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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
Épisodes
  • Open Architecture with Intent: Building a Smarter Tech Ecosystem with Dessy Prasad

    Open Architecture with Intent: Building a Smarter Tech Ecosystem with Dessy Prasad
    Oct 13 2026
    Episode 166: This week, Kyle Van Pelt talks with Dessy Prasad, COO at Northwest Asset Management and RIA Innovations. Dessy began her career at Northwestern Mutual in Seattle as a financial representative on the insurance side, working alongside investment advisors and their teams. She joined Northwest Asset Management 11 years ago and helped support its growing advisor platform and operational infrastructure. Kyle and Dessy explore how advisory firms can give advisors flexibility without allowing their technology and operations to become fragmented. Dessy shares why the CRM serves as the central hub for their workflows, how her team customizes support around individual practices, and when outsourcing can free advisors to spend more time with clients. They also discuss onboarding, communication, AI note takers, specialized versus general-purpose AI tools, and why cybersecurity and compliance have to be part of every technology decision. In this episode: (00:00) - Intro (01:25) - Dessy’s money moment (04:11) - From open architecture to architecture with intent (05:23) - Building a tech ecosystem around a central hub (06:51) - Customizing workflows without creating chaos (07:58) - Evaluating AI tools for advisors (11:35) - When outsourcing starts to make sense (13:05) - Choosing the right RIA support model (14:28) - Using communication and workflows to improve execution (15:57) - Using CRM workflows to keep onboarding on track (17:01) - How the firm is evaluating AI tools (19:23) - Dessy's outlook on the future of financial services (20:41) - Building compliance into technology evaluation (21:37) - Dessy’s Milemarker Minute Key Takeaways Curate your tech stack around a central hub. Open architecture works best with intent: start with the system your team logs into every day, then add only the tools that have a clear purpose and work together. A connected platform is easier for advisors to adopt than a long list of tools. Vet AI tools before you adopt them. Note takers can take real administrative work off an advisor’s plate, but they also handle sensitive client information. Reviewing a vendor’s documentation and talking with its engineers and compliance team helps confirm that PII stays protected. Protect the work only you can do. When administrative and back-office responsibilities begin taking time away from client relationships, firms have to decide whether to add internal capacity or outsource. The goal is to give advisors more room to focus on the work where they create the most value. Operational excellence comes down to communication. Taking the time to understand each practice shows what an advisor actually needs, and onboarding is where that matters most. Automated workflows that alert every team, paired with steady personal contact, keep a stressful transition from slipping through the cracks. Quotes “A crucial part of having a healthy ecosystem is not just adding a bunch of tools, but rather having a platform where everything has a purpose.” ~ Dessy Prasad “As an advisor, your key strengths are usually building and maintaining client relationships. It's kind of hard to do when you're bogged down with too many back-end projects.” ~ Dessy Prasad “We’ve gone from trying to connect to a bunch of different tools to asking ourselves what tools work to create the best ecosystem for our advisors.” ~ Dessy Prasad Links Dessy Prasad on LinkedIn Northwest Asset Management RIA Innovations Nelly Mubashi on LinkedIn Northwestern Mutual Salentica Jump Zocks The Secret by Rhonda Byrne Connect with our hosts Milemarker.co Kyle on LinkedIn Jud on LinkedIn Subscribe and stay in touch Apple Podcasts Spotify YouTube
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    24 min
  • Scaling with Soul: Growing an Advisory Firm Without Losing What Matters with Grace Balestrieri

    Scaling with Soul: Growing an Advisory Firm Without Losing What Matters with Grace Balestrieri
    Oct 6 2026
    Episode 165: This week, Kyle Van Pelt talks with Grace Balestrieri, Senior Director of Client Experience Operations at Brighton Jones. Grace began her career in software, where her work spanned implementation, customer experience, and operations. She now brings that playbook to wealth management, building the systems, processes, and technology that let advisors focus on clients. Kyle and Grace discuss what "scaling with soul" means in practice and why growth can't come from simply adding people, tools, and complexity. Grace unpacks how Brighton Jones' Centralized Administrative Office brings custodian expertise to high-volume work, and why firms building one should plan for a learning runway and staff ahead of demand. She also shares how the firm's training program is evolving into Richer Life University, what advisors can borrow from B2B sales about activity and referrals, and why she believes technology will make relationships the real differentiator. In this episode: (00:00) - Intro (01:19) - Grace's money moment (03:05) - Bringing a software mindset into wealth management (05:13) - Why firms shouldn't overlook talent from outside the industry (06:36) - What it means to scale with soul (07:56) - How centralized operations help advisors scale (10:17) - Building expertise you don't have yet (13:46) - Inside Brighton Jones University (14:54) - Expanding into Richer Life University (16:01) - Finding the right career path inside a firm (17:23) - What wealth management can learn from B2B sales (20:58) - Grace's outlook on the future of the wealth management industry (22:48) - Staying human in an age of AI (24:30) - Grace's Milemarker Minute Key Takeaways Scale with systems, not headcount. Adding people, tools, and complexity only goes so far. Better processes, consistency, and technology free advisors for the relationship work that depends on their judgment and that clients value most. Centralize high-volume work with specialists. A dedicated team that knows each custodian's nuances reduces not-in-good-order paperwork and back-and-forth. It's also easier to measure and improve than the same work spread across a firm. Give centralization time to earn trust. Efficiency and adoption won't arrive on day one. Plan a runway for the team to learn and for advisors to build confidence, and staff for capacity before the volume ramps. Use technology to make the human side of advice more valuable. As AI removes more administrative work and levels parts of the competitive landscape, the opportunity is to turn that reclaimed capacity into stronger conversations, greater trust, and deeper client relationships. Quotes "We can't just ask people to work harder and hire and hire and hire more people and add complexity and add more tools. What we have to think about is better technology, better process, more consistency across the firm, better ways we service clients so that we can maintain the soul." ~ Grace Balestrieri "You can teach the industry. People, as fast learners, can grow and evolve and understand the nuances, but you can't teach the skill set, the experience, the judgment, the critical thinking." ~ Grace Balestrieri "Plan the runway for the team to learn, for people to build the trust, to work out the kinks, and know that your ROI isn't going to be immediate." ~ Grace Balestrieri Links Grace Balestrieri on LinkedIn Brighton Jones Outreach WALL-E The Book Club for Troublesome Women 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 Milemarker Studio Milemarker Studio 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 MilemarkerStudio.co.
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    27 min
  • Why Expertise Alone Isn't Enough for Ultra-High-Net-Worth Families with Kristina Baron

    Why Expertise Alone Isn't Enough for Ultra-High-Net-Worth Families with Kristina Baron
    Sep 29 2026
    Episode 164: This week, Kyle Van Pelt talks with Kristina Baron, Co-Managing Partner and Managing Director at Oxford Financial Group. Kristina started in the industry as a high school intern in a financial advisor's office and later worked at Goldman Sachs before joining Oxford. Today she helps lead a team that serves roughly 700 families across the country. Kyle and Kristina explore what it takes to coordinate advice for families whose needs span investments, estate planning, taxes, trusts, outside advisors, and multiple generations. Kristina shares why understanding a family’s values should precede any solution, how Oxford structures teams and communication to make complexity manageable, and why continuity depends on giving younger generations a voice. They also discuss data integrity, connected technology, practical AI applications, and Kristina’s concerns about how consolidation and pressure for new revenue streams could reshape the RIA landscape. In this episode: (00:00) - Intro (01:31) - Kristina's money moment (04:56) - Why understanding has to come before expertise (07:10) - Coordinating estate planning across jurisdictions (10:05) - Standing out when every firm says it serves families like yours (15:38) - Working alongside a family's other advisors (18:12) - Making a complex service model feel simple (19:46) - Planning for every generation of the family (23:23) - Why communication breaks down between generations (27:14) - Building the data foundation before layering on technology (30:08) - Where AI fits in serving ultra-high-net-worth families (33:33) - Kristina's outlook on the future of the wealth management industry (36:43) - Kristina's Milemarker Minute Key Takeaways Understand the family before designing the solution. Technical expertise only goes so far when several generations, advisors, and priorities are involved. Open-ended questions about values, concerns, and goals help determine what the family actually needs before specialists begin solving for it. Coordination matters as much as specialization. Complex families may work with attorneys, CPAs, insurance professionals, and multiple wealth managers at once. Shared communication, clearly assigned follow-up items, and a coordinated team help keep good individual advice from becoming a fragmented overall plan. Bring the next generation into the conversation before a transition happens. Continuity becomes harder when a family structure reflects only the founder generation’s priorities. Families can preserve important values while still giving later generations enough context and voice to understand, engage with, and eventually help shape the plan. Build the data foundation before expecting more from AI. Clean information and connected systems reduce manual work and give AI more useful problems to solve. The opportunity is to accelerate analysis and information retrieval while preserving human judgment and the personal interaction that complex families still value. Quotes "Facts help drive decision-making, but I think feelings and values drive even more important decision-making." ~ Kristina Baron "We can't fool ourselves that we're the best at everything, so we need to work together as a team to accomplish it, and really understand what it is that you're trying to solve for." ~ Kristina Baron "There's a way to still hold true to the values of generation one, while also allowing conversations and evolution into what's really important for generation two and beyond." ~ Kristina Baron Links Kristina Baron on LinkedIn Oxford Financial Group Jeffrey H. Thomasson — Founder and CEO of Oxford Financial Group Morningstar Direct Goldman Sachs Kubota Marie Benedict What Got You Here Won't Get You There by Marshall Goldsmith and Mark Reiter Good to Great by Jim Collins Unreasonable Hospitality by Will Guidara Connect with our hosts Milemarker.co Kyle on LinkedIn Jud on LinkedIn Subscribe and stay in touch Apple Podcasts Spotify YouTube
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    40 min
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