Madison Advisory AI Podcast

Amanda Verner Thompson

The Madison Advisory AI Podcast explores how leaders navigate a world where technology and AI are accelerating decisions—but where judgment, trust, and experience still matter more than ever. Hosted by Amanda Verner Thompson, a healthcare investment banker and founder of Madison Advisory AI, the show features candid conversations with founders, operators, advisors, and executives who understand that good advice isn't about products or algorithms—it's about asking the right questions at the right time. Each episode examines how trusted advisors think through complexity, make decisions in moments that matter, and use technology as an amplifier—not a replacement—for seasoned judgment. For leaders who value substance over speed, and perspective over hype.

  1. Jul 13

    The Human Side of the Close: Trust, Judgement, and Talking Founders Off the Ledge

    What actually gets a deal across the finish line? After more than 20 years advising founders through business exits, Todd Hutchinson has learned it's rarely the numbers — it's the trust, judgment, and emotional steadiness required in the final stretch, when doubt and regret tend to surface. In this episode, host Amanda Verner Thompson sits down with Todd Hutchinson, Managing Partner at MDR & Associates, to explore the deeply human work of guiding an owner through the sale of their business. Todd compares the advisor's role to that of a sports agent — negotiating on behalf of the founder while keeping them steady on the sidelines — and explains why the deals he works on often "die" more than once before they close. The conversation gets at something every founder considering an exit should understand: selling a business is one of the most personal decisions an owner ever makes, and no amount of automation replaces the person on the other end of the phone when the process gets hard.   In this conversation: Why building a personal relationship with the founder — sometimes 12 to 18 months before a sale — is the foundation of a successful closeThe "small deaths" of a deal: the forgotten lease, the departing employee, the outside party who surfaces at the worst momentWhy doubt and regret, not valuation, are the most common breakdowns in the final stretchHow Todd's firm screens for founders who are genuinely ready to sell — and why they take on only a handful of clients at a timeWhere AI helps in the M&A process, and where the human element remains irreplaceableWhat Todd wishes founders understood about deal readiness well before they go to market  A moment from the episode: "AI is not going to get on the phone with my owner and talk them off the ledge. That has to be me." About the Guest Todd Hutchinson is Managing Partner at MDR & Associates, where he has spent more than two decades advising founders and business owners through exits. His approach centers on long-term relationships, in-person trust-building, and a deep understanding of the emotional realities of selling a business. Connect with Todd LinkedIn: https://www.linkedin.com/in/toddhutchinson1/   About the Host Amanda Verner Thompson is the founder of Madison Advisory AI, a healthcare services and behavioral health M&A and capital advisory firm. With nearly two decades of investment banking experience, she advises founders and operators on sell-side M&A, capital raises, and ownership transitions. The Madison Advisory AI Podcast features conversations with founders, operators, and investors on strategy, capital, and the human judgment behind high-stakes decisions. Connect with Amanda: https://www.linkedin.com/in/amanda-verner-thompson/ Website: https://www.madisonadvisory.ai/

    The Human Side of the Close: Trust, Judgement, and Talking Founders Off the Ledge

  2. Jun 29

    When Deals Blow Up: The Cost of Waiting Too Long

    Some advisors get called when things are going well. Robert Stevens gets called when the deal has already broken. In this episode of the Madison Advisory AI Podcast, Amanda Verner Thompson sits down with Robert Stevens — a turnaround and restructuring specialist who has spent decades inside receiverships, workouts, and high-stakes situations where capital, regulation, ego, and reality collide. His job isn't to predict success. It's to recover value after failure. Robert walks through what the first 72 hours of a blown-up deal actually look like, the earliest warning signs investors tend to ignore, and the single mistake he sees in every case: waiting too long. He explains why distressed situations rarely fail all at once, how the fear of taking "permanent" action keeps stakeholders frozen, and why — in his words — not taking action is itself an action, and usually a bad one. The conversation also gets practical on AI. Robert shares how he links thousands of company files into tools like Perplexity and runs forensic queries in minutes — work that once took a room full of people weeks. It's a clear-eyed look at AI as an operational tool for precision and speed, including where it still falls short and why a strong prompt and complete data matter more than the platform you choose. Along the way, Robert draws on nearly five decades in Taekwondo to talk about conflict, composure, and leading when respect isn't automatic. In this episode: What the first 72 hours of a distressed situation look likeThe earliest signals investors tend to ignoreHow to tell a salvageable situation from a write-offUsing AI for forensic clarity in restructuringsWhy waiting is the most common — and most costly — mistake  About the Guest Robert Stevens is the Founder of Strongbow Advisors, Inc., where he serves as a court-appointed receiver and restructuring advisor in distressed and high-risk business matters across more than 30 state and federal jurisdictions. His practice focuses on distressed operating companies, securities enforcement receiverships, and fiduciary appointments where operational control and the preservation of stakeholder value are the primary mandates. A federally admitted expert witness in SEC enforcement proceedings, he also serves as President and Managing Director of Somerset Capital and is a ninth-degree black belt and founder of a 40-plus-year Taekwondo program. He holds a legal background from Pepperdine University. Connect with Robert on LinkedIn: https://www.linkedin.com/in/somersetstevens/   About the Host Amanda Verner Thompson is the Founder & CEO of Madison Advisory AI, a boutique advisory firm focused on healthcare services and behavioral health, specializing in capital raises and sell-side M&A. With nearly two decades of investment banking experience, she advises founders, operators, and investors navigating growth, capital, and ownership transitions. Learn more: https://www.madisonadvisory.ai/ Connect with Amanda on LinkedIn: https://www.linkedin.com/in/amanda-verner-thompson/

    When Deals Blow Up: The Cost of Waiting Too Long

  3. Jun 22

    The Hidden Cost of AI in Fundraising: Efficiency Up, Effectiveness Down

    Everyone wants to know what AI can automate. The more useful question is what happens when you actually try. In this episode, Amanda Verner Thompson sits down with Jeffrey Fidelman, a capital advisor who has guided hundreds of early and growth-stage companies through raising capital. Jeffrey did what most firms only talk about: he built AI into his investor outreach, scaled it roughly fourfold — and then pulled it back out when the numbers told the real story. The throughline is a distinction every founder and operator should internalize: efficiency and effectiveness are not the same thing. As outreach volume climbed, conversions fell. Analysts were reading AI-generated personalization to investors they'd never researched, and had nothing to say once the script ran out. We get into: Why most raises take six to nine months — and what founders consistently misunderstand about how investors actually decideThe difference between efficiency and effectiveness, and how automation quietly eroded resultsWhat kills a raise before it starts: over-representation, raising before you're ready, and a lack of convictionHow AI has reset the definitions of pre-seed, seed, and Series A — and what metrics actually matter at each stageWhy fundraising is both storytelling and analysis, and where AI still produces work that doesn't hold upThe human element capital can't automate: judgment, relationships, and the founder who just needs to know they're not aloneThis is a grounded conversation about where AI genuinely helps a raise, where it creates false confidence, and why the decision to walk away from a tool that looked good on paper is often the right one.   About the Guest Jeffrey Fidelman is a capital advisor with more than a decade of experience helping early and growth-stage companies raise capital, position themselves, and navigate how investors evaluate opportunities. His firm operates a managed "Fundraise as a Service" model, combining investor research, qualification, and outreach with the relationship work that capital formation still depends on. Connect with Jeffrey on LinkedIn: https://www.linkedin.com/in/jeffreyfidelman/   About the Host Amanda Verner Thompson is the Founder & CEO of Madison Advisory AI, a boutique advisory firm focused on healthcare services and behavioral health — primarily sell-side M&A and capital raises. With nearly two decades of investment banking experience, Amanda advises founders and operators navigating growth, capital, and ownership transitions. The Madison Advisory AI Podcast features conversations at the intersection of strategy, leadership, and AI. Connect with Amanda on LinkedIn: https://www.linkedin.com/in/amanda-verner-thompson/ Learn more about Madison Advisory AI: https://www.madisonadvisory.ai/

    The Hidden Cost of AI in Fundraising: Efficiency Up, Effectiveness Down

  4. Jun 15

    The Cost of Indecision: Leadership, Trust, and Judgment Under Pressure

    When capital is constrained and options are narrowing, what separates the companies that recover from those that don't? More often than not, it isn't the numbers — it's the willingness to make hard decisions before they become forced ones.   In this episode, Amanda Verner Thompson sits down with Rick Rosenbloom, founder and managing partner of Fuel Break Capital Partners, who has spent more than three decades across bankruptcy law, distressed investing, restructuring, and special situations advisory. Rick brings a forensic view of why companies fail — and what leaders, boards, and investors can do long before distress ever shows up in the financials.   The conversation moves from the discipline of decision-making under pressure to the human dynamics that decide outcomes: why most restructurings are operational and management problems dressed up as financial ones, why credibility and trust carry distressed situations, and why the judgment and relationships behind a deal still can't be handed to a model.   In this episode: Why indecision is the costliest decision a leader can makeThe forensic mindset: working backward from failure to find its real causeWhy restructuring is usually a leadership problem, not a financial oneHow data and AI have leveled the playing field — and made financing more rigidWhat credibility and trust actually determine when the stakes are highWhat CEOs and boards should be doing before distress appears in the numbers  About the Guest Rick Rosenbloom is founder and managing partner of Fuel Break Capital Partners. Over more than three decades, he has worked across bankruptcy law, distressed investing, restructuring, and special situations advisory, helping companies, boards, and investors navigate moments where judgment matters more than models. Trained as both a lawyer and an MBA, Rick now advises clients seeking capital outside the traditional bounds of banks and private equity, bringing deep market knowledge and a candid, reality-based approach to complex financing. 🔗 Connect with Rick: https://www.linkedin.com/in/rickrosenbloom/   About the Host Amanda Verner Thompson is Founder & CEO of Madison Advisory AI, a boutique advisory firm working at the intersection of strategy, leadership, and AI in healthcare and behavioral health. With nearly two decades of healthcare investment banking experience, she advises founders and operators on sell-side M&A, capital raises, and ownership transitions. The Madison Advisory AI Podcast features candid conversations with the founders, operators, and investors shaping the future of healthcare and behavioral health. 🔗 Website: https://www.madisonadvisory.ai/ 🔗 LinkedIn: https://www.linkedin.com/in/amanda-verner-thompson/

  5. Jun 8

    You Can't AI Your Way to a Sale in Healthcare: Why Founders Must Sell Before They Hire

    Most digital health founders know how to build. Some know how to raise. Far fewer know how to translate early traction into a repeatable revenue engine — and that gap is where companies stall, burn capital, and make expensive hiring mistakes. In this episode, Amanda sits down with Kirk Barnes, founder of TransPharMed and a digital health commercialization strategist with a career spanning pharma, startups, incubators, and innovation ecosystems. Kirk has spent decades helping founders navigate the difficult transition from founder-led sales to scalable commercial infrastructure — and he doesn't sugarcoat what most get wrong. They cover where digital health founders consistently misfire on their first sales hire, why healthcare is not generic SaaS, how a single bad hire can cost a startup $400,000 or more, why AI can support but not replace trust in complex sales environments, and why founders need to master the sale before they hand it off to anyone else. If you're a founder preparing to scale your commercial team — or an investor watching portfolio companies burn through runway on the wrong hires — this conversation is worth your full attention.   Topics Covered Founder-led sales and when to transitionThe true cost of a bad first sales hire in digital healthWhy healthcare is not generic SaaSHow to structure your first commercial hire correctlyAI's role in sales preparation and workflow — and where it falls shortWhy trust and human connection still drive complex healthcare dealsCapital allocation mistakes early-stage founders makeWhy raising money is not a milestone worth celebrating  About the Guest Kirk Barnes is a digital health commercialization strategist and the founder of TransPharMed. He has worked across pharma, biotech, startups, and innovation ecosystems helping companies build the sales infrastructure and mindset needed to scale. Kirk also founded the Digital Health Sales Institute, a resource for founders learning to sell before they hire. 🔗 Connect with Kirk: https://www.linkedin.com/in/kirkbarnes/   About the Host Amanda Verner Thompson is the Founder & CEO of Madison Advisory AI and a former healthcare investment banker with two decades of experience advising healthcare services companies, founders, and investors on growth, strategy, and transactions. Through the Madison Advisory AI Podcast, Amanda leads conversations with founders, operators, investors, and executives navigating leadership, decision-making, and AI adoption across healthcare and founder-led businesses. 🔗 Website: https://www.madisonadvisory.ai/ 🔗 LinkedIn: https://www.linkedin.com/in/amanda-verner-thompson/

  6. Jun 1

    The Long Build: How EyeQue Grew a Decade Without Venture Backing

    Episode Summary Most healthcare technology companies are built on venture timelines. John Serri built EyeQue on a different premise — that the technology would eventually matter enough to justify the long game. Founded in 2015, EyeQue set out to make accurate vision testing accessible through a smartphone. Nearly a decade later, the company holds 35 patents, operates across direct-to-consumer and B2B channels, and is now integrating AI to reduce support burden, accelerate development, and improve testing accuracy. In this conversation, John and Amanda cover what it takes to build in a regulated healthcare market without venture backing — navigating FDA registration, evolving from D2C to a telemedicine platform, and making capital decisions across multiple market cycles. They also dig into EyeQue's current inflection point and how John is weighing equity investment versus a strategic partnership for the next phase of growth.   Key Themes Building without venture capital — discipline and trade-offs of a decade-long independent buildD2C to telemedicine — how regulatory realities and COVID shaped EyeQue's evolutionAI as an operational tool — cutting support costs, accelerating development, speeding up testingThe vision care market — the myopia epidemic, aging population, and provider shortageCapital strategy — equity investment versus strategic partnership at an inflection pointWhat investors get wrong — why understanding the technology matters as much as the return  About the Guest John Serri is the CEO and Founder of EyeQue Inc, which he co-founded in 2015 to rethink vision testing using smartphones, optical hardware, and telemedicine infrastructure. EyeQue has developed 35 patents, registered seven devices with the FDA, and scaled across D2C and B2B channels. John brings a background in aerospace and physics to healthcare technology and is based in Pleasanton, California.   About the Host Amanda Verner Thompson is the Founder & CEO of Madison Advisory AI and a former healthcare investment banker with nearly two decades of experience advising healthcare services companies, founders, and investors on growth, strategy, and transactions. Through the Madison Advisory AI Podcast, Amanda leads conversations with founders, operators, investors, and executives navigating leadership, decision-making, and AI adoption across healthcare and founder-led businesses. Website: https://www.madisonadvisory.ai/ LinkedIn: https://www.linkedin.com/in/amanda-verner-thompson/

    The Long Build: How EyeQue Grew a Decade Without Venture Backing

  7. May 18

    Technology May Be Our Greatest Hope for Suicide Prevention

    Episode SummaryAs technology becomes embedded in daily life, the conversation around mental health has grown more complex. We hear constantly about the risks. But there is a less discussed perspective: technology may be one of our most powerful tools for improving mental health outcomes and preventing suicide.   Dr. Dan Reidenberg has spent decades at the forefront of suicide prevention. He serves as Managing Director at the National Council for Suicide Prevention and is the founder of Safe Online Standards — the world's first rating system for technology companies on mental health and wellbeing.   In this conversation, we explore the dual nature of technology in mental health, what leaders most misunderstand about suicide prevention, the responsibility of technology platforms, and why Dan believes AI may be the field's greatest source of hope. Key Themes•      The dual role of technology — risk and protective factor in mental health •      How algorithms amplify mental health vulnerability •      Why suicide never has a single cause — and what that means for prevention •      What leaders most misunderstand about suicide in the workplace •      Safe Online Standards: the world's first rating system for social media platforms •      AI as a protective factor — 24/7 access to support when clinicians aren't available •      The human-in-the-loop imperative in behavioral healthcare •      Why young people's willingness to talk gives Dan his greatest hope   About the GuestDr. Dan Reidenberg is one of the leading voices in suicide prevention and behavioral health. He serves as Managing Director at the National Council for Suicide Prevention and is the founder of Safe Online Standards — the world's first comprehensive rating system for technology companies on mental health, wellbeing, suicide, self-harm, and eating disorders, released February 2026. Throughout his career he has advised technology companies, healthcare organizations, and corporate leaders on evidence-based approaches to prevention and breaking through stigma.   LinkedIn: https://www.linkedin.com/in/dan-reidenberg-9264864/ Safe Online Standards: https://www.safeonlinestandards.org/     About the HostAmanda Verner Thompson is the founder of Madison Advisory AI and host of the Madison Advisory AI Podcast. With nearly two decades of investment banking experience, she has advised founders, operators, and investors on healthcare and behavioral health transactions — from capital raises to sell-side M&A. Madison Advisory AI is a boutique advisory firm at the intersection of strategy, capital, and AI adoption, focused on healthcare services and behavioral health.   LinkedIn: https://www.linkedin.com/in/amanda-verner-thompson/ Madison Advisory AI Website: https://www.madisonadvisory.ai/ Crisis ResourcesIf you or someone you know is struggling, support is available 24 hours a day, 7 days a week.   988 Suicide & Crisis Lifeline: Call or text 988 (US) Crisis Text Line: Text HOME to 741741

    Technology May Be Our Greatest Hope for Suicide Prevention

  8. May 11

    The Decisions That Create Value Happen Before the Deal

    Episode Summary Most founders don’t realize they’re leaving value on the table until a banker walks in the door and by then, much of the story is already written. In this episode of the Madison Advisory AI Podcast, Amanda sits down with Sterling Morris to discuss the decisions that shape enterprise value long before a transaction ever begins. Drawing from his background in investment banking and corporate development, Sterling shares a practical perspective on what founders in the $5M–$50M revenue range consistently overlook: operational discipline, transferability, and the hidden risks that surface during diligence. The conversation explores why many founder-led businesses become overly dependent on the founder themselves, how key man risk directly impacts deal structure and valuation, and why communication and judgment become even more valuable as AI automates more execution-oriented work. Amanda and Sterling also discuss the reality of AI adoption for smaller businesses: where it creates leverage, where it creates noise, and why founders need trusted advisors to navigate a rapidly changing environment. This is a grounded conversation about leadership, value creation, and decision-making under uncertainty, not just during a transaction, but in the years leading up to one.   Key Themes Value Creation Starts Before the Transaction: Many of the issues that impact valuation — financial reporting gaps, operational inefficiencies, customer concentration, and founder dependency — are created years before a sale process begins and become far harder to fix once diligence is underway. The Hidden Impact of Key Man Risk: Buyers are often evaluating whether a business can operate independently after the founder exits. AI as Leverage Not Replacement: AI can accelerate research, drafting, and operational efficiency, but it cannot replace trust, accountability, context, or human judgment. Communication as a Competitive Advantage: As more execution becomes automated, communication, critical thinking, and relationship-building become even more important differentiators for founders, operators, and advisors.   About Sterling Morris Sterling Morris brings experience across investment banking, corporate development, growth strategy, and founder advisory. Throughout his career, he has worked alongside founder-led businesses navigating growth, operational scaling, M&A processes, and strategic transitions. His current work focuses primarily on businesses in the $5M–$50M revenue range, helping founders think through the operational, financial, and strategic decisions that ultimately drive long-term enterprise value. Website: https://www.acuxcel.com/ LinkedIn: https://www.linkedin.com/in/sterlinglmorris11/   About the Host Amanda Verner Thompson is the Founder & CEO of Madison Advisory AI and a former healthcare investment banker with nearly two decades of experience advising healthcare services companies, founders, and investors on growth, strategy, and transactions. Through the Madison Advisory AI Podcast, Amanda leads conversations with founders, operators, investors, and executives navigating leadership, decision-making, and AI adoption across healthcare and founder-led businesses. Website: https://www.madisonadvisory.ai/ LinkedIn: https://www.linkedin.com/in/amanda-verner-thompson/

    The Decisions That Create Value Happen Before the Deal
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About

The Madison Advisory AI Podcast explores how leaders navigate a world where technology and AI are accelerating decisions—but where judgment, trust, and experience still matter more than ever. Hosted by Amanda Verner Thompson, a healthcare investment banker and founder of Madison Advisory AI, the show features candid conversations with founders, operators, advisors, and executives who understand that good advice isn't about products or algorithms—it's about asking the right questions at the right time. Each episode examines how trusted advisors think through complexity, make decisions in moments that matter, and use technology as an amplifier—not a replacement—for seasoned judgment. For leaders who value substance over speed, and perspective over hype.

Information

  • Creator
    Amanda Verner Thompson
  • Years Active
    2026
  • Episodes
    26
  • Rating
    Clean
  • Copyright
    © 2026 Amanda Verner Thompson
  • Show Website
    Madison Advisory AI Podcast