Reading the Room: Greg Cantone on Building a Practice Around the People You Serve

Most advisors spend years perfecting their pitch. Greg Cantone spent twelve years perfecting something harder: reading an audience in real time and adjusting on the fly.

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.

In episode 21 of Gray to Great, Greg joins the podcast to talk about what those two worlds have in common, why communication is the most underrated skill in the advisory business, and what one of the most difficult chapters of his career taught him about resilience.

The Stage and the Committee Room

When Greg talks about his stand-up background, he is not telling a fun origin story. He is describing the training ground for every client interaction he has had since.

“There was a lot of overlap in doing stand-up and my professional career in finance,” Greg says. “A lot of it being just being able to read the room. If something wasn’t hitting or something wasn’t making sense, being able to repolish the message or refocus the energy in a way that I knew it was landing.”

That skill does not come from a training manual. It comes from standing in front of an audience, night after night, and learning to pay attention. Learning when to pause. Learning when to go back and clarify. Learning that the most important thing in any room is not what you are saying. It is whether the person across from you is actually receiving it.

For Greg, that lesson transferred directly to retirement plan advising. Whether he is presenting to an investment committee, sitting down with a plan participant, or walking a plan sponsor through a regulatory change, the objective is the same: make it land.

Detach From the Outcome

The most striking moment in Greg’s episode has nothing to do with communication. It has to do with resilience.

In his early thirties, Greg was part of one of the largest bank failures in US history. It was not something he anticipated having on his resume. What it gave him, after enough time and distance, was one of the most important mindset shifts of his career.

“You are not attached to the outcome. You are attached to your product and your result and what you create. And there is a lot of beauty in that.”

That is not a platitude. It is a hard-won perspective that took years to arrive at. Greg is candid about the fact that it was not easy in the moment. But on the other side of it, the lesson is clear: the advisors who navigate difficult chapters are the ones who stay focused on what they can control and do not let the outcome define them.

That mindset carries into how Greg approaches every new business conversation, every lost deal, and every moment where the result does not go the way he planned. The work is what matters. The output is what you own.

More People, More Impact

Greg did not end up in retirement plan advising by accident. Early in his career at Merrill Lynch, he saw two paths in front of him: ultra high net worth private wealth, where most advisors aspired to be, or retirement plans, where the clients were more varied and the need was far greater.

He chose the latter. Not because it was easier, but because of what it made possible.

“Being able to help a much broader range of participants or employees through a company’s retirement plan just felt like the most effective way to help the most amount of people.”

That conviction has never left him. Today Greg focuses on mid-sized businesses, where one trusted advisor can make a meaningful difference not just for the plan sponsor but for every employee sitting in that enrollment meeting.

That is impact at scale. And for Greg, it is the whole point.

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.

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Disclosures:

Greg Cantone is a Wealth Manager with Citizens Private Wealth. Citizens Private Wealth is a registered investment adviser and a wholly owned subsidiary of Citizens Bank, N.A. Brokerage services are offered through Citizens Securities, Inc., a registered investment adviser and member of FINRA and SIPC. Citizens Private Wealth, Citizens Securities, Inc., and Citizens Bank, N.A. are affiliated entities. Great Gray is not affiliated with Citizens Private Wealth, Citizens Securities, Inc., or Citizens Bank, N.A. The views, opinions, and strategies expressed herein reflect Greg Cantone’s judgment as of the recording date, are subject to change without notice, and may not represent the views of Citizens Private Wealth or its affiliates. This material is provided for informational purposes only and does not constitute investment advice or a recommendation to buy or sell any security. References to specific securities, strategies, or market conditions are for illustrative purposes only.

Greg Cantone and Citizens Private Wealth 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.