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

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 close * The "small deaths" of a deal: the forgotten lease, the departing employee, the outside party who surfaces at the worst moment * Why doubt and regret, not valuation, are the most common breakdowns in the final stretch * How Todd's firm screens for founders who are genuinely ready to sell — and why they take on only a handful of clients at a time * Where AI helps in the M&A process, and where the human element remains irreplaceable * What 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/ [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/ [https://www.linkedin.com/in/amanda-verner-thompson/] Website: https://www.madisonadvisory.ai/ [https://www.madisonadvisory.ai/]

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 like * The earliest signals investors tend to ignore * How to tell a salvageable situation from a write-off * Using AI for forensic clarity in restructurings * Why 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/ [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/ [https://www.madisonadvisory.ai/] Connect with Amanda on LinkedIn: https://www.linkedin.com/in/amanda-verner-thompson/ [https://www.linkedin.com/in/amanda-verner-thompson/]

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/]