AI for Advisors

What happens when AI gives legal advice — and gets it wrong? In this episode, Mark Heynen and James Cantwell sit down with Matt Morris and Mike Bennett from Encore Estate Plans to unpack their viral study comparing ChatGPT, Claude, Perplexity, and Google AI to human estate-planning experts. The results? Some bots aced the basics, others literally gave up halfway through.From hilarious “ChatGPT Law School” jokes to serious insights about legal accuracy, the conversation explores where AI helps, where it fails, and why human oversight still matters when your life’s assets are on the line. The Encore team also reveals how they’re building their own guarded LLM — trained on four years of real advisor chats — to deliver trustworthy automation without crossing the line into unauthorized legal advice.Along the way, the group debates VC vs. bootstrapped growth, Harvard’s new “Work Slop” study, and even the future of digital legacies (“Can your trustee delete your browser history?”). It’s a smart, funny, and candid look at the intersection of AI, trust, and mortality — and one you won’t forget.Listen in to learn why estate planning is becoming the next frontier of human-in-the-loop AI.

In this episode of AI for Advisors, hosts Mark Heynen and James Cantwell welcome Reed Colley, President of Orion Advisor Technology, for a deep-dive into how Orion is driving AI innovation in wealth management. Reed, a seasoned entrepreneur and founder of Black Diamond and Summit Wealth Systems, shares insights from his journey—from startup “pirate” to leading a “Navy” of enterprise solutions.They explore Orion’s Denali data architecture, the evolving role of agentic AI, and how wealth tech firms can balance scale versus specialization in the age of open ecosystems. The discussion also touches on the future of CRM evolution, AI orchestration tools like AgentKit, and how voice and natural language interfaces are redefining advisor workflows.From Pirate to Navy: Reed compares startup agility to enterprise structure—both necessary for innovation at scale.The Power of Data Architecture: Orion’s Denali platform unifies disparate systems into a cohesive data ecosystem, enabling AI-driven insights.Agentic AI is the Next Wave: AI will shift from static tools to autonomous, outcome-focused agents capable of daily decision support.Scale vs. Specialization: Larger firms like Orion can leverage their data scale, while startups can still win with speed, creativity, and niche focus.Open Ecosystems Matter: Success in AI-driven wealth tech will depend on open APIs, interoperability, and flexible integration between systems.The Human Element Remains Central: AI should enhance—not replace—advisor-client relationships by automating repetitive tasks and amplifying human insight.Key TakeawaysThe Future Is Conversational: Voice and natural-language-driven workflows will soon dominate advisor platforms, moving beyond screens and manual data entry.

In this episode, Mark Heynen and James Cantwell speak with Parker Ence, CEO and co-founder of Jump, about how AI is reshaping the advisor workflow. Parker shares how Jump evolved from a data-aggregation startup to one of the fastest-growing AI meeting assistants in wealthtech. They discuss the challenges of scaling an AI company in a regulated industry, the role of timing and product focus in driving adoption, and how intelligent automation can strengthen advisor–client relationships. The conversation also covers Jump’s recognition at the WealthManagement.com Industry Awards, the future of “agentic AI,” and what’s next for technology-enabled growth in financial services.Key Takeaways: Jump pivoted from data aggregation to become an AI meeting assistant built for financial advisors.Rapid growth from 16 to 120 employees underscored the power of timing and product focus.Parker explains how Jump gained traction despite compliance and adoption hurdles.The platform now spans pre-, post-, and in-meeting intelligence beyond simple note-taking.“Agentic AI” will depend on trust, data access, and responsible integration.AI can enhance advisor efficiency while keeping client relationships personal.Parker predicts deeper AI integration to drive smarter, more connected advisor workflows.Learn more about Parker Ence | JumpWebsite: https://jump.ai LinkedIn: https://www.linkedin.com/in/parkerence

Is AI the key to helping advisors scale—or just another shiny tool adding to tech stack chaos? In this episode of AI for Advisors, Mark and James sit down with two leaders tackling the problem from very different angles: Dr. Sindhu Joseph, CEO of CogniCor, and David DeCelle, founder of Model FA.Dr. Sindhu shares her journey from 25+ years in AI research to building CogniCor’s co-pilot platform, designed to help advisors move from reactive to proactive and expand access to financial advice beyond just the affluent. David brings his perspective as an advisor-turned-coach, showing how AI can free up time, scale growth, and even reshape advisor-client relationships without replacing the human touch.We dive into some of wealthtech’s most pressing debates:Efficiency vs. Effectiveness: Can AI truly help advisors scale and deepen relationships, or do most tools just create more busywork?CRMs vs. AI Platforms: Are CRMs just “glorified databases” destined to be disrupted by AI layers built around client interactions?Adoption & Pitfalls: Why advisors often “play business” with endless tool demos instead of focusing on real growth.AI + Coaching: How note takers, automations, and micro-coaching tools are transforming not just administration, but advisor training itself.The Future UI: Is the next paradigm less about tabs and dashboards—and more about AI-powered conversation layers?This episode is a must-listen for RIAs, coaches, and wealthtech pros navigating the balance between hype, adoption, and real advisor impact.Subscribe for more insights into AI for Financial Advisors!Guest Information:Dr. Sindhu Joseph, CEO of CogniCor → https://www.cognicor.comDavid DeCelle, Model FA → https://www.modelfa.com(TIMESTAMPS)00:58 – Sindhu’s Background: 25 years in AI, patents, and founding CogniCor03:10 – Effectiveness vs. Efficiency: Can AI make advisors proactive instead of reactive?07:01 – Transition to David: Advisor → Consultant → Model FA founder11:12 – From Anti-AI to Pro-AI: Why David pivoted to embrace AI (while staying pro-human)14:53 – Hinton’s Wrong Bet: Why advisors won’t be replaced like radiologists weren’t18:06 – Sindhu’s Take: Tech fragmentation and why AI should unify—not add tabs23:27 – Future UI Paradigm: From tabs to conversational AI layers27:22 – Coaching with AI: How David helps advisors adopt tools for growth29:39 – Proactive Capacity Planning: Using AI to prevent advisor burnout31:02 – Automating Follow-Ups: How note takers save 10–15 hours weekly35:27 – Beyond Admin Tasks: From efficiency → advisor skill-building36:24 – Firm-Level AI: Business intelligence, risk detection, and segmentation39:55 – CRMs vs. AI: Will CRMs adapt—or be replaced by AI-driven interaction layers?

In this episode of AI for Advisors, hosts Mark Heynen and James Cantwell engage with Mark Gilbert, co-founder of Zocks, discussing the evolution of AI in financial services. They explore the unique approach Zocks takes towards privacy and compliance, the implications of AI in government, and the future of note-taking and wealth management. The conversation also touches on the challenges and opportunities presented by AI, the role of CRMs, and best practices for vetting AI solutions in the industry.takeawaysMark Gilbert has a rich background in tech and finance.Zocks focuses on privacy by not recording conversations.AI is transforming the way advisors manage client interactions.The Future Proof conference showcased innovative ideas in finance.AI can help advisors offer more services efficiently.Concerns about recording conversations are prevalent among clients.The role of AI in government is emerging, as seen in Albania.Zocks aims to redefine note-taking in financial services.Consolidation in the wealth tech landscape is expected.Advisors should try multiple AI solutions to find the best fit.AI's Role in Transforming Financial Services

In this episode, James Cantwell and Mark Heynen discuss their experiences at the Future Proof conference, highlighting the vibrant atmosphere, networking opportunities, and the emergence of AI technologies in the financial advisory space. They delve into key insights from Michael Kitces regarding the importance of client engagement over technology, and share their thoughts on innovative tools that enhance client relationships. The conversation also covers highlights from the demo drop, predictions for future trends in wealth tech, and the evolving role of technology in financial services.TakeawaysFuture Proof is a unique networking opportunity for financial advisors.AI assistants are becoming increasingly prevalent in the financial sector.Michael Kitces emphasizes the importance of client engagement over technology.Delegation is crucial for enhancing productivity in advisory firms.The next generation of clients expects higher tech savviness from advisors.Innovative tools like Knapsack Outreach can streamline client communication.The demo drop showcased exciting new AI-driven platforms.Future trends may include more customized visualizations in financial advice.Note-taking is becoming a standard feature across platforms.The Future Proof conference fosters strategic thinking among advisors.

In this episode, Mark and James host Ben Olsen and Kai Bogdanovich to discuss the practical applications of AI in wealth management. They explore the expectations financial advisors have regarding AI, the strategies for implementing AI solutions, and the importance of understanding the limitations of AI technology. The conversation also touches on the current trends in AI usage among financial advisors, the challenges of integrating AI into existing systems, and the future of AI in enhancing client relationships. The guests share insights from their experiences and provide practical advice for advisors looking to leverage AI effectively.TakeawaysAI is not just a feature; it's a foundational technology.Financial advisors have varying expectations of AI's capabilities.It's essential to identify specific problems before implementing AI solutions.The five whys technique helps in understanding root causes of issues.AI can enhance client relationships by providing personalized insights.Many advisors are still hesitant to adopt AI due to trust issues.Successful AI implementation requires a balance of applying, buying, and building solutions.Data lakes can provide significant benefits but come with high costs.Automation can save time in meeting preparation and follow-up tasks.AI should be seen as a tool to enhance, not replace, human relationships.Unlocking AI's Potential in Wealth ManagementThe Future of Financial Advisory: AI Insights"AI isn't just a game changer.""AI is commoditized intelligence.""Not everything's a nail."Chapters00:00 Introduction to AI for Advisors01:12 Meet the Guests: Ben and Kai02:32 Diverse Backgrounds in Finance and Data Science04:08 Expectations of AI in Wealth Management05:53 Approaching AI Solutions: Internal Strategies08:08 Best of LinkedIn: AI Usage Insights10:14 AI in Advisory Practices: What's Working?19:39 Effective AI Applications in Meetings22:43 Building vs. Buying AI Solutions23:16 Automation in Client Management25:27 Enhancing Advisor Efficiency with AI30:33 The Role of AI in Financial Advisory34:12 Building vs. Buying AI Solutions39:12 Data Lakes and Their Importance43:36 Final Thoughts on AI in Finance

We unpack the hype vs. reality of enterprise AI, why that viral “95% of AI pilots fail” headline was misleading, and where adoption is actually working—especially when human teams and focused, vertical tools move in lockstep. We also compare healthcare’s scribe wave with wealth management, and spotlight emerging tools from big banks and big tech.  00:00 Debunking LinkedIn Studies01:11 The State of AI: Is It Working?  — AI Adoption Challenges and Insights  — The Role of Human Support in Technology01:25 Integrating Technology and Human Resources05:16 Future of AI in Wealth Management08:04 Healthcare and Finance: A Comparative Analysis14:01 Emerging AI Tools in FinanceKey TakeawaysHeadlines ≠ data. The widely shared “95% failure” stat conflated not attempting custom AI with failing at it; vertical, domain-specific deployments show materially better outcomes.  Humans x AI > either alone. Firms that add trained support staff alongside tech see greater revenue and well-being than those chasing tool count alone.  Point-tool fatigue is real. Frankenstacks (10–15 tools stitched together) erode compliance and morale; plan broader platforms from day one—even if you ship features progressively.  Healthcare offers a preview. Epic’s AI scribe push signals what happens when AI is embedded in the system everyone already uses; expect similar dynamics in finance as core platforms bundle AI.  Independents need a plan. As large banks roll custom AI (e.g., internal assistants for discovery and analysis), RIAs and broker-dealers must decide: build, buy vertical, or ride bundles from Microsoft/Google.  Enjoying the show? Subscribe, share with a colleague, and ping us if you’d like to be a guest—we’re lining up voices from wealth, healthcare, and AI tooling.  Get in touch with the hosts: ⁠Mark Heynen⁠ & ⁠James Cantwell⁠

In this conversation, Mark Heynen and James Cantwell discuss the current state of AI in wealth management. They explore the challenges of CRMs, the importance of data integration, and the evolving role of note-taking technology. The discussion also touches on the impact of AI on productivity and the need for systems of record to adapt to new technologies. They conclude with thoughts on future guests and the direction of the industry.

In our very first episode of AI for Advisors, Mark Heynen (serial entrepreneur & co-founder of Knapsack AI) and James Cantwell (WealthTechSelect, longtime wealth management consultant) dive into the big questions shaping the future of advice:Can AI really make better judgments than humans?Will financial advisors be replaced by algorithms, or will AI simply become their most powerful tool?How are tools like ChatGPT, Claude, and Perplexity actually being used (or not used) in real advisor workflows?What happens to fees, client ratios, and the advisor’s role as technology scales?We also explore the latest AI news—from ChatGPT-5’s mixed reception to Perplexity’s headline-grabbing bid for Chrome—and what it all means for wealth management professionals.This is a candid, exploratory conversation about where AI meets human judgment, trust, and client relationships in financial services. If you’re a financial advisor, WealthTech founder, or just curious about how AI is reshaping money, this episode is for you.👉 Connect with us on LinkedIn (Mark Heynen, James Cantwell) or message us if you’d like to share your perspective as a future guest.