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Next Mile

Next Mile

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 Next Mile is a podcast about bringing together the people and technology shaping the wealth management industry. Brought to you by Milemarker.Copyright © Milemarker Inc. Economie Finances privées Marketing et ventes
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    Épisodes
    • How to Build a Firm That Outlasts You with Tyson Ray

      How to Build a Firm That Outlasts You with Tyson Ray
      Jan 20 2026
      Episode 128: This week, Kyle Van Pelt talks with Tyson Ray, CEO, Founding Partner, and Senior Wealth Advisor at FORM Wealth Advisors. Tyson helps financial advisors exit their businesses with clarity, confidence, and no regrets. He's been recognized as a Forbes Best-in-State Wealth Advisor, AdvisorHub Advisors to Watch, and Barron's Top 1200 Advisor. Kyle and Tyson discuss what it takes to build a successful wealth advisory practice that balances growth, client care, and community impact. Tyson shares the strategies, leadership mindset, and values that have guided his career to success. He also discusses his SPACE (See, Prepare, Act, Commit, Exit) framework, which reveals how advisors can exit their practice confidently and fully compensated, while keeping their clients' interests first and foremost. In this episode: (00:00) - Intro (02:12) - Tyson's money moment (05:48) - Valuable lessons Tyson learned during the early stages of his career (07:26) - How to build a career that lasts a lifetime (10:23) - The power of structure, boundaries, and accountability in scaling a firm (13:51) - The SPACE framework (21:29) - The importance of building a multi-generational team (30:07) - How Tyson finds and trains his team members (32:52) - Why you should “never enter data twice” (34:59) - Tyson's outlook on the future of the industry (40:36) - Tyson's Milemarker Minute Key Takeaways Great leadership begins with humility. The best leaders don't pretend to have all the answers. They listen, learn, and grow alongside their teams. Don't let fear define your future. If you know a change is necessary for growth, don't let fear hold you back from what is ultimately the right thing for your firm's long-term health and your own personal well-being. Invest in the next generation of advisors. Intentionally recruit and mentor younger team members to build a truly multi-generational firm—one where clients feel confident their advisor won’t retire before they do, and where modern, responsive service comes naturally. Make space for succession. You cannot effectively plan for your future or your firm without intentionally creating the time and mental room to do it. The succession process is not just about selling or retiring; it's about seeing a vision, committing to the necessary actions, and exiting with confidence and purpose. Quotes "You can't let fear prevent you from doing what's right." ~ Tyson Ray "The reason most of us don't do planning for ourselves is that we don't create the space to do it." ~ Tyson Ray "How to build your business is to hire caretakers of what you've built to free you up, because most likely, you are the rainmaker." ~ Tyson Ray Links Tyson Ray on LinkedIn FORM Wealth Advisors Total Succession Connect with our hosts Milemarker.co Kyle on LinkedIn Jud on LinkedIn Subscribe and stay in touch Apple Podcasts Spotify YouTube Produce game-changing content with Turncast Turncast helps your company grow by producing top-quality content and fostering transformative conversations. We specialize in content generation, podcasting, digital strategy, and audience growth for fintech and financial services companies. Learn more at Turncast.com.
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      43 min
    • The Operating System Behind Scalable Advisory Firms with Matt Regan

      The Operating System Behind Scalable Advisory Firms with Matt Regan
      Jan 13 2026
      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 Subscribe and stay in touch Apple Podcasts Spotify YouTube Produce game-changing content with Turncast Turncast helps your company grow by producing top-quality content and fostering transformative conversations. We specialize in content generation, podcasting, digital strategy, and audience growth for fintech and financial services companies. Learn more at Turncast.com.
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      36 min
    • Scaling White-Glove Client Experiences with Sarah Simmer

      Scaling White-Glove Client Experiences with Sarah Simmer
      Jan 6 2026
      Episode 126: This week, Kyle Van Pelt talks with Sarah Simmer, Partner and Senior Wealth Advisor at Heritage Wealth Advisors. Sarah delivers customized wealth management and tax planning services to individuals and families, with a special focus on multi-generational households. Sarah talks with Kyle about what world-class client experience truly requires, especially for ultra-high-net-worth families. She shares the tactical side of scaling a white-glove firm, highlighting the importance of rigorous client segmentation, the courage to have difficult fee conversations, and how to use data to determine exactly who you should and shouldn't be serving. In this episode: (00:00) - Intro (03:10) - Sarah's money moment (06:11) - How Sarah's mother influenced her career in wealth management (09:13) - How an auditor's mindset translates to serving high-net-worth families (10:30) - What client experience means for ultra-high-net-worth families (13:16) - How Sarah uncovers and manages client expectations (17:55) - Why proactively discussing fees can reinforce value (22:46) - How Heritage scales white-glove service to ultra-high-net-worth clients (30:03) - How a scaled white-glove service feels personalized (34:08) - Sarah's outlook on the future of the financial services industry (36:22) - Sarah's Milemarker Minute Key Takeaways Client experience is not a deliverable. It's the whole relationship. The client's perception is the reality. Leaders need a consistent feedback loop to ensure the experience matches the intent. Audit-trained minds bring hidden superpowers. Learning how to learn quickly and diagnose problems is often more valuable than specific industry knowledge. Don't fear the fee conversation. While many leaders shy away from this topic, proactively raising it allows you to realign expectations. If the client hesitates on the fee, it's an immediate signal that there is a disconnect in the perceived value of the service being delivered. Providing white-glove services at scale requires a personalized approach. White-glove service feels impossible to scale unless you define exactly who fits in which bucket. Quotes "At the end of the day, we're a people business, so the client's experience is their reality. We can think we're doing a fantastic job, but if the client has a terrible experience through all of it, we're not going to stay in business." ~ Sarah Simmer "If you believe in the value you're providing to your clients, you shouldn't be scared to check in with them on how that fee feels." ~ Sarah Simmer "If we can focus on making the information and the story we're trying to get to the client more aligned with the types of experiences they enjoy, that's the goal." ~ Sarah Simmer Links Sarah Simmer on LinkedIn Heritage Wealth Advisors PwC Dee Ann Remo KPMG International McKinsey A Bit Much Northanger Abbey Connect with our hosts Milemarker.co Kyle on LinkedIn Jud on LinkedIn Subscribe and stay in touch Apple Podcasts Spotify YouTube Produce game-changing content with Turncast Turncast helps your company grow by producing top-quality content and fostering transformative conversations. We specialize in content generation, podcasting, digital strategy, and audience growth for fintech and financial services companies. Learn more at Turncast.com.
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      41 min
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