Next Mile

Milemarker

Next Mile is a podcast about bringing together the people and technology shaping the wealth management industry. Brought to you by Milemarker.

  1. The Operating System Behind Scalable Advisory Firms with Matt Regan

    6D AGO

    The Operating System Behind Scalable Advisory Firms with Matt Regan

    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.

    36 min
  2. Scaling White-Glove Client Experiences with Sarah Simmer

    JAN 6

    Scaling White-Glove Client Experiences with Sarah Simmer

    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.

    41 min
  3. Why Wealth Tech Still Feels Broken

    12/30/2025

    Why Wealth Tech Still Feels Broken

    Episode 125: In this special New Year's 2025 episode, Kyle Van Pelt brings together four standout voices to explore why wealth technology still feels broken—and what actually fixes it. Jeremy Nelson explains how rising client complexity demands centralized planning and operational tech that can truly scale. Art Ambarik shares how fragmented data and poor transitions create bottlenecks that distract advisors from clients. Kylie Felker shows how efficient systems make room for unreasonable hospitality and deeply human service. And Terry Parham Jr outlines how impact, efficiency, and effectiveness improve when firms own and streamline their data. Together, these conversations reveal how better integration—not more tools—is the path forward. In this episode: (00:00) – Intro (00:30) – Jeremy Nelson on rising client complexity and why centralized tech is essential for scale (03:25) – Art Ambarik on data bottlenecks, advisor transitions, and removing operational friction (08:30) – Kylie Felker on using efficient systems to create unreasonable hospitality for clients (15:30) – Terry Parham Jr on evaluating wealth tech through impact, efficiency, and effectiveness Links  Jeremy on LinkedIn: https://www.linkedin.com/in/jeremy-my-element-wealth/  Element Wealth: https://myelementwealth.com/ Art Ambarik on LinkedIn: https://www.linkedin.com/in/arthur-ambarik-cfp%C2%AE-75359457/  Perigon Wealth Management: https://www.perigonwealth.com/  Kylie Felker on LinkedIn: https://www.linkedin.com/in/kyliekotowskifelker/  Foster Victor Wealth Advisors: https://fostervictor.com/  Terry Parham Jr on LinkedIn: https://www.linkedin.com/in/tepjr/  Innovative Wealth Building: https://innovativewealthbuilding.com/  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.

    18 min
  4. What It Takes to Build the Next Generation of Talent

    12/23/2025

    What It Takes to Build the Next Generation of Talent

    Episode 124: In this special Christmas 2025 episode, Kyle Van Pelt brings together four standout voices to explore what it takes to identify, attract, develop, and retain the next generation of talent. Daniel Spurgeon shares how firms can spot potential early and create intentional career pathways instead of reactive hires. Kristen Oziemkowski explains what today’s young professionals are really looking for—and how purpose, culture, and clarity drive attraction. Eric Kittner highlights the power of mentorship, in-person learning, and real responsibility in developing talent. And Matt Matrisian makes the case that long-term growth, trust, and investment are essential to retention. Together, these conversations offer a practical roadmap for building teams that thrive well into the future. In this episode: (00:00) - Intro (00:54) – Daniel Spurgeon on identifying potential early and building intentional career pathways (07:32) – Kristen Oziemkowski on attracting young professionals through purpose, culture, and clarity (16:53) – Eric Kittner on developing the next generation through mentorship and real responsibility (24:52) – Matt Matrisian on retaining talent by investing in growth, trust, and long-term vision Links  Daniel Spurgeon on LinkedIn Commonwealth Financial Services Kristen Oziemkowski on LinkedIn The Mather Group Eric Kittner on LinkedIn Moneta Group Matt Matrisian on LinkedIn Signature Estate & Investment Advisors 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.

    32 min
  5. How Planning Drives Better Investment Decisions with Tim Thomas

    12/16/2025

    How Planning Drives Better Investment Decisions with Tim Thomas

    Episode 123: This week, Kyle Van Pelt talks with Tim Thomas, Chief Investment Officer and Wealth Manager at Badgley Phelps Wealth Managers. Tim joined Badgley Phelps in 2008 and brings more than two decades of experience in financial planning and portfolio management. He specialized in security analysis and selection, portfolio construction, asset allocation, and alternative investments. Tim shares with Kyle about the mechanics of modern portfolio construction. He discusses why the financial plan must be the north star for investment strategy, how to navigate the noisy and rapidly democratizing world of alternative investments, and how AI is changing the backend of advisory work without replacing the human connection. In this episode: (00:00) - Intro (01:33) - Tim's money moment (02:57) - Marrying financial planning with investment strategy (03:56) - How investing has changed over time (06:18) - The rise in alternative investments (09:55) - Understanding alts as more than one asset class (16:24) - How Badgley Phelps helps clients navigate the nuances of alts (18:27) - Managing M&A and the acquisition of Marshall & Sullivan (21:45) - How Badgley Phelps approaches holistic planning (23:40) - Tim's thoughts about the future of the industry (27:25) - Tim's Milemarker Minute Key Takeaways Planning is a strategy. Investments are implementation.  The most effective portfolios are built after the cash flow model is complete.  By understanding the client's lifestyle needs and success rates first, you can determine the specific hurdle rate required to achieve their goals.  Democratization of alts is exciting, but operational risk is real. Alternative investments are booming, but they shouldn't be added to a portfolio just because they are trendy or accessible. Customization beats cookie-cutter strategies. Whether it's equities, fixed income, or alts, thoughtful leaders build client portfolios around client-specific needs — income, growth, risk tolerance, or liquidity — instead of defaulting to one-size-fits-all recommendations. The quarterback model vs. the generalist. There is a massive industry push to bring tax, legal, and estate planning in-house. Sometimes, building a bespoke team of external experts serves the client better than a one-size-fits-all internal department. Quotes "Planning has really come to the forefront, and the investments are critically important because that is the implementation of the plan. But the planning has definitely risen in prominence, and it has a much bigger role than it used to." ~ Tim Thomas "It's just incredible to see how fast alts have grown in prominence and how big an allocation they're getting in portfolios these days. We're missing out on some opportunities by not having them." ~ Tim Thomas "When you think about technology, computers are really good at crunching a lot of data, sorting, and solving a lot of different things at the same time. What they can't replace is that conversation with a client." ~ Tim Thomas Links  Tim Thomas on LinkedIn Badgley Phelps Wealth Managers Vanguard iCapital CAIS Focus Financial Partners Marshall & Sullivan, Inc. Chip War: The Fight for the World's Most Critical Technology Boom: Bubbles and the End of Stagnation 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.

    30 min
  6. Beyond Referrals: Transforming Advisor Growth with Eden Ovadia

    12/10/2025

    Beyond Referrals: Transforming Advisor Growth with Eden Ovadia

    Episode 122: This week, Kyle Van Pelt talks with Eden Ovadia, Co-Founder of FINNY. Before FINNY, Eden worked on the private equity team at Boston Consulting Group, where she advised on major M&A deals across the wealth management space. Driven by her background in AI and engineering, and inspired by the wealthtech industry's shifting dynamics, Eden co-founded FINNY to help advisors build predictable, personalized, and tech-enabled organic growth engines.  Eden discusses why the wealth management industry is ripe for innovation and disruption. She also shares why referrals are no longer enough to drive organic growth, and how FINNY rewrites the marketing playbook using machine learning to create hyper-personalized, high-propensity matches between advisors and prospects. In this episode: (00:00) - Intro (02:18) - Eden's money moment (04:12) - Innovation in wealth management (07:28) - Why referrals are no longer enough to grow organically (09:25) - How FINNEY rewrites the traditional marketing playbook (16:16) - The power of niching and segmentation in organic growth (18:14) - Introducing the F-score: FINNY's proprietary machine learning algorithm (22:56) - What it takes to build an advisor-first tech stack (24:18) - FINNY's future goals (25:39) - FINNY's outlook on the future of the wealth management industry (28:51) - Eden's Milemarker Minute Key Takeaways Referrals are great. But they're no longer enough to grow organically. Referrals are a linear expansion tied to an advisor's personal time and energy. True scalability requires building an engine that works in the background for you. Consumer behavior has changed. Your growth strategy should, too. The next generation of clients shops for everything digitally, including financial guidance. They expect personalized, tech-enabled experiences.  Niche and segment. The firms breaking out from the pack are the ones that define exactly who they serve. Not "retirees," but "retirees selling a dental practice." Not "business owners," but "HVAC operators with succession on their minds." Precision builds trust, and trust accelerates conversion. Organic growth must become intentional and operationalized. The fastest-growing firms don't stumble into growth. They measure it, build systems for it, and treat it with the same seriousness as investing or planning. Growth becomes predictable when it becomes part of your operating rhythm. Quotes "Referrals will always be king. The problem with referrals is that they grow with every advisor's time, energy, and resources. It doesn't scale exponentially. It scales with your time and money" ~ Eden Ovadia "If you're an advisor who wants to build a generational business, you need to start building and investing effort in creating a growth engine, because referrals will decline year over year." ~ Eden Ovadia "If you believe that there's going to be a lack of a hundred thousand advisors in the near future, we view FINNY as the tool that can serve as the optimization layer between the supply of financial advisors and the demand for financial advice." ~ Eden Ovadia Links  Eden Ovadia on LinkedIn FINNY Brian Chesky Y Combinator Boston Consulting Group JUMP AI Zocks Outliers Never Split the Differences 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.

    32 min
  7. Connecting Advisors and Investors to the Innovation Economy with Mark Buffington

    12/02/2025

    Connecting Advisors and Investors to the Innovation Economy with Mark Buffington

    Episode 121: This week, Kyle Van Pelt talks with Mark Buffington, CEO at BIP Capital and Managing Partner at BIP Ventures. Since founding BIP Capital, Mark has helped shape the firm into one of the most active and respected investment brands outside Silicon Valley. He’s also spearheaded several of its most forward-thinking initiatives, from a private-equity Evergreen BDC to a proprietary deep-data AI platform and a Performance Engineering framework built to create category-leading companies and deliver premium exits. Mark and Kyle explore what it takes to build a wealth advisory practice that blends growth, service, and innovation. Mark explains the regulatory and educational hurdles that have historically kept most individuals at arm’s length from the innovation economy—and the unconventional solution BIP created to bridge that gap. He also breaks down how BIP adapted “performance engineering” principles from its tech portfolio to transform business culture and fuel record-breaking growth in the wealth management space. In this episode: (00:00) - Intro (02:30) - Mark's money moment (08:50) - Why individuals struggle to access private markets (15:08) - How BIP connects investors to alternative and private market opportunities (23:32) - Bringing “performance engineering” into BIP’s business strategy (27:46) - The challenge of building a sales culture on top of a service culture (31:43) - The internal and external tech stack powering BIP’s growth (37:15) - Mark’s outlook on the future of financial services (43:16) - Mark's Milemarker minute Key Takeaways A sales culture can enhance—not replace—service excellence. A strong service-driven culture doesn’t conflict with growth. When layered thoughtfully, a disciplined sales and marketing process amplifies the value you deliver while expanding your firm’s reach. The traditional advisory value proposition isn’t enough. As the industry becomes more complex and competitive, simple asset allocation or basic planning won’t consistently attract or retain clients. Advisors need differentiated value supported by expertise, technology, and innovation. Technology is a strategic advantage when you control it. Building or owning your tech and data enables better decisions, stronger efficiency, and a better client experience—especially as AI accelerates what’s possible. Innovation removes structural barriers. Regulation, access limitations, and operational friction often hold back growth. Firms that find creative ways to overcome those barriers can separate themselves from competitors and unlock new opportunities. Quotes "The market shifted. Traditional advisors that provide basic asset allocation and some basic planning are not enough to win and keep business consistently." ~ Mark Buffington "In a world where advisors are increasingly under competitive pressure, how do we give them an advantage? Technologically, with AI and with private market products, and in ways that integrate with their workflows." ~ Mark Buffington "We are in the advice business, but we're also in the worry elimination business. The real value to individuals with complex lives, who are raising kids and trying to manage their own careers, is to take that worry and concern off their plates." ~ Mark Buffington Links  Mark Buffington on LinkedIn Bill Harris BIP Capital BIP Ventures BIP Wealth iCapital CAIS Charles Schwab Christy Johnson Andrew Somoza Hart Williford Tamarac | Envestnet Orion Advisor Solutions Envestnet | MoneyGuide eMoney Advisor Plaid Skin in the Game Connect with our hosts Milemarker.co Kyle on LinkedIn Jud on LinkedIn Subscribe and stay in touch Apple Podcasts Spotify YouTube

    47 min
  8. Building a Tech Stack That Scales With Your Firm

    11/25/2025

    Building a Tech Stack That Scales With Your Firm

    Episode 120: As firms enter strategic planning season, Kyle Van Pelt brings together the strongest technology insights from four standout leaders. Nelly Mubashi explains the operational realities of supporting multiple advisor-selected platforms. Carrie Delgott highlights why consolidation into a unified stack unlocks collaboration and efficiency. Phillip Hamman shares how long-term planning and thoughtful automation free advisors to deliver “unreasonable hospitality.” And Michael Batnick offers a candid look at integration frustration inside a hyper-growth firm. Whether you’re expanding advisor choice or tightening your stack, this episode clarifies what it takes to build a scalable, integrated tech ecosystem that truly serves your team. In this episode: (00:00) - Intro (00:54) - Nelly Mubashi on supporting advisors across multiple platforms like Tamarac and Orion (05:01) - Carrie Delgott on why aligning the firm around one tech stack drives efficiency and collaboration  (07:14) - Phillip Hamman on using technology to free up advisors and deliver “unreasonable hospitality” (12:04) - Michael Batnick on the challenges of selecting tools that integrate well in a fast-growing firm Links  Nelly Mubashi on LinkedIn Northwest Asset Management Carrie Delgott on LinkedIn Wescott Financial Advisory Group Phillip Hamman on LinkedIn Linscomb Wealth Michael Batnick on LinkedIn Ritholtz Wealth Management 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.

    17 min
5
out of 5
9 Ratings

About

Next Mile is a podcast about bringing together the people and technology shaping the wealth management industry. Brought to you by Milemarker.

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