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Episode 167: This week, Kyle Van Pelt talks with Marcos Segrera, Principal, Wealth Manager, and Director of Growth & Development at Evensky & Katz/Foldes Wealth Management. Marcos began his career in insurance before moving into the RIA channel, where his work now spans client advice, advisor development, growth strategy, and the firm’s next generation of leadership. Kyle and Marcos explore why sales is really a transfer of confidence, and why RIAs need to invest more intentionally in developing young advisors. Marcos shares how Evensky & Katz is expanding its approach to marketing and content as AI makes authentic human connection more valuable. They also discuss “funded contentment,” the role of advisors as guides, and why firms preparing for AI should focus first on clean data, documented workflows, and client-facing talent.  In this episode: (00:00) - Intro (02:33) - Marcos's money moment (06:31) - Why learning to sell still matters (10:09) - Developing advisors straight out of college (14:37) - Why Evensky & Katz is investing in content (19:45) - Why authenticity matters more in the age of AI (21:57) - Finding purpose beyond financial success (27:01) - Why AI won't replace human connection (29:49) - The value of an advisor who challenges you (32:12) - Preparing a 40-year-old firm for AI (35:41) - Designing the workflow before choosing the technology (37:07) - Marcos's outlook on the future of the wealth management industry (41:21) - Marcos's Milemarker Minute Key Takeaways Treat sales as a transfer of confidence. Technical expertise matters, but advisors still need the ability to connect, communicate, and help people feel confident making decisions. Developing those skills should be part of advisor training rather than something firms expect people to pick up on their own. Use AI to strengthen the human experience, not replace it. As information and automated advice become easier to access, trusted human judgment may become more valuable. The opportunity is to let technology handle more of the mechanics while advisors spend more time understanding clients, challenging assumptions, and navigating consequential decisions. Do the operational work before chasing the newest AI tool. Clean data and well-documented workflows determine what technology can actually improve. Before automating a process, understand how it works today, why each step exists, and whether the result improves the client experience rather than simply creating internal efficiency. Ask clients what they want to avoid. A question about goals can feel abstract, while a question about what someone is trying to avoid often reveals what matters most. Portfolios, tax strategies, and insurance then serve those bigger conversations. Quotes "Sales is a transfer of confidence." ~ Marcos Segrera “People tell you what their goals are when they tell you what they’re trying to avoid.” ~ Marcos Segrera “The people talking about it the most are the ones doing the least with it because they’re the ones getting to the quickest solution, which is probably not where you wanted to be anyway.” ~ Marcos Segrera “You should delegate everything that it’s humanly possible to delegate because you cannot delegate going to dinner with your wife. You cannot delegate taking your kid to school in the morning.” ~ Marcos Segrera Links  Marcos Segrera on LinkedIn Evensky & Kats / Folds Wealth Management Prudential AXA UBS Merrill Lynch J.P. Morgan University of Florida To Sell Is Human by Daniel Pink Shaping Wealth The Geometry of Wealth by Brian Portnoy The Money Guy Show Joe Schmitz Jr. From Strength to Strength by Arthur C. Brooks Dodge Viper Connect with our hosts Milemarker.co Kyle on LinkedIn Jud on LinkedIn Subscribe and stay in touch Apple Podcasts Spotify YouTube

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

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.

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

Episode 163: This week, Kyle Van Pelt talks with Megan Carpenter, CEO and Co-Founder at Ficomm Partners. Megan entered the industry through a college internship and started her own marketing consultancy at 29 before co-founding Ficomm with Jason Lahita. She has since refocused the firm exclusively on RIAs, working as an embedded growth partner that pairs marketing strategy with advisor coaching. Kyle and Megan explore what Ficomm's research reveals about the path from referral to hired advisor. Megan shares why the wealthiest investors turned out to be the least referral-reliant segment surveyed, and how younger investors now use four or more touchpoints before reaching out. They discuss the "referral-only" website approach, why the prospect experience begins long before the first meeting, and how advisors can create content that fits them and still reach clients where they are. Megan also examines AI discovery and why she sees marketing becoming a leadership responsibility. In this episode: (00:00) - Intro (02:08) - Megan’s money moment (04:26) - How Ficomm evolved from PR firm to embedded growth partner (08:15) - Finding your niche as your business evolves (13:45) - What research reveals about how investors find advisors (19:10) - Building trust after the referral (21:29) - Does the "referral-only" website still work? (25:22) - The overlooked opportunity in serving the mass affluent (26:46) - Starting the client experience before the first meeting (30:32) - Creating content that fits you and your ideal clients (34:58) - How AI tools are changing advisor discovery (39:01) - Megan’s outlook on the future of the wealth management industry (41:32) - Megan’s Milemarker Minute Key Takeaways Referrals get you on the list, not the client. Megan’s research suggests prospects often investigate an advisor before ever making contact. Your website and content need to reinforce the recommendation and demonstrate whom you understand and serve. Define your ideal client, but leave room to evolve. Early-stage businesses often need to work with the clients they can attract. The goal is to build around shared values, strong relationships, and the people you can genuinely serve well, then narrow your focus as the business matures. The prospect experience is part of the client experience. Nearly three-quarters of investors surveyed chose an advisor who demonstrated an understanding of their specific needs. Show that understanding in your messaging and first touchpoints, not just after the engagement letter is signed. Build a growth engine that fits who you are. Match your clients’ preferred channels with your team’s strengths. Megan uses conversations and speaking engagements as source material that her team repurposes, without requiring her to become an active personal social media publisher. Quotes "Referrals really get you onto the list, but don't necessarily get you the client. What's changed is not necessarily the value of the referral, but what happens immediately following the referral." ~ Megan Carpenter "Contrary to what the industry thinks, the wealthiest investors are actually the least referral-reliant segment that we surveyed." ~ Megan Carpenter "All AI is really doing is collapsing the gap between being findable and being worth finding." ~ Megan Carpenter “The firms that win will have marketing at the leadership table, not in a support role.” ~ Megan Carpenter Links  Megan Carpenter on LinkedIn Ficomm Partners The New Growth Equation Jason Lahita Goldman Sachs BlackRock Absolute Engagement Julie Littlechild Michael Kitces James Conole Beautiful Chaos by Jessica Urlichs Harry Potter Connect with our hosts Milemarker.co Kyle on LinkedIn Jud on LinkedIn Subscribe and stay in touch Apple Podcasts Spotify YouTube

Episode 162: This week, Kyle Van Pelt talks with Brian Fernandez, President at Krilogy. Brian brings more than 20 years of experience working with complex family office needs and continues to serve clients as an advisor. As the firm’s integrator, he pairs that client perspective with a focus on operational excellence, helping translate its founder’s vision into execution. Kyle and Brian explore how investing ahead of demand prepares an advisory firm for its next stage of growth. Brian explains how Krilogy uses EOS to create accountability, develops future partners through internal training, and reinforces culture as its team expands. They also discuss the ongoing responsibilities of building software, the importance of mastering tools before adding more, and the staffing demands behind family office services. Throughout the conversation, Brian considers how firms can expand their capabilities while remaining attentive to the people they serve. In this episode: (00:00) - Intro (01:16) - Brian's money moment (03:15) - Investing ahead of growth  (04:59) - Building a culture of organic growth  (08:05) - What makes a great integrator  (13:18) - The meaning behind Krilogy's name and its core purpose (16:27) - Developing the next generation of advisors (19:28) - How Krilogy preserves its culture despite rapid growth (21:08) - Building a platform for entrepreneurial advisors (23:02) - Krilogy's current tech stack and how it's evolving  (24:25) - Build vs buy: How Krilogy evaluates technology investment decisions  (26:22) - What's next for Krilogy (28:03) - Why customized advice is harder than scaling a manufactured product  (29:07) - Brian's outlook about the future of the financial services industry (33:44) - Brian's Milemarker Minute Key Takeaways Invest ahead of the growth curve. Don't wait until your firm is overwhelmed to build the people, systems, and infrastructure you'll need. Sustainable momentum comes from building executive capacity, infrastructure, and talent pipelines before reaching the next phase of growth.  Create a system for turning ideas into action. Visionaries need room to generate ideas, while operators need a process for prioritizing them. Separating idea generation from problem-solving can keep both sides productive.   Build your talent pipeline instead of waiting for talent to appear. Developing people internally can create advisors who understand both the technical side of the business and its culture and values. Training next-generation leaders through structured, in-house development systems builds deep cultural alignment and ensures senior leaders naturally step up to mentor incoming cohorts.   Culture has to become institutionalized as you scale. Strong cultures can't depend on one founder or executive. Teach the values consistently and give employees the confidence to hold one another accountable.  Quotes "You need one central advisor to coordinate everything. You may have a number of great advisors, but somebody has to own it." ~ Brian Fernandez "If we're creating human experience, as good as AI gets, I still think we're going to have the opportunity to be really trusted advisors and do the work that really is the emotional stuff around families, retirements, or selling businesses." ~ Brian Fernandez "When I think about what a true family office means, it's about the complexity of the clients and the depth to which the advisors have to go. And it's also the frequency with which you're dealing with things." ~ Brian Fernandez Links  Brian Fernandez on LinkedIn Krilogy Kent Skornia Envestnet | MoneyGuide  So Good They Can't Ignore You Connect with our hosts Milemarker.co Kyle on LinkedIn Jud on LinkedIn Subscribe and stay in touch Apple Podcasts Spotify YouTube

Episode 161: This week, Kyle Van Pelt talks with Scott Hanson, Cofounder at Allworth Financial. Scott helped build the firm and led it through acquisitions, private equity ownership, and recapitalization before stepping aside as CEO. Drawing on experience as both a buyer and seller, he wrote The Private Equity Advantage to help business owners approach succession with greater clarity and intention. Kyle and Scott explore what separates a successful transaction from simply getting a deal done. Scott explains why growth and cultural fit matter, how deal terms shape outcomes, and why planning should begin well before a letter of intent. They also discuss choosing experienced legal counsel, communicating change to employees, and preparing emotionally for a different role. Scott reflects on his own transition out of leadership and shares why understanding your strengths—and defining success on your own terms—is essential to building a fulfilling next chapter. In this episode: (00:00) - Intro (02:52) - Debunking private equity myths  (05:53) - Why integration is harder than closing the deal  (07:13) - The current state of M&A in wealth management (10:33) - The mindset that makes an acquisition successful  (13:47) - Structuring a tax-efficient transaction   (15:56) - How to choose the right M&A attorney  (19:36) - Preparing for life after selling a business (24:21) - Identifying the strengths that give you energy (25:36) - Communicating a transaction to your team  (28:36) - What's next for large private equity-backed firms  (31:48) - Scott's Milemarker Minute Key Takeaways Build a growing business before you think about selling. The strongest acquisition candidates aren't simply profitable—they have organic growth, momentum, and a clear plan for continued expansion.  Integration is where value gets created. Doing a deal is the easy part. The harder work is combining organizations in ways that improve the experience for clients, advisors, and employees. Know what you're giving up and what you're gaining. Selling a firm means exchanging some control for liquidity, resources, and potentially greater growth opportunities. The clearer founders are about that tradeoff, the more likely they are to thrive afterward.  Define success on your own terms. The next chapter doesn't have to look like someone else's. Understanding your unique abilities, what energizes you, and what you want from life can help shape a more fulfilling path after stepping away from leadership.  Quotes "For firms to be acquired, they have to be growing. And if they're not growing, there has to be some plan in place to make sure that there's growth, because that growth is super important for the buyer." ~ Scott Hanson "Doing the deal is the easy part. Integrating the organizations, that's where the work is." ~ Scott Hanson "I think what makes a successful integration and transaction is when the seller has the right kind of mindset. Understanding what the exchange is, what you're gaining, and what you're giving up—those who are clear on that do extremely well." ~ Scott Hanson Links  Scott Hanson on LinkedIn Allworth Financial The Private Equity Advantage Ian Wenik Focus Financial Partners Life Is in the Transitions 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.

Episode 160: This week, Kyle Van Pelt talks with Joe Schmitz Jr, Founder and CEO at Peak Retirement Planning. Joe built the firm around a tax-focused, 5 Pillar Approach that helps Midwestern millionaires nationwide grow and protect their wealth. A Certified Kingdom Advisor (CKA®), Joe also helps clients approach retirement with purpose and steward their wealth in alignment with their values. Joe talks with Kyle about the marketing and talent engine of fast-growing RIAs. He shares why Peak focuses on developing talent internally, how its intensive training programs prepare advisors for real client conversations, and why coaching is such an important part of the firm's culture. Joe also explains how a strong marketing engine has helped Peak expand its reach, define a specific niche, and build trust with prospective clients through YouTube, books, and other content. In this episode: (00:00) - Intro (00:54) - Joe's money moment (02:09) - Building technical depth and soft skills in young financial advisors (04:28) - Why Peak focuses on developing talent internally  (06:10) - Inside Peak's training programs: Peak University and Peak Bootcamp  (09:40) - How Peak structures its training programs (14:44) - Why Peak sees itself as a media and marketing company first (17:10) - How Joe turns marketing knowledge into action  (19:00) - What YouTube has done for Peak Retirement Planning (20:38) - What motivated Joe to build a YouTube presence  (23:12) - How Joe builds Peak's long-term enterprise value (25:54) - Balancing marketing-driven growth with service capacity (28:34) - Peak's 'no creativity' policy and 'no shiny objects' marketing strategy (29:51) - The marketing checklist behind every piece of Peak content  (30:58) - How Peak's core messaging came together  (34:13) - Why Joe writes books instead of chasing other content formats  (36:11) - How Peak leverages technology for growth (38:45) - What Peak's purpose-driven conversation is all about (40:11) - Joe's Milemarker Minute Key Takeaways Build the talent you need instead of waiting for it to appear. If experienced hires aren't the right fit, create an environment that develops people from the ground up. A strong training program can become a long-term competitive advantage. Turn your best people into coaches. Developing talent becomes more scalable when experienced team members teach and mentor others.  Hold high standards for quality and brand detail. Every outward-facing material—from digital media to printed mailers—reflects the quality of a firm's work. Holding internal operations to high standards builds immediate credibility with potential clients. Build branding around real client pain points and identities. Developing authentic marketing messaging requires paying close attention to client conversations.  Treat content as a long-term asset. Books, videos, articles, and podcasts can keep building credibility and generating opportunities long after they're published.  Quotes "I think so many people are afraid to put time, effort, and money into marketing, and that's the biggest shortfall." ~ Joe Schmitz Jr. "There are so many shiny objects out there that people can go to. Don't go out there and try to do everything. Focus on one or two things to start that add value, that add a great return on investment, that you enjoy doing, and then see the success from there." ~ Joe Schmitz Jr. "If anything ever goes out from our firm, it better be done with excellence because that's all people know about the work we do." — Joe Schmitz Jr. Links  Joe Schmitz Jr. on LinkedIn Peak Retirement Planning I Hate Taxes Midwestern Millionaire The 2% Club Hazel AI Chop Wood Carry Water The Energy Bus  How to Win Friends and Influence People Make Your Bed Splitting Heirs The New Retirementality Kingdom 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.

Episode 159: This week, Kyle Van Pelt talks with Melissa Caro, Founder at My Retirement Network. For the past decade, Melissa has studied real advisor conversations to understand what communication behaviors build stronger client relationships. Today, she helps advisory firms close the client language gap through digital learning, live coaching, conversation analysis, and AI-powered insights that turn real client meetings into learning opportunities. Melissa talks with Kyle about why the best financial advice starts with the right conversation. They explore why wealth management is a people business first, how to make discovery meetings feel less like data collection and more like meaningful conversations, and how advisors can use AI and technology to create more room for human connection.  In this episode: (00:00) - Intro (02:08) - Melissa's money moment (04:15) - What Melissa learned on the trading floor (05:50) - Melissa’s transition from equity trading to advisor coaching  (08:06) - What separates elite advisors from the rest  (10:14) - How to make discovery conversations more engaging  (14:36) - Why soft skills are as important as technical skills  (17:45) - Practical ways for new advisors to build communication skills  (19:41) - The difference between coaching next-gen and seasoned advisors (22:59) - How AI is changing the dynamics of human connection  (25:19) - How overbuilt, poorly integrated tech stacks hurt advisor behavior (28:24) - Melissa's outlook about the future of wealth management (30:51) - Melissa's Milemarker Minute Key Takeaways Put the relationship before the financial plan. The strongest advisors know that trust and engagement come first, and then use their technical knowledge to support the relationship. Turn data gathering into a conversation. Instead of treating discovery as an intake form, use open-ended questions and genuine curiosity to uncover what actually matters to clients.  Don't rush past the important moments. A simple answer—like a client's expected retirement date—can open the door to deeper conversations about identity, fears, goals, and expectations. Those insights can make the financial plan feel collaborative rather than prescriptive.  Use technology to become more present, not less. AI can remove administrative work such as note-taking, but advisors need to retrain themselves to use that extra capacity for deeper client engagement.  Quotes "The real elite advisors know that you need to engage with people, build trust, and build those relationships first." ~ Melissa Caro "What makes a great associate isn't necessarily the same as the characteristics you translate into what makes a great lead advisor." ~ Melissa Caro "You can turn anything that is considered a hard data point into a soft data point if you just ask open-ended questions. That's where the moment is—that's where your gold is." — Melissa Carro Links  Melissa Caro on LinkedIn My Retirement Network Julie Littlechild on LinkedIn Pink Floyd - The Dark Side Of The Moon The StorySelling Method On the Shortness of Life 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.

Episode 158: This week, Kyle Van Pelt talks with Michael Batnick, Managing Partner at Ritholtz Wealth Management. Michael began his career in sales at a life insurance company. Today, he focuses on helping clients navigate the challenges of long-term investing and achieve their financial goals.  Michael talks with Kyle about how AI is disrupting the wealth management industry. He discusses the realities of rising technology spend, the limits of AI-driven efficiency in human relationships, and how firms can use AI to improve advisor training. Michael also shares the concept behind Exhibit A—Ritholtz's custom-branded visual storytelling and charting software platform—and the importance of building intuitive technology that genuinely makes people's lives easier.  In this episode: (00:00) - Intro (02:26) - Navigating AI hype vs. operational realities  (04:24) - Michael's thoughts on technology spending (07:01) - Why AI won't systematically double an advisor's client capacity (11:21) - How AI could transform training for young advisors  (15:57) - Private equity and the changing advisor landscape  (19:24) - The debate between cash flow and enterprise value  (23:09) - The concept behind Exhibit A (25:52) - Are RIAs becoming wirehouses in disguise?  (28:32) - Why large RIAs struggle to reach the public markets  (31:19) - Michael's outlook for the wealth management industry  (32:38) - The future of multi-custodial RIAs  (35:23) - Michael's Milemarker Minute Key Takeaways Don't confuse efficiency with capacity. AI can automate preparation, documentation, and follow-up, but human capacity for real, meaningful conversations has a ceiling regardless of how much prep work gets automated. Rethink how you train the next generation of advisors. Build a training engine, not just a productivity tool. If AI tools can simulate practice scenarios and give real-time coaching feedback, use them to compress the learning curve for junior talent instead of burning your best chances on people who might not be ready yet.  Question industry narratives before adopting them. Just because a structure worked for someone else doesn't mean it's automatically right for your business. Figure out what you actually need.  Make technology so intuitive that clients barely notice it. When software is genuinely easy to use, adoption grows, support needs drop, and businesses can scale more sustainably.  Quotes "There's never been more excitement and also more confusion about the future of where we're going." ~ Michael Batnick  "I think a lot of people are really excited about the promise of AI and what it's going to do to change our industry, our jobs, our margins, and the way that we communicate with clients. But I don't think we know what that looks like, which is fine, totally fine and normal." ~ Michael Batnick "Dealing with clients is exhausting, mentally and emotionally. It takes a lot out of you." ~ Michael Batnick Links  Michael Batnick on LinkedIn Ritholtz Wealth Management Future Proof Matt Cerminaro Exhibit A For Advice Ian Wenik Creative Planning Altruist Jason Wenk Powerhouse by James Miller 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.

Episode 157: This week, Kyle Van Pelt talks with Libby Buckley, Director of Wealth Administration & Marketing at Parable Wealth Partners. Libby leads the firm's client experience and team culture, bridges connections between clients, partner businesses, and non-profits, and creates experiences that help people rethink their wealth's potential to create change.  Libby talks with Kyle about how radical hospitality translates into the wealth management space. She discusses how firms can preserve high-touch, authentic human relationships as AI adoption accelerates, how to design thoughtful and memorable client experiences, and how organizations can scale without losing sight of their core purpose.  In this episode: (00:00) - Intro (00:57) - Libby's money moment (05:32) - Libby's definition of radical hospitality in wealth management (08:05) - Client events that create meaningful connections  (09:56) - Why AI makes authenticity even more valuable (11:52) - Practical advice for building soft skills and radical hospitality habits  (16:12) - How culture drives Parable's organic growth  (18:31) - Scaling without losing authenticity  (21:08) - Libby's outlook on the future of the financial services industry (24:08) - Libby's Milemarker Minute Key Takeaways Use efficiency to create better relationships. AI can save time, but its greatest value is giving leaders more opportunities to invest in conversations, trust, and meaningful client experiences. People remember how you made them feel. Exceptional service solves problems, but genuine hospitality creates lasting relationships by helping people feel seen, understood, and valued. Culture is something you protect. As organizations scale, intentional hiring, regular team development, and shared purpose become essential for maintaining the culture that fuels long-term success. Personalization goes beyond using someone's name. Understanding people's preferences, interests, and communication styles creates experiences that feel thoughtful instead of transactional. Quotes "We think of money as the invitation, not the destination. So, wealth is not something to accumulate, but something to activate." ~ Libby Buckley "If you don't know who you are, who you want to serve, and how you're going to do that uniquely, quit. Authenticity is going to matter so much more moving forward." ~ Libby Buckley "How do you show up, and how do you want to show up for clients and your team, I think is going to be one of the biggest contenders moving forward." ~ Libby Buckley Links  Libby Buckley on LinkedIn Parable Wealth Partners Unreasonable Hospitality Paterson Center The Ideal Team Player The Art of Gathering Chief Joy Officer 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.

Episode 156: This week, Kyle Van Pelt talks with Ian Wenik, Editor at Citywire. Ian covers the independent wealth management industry with a focus on RIAs, mergers and acquisitions, advisor technology, and the business forces reshaping financial advice. Through his reporting and conversations with industry leaders, he has developed a front-row view of the trends driving growth across the advisory landscape. Kyle and Ian explore what separates today's fastest-growing RIAs from the rest of the industry. They discuss why competition for acquisitions continues to intensify, how firms can balance scale with independence, and why organic growth remains the ultimate differentiator. They also examine Schwab's latest referral changes, AI's potential to level the playing field for mid-sized firms, emerging technology trends, and what Ian believes the future holds for advisors building the next generation of great firms. In this episode: (00:00) - Intro (03:25) - A preview of Citywire's fastest-growing RIAs report  (05:47) - Why the M&A market is becoming more competitive  (08:00) - Why large RIAs struggle to reach the public markets (11:02) - Are RIAs becoming the new wirehouses?  (13:21) - Deal structures that don't work (16:05) - Schwab's referral changes and what they mean for RIAs  (22:06) - What's driving organic growth today (25:21) - How AI can help mid-sized firms compete  (27:00) - Ian's advice for firms that want to stay independent (27:58) - Technology trends among the fastest-growing firms (29:16) - Ian's outlook on the future of the financial services industry (30:41) - Ian's Milemarker Minute Key Takeaways Deep expertise creates opportunities. Whether investing, acquiring businesses, or serving clients, deep subject-matter expertise allows firms to spot hidden value and underrated talent before the broader market takes notice.  Ownership drives commitment. If you want entrepreneurial people to stay engaged, give them meaningful opportunities to build equity rather than relying solely on compensation. Optimize organic growth strategies for modern discovery. Traditional search and referral channels are evolving. To maintain a strong pipeline, leaders must diversify their acquisition strategies—leveraging digital media, strategic partnerships, and AI-driven search visibility. Use AI to create more time for people, not less. Automating operational work improves efficiency, but relationships and trust remain the foundation of exceptional client service. Let AI handle the back office so you can spend more time on the conversations that actually grow the business. Quotes "For the public markets to open up to RIAs, you need a really strong, well-capitalized firm, a strong balance sheet, a clean operating and capital structure, strong cash flows, and high organic growth." ~ Ian Wenik "The reason that we've seen so many transactions fail is that the transactions are structured in a way where it's cash-heavy, short earn-out. It allows the founders to cash themselves out. They peace out after maybe a year, and you have a second generation that's actually managing the underlying client book of business that has no incentive to stick around." ~  Ian Wenik "Invest in what you do best. Remember why you got into this business. If you focus on that core business, as long as you maintain a baseline level of profitability, a lot of things will fall into place." ~ Ian Wenik Links  Ian Wenik on LinkedIn Citywire Edelman Financial Engines Focus Financial Partners Creative Planning Cerity Partners LPL Financial  Morgan Stanley  Future Proof Joshua Brown Goldman Sachs  Moneta Group Carson Group  Peter Mallouk Charles Schwab  Orion Advisor Solutions  Movement 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.

Episode 155: This week, Kyle Van Pelt talks with Julie Littlechild, Founder and CEO at Absolute Engagement. Julie is a recognized leader in client engagement, investor behavior, and referral growth. Through years of advisor and investor research, she has helped firms better understand the emotional drivers behind client decisions and build stronger, more personalized advisory relationships. Kyle and Julie explore why understanding how clients feel is just as important as understanding their financial goals. Julie explains how behavioral data—especially around confidence and concerns—helps advisors uncover more meaningful conversations, personalize communication, and strengthen trust over time. They also discuss why client experience is becoming a key competitive advantage, how AI should enhance rather than replace human connection, and practical ways firms of every size can create experiences that resonate with both today's clients and the next generation. In this episode: (00:00) - Intro (01:33) - Julie's money moment (04:52) - Understanding the confidence and concern indices (04:52) - Understanding the confidence and concern indices (06:52) - Using behavioral data to personalize the client experience (10:00) - Why CRM integrations make behavioral data more actionable (14:35) - The growing role of client experience leadership (17:04) - Why efficiency alone isn't a competitive advantage (19:18) - Practical ways smaller firms can elevate the client experience (22:06) - Making client appreciation events more meaningful (25:21) - Generational shifts and the "juggle generation" (27:54) - Julie's outlook on the future of financial services (29:23) - Julie's Milemarker Minute Key Takeaways Behavioral data creates better conversations, not just better reporting. Measuring client confidence and concerns gives advisors a practical starting point for uncovering what clients are truly thinking and feeling, leading to deeper, more meaningful relationships. Personalization starts with understanding what matters most. Advisors who know what clients are worried about can tailor conversations, communication, events, and resources in ways that feel genuinely relevant instead of generic. Technology should amplify human connection. AI and behavioral insights are most valuable when they create more time—and better context—for advisors to build trust, empathy, and lasting relationships. Client experience is becoming a true competitive advantage. Operational efficiency is increasingly expected. The firms that stand out will be the ones that consistently make clients feel understood, supported, and confident about the future. Quotes "Think about the experience not only as the conversations that advisors have with their clients, but the communications they share, the events that they run, and the offer that they have in place." ~ Julie Littlechild "We are at a point now where we can see the connection between data, technology, and human connection. I think we're starting to understand that, 'If I can capture this insight and have this data and do that effectively, comfortably, and consistently, I can create a more human experience.'" ~ Julie Littlechild "Efficiency does not set you apart. No one ever said, 'My life has been impacted by my advisor because they have some incredible workflows.'" ~ Julie Littlechild Links  Julie Littlechild on LinkedIn Absolute Engagement Good to Great 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.

Episode 154: This week, Kyle Van Pelt talks with Jason Borek, Chief Growth Officer at The Pinnacle Group. Jason has extensive experience in the financial services industry, with a focus on distribution and sales. At The Pinnacle Group, he is responsible for implementing the firm's enterprise-level business strategies.  Jason talks with Kyle about why insurance remains dramatically underutilized in wealth management, why advisors struggle to implement it, and what needs to change for it to become a meaningful part of holistic planning. He also shares how Pinnacle closes the gap between insurance manufacturers and financial advisors, where AI and technology fit into the future of distribution, and why emotional intelligence will define the next generation of great advisors.  In this episode: (00:00) - Intro (01:17) - Jason's money moment (04:38) - Inside The Pinnacle Group's core businesses  (06:35) - Why only 2% of wealth management firms use insurance  (09:59) - How and when should insurance be used in client portfolios (15:21) - How AI and data impact the future of advisor workflows  (21:17) - Will technology replace distribution in asset management or enhance it?  (23:52) - Jason's thoughts on emotional intelligence—innate or taught (27:32) - Jason's outlook on the future of wealth management (30:55) - What it takes to run a multicustodial firm  (33:51) - Jason's Milemarker Minute Key Takeaways Lead with culture and language, not product. The industry's biggest mistake has been pushing solutions before understanding the people they're meant for. Breaking into new markets isn't about forcing a pre-existing product. It's about learning how your audience thinks, operates, and communicates. Real traction comes from building bridges, not delivering pitches.   Don't confuse education with implementation. Education alone doesn't move people to action. Pair any new strategy or message with real people who can sit in the room and walk clients or stakeholders through the hard follow-up questions. Materials build awareness. People build trust. Treat clean data as your foundation, not an afterthought. You cannot begin to solve a client's problem or identify new opportunities without clean, accurate data. Clean data is the modern business currency. Without it, organizations cannot deliver true, personalized value. Don't mistake efficiency for engagement. Technology creates capacity. But its value only shows up if you reinvest that time into deeper relationships. Otherwise, you're not more effective, you're just more efficiently absent.  Quotes "About 2% of revenues come from the sale of insurance products within the wealth management space. And part of the reason why is that our industry is terrible at listening. The insurance industry has forever been a hammer looking for a nail." ~ Jason Borek "If we're going to move into a marketplace where 97% of the people who do business with us do not sell insurance as their primary means of revenue, we'd better take some time to understand how they communicate." ~ Jason Borek "Without the technology creating more client engagement, all you've then become is more efficiently absent." — Jason Borek Links  Jason Borek on LinkedIn The Pinnacle Group New York Life Insurance Holland & Knight Marshall & Stevens  Angeles Investments Cameron Rogers Altruist Jason Wenk Nimesh Patel The Explicit Gospel 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.

Episode 153: This week, Kyle Van Pelt talks with Brett Bernstein, CEO & Co-founder at XML Financial Group. Brett is an active financial advisor assisting clients with his holistic approach to goal-setting and problem-solving. Before co-founding XML in 2004, he was a Vice President and Senior Financial Advisor at Merrill Lynch. He is also a serial entrepreneur, actively investing in many startups, and has led his firm through three acquisitions. Brett talks with Kyle about why advisors are going independent. He discusses why independence continues to attract both advisors and clients, what it takes to build trust and brand recognition as an independent advisory firm, and how firms can balance scale with personalization. Brett also addresses the realities of scaling a modern advisory firm, including aligning operations across multiple teams, attracting the next generation of investors, investing in cybersecurity, and thoughtfully adopting AI without compromising compliance.  In this episode: (00:00) - Intro (02:03) - Brett's money moment (05:34) - How to build brand credibility and trust as an independent firm (07:52) - How Brett defines independence (11:36) - Unifying operations and compliance while preserving advisor autonomy  (13:15) - XML's social media and content strategy  (18:15) - Referrals, seminars, and community-driven growth strategies (20:04) - How to build a successful business from the ground up (22:08) - Cybersecurity as a non-negotiable investment (25:02) - How XML adapts to technology and AI (27:17) - Leading with compliance: XML's approach to using AI (29:16) - What Brett thinks about data and AI  (31:24) - What the future holds for XML Financial Group (33:53) - Brett's Milemarker Minute Key Takeaways Don't chase growth. Build for it. Sustainable growth starts from the ground up. Focus on your real costs, your people, and your clients’ needs first. Then let those realities define your growth targets. Reach the next generation before you need to. If your client base is aging, the clock is ticking. The children and grandchildren of your current clients are the next relationship to build. Connect and meet them where they're at.  Invest in expertise where it matters most. Cybersecurity, compliance, and technology aren't DIY functions. The cost of not investing is far greater than the cost of doing it right. Technology is a multiplier, not a replacement. AI and automation should enhance your ability to serve clients, not replace human relationships. Human connection, trust, and community engagement will always be core to advisory businesses, no matter how advanced technology becomes.  Quotes "More money has been going to independent platforms. More people are starting their own firms. They're realizing that independence is a lot of times better for the client." ~ Brett Bernstein "I want the people to continue doing what made them great and what the clients love." ~ Brett Bernstein "AI needs to be your partner. Don't look at it as a replacement. And if you can lean into it as your partner, you're going to be better as a firm and better for your client." ~ Brett Bernstein Links  Brett Bernstein on LinkedIn XML Financial Group Merrill Lynch So What Else  Focus Financial Partners 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.