Matt Regan, CEO of Wealthcare Capital Management, joins me to explore the forces reshaping the wealth management industry and what RIAs must do to thrive in the decade ahead.

We discuss the accelerating shift of assets toward independent advisors, the realities behind fee compression, the role of technology in building scalable practices, and the shortage of next-generation advisors. Matt also shares candid insights on regulatory pressures, the impact of robo-advisors, and why outsourcing non-revenue-generating activities is critical to growth and enterprise value.

Whether you’re an advisor, investor, or simply curious about where wealth management is headed, this conversation offers practical insights and a clear-eyed view of the future.

In this episode, I’m joined by Leigh Hoagland, co-founder and former CEO of New York Private Finance and now senior advisor to the firm. Leigh shares the backstory of a borrower we’ll call “Bob”—a food entrepreneur who used a loan from NYPF to buy out a minority partner and retain full control of his company.

We explore:

• Why Bob borrowed personally instead of through the company
• How we structured the loan using a blend of illiquid private equity and a participating interest
• What made this deal a win for the borrower—and for NYPF
• How our model differs from mezzanine debt and other private credit providers

Leigh also shares reflections from his time at Bankers Trust and Deutsche Bank, and explains how regulatory shifts gave rise to the NYPF model.

Will Bowmer, Managing Director and Co-Head of Technology at Lincoln International, joins David to share his path from corporate law to investment banking, including his time navigating the Lehman Brothers bankruptcy. Will discusses building Lincoln’s tech banking practice in San Francisco, the firm’s strength in valuing private companies and private markets, and how AI is reshaping dealmaking and advisory work. Along the way, he reflects on lessons from past market cycles and what’s driving today’s technology M&A landscape.