The Advisors Edge Podcast

Tired of the same boring financial services podcasts? The Advisors Edge Podcast breaks the mold. This isn’t just another show about theory and outdated advice. We’re bringing you the real stories, the cutting-edge tech, and the bold strategies that will give you the competitive edge you need to dominate in today’s fast-paced industry. Hosted by insiders who know the game, each episode delivers conversations with top leaders, innovators, and disruptors from across the financial services world. Whether it’s AI, fintech, valuations, regulatory compliance, or cybersecurity—we’re covering it. If you’re a financial advisor, RIA, or leader in this space, this is where you’ll find the strategies that actually move the needle . You won’t just leave with more information—you’ll leave with a blueprint to sharpen your skills, elevate your business, and stay ahead of the competition. If you want to play it safe, go listen to something else. If yo

The Advisors Edge Podcast is a business podcast hosted by Rob Jacomen & Chad Ramberg, with 49 episodes on record and a Required Pod Score of 80.

Rob Jacomen & Chad Ramberg hosts The Advisors Edge Podcast, a business show with 49 episodes published.

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  Episode #15

  S2E15 | RIAs Can't Automate What They Haven't Standardized

  Sep 22, 20261h 13mS2

  AI is moving quickly inside advisory firms. But before an RIA starts automating more of its work, there is a more fundamental operating question: Is there a clear process to automate in the first place? In this episode of The Advisor’s Edge Podcast, Rob leads a discussion with Chad Ramberg and Ryan Closs of Box Professional Insurance about the emerging risks and operating challenges facing RIAs as firms adopt AI, automate more work, manage cybersecurity concerns, and try to build more consistent organizations. One of the central themes is simple: technology does not eliminate the need for human judgment, clear standards, or documentation. Ryan contrasts “hero-led” organizations where critical knowledge and judgment live primarily inside individual people with process-centered organizations that create standards for how work gets done. That becomes especially important when firms start introducing AI and automation. WHAT YOU’LL DISCOVER ✅ Why firms need a clear standard before they can reliably automate a process ✅ What happens when employees adopt AI individually without firm-wide expectations ✅ Why using AI does not remove the professional’s responsibility for the final work ✅ How standardization can strengthen—not replace—human judgment ✅ Why documentation matters when decisions and workflows vary across the firm ✅ How cybersecurity and social-engineering risks are creating new operational questions for RIAs ✅ Why some apparent AI problems are really process problems ✅ How incremental process improvement can make an advisory firm more consistent over time For RIA owners and advisory firm leaders, the question is not simply whether the firm should use AI. It is whether the organization has enough clarity around its processes, responsibilities, and standards to use new technology intentionally. Because automation can accelerate a process. It cannot create a good process where one does not already exist. A practical conversation for RIA leaders thinking seriously about AI, automation, risk, documentation, and building a more durable operating organization. FEATURED EXPERTS Chad Ramberg President, Box Professional Insurance https://www.linkedin.com/in/chad-ramberg-71278533/ Ryan Closs RIA Risk Advisor, Box Professional Insurance https://www.linkedin.com/in/ryan-closs/ ABOUT THE SPECIAL GUEST HOST Rob Jacomen Founder & CEO, Insurance Distribution Architects https://www.linkedin.com/in/rob-jacomen/ SPONSOR Special thanks to Box Professional Insurance for supporting Advisor’s Edge. Box Professional Insurance was built around the belief that an RIA’s business insurance advisor should understand the advisor’s world and the risks they face. Learn more: https://www.boxproinsurance.com CHAPTERS 00:00 — Introduction and the current state of the RIA industry 04:00 — Emerging AI risks for advisory firms 07:38 — AI, professional responsibility, and E&O questions 14:06 — Why human judgment still matters 15:45 — AI-assisted communication and advisor responsibility 24:08 — Cybersecurity and social-engineering risks 34:04 — What happens when a potential client risk surfaces 39:24 — Reducing friction in the insurance application process 48:31 — Automation, underwriting, and human judgment 50:25 — Why you can’t automate what you haven’t standardized 54:06 — How standardization can elevate human judgment 01:04:02 — Continuous improvement inside the firm 01:07:00 — The AI risk leaders may not see 01:09:43 — Closing thoughts DISCLAIMER The views shared in this episode reflect the perspectives of the hosts and featured experts. They are not financial advice or investment recommendations. Always consult a qualified professional regarding your specific situation.

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  Episode #14

  S2E14 | What Happens When Your RIA’s Cybersecurity Plan Gets Tested?

  Sep 8, 202645 minS2

  Having a cybersecurity plan is one thing. Knowing what happens when your firm actually has to use it is another. For RIAs, that difference can expose practical gaps that have little to do with buying another security tool: unclear responsibilities, providers assuming someone else owns a task, missing response information, communication breakdowns, and continuity plans that haven't been tested under pressure. In this episode of The Advisor’s Edge Podcast, Chad Ramberg and Charles “Chuck” Failla, CFP® sit down with Lyman Terni, Partner at Havoc Defense, LLC, to explore what happens when an RIA takes its cybersecurity and incident-response planning off the page and actually tests it. Lyman walks through tabletop or “bench” exercises designed to simulate real incidents and uncover problems before the firm has to respond to an actual event. The conversation goes beyond the exercise itself, exploring how IT, compliance, insurance and firm leadership coordinate during an incident and what firms can learn by testing scenarios involving compromised email accounts, ransomware, backups, system outages and alternative communication. IN THIS EPISODE, WE COVER: - Why a successful tabletop exercise can be one that finds problems - How assumed responsibilities can create gaps between IT, compliance and firm leadership - What a tabletop or bench test actually looks like - Why incident response requires coordination beyond the IT team - Why an IT provider's standard response may not account for an RIA's operating environment - What firms should think through when testing business email compromise and ransomware scenarios - Why backup and recovery planning needs to be understood before an incident - What happens when a critical system such as Office 365 becomes unavailable - Why firms need another way to communicate when their normal communication channel is down - How smaller RIAs can begin improving preparedness without assuming every improvement requires another technology purchase The goal isn't to prove that a cybersecurity plan is perfect. As Lyman explains, finding problems is part of what makes the exercise useful. Testing gives the firm an opportunity to uncover assumptions, clarify responsibilities, and understand how its response would actually work before the plan is needed for real. ABOUT THE GUEST Lyman Terni is Partner at Havoc Defense, LLC . Havoc Defense is a managed service provider focused on security-first IT management and security services. The firm works with RIAs, broker-dealers, accounting firms, lawyers, and high-net-worth families. Lyman's background includes financial services, regulatory compliance, cybersecurity advising, and IT. Connect with Lyman: LinkedIn: https://www.linkedin.com/in/lymanterni/ Website: https://havocdefense.com/ ABOUT THE HOSTS Chad Ramberg President, Box Professional Insurance https://www.linkedin.com/in/chad-ramberg-71278533/ Charles “Chuck” Failla, CFP® Founder, Sovereign Financial Group & GoRIA https://www.linkedin.com/in/charlesfailla/ https://www.goria.com The Advisor’s Edge Podcast brings together practical conversations for financial advisors, RIA leaders, fiduciaries, and firm builders navigating the decisions that shape their firms, clients, risk, compliance, and long-term durability. SPONSOR Special thanks to Box Professional Insurance for supporting The Advisor’s Edge Podcast. Box Professional helps RIAs understand where operational and risk exposure actually shows up before it becomes a claim. Learn more: https://www.boxproinsurance.com CHAPTERS 00:00 — Introduction: Lyman Terni of Havoc Defense 02:00 — What Is a Bench Test or Tabletop Exercise? 05:03 — How Testing Exposes Assumed Responsibilities 08:00 — Why Coordination Gets Harder as an RIA Grows 09:10 — Who Should Be Involved in an Incident Response Test? 14:23 — What Actually Happens During a Tabletop Exercise? 18:06 — Who Gets Called First After a Cyber Incident? 20:00 — Understanding the Incident-Response Timeline 22:23 — Why RIAs May Need More Than a Generic IT Response 25:20 — Ransomware: What Lyman Is Seeing 30:07 — Cloud Storage, Backup, and Redundancy 32:50 — What Happens If Office 365 Goes Down? 38:35 — What RIAs Should Take Away From the Conversation 40:40 — Lyman’s Path Into Cybersecurity and RIAs 43:39 — What Lyman Wants to Be Known For DISCLAIMER This podcast is for educational purposes only and should not be considered investment, legal, tax, or insurance advice. The views expressed are those of the hosts and guests and do not necessarily reflect the views of their firms or affiliates.

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  Episode #13

  S2E13 | Before Your RIA Adds More AI, Ask This Question feat. Daleele Alison

  Aug 25, 202659 minS2

  Adding more AI to an already complicated technology stack doesn't automatically make an RIA more efficient. Before adding another tool, there's a more important question to answer: What problem are you actually trying to solve? In this episode of The Advisor’s Edge Podcast, Chad Ramberg, Charles “Chuck” Failla, CFP®, and Rob Jacomen sit down with Daleele Alison, CEO of RooksDM, for a practical conversation about how RIAs can approach AI and technology decisions more deliberately. Daleele explains why the process should begin with understanding the business problem—not the technology. From there, the conversation moves into the operating foundation underneath effective AI adoption: data quality, sources of truth, technology consolidation, workflow inefficiencies, internal governance, security tradeoffs, and human oversight. Daleele also explains why firms need to understand where their data actually lives and establish standards around which systems serve as the source of truth before expecting automation to move information reliably across the technology stack. The conversation ultimately goes beyond technology itself. Chuck and Rob explore how AI can reduce administrative friction while giving advisors more capacity to be present with clients, strengthen relationships, and focus on work where human judgment still matters. Chuck shares a practical example of AI-assisted meeting notes allowing him to focus more fully on the client conversation. IN THIS EPISODE Why RIAs should define the problem before deciding whether AI is the solution How technology sprawl can create more maintenance, training, integration, and operational complexity Why AI-generated insights still depend on the quality of the underlying data How firms can establish sources of truth across CRM, planning, and other systems Where to look for operational friction before automating another workflow Why technology decisions may benefit from an internal technology committee How specialized AI agents could change advisory-firm workflows Why security and third-party access remain part of the technology decision Where human review belongs as AI becomes more embedded in firm workflows How advisors can use AI to create more capacity for client conversations and relationships Daleele's core message is straightforward: don't start with the tool. Start with the problem. ABOUT THE GUEST Daleele Alison CEO of RooksDM Daleele Alison is a technology leader, entrepreneur, and Microsoft Partner focused on helping businesses operate more efficiently through technology. As CEO and cofounder of RooksDM, Daleele works with firms to identify technology and operational challenges and determine where integrations, automation, data architecture, and other technology solutions can help address them. In the episode, Daleele explains that RooksDM's work with RIAs grew from seeing firms use multiple technologies that often did not communicate effectively with one another. LinkedIn: https://www.linkedin.com/in/daleele-alison/ Website: https://rooksdm.com/ ABOUT THE HOSTS Chad Ramberg President, Box Professional Insurance https://www.linkedin.com/in/chad-ramberg-71278533/ Charles “Chuck” Failla, CFP® Founder, Sovereign Financial Group & GoRIA https://www.linkedin.com/in/charlesfailla/ https://www.goria.com Rob Jacomen Founder & CEO, IDA https://www.linkedin.com/in/rob-jacomen/ SPONSOR Special thanks to Box Professional Insurance for supporting The Advisor's Edge Podcast. You already know the back office is where the liability hides. The miscalculated fee. The onboarding step that got skipped. The vendor handling client data you've never actually vetted. Most RIA insurance policies weren't built with any of that in mind. BPI was. They help advisors find the exposure before it finds them. Take the FREE C³ Coverage Diagnostic and get your score in under 2 minutes. RIA Coverage Diagnostic Assessment: https://www.boxproinsurance.com/ CHAPTERS 00:00 — Meet Daleele Alison, CEO of RooksDM 04:00 — Are RIAs Adding Too Much Technology? 05:00 — Start With the Problem, Not the AI Tool 09:00 — AI, CRM Data & “Garbage In, Garbage Out” 12:00 — Security & Third-Party Technology Tradeoffs 13:00 — Building a Source of Truth for Firm Data 19:00 — Is Your RIA Operationally Ready for AI? 25:00 — Why Firms Need a Technology Committee 27:00 — Specialized AI Agents & Where This Could Go 37:00 — What Becomes More Valuable in an AI-Driven World? 40:00 — Will AI Replace Financial Advisors? 45:00 — Human Review & AI-Generated Work 48:00 — AI-Assisted Compliance Review 50:00 — Finding the Real Constraint Inside the Firm 55:00 — Daleele on Integrity & Legacy DISCLAIMER The views shared in this episode reflect the perspectives of the hosts and guest. They are not financial advice or investment recommendations. Always consult a qualified professional regarding your specific situation.

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  Episode #12

  S2E12 | The Tech Gaps RIAs Don’t Know to Look For feat. Regina Schumaker

  Aug 11, 202645 minS2

  A technology problem inside an advisory firm rarely stays isolated to technology. An email change can affect archiving. An old employee credential can remain active. A computer prepared before a breakaway can still contain programs controlled by the old firm. And when a device, system, or access point disappears, the firm's recovery plan suddenly matters. Those are the technology gaps advisors may not know to look for until something changes. In this episode of Advisor’s Edge, Chad Ramberg sits down with Regina Schumaker, Founder of SchurTech Solutions, LLC, to discuss the technology issues that show up inside real advisory practices—and why understanding the advisor's operating environment matters when technology intersects with compliance, cybersecurity, transitions, and day-to-day productivity. Regina brings more than 30 years of technology experience, including nearly two decades working directly with financial advisors inside a broker-dealer environment. Rather than treating technology as a collection of isolated tools, Regina explains why advisors need to understand how their systems connect—and what can happen when one part changes. IN THIS EPISODE, WE COVER: Why financial-advisor technology needs differ from those of a typical small business How overlapping tools and old employee credentials can create unnecessary operational gaps Why advisors may not know which technology questions they should be asking What advisors can overlook when leaving a broker-dealer or transitioning to an independent RIA Why email archiving, secure communication, devices, and software access need attention during a transition How technology troubleshooting can create new problems when the entire workflow isn't understood Why cybersecurity starts with individual behavior as well as monitoring tools The practical role of MFA, VPNs, backups, and safer technology habits Why recovery planning still matters in increasingly cloud-based advisory firms The larger lesson isn't that RIAs need more technology. It's that the technology they already depend on needs to support the way the firm actually operates. ABOUT THE GUEST Regina Schumaker is the Founder of SchurTech Solutions, LLC. Regina brings more than 30 years of experience helping people solve technology problems, including nearly two decades supporting financial advisors inside a national broker-dealer. Her experience spans advisor operations, technology support, Microsoft 365, device troubleshooting, vendor coordination, cybersecurity practices, and technology workflows within financial-services environments. Through SchurTech Solutions, Regina provides relationship-driven technology support for financial advisors and small businesses. Guest Website: https://www.schurtechsolutions.com/ ABOUT THE HOST Chad Ramberg is President of Box Professional Insurance and host of Advisor’s Edge. Advisor’s Edge focuses on the real-world decisions that shape advisory firms—from risk and compliance to operations, technology, client relationships, and long-term firm durability. SPONSOR Special thanks to Box Professional Insurance for supporting the Advisor's Edge Podcast. You already know the back office is where the liability hides. The missed onboarding step. The overlooked vendor relationship. The client data exposure you didn't realize existed. Most RIA insurance policies weren't designed with those risks in mind. BPI was. Take the FREE C³ Coverage Diagnostic and better understand your firm's risk profile. https://www.boxproinsurance.com/ CHAPTERS 00:00 — Why Advisor Technology Gets Complicated 02:00 — Regina Schumaker’s Path Into Advisor Technology 05:00 — Technology Support Built Around Financial Advisors 07:00 — What Does an MSP Actually Do? 10:00 — Making Technology Work for the Advisor 13:00 — Why Advisor Technology Is Different 17:00 — The Technology Side of an RIA Breakaway 22:00 — Understand the Problem Before You Fix It 27:00 — Cybersecurity Starts With Individual Behavior 32:00 — Cloud Systems, Security Monitoring & Backups 36:00 — Why Regina Built SchurTech Solutions 39:00 — The Entrepreneurial Side of Building the Business 43:00 — Final Takeaways for Advisors DISCLAIMER The views shared in this episode reflect the perspectives of the host and guest. They are not financial advice or investment recommendations. Always consult a qualified professional regarding your specific situation.

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  Episode #11

  S2E11 | The Founder Trap Keeping RIAs From Scaling feat. Jarrod Upton

  Jul 29, 202639 minS2

  Most advisory firms don't stop growing because they run out of clients. They stop growing because the systems, leadership habits, and decision-making that created early success eventually become the very things holding the firm back. In this episode of Advisor's Edge, Chad Ramberg sits down with Jarrod Upton, MBA, MS, CFP®, Professional EOS Implementer at EOS Worldwide, for a conversation about one of the biggest transitions firm owners face: evolving from being the center of the business to building a business that can grow beyond them. Together, they explore why founder dependency limits scale, how leadership must evolve as firms grow, the importance of organizational clarity, and why succession planning begins long before ownership changes hands. If your advisory firm is growing—or you're trying to build a business that can thrive without depending on you—this conversation offers practical leadership lessons grounded in real operational experience. WHAT YOU'LL LEARN • Why founder dependency quietly limits growth • The leadership shift required to scale beyond yourself • What "delegate and elevate" actually looks like • Why organizational clarity creates accountability • How strong core values influence hiring and decision-making • Why founders must "let go to grow" for succession to succeed ABOUT THE GUEST Jarrod Upton, MBA, MS, CFP® is a Professional EOS Implementer with EOS Worldwide. He works with entrepreneurial leadership teams to improve organizational clarity, accountability, execution, and long-term business growth using the Entrepreneurial Operating System® (EOS). Guest LinkedIn https://www.linkedin.com/in/jarrodupton/ Company Website https://www.eosworldwide.com/ ABOUT THE HOST Advisor's Edge is hosted by Chad Ramberg. Each episode features conversations with experienced operators, firm builders, and industry leaders exploring the strategic, operational, leadership, and fiduciary challenges facing today's independent advisors and wealth management firms. Chad Ramberg President, Box Professional Insurance https://www.linkedin.com/in/chad-ramberg-71278533/ SPONSOR Special thanks to Box Professional Insurance for supporting the Advisor's Edge Podcast. You already know the back office is where the liability hides. The missed onboarding step. The overlooked vendor relationship. The client data exposure you didn't realize existed. Most RIA insurance policies weren't designed with those risks in mind. BPI was. Take the FREE C³ Coverage Diagnostic and better understand your firm's risk profile. https://www.boxproinsurance.com/ CHAPTERS 00:00 — Introduction 01:52 — Defining What Growth Really Means 06:12 — Growth Stops Being About Getting Clients 10:48 — What Got You Here Won't Get You There 11:49 — If You Can't Delegate, You Can't Elevate 18:55 — Let Go to Grow 19:04 — Your Core Values Should Cost You Business 20:19 — Why Succession Starts Long Before Retirement 27:36 — Building a Business That Outlives the Founder 34:12 — Final Leadership Takeaways 36:41 — Closing Thoughts DISCLAIMER This episode is for informational and educational purposes only and should not be construed as investment, legal, tax, insurance, compliance, or business advice.

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