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

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 decide * The difference between efficiency and effectiveness, and how automation quietly eroded results * What kills a raise before it starts: over-representation, raising before you're ready, and a lack of conviction * How AI has reset the definitions of pre-seed, seed, and Series A — and what metrics actually matter at each stage * Why fundraising is both storytelling and analysis, and where AI still produces work that doesn't hold up * The human element capital can't automate: judgment, relationships, and the founder who just needs to know they're not alone This 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/ [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/ [https://www.linkedin.com/in/amanda-verner-thompson/] Learn more about Madison Advisory AI: https://www.madisonadvisory.ai/ [https://www.madisonadvisory.ai/]

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 make * The forensic mindset: working backward from failure to find its real cause * Why restructuring is usually a leadership problem, not a financial one * How data and AI have leveled the playing field — and made financing more rigid * What credibility and trust actually determine when the stakes are high * What 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/ [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/ [https://www.madisonadvisory.ai/] 🔗 LinkedIn: https://www.linkedin.com/in/amanda-verner-thompson/ [https://www.linkedin.com/in/amanda-verner-thompson/]

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 transition * The true cost of a bad first sales hire in digital health * Why healthcare is not generic SaaS * How to structure your first commercial hire correctly * AI's role in sales preparation and workflow — and where it falls short * Why trust and human connection still drive complex healthcare deals * Capital allocation mistakes early-stage founders make * Why 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/ [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/ [https://www.madisonadvisory.ai/] 🔗 LinkedIn: https://www.linkedin.com/in/amanda-verner-thompson/ [https://www.linkedin.com/in/amanda-verner-thompson/]

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 build * D2C to telemedicine — how regulatory realities and COVID shaped EyeQue's evolution * AI as an operational tool — cutting support costs, accelerating development, speeding up testing * The vision care market — the myopia epidemic, aging population, and provider shortage * Capital strategy — equity investment versus strategic partnership at an inflection point * What 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/ [https://www.madisonadvisory.ai/] LinkedIn: https://www.linkedin.com/in/amanda-verner-thompson/ [https://www.linkedin.com/in/amanda-verner-thompson/]

Technology May Be Our Greatest Hope for Suicide Prevention

EPISODE SUMMARY As 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 GUEST Dr. 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/ [https://www.linkedin.com/in/dan-reidenberg-9264864/] Safe Online Standards: https://www.safeonlinestandards.org/ [https://www.safeonlinestandards.org/]     ABOUT THE HOST Amanda 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/ [https://www.linkedin.com/in/amanda-verner-thompson/] Madison Advisory AI Website: https://www.madisonadvisory.ai/ [https://www.madisonadvisory.ai/] CRISIS RESOURCES If 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