Episode 127: This week, Kyle Van Pelt talks with Matt Regan, President at Wealthcare. With more than two decades in the financial services industry, Matt has helped build several transformative business models, including launching the retail brokerage and OpenIPO system at WR Hambrecht+Co. His work has consistently focused on scaling world-class organizations with a strong commitment to the client experience.

Kyle talks with Matt about building scalable, sustainable advisory businesses at the intersection of technology and operations. Matt shares his journey into wealth management, the evolution of Wealthcare from planning software to a full-service platform, and how standardized systems drive organic growth and enterprise value. They dive into affiliation models, M&A strategy, talent challenges, and the future of advice in an AI-driven world—especially for emerging advisors and smaller clients.

In this episode:

(00:00) - Intro

(02:44) - Matt's money moment 0.

(03:58) - Wealthcare's origin story

(06:20) - Wealthcare's affiliation model

(12:24) - Common pitfalls in M&A

(14:04) - The talent gap and finding Gen 2 successors

(15:33) - Matt's thoughts about the future of M&A

(19:34) - What it takes to build a firm from $0 to $100M in today's market

(22:47) - The role of AI in serving HENRYs (High Earners, Not Rich Yet)

(26:50) - Why soft skills are the new hard currency

(28:27) - Matt's outlook on the future of the industry

(32:37) - Matt's Milemarker Minute

Key Takeaways

Standardization creates enterprise value. A repeatable operating system is what turns an advisory practice into a real business. Consistency across planning, investments, client service, and operations becomes your biggest growth lever.

Tech-enabled platforms only matter if the tech actually supports the advisor's workflow. A true tech platform is not a stack of tools. It's a single operating system that connects planning, investments, trading, and service in one experience. 

"Date before you marry" might be the future of advisor M&A. Affiliation provides an opportunity for advisors to integrate systems, see the culture, and test-fit a partner long before selling the firm. It reduces regret and increases alignment.

Not every acquisition is a good acquisition. Great M&A means buying businesses you can meaningfully improve.

Quotes

"What the founder of this firm preached was that you should do things in a very systematic, repeatable way. It's the only way you scale. It's the only way you grow organically." ~ Matt Regan

"[Being a financial advisor] takes an incredible amount of resilience and aggressive dedication to building a business. And it's not for the faint of heart." ~ Matt Regan

"Progress empowers the people who work for us here and creates career paths and a valuable professional life for Wealthcare's employees. I care deeply about the people who work here. And I want to see them not only succeed financially, but become happy people." ~ Matt Regan

Links 

Matt Regan on LinkedIn

Wealthcare Capital Management

Wells Fargo

Fidelity Investments

Orion Advisor Solutions

Charles Schwab

Morgan Stanley

The Passenger

Blood Meridian

Connect with our hosts

Milemarker.co

Kyle on LinkedIn

Jud on LinkedIn

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YouTube

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