG’s proprietary quantitative and qualitative scoring methodology. The investment vehicles do not pay to be evaluated and scored; nor do the companies that provide services to the investment vehicles pay for them to be evaluated and scored, but those companies may have commercial relationships and affiliations with RPAG. In addition, RPAG’s affiliate, Great Gray Trust Company, LLC, offers CITs, some of which include fee classes with customized pricing that it makes available to RPAG subscribers.    Great Gray Trust Company, LLC (“Great Gray”) serves as trustee and provides administrative services for collective investment trust funds (“Great Gray CITs”) that are scored by RPAG. Great Gray and RPAG are wholly owned by Great Gray Group, LLC (“Great Gray Group”). Great Gray has a commercial relationship with RPAG that does not involve the evaluation and scoring of Great Gray CITs.

    23 min
  4. 10. The Lead Generation Blueprint for Retirement Plan Advisors | Steven Puckett

    09/25/2025

    10. The Lead Generation Blueprint for Retirement Plan Advisors | Steven Puckett

    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 finance industry. Fun fact: Steven arrives before the rest of his office to maintain best practices of seemingly "old-fashioned" cold calling to gain new business. More About Steven Puckett:Steve manages and consults on retirement plans in the areas of investment advisory services, fiduciary services, forensic plan audits, fiduciary risk mitigation solutions, compliance assistance, and fee audits for 403(b) plans, 401(k) plans, 457 plans, Defined Benefit plans, and Non-Qualified Plans. With over 30 years of experience in the retirement plans industry, Steve has assisted and consulted with hundreds of companies with their retirement plans concerns. Prior to joining FPP, Steve held senior level positions at HANYS Benefit Services, Gallagher Retirement Services, MetLife, Oppenheimer Funds, and Nicholas Applegate Capital Management. Steven has been a featured retirement plans speaker at the American Bar Association (ABA), Securities Industry Association (SIA) conference and the National Tax Sheltered Accounts Association (NTSAA) national conferences. Steven has been named as one of the Top 100 retirement plan advisors in the United States by Plan Sponsor Magazine in 2015 and 2016. He was also named as one of the Top Retirement Advisers by The Financial Times in 2017, 2018, 2019, 2020, and 2021.  Steve was also named one of the Top 300 in the years 2008, 2009, 2010. Steven has been awarded his Accredited Investment Fiduciary designation (AIF®) from the University of Pittsburgh, the Certified Plan Fiduciary Advisors (CPFA®) from the National Association of Plan Advisors (NAPA), and the Chartered Retirement Plan Specialist (CRPS®) designation from the College for Financial Planning. Steve earned his Bachelor’s Degree (BBA) in Finance from the University of Iowa. Steven resides with his family in Westfield, New Jersey. Disclosure: Steven Puckett is the managing member of Fiduciary Pension Partners.  Fiduciary Pension Partners is a registered investment adviser with its principal place of business in the State of New Jersey. Registration does not imply a certain level of skill or training.  The content provided herein is not intended to provide specific legal, tax, financial or other professional advice. Mr. Puckett was not compensated for his participation in this program.

    28 min
  5. 9. Applying Unreasonable Hospitality to Closing the Retirement Plan Access Gap | Phil Senderowitz

    09/17/2025

    9. Applying Unreasonable Hospitality to Closing the Retirement Plan Access Gap | Phil Senderowitz

    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 Advisor Representative with Global Retirement Partners. As a Managing Director for Strategic Retirement Partners, Phil is responsible for servicing clients, as well as growing the firm’s practice in the Central Florida market. He is a specialist in investment due diligence processes, fiduciary best practices, and provider benchmarking. Phil also provides extensive experience in delivering customized employee education services to help promote more positive retirement outcomes. With more than two decades of industry experience, Phillip has served as Chief Investment Officer for Chepenik Financial and also as a Private Financial Advisor at SunTrust Bank. Phillip is a Chartered Financial Analyst (CFA) and a Certified Financial Planner (TM) professional. He is a regular speaker at industry conferences, actively serves on the board of several community organizations, and is a trustee of the City of Maitland Police & Fire Pension Fund. Phillip lives in Orlando, Florida with his wife, two sons. He is an avid runner and has completed three marathons. He also enjoys reading and spending family vacations skiing.

    28 min
  6. 8. Private Markets in Defined Contribution Plans: Navigating the New Frontier, Part 2 | Charlotte Hickey, Zachary Rosenoff

    09/12/2025

    8. Private Markets in Defined Contribution Plans: Navigating the New Frontier, Part 2 | Charlotte Hickey, Zachary Rosenoff

    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 on retirement plans, the importance of understanding new terminology, and the need for financial advisors to build trust with clients. The conversation emphasizes the shift from focusing on optionality in investment choices to prioritizing participant outcomes, highlighting the growing role of alternative assets in retirement portfolios. The opinions and thoughts expressed here are those of the individual speaker providing them based on their professional and personal experience and does not represent the views or opinions of Marsh & McLennan Agency, its parent companies or any of its affiliated companies.

    19 min
  7. 7. Private Markets in Defined Contribution Plans: Navigating the New Frontier, Part 1 | Charlotte Hickey, Zachary Rosenoff

    09/05/2025

    7. Private Markets in Defined Contribution Plans: Navigating the New Frontier, Part 1 | Charlotte Hickey, Zachary Rosenoff

    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 on retirement plans, the importance of understanding new terminology, and the need for financial advisors to build trust with clients. The conversation emphasizes the shift from focusing on optionality in investment choices to prioritizing participant outcomes, highlighting the growing role of alternative assets in retirement portfolios. The opinions and thoughts expressed here are those of the individual speaker providing them based on their professional and personal experience and does not represent the views or opinions of Marsh & McLennan Agency, its parent companies or any of its affiliated companies.

    22 min
  8. 6. The Power of Specialization for Retirement Plan Advisors | Rick Unser

    08/01/2025

    6. The Power of Specialization for Retirement Plan Advisors | Rick Unser

    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 learning and adaptation in the financial services industry. More About Rick:Rick Unser is on a mission to positively influence the retirement outcomes of 10 million people.  His experience in the trenches, insatiable curiosity and constant need to separate the forest from the trees has put him in the watchtower of an industry managing quickly shifting demographics, product and platform innovation, and everchanging regulation.  Come join Rick as he challenges conventional thinking and champions positive change:• on Forbes: become a reader of his Forbes column on the 401(k) and workplace retirement plan topics• on your podcast player: listen to his podcast, 401(k) Fridays, where I interview industry experts from public policy thinktanks, asset management, and leading service providers.

    35 min
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Ratings & Reviews

5
out of 5
4 Ratings

About

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.

Information

  • Creator
    Great Gray Trust Company
  • Years Active
    2K
  • Episodes
    13
  • Rating
    Clean
  • Copyright
    ©2025 Great Gray Trust Company, LLC. All rights reserved. Please see disclosures for important information.
  • Show Website
    Gray to Great

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