Most American families procrastinate on estate planning—over 50% have no plan at all. But Cody Barbo, founder and CEO of TrustAndWill (the nation's leading digital estate planning platform), reveals why this isn't a knowledge problem. It's an anxiety problem.

In this episode of Contrasting Viewpoints, Ray Sclafani and Mark Hurley explore the real opportunity ahead for financial advisors who make estate planning a core service. Cody shares why his startup has helped 1.3 million families—and how he got there by recognizing that clients are worried about money more than ever before. The conversation covers why traditional estate planning failed to solve this problem, how digital platforms change the equation for advisors, and why over 50% of clients would consider switching advisors if their current advisor didn't offer estate planning capability.

Whether you're looking to add a competitive service, deepen client relationships, or unlock a new revenue stream, this episode reveals the business case for estate planning in your practice today.

About Our Guest:

Cody Barbo | Founder & CEO, TrustAndWill

Cody Barbo is a serial entrepreneur and founder of TrustAndWill, the nation's leading digital estate planning platform serving 1.3+ million families. With 16 years of entrepreneurial experience and a mission to make estate planning accessible to everyday American families, Cody has built TrustAndWill into a 50+ million dollar revenue business in just seven years, with backing from strategic investors including UBS, Northwestern Mutual, American Express, USAA, and others.

Before TrustAndWill, Cody built a hospitality tech platform serving restaurants and hotels, raising millions in venture capital. His personal catalyst for TrustAndWill came in late 2017 when he recognized that millions of Americans know they should address estate planning but continue to postpone—creating both a business opportunity and a human need.

Today, 26,000 financial advisors use TrustAndWill as part of their client service delivery, and Cody is focused on continuing to partner with the wealth management industry to solve the estate planning gap. He speaks regularly at industry conferences and contributes research on advisor best practices and client engagement strategies.

About Our Hosts:

Mark Hurley

Mark Hurley is CEO of Digital Privacy and Protection, a cybersecurity specializing in serving clients of financial advisory firms and other professionals. Prior to that, he was CEO of Fiduciary Network, an acquirer of minority interests in RIAs. From 1998 to 2004, he was CEO of Undiscovered Managers, a mutual fund company that was sold to JP Morgan Asset Management. He began his career as an investment banker in the financial services division of Goldman Sachs, where he specialized in asset management. He is a graduate of the United States Military Academy at West Point and holds an M.B.A. from the Stanford Graduate School of Business.

To learn more about Mark Hurley and Digital Privacy and Protection visit dpripro.com

Ray Sclafani

Ray Sclafani is the Founder and CEO of ClientWise, a premier business and executive coaching firm serving financial advisors, advisory teams, and wealth management leaders nationwide. A recognized authority on advisory firm growth, leadership, succession, and enterprise development, Ray brings 20+ years of experience in financial services, including a distinguished tenure at AllianceBernstein where he served as one of the company's top sales professionals and executive leaders.

As a Professional Certified Coach (PCC) and Master Certified Neuro-Linguistic Programmer, Ray has coached many of the industry's top-performing advisory firms and teams, including those at Merrill Lynch, Morgan Stanley, LPL, Raymond James, Ameriprise, and Northwestern Mutual. He is the host of the Building the Billion Dollar Business podcast, co-host of Contrasting Viewpoints published by Financial Advisor magazine, and author of You've Been Framed (Wiley, 2015).

Ray's thought leadership and impact have been recognized through multiple 2026 awards: Finalist for Chief Executive Officer of the Year at the Wealth Management Industry Awards, Finalist for Thought Leader of the Year in the Advisory Support Platform Category at the ThinkAdvisor Luminaries Awards, and Top Financial Advisor Coaching Service 2026 from Financial Services Review.

To learn more about Ray Sclafani and ClientWise visit www.clientwise.com

AI is no longer a future consideration for advisory firms. It's an operating decision advisors are making right now, and this episode digs into what that decision actually involves. Ray Sclafani and Mark Hurley open with their usual contrasting lenses (Mark on custodial economics and market structure, Ray on talent and culture) before turning to Matt Halloran, Chief Evangelist at Zocks, for a candid look at how AI assistants are reshaping day-to-day practice management.

Matt unpacks why plugging client data into consumer AI tools like ChatGPT or Claude carries real compliance risk, why connecting AI directly to a CRM can mean the AI provider learns from and effectively owns that client data, and how purpose-built platforms are designed to avoid that exposure. Mark presses him on breach liability and third-party attack vectors, while Ray challenges whether automating entry-level work strips junior advisors of the judgment they need to develop. The conversation also covers where AI should responsibly learn about clients: through structured, advisor-reviewed processes rather than open access to historical records.

Listeners walk away with a clearer framework for evaluating AI tools and the compliance questions worth asking before connecting any AI system to client data.

About Our Guest:



Matt Halloran is Chief Evangelist at Zocks, the privacy-first AI assistant platform built for financial advisors, where he leads AI education and adoption for advisors and firms. A three-time author, TEDx speaker, and advisor coach with more than 15 years of practice management experience, Matt holds an MS in mental health and life coaching and has appeared on more than 1,000 podcasts. He's known for championing a human-centered approach to leadership and client communication, making him a credible voice on where automation should and shouldn't take over in an advisory practice.

About Our Hosts:

Mark Hurley

Mark Hurley is CEO of Digital Privacy and Protection, a cybersecurity specializing in serving clients of financial advisory firms and other professionals. Prior to that, he was CEO of Fiduciary Network, an acquirer of minority interests in RIAs. From 1998 to 2004, he was CEO of Undiscovered Managers, a mutual fund company that was sold to JP Morgan Asset Management. He began his career as an investment banker in the financial services division of Goldman Sachs, where he specialized in asset management. He is a graduate of the United States Military Academy at West Point and holds an M.B.A. from the Stanford Graduate School of Business.

To learn more about Mark Hurley and Digital Privacy and Protection visit dpripro.com

Ray Sclafani

After 20 years at AllianceBernstein, Ray Sclafani founded and heads ClientWise, the premier coaching and training company exclusively serving the financial services industry. Ray’s passion for serving leaders, advisors, and companies in the financial services sector is reflected in ClientWise and its unique coaching programs and team of credentialed coaches that help advisors and companies find the next level of professional excellence and financial success with greater focus and ease.

Ray’s experience as a seasoned specialist in coaching and training in the financial sector mirrors his long and profitable history in the industry. In his 20 years at AllianceBernstein, Ray was one of the company’s top sales professionals and executive leaders. His knowledge of how to create and execute on highly successful sales plans and build long lasting client connections was later utilized as founder and Managing Director of the Advisor Institute at AllianceBernstein.

As a complement to his coaching skills, he also holds a Master’s Certification in Neuro-Linguistics from the International Association for Neuro-Linguistic Programming and has participated in The Strategic Coach® Program for 17 years.

Ray’s book, You’ve Been Framed: How to Reframe Your Wealth Management Business and Renew Client Relationships, was published by Wiley in 2015. Ray holds a BA from Baylor University. He lives in Flower Mound, Texas with his wife and true life partner, Beth. Their two sons and Beth continually inspire his work and his passion for excellence.

To learn more about Ray Sclafani and ClientWise visit www.clientwise.com