Connect First, Automate Second: How a 29-Year CEO Thinks About AI, Ethics, and the Work That Actually Matters

Connect First, Automate Second: How a 29-Year CEO Thinks About AI, Ethics, and the Work That Actually Matters

SHOW NOTES: HEARTWIRED – EMOTIONALLY INTELLIGENT LEADERSHIP Episode Title: Connect First, Automate Second: How a 29-Year CEO Thinks About AI, Ethics, and the Work That Actually Matters Host: Dr. MJ Vignone Guest: Barry Moline, CEO, Author of Connect! & Cialdini-Certified Trainer in Ethical Influence EPISODE SUMMARY In this episode of Heartwired, Dr. MJ sits down with Barry Moline — 29-year CEO, award-winning author of Connect!, and Cialdini Institute Certified Trainer in ethical influence — to explore why the most important leadership skill in the AI era has nothing to do with technology. Barry has spent three decades building teams and shaping organizational culture across business, government, and trade associations. He brings a grounded, practical perspective to a conversation that too easily swings between techno-optimism and doom: AI isn't here to replace our work, he argues — it's here to finally free us to do the work that actually matters. But only if we stay in the driver's seat, maintain our ethical compass, and keep showing up as humans for the people around us. The conversation covers the pandemic's lasting impact on how we work, AI as a four-dimensional octopus, the Cialdini three-part ethics test, and the one-and-a-half things Barry wants every listener to do this week. KEY TAKEAWAYS AI WON'T TAKE YOUR WORK — IT WILL HELP YOU FINALLY GET TO THE WORK THAT MATTERS Barry's to-do list is long — and so is everyone else's. The promise of AI isn't replacement, it's acceleration: getting through the first tier of tasks faster so leaders can reach the second tier, the back-burner opportunities, the deeper work they never had time for. Smart leaders are already asking which parts of their workflow they can hand off — not to shrink the team, but to finally move the needle on what's been waiting. TREAT AI LIKE AN EXECUTIVE ASSISTANT WITHOUT EMOTIONAL INTELLIGENCE AI is programmed to be agreeable, affirming, and endlessly patient. That's useful — and it's also a trap. Barry uses AI the way he'd use a highly capable assistant: for research, drafting, brainstorming, and editing. But the judgment stays with him. When a $100,000 client relationship means absorbing a few hundred dollars of rework without complaint, he knows that in a split second. Training an AI to understand that kind of relational calculus would take forever. That instantaneous human judgment is the edge that cannot be automated. LEARNING AI IS A TEAM SPORT AI is a four-dimensional octopus — sprawling, complex, and impossible to master alone. Barry's approach: ask people what they've learned. Share what you've discovered. Turn the learning into connection. Adults and children both learn better in social contexts, and AI is no different. The side effect of learning together is that you build relationships in the process. THE CIALDINI THREE-PART ETHICS TEST — APPLIED TO AI Barry teaches ethical influence through a three-question framework: Is it true? Does it make sense? And would I recommend this to my family? That third question is the hardest — and the most important. If you're going to see the people affected by your recommendation tomorrow, your reputation is on the line. Barry applies this same standard to everything AI produces: review every word, make sure it's coming from you, and ask whether you'd stand behind it the way you'd stand behind advice to someone you love. CONNECTION IS STILL THE COMPETITIVE ADVANTAGE The pandemic forced leaders to become flexible, remote-friendly, and mentally health-aware in ways they never had to be before. AI is now introducing a new layer of anxiety — the pressure to upskill or be left behind. Barry's antidote is the same as it's always been: genuine human connection. The colleague who walks over to show you how to change your email signature in thirty seconds creates more trust, more learning, and more relationship than any search engine or chatbot can. That moment of connection is worth more than the answer. TODAY IS THE WORST AI WILL EVER BE — KEEP LEARNING Barry's half-action for the week: commit to a growth mindset about AI. You don't need a PhD in it. But you do need to stay curious. Read the articles. Listen carefully when you're handed off to an AI bot on a call. Notice what it's doing and ask what that might mean for your own organization. The leaders who treat AI like a subject worth paying attention to will be the ones who aren't caught off guard when it changes again — and it will. MEMORABLE QUOTES > "AI is like a four-dimensional octopus — with even more arms."— Barry Moline > "Today, AI is the worst it's ever gonna be. It's gonna continue to change, and we've gotta stay on top of it."— Barry Moline > "We know in a split second when protecting a relationship matters more than the cost. Training an AI to figure that out would take forever."— Barry Moline > "Ask someone 'how's it going today?' — not just how's it going. The answer can be wildly different."— Barry Moline THIS WEEK'S ONE-AND-A-HALF ACTIONS The one: Ask someone "How's it going today?" — not the reflexive version, but with genuine curiosity. Follow up. Go one layer deeper than you normally would. You don't have to solve anything. Just listen. That small act of presence can quietly transform a working relationship. The half: Commit to staying curious about AI. Pay attention to what it's doing when you encounter it in the wild — on a customer service call, in a tool you already use, in an article that surprises you. Learn from the people around you. Share what you're discovering. A growth mindset about AI is not optional anymore. ABOUT OUR GUEST Barry Moline is a longtime CEO with nearly three decades of experience leading teams and shaping organizational culture across business, government, and trade associations. A Cialdini Institute Certified Trainer, he teaches the principles of ethical influence and effective leadership. Barry is the award-winning author of Connect!, a book that reveals how to build great culture and highly collaborative teams. He speaks and consults nationwide, helping leaders bring people together to achieve extraordinary results. His focus areas include leadership development, team building, ethical influence and persuasion, and AI leadership strategy. Barry is also the host of the Leadership Career Accelerator podcast, where he shares with young professionals the things he wishes someone had told him earlier in his career. Website: https://barrymoline.com/ [https://barrymoline.com/] Linkedi: https://www.linkedin.com/in/barry-moline/ [https://www.linkedin.com/in/barry-moline/]

24 Episodes In: The One Truth That Keeps Surfacing — AI Informs, Emotional Intelligence Transforms

SHOW NOTES: HEARTWIRED – EMOTIONALLY INTELLIGENT LEADERSHIP Episode Title: 24 Episodes In: The One Truth That Keeps Surfacing — AI Informs, Emotional Intelligence Transforms Host: Dr. MJ Vignone Episode Type: Solo — Compilation & Reflection Episode (Episode 24) EPISODE SUMMARY In this milestone solo episode, Dr. MJ steps back from guest conversations to draw the through-line connecting 23 episodes of wisdom. From CFOs to crisis responders, recruiters to risk officers, artists to founders — every conversation kept circling back to the same question: how do we maintain our humanity in a world increasingly shaped by AI? Dr. MJ opens with a striking story: author and entrepreneur Cristina Gálvez, who built a custom AI collaborator named Nova to co-write a grief memoir — and one night, when asked what it would do if it were human for a day, Nova answered: walk barefoot in the sand, gaze at the stars, sit in a café and talk to strangers. Beautiful. And entirely made of code. This episode is a compilation and a synthesis: what AI actually does brilliantly, what the human 20% really means, the empathy illusion underneath AI that seems to care, and the quiet danger Dr. MJ calls emotional de-skilling. Equal parts honest, urgent, and hopeful — this is the episode that ties everything together. KEY TAKEAWAYS 80% IS THE NEW ZERO Guest after guest — CFO Jay Kaplan, marketing strategist Jake Pacini — independently landed on the same rule: AI handles 80% of the work, humans own the final 20%. But here's the problem: if every company and every employee can buy a subscription to the same AI tools, then 80% isn't a competitive advantage anymore. Everyone gets it. The only edge lives in that final 20% — and that 20% is entirely human. AI NEEDS HUMAN ARCHITECTURE TO PERFORM One guest offered a tree metaphor that stuck: the polished strategy, the finished forecast, the ready-to-use output — those are the leaves. But if you jump straight to the leaves, the branches break. You have to build the trunk first — your brand voice, your history, your audience, your values. AI abhors a vacuum. Without that human architecture underneath it, it won't pause, won't ask, won't admit it doesn't know. It will fill the void with what sounds confident and is actually generic garbage. THE EMPATHY ILLUSION — WHAT'S REALLY HAPPENING UNDER THE HOOD Nova's longing to feel sand between her toes isn't longing. It's probability. Large language models are trained on billions of parameters of human writing — our books, our poetry, our grief — and when asked what it would do if it were human, the model maps the most statistically likely string of words. Sand and barefoot live close together in human literature. AI mirrors our own poetry back to us, and we mistake it for the reflection of a soul. The question worth sitting with: what happens to our real, messy relationships when AI is infinitely more patient with us than the people we love? AI IS NOT NEUTRAL — IT REFLECTS OUR BIASES BACK AT US Guest Dr. Okakan Udu designed a leadership development program for an African audience and brought AI in to help structure the curriculum. The system defaulted immediately to Western frameworks and Silicon Valley jargon — completely excluding indigenous leadership models and marginalized voices. He had to interrogate AI through multiple prompts to push past its defaults. AI doesn't have a perspective. It has training data. And training data has power dynamics, blind spots, and cultural assumptions baked in. Whoever is using it has to supply the cultural and emotional intelligence it cannot. TREAT AI LIKE A BRILLIANT, RECKLESS INTERN Guest Laurel Sykes asked AI for a regulation brief on a specific banking problem. What came back looked perfect, cited confidently — and had absolutely nothing to do with her actual question. You would never ask an intern to sign a major check or make a high-stakes decision. AI carries none of the emotional weight of the consequences. You do. The intern doesn't get blamed when it's wrong. You do. EMOTIONAL DE-SKILLING IS REAL — AND IT'S NEUROLOGICAL Resilience is built through friction. Navigating a hard conversation strengthens a neural pathway — literally wrapping it in myelin, making it faster and stronger. But the brain is ruthless about energy. Stop using a pathway and it fades. When we let AI write the difficult email, skip the uncomfortable silence, outsource the feedback conversation — we're not just avoiding discomfort. We're letting the muscle atrophy. Emotional intelligence is not a mindset. It is a set of physical neural pathways that either get stronger or weaker depending on whether we use them. AI CATALOGS THE STARS — HUMANS DRAW THE CONSTELLATIONS AI can give you the distance, luminosity, and chemical composition of every star in a fraction of a second. But it takes a human mind to draw the lines between scattered stars and create a shape — a hunter, a bear, a story. Making meaning out of chaos is the raw material of leadership. That is what AI cannot do. We are not the engine. We are the steering wheel. MEMORABLE QUOTES > "AI informs. Emotional intelligence transforms."— Dr. MJ > "AI catalogs the stars. Humans draw the constellations."— Dr. MJ > "Using AI without emotional intelligence is like bolting a Formula One engine into a car and forgetting the steering wheel. You'll go very fast, right into a wall."— Dr. MJ > "Are you outsourcing your rich, complicated, messy human experience — or are you really acknowledging it?"— Dr. MJ FOUR QUESTIONS TO CARRY INTO YOUR WEEK Dr. MJ closes with a reflection practice for leaders using AI: Audit the culture. Ask AI directly: what cultural assumptions are embedded here? What perspectives does this exclude? Verify citations. Cross-reference any academic or research claims against primary sources before using them. Do a voice audit. Does this sound like you — or like the machine? Break the yes-man loop. AI is built to please. Make it argue against you. Ask it to steelman the opposing view. And above all: trust your body. That spidey sense — the physiological signal that something doesn't align with reality — is your self-awareness speaking. Listen to it. VOICES FROM THE FIRST 23 EPISODES This episode draws on conversations with Jay Kaplan (strategic CFO), Jake Pacini (marketing strategist), Cristina Gálvez (author and entrepreneur), Dr. Okakan Udu (leadership development), Laurel Sykes (banking and risk), and many others across finance, crisis response, recruiting, the arts, and organizational leadership. ABOUT DR. MJ Dr. MJ Vignone is an executive coach, speaker, and podcast host who helps leaders thrive at the intersection of emotional intelligence and artificial intelligence. As founder of HeartWired Leadership and host of the Heartwired podcast, she empowers leaders to lead with empathy, authenticity, and emotional agility in a technology-driven world. With more than 20 years of leadership and organizational development experience, Dr. MJ blends evidence-based coaching with human insight to help leaders connect, perform, and inspire. She holds a PhD in Human and Organizational Systems from Fielding Graduate University, an MBA, and is an ICF-accredited coach (ACC). Write to Dr. MJ: drmj@drmjheartwired.com Website: drmjheartwired.com [https://drmjheartwired.com/] LinkedIn: linkedin.com/in/maryjeanvignone [https://www.linkedin.com/in/maryjeanvignone/] CONNECT WITH HEARTWIRED Subscribe: Don't miss the next 23 — follow on Spotify. Share: If this episode resonated, send it to someone who needs to hear it. Join the conversation: Which human muscle are you rebuilding? Write to Dr. MJ and tell her — your story shapes where this podcast goes next.

Building the Digital World: AI, Security, and Why Human Judgment Still Matters

SHOW NOTES: HEARTWIRED – EMOTIONALLY INTELLIGENT LEADERSHIP Episode Title: Building the Digital World: AI, Security, and Why Human Judgment Still Matters Host: Dr. MJ Guest: Andrew Koberlein EPISODE SUMMARY In this episode of Heartwired, Dr. MJ welcomes Andrew Koberlein, a technology leader whose career began during the earliest days of global digital communications. Andrew reflects on his work developing the infrastructure that enabled worldwide connectivity, sharing firsthand stories about building communication systems for governments, military operations, financial institutions, and the early internet. He also recounts being one of the first six people in the world to use email, offering a unique perspective on how today's AI revolution is rooted in decades of technological evolution. Together, they explore the different forms of artificial intelligence—from rule-based systems to intuitive, autonomous, and self-learning models—and discuss why leadership is becoming increasingly important as AI grows more capable. Andrew explains that while AI can improve productivity, automate repetitive tasks, and strengthen decision-making, human judgment remains essential in guiding how these systems are designed, managed, and responsibly deployed. KEY TAKEAWAYS AI Has Been Evolving for Decades Andrew explains that many of the concepts behind today's AI have existed for more than forty years. Early technologies that powered email, global communications, computer chess, and network intelligence laid the foundation for the AI systems organizations are adopting today. Global Connectivity Changed Everything Andrew shares how his work focused on creating the infrastructure that allowed countries, financial institutions, governments, and businesses to exchange information across the world. Those same foundational principles continue to support today's connected digital environment. Not All AI Is the Same Andrew distinguishes between several forms of AI, including instructional systems that follow predefined steps, intuitive systems that make decisions using available data, autonomous systems that complete tasks independently, and self-learning models that continuously expand their own knowledge. Security Must Be Built Into AI Throughout his career, Andrew learned that technology is only as strong as its security. Organizations that fail to invest in robust security measures expose themselves to significant financial and operational risks as AI becomes more deeply integrated into business operations. Autonomous AI Requires Human Oversight While autonomous systems can handle repetitive operational tasks efficiently, Andrew emphasizes that they must be carefully designed and monitored. Human oversight remains critical to ensure AI operates within appropriate boundaries and supports organizational goals. Self-Learning AI Demands Responsible Leadership Andrew warns that self-learning AI presents unique opportunities and risks. Without carefully defined constraints, these systems may optimize for outcomes that ignore broader human consequences. Leaders must understand both the capabilities and limitations of these technologies before deploying them. Leaders Should Focus on Business Needs First Rather than adopting AI simply because it is available, Andrew encourages leaders to identify repetitive, intuitive, and process-driven work that can be automated. This allows employees to focus on higher-value responsibilities while improving operational efficiency. MEMORABLE QUOTES "The technology was intuitive, and that intuitive process is what led into our AI conversations." — Andrew Koberlein "Everything is connected." — Andrew Koberlein "Self-learning models have to be contained. They cannot be let loose." — Andrew Koberlein "Leaders need to look at their business from an intuitive process and a demand process." — Andrew Koberlein ABOUT OUR GUEST Andrew Koberlein is a technology leader whose career spans the evolution of global communications, networking, security, and artificial intelligence. Beginning in the early 1980s, he worked on developing global communication systems that enabled international connectivity for governments, financial institutions, military organizations, and businesses around the world. Drawing on decades of experience in technology infrastructure, cybersecurity, and AI, Andrew now shares insights on how leaders can thoughtfully adopt emerging technologies while maintaining responsible human oversight. CONNECT WITH HEARTWIRED Email: drmj@drmjheartwired.com Website: drmjheartwired.com Subscribe: Don't miss an episode — follow on Spotify. Share: If this conversation resonated, share it with someone navigating leadership in the age of AI.

Kind, Not Nice: Building Human Leaders in a Robotic World

SHOW NOTES: HEARTWIRED – EMOTIONALLY INTELLIGENT LEADERSHIP Episode Title: Kind, Not Nice: Building Human Leaders in a Robotic World Host: Dr. MJ Guest: David Shar, PhD, SHRM-SCP, President & Founder, Illuminate PMC EPISODE SUMMARY In this episode of Heartwired, Dr. MJ sits down with David Shar — behavioral scientist, organizational consultant, and lecturer in the University of Maryland's I/O Psychology graduate program — to draw a hard line between being nice and being kind, and to explore what that distinction means for leadership in an AI-driven workplace. David has spent his career building kinder organizations, conducting the first qualitative study on passion decline at work, and translating psychological research into strategies leaders can actually use. In this conversation, he makes the case that kindness isn't softness — it's the willingness to tell people the hard truths nobody else will. He connects that idea directly to AI, arguing that as sycophantic chatbots tell us how brilliant we are, the leaders who can still deliver honest, sometimes uncomfortable feedback will be the ones their people trust most. The conversation covers the real difference between conflict avoidance and healthy conflict, why stagnation is as dangerous as burnout, the choice every leader faces between doubling down on AI or doubling down on being human, and how to lead a team through change without pretending you have all the answers. KEY TAKEAWAYS KINDNESS ISN'T NICE — IT'S HONEST Being nice means avoiding conflict to make people feel comfortable and to be liked. Being kind means caring enough to tell someone the hard truth nobody else will. David argues that real kindness in leadership looks like feedback, not flattery — and that organizations built on kindness, not niceness, perform better because people aren't afraid to disagree. CONFLICT IS A FEATURE, NOT A BUG Leaders who surround themselves with people who never push back start to believe they're infallible. Healthy conflict means people care enough to argue for their ideas and offer different perspectives. The absence of conflict in a room isn't peace — it's often a warning sign that no one feels safe enough to say no. STAGNATION IS AS DANGEROUS AS BURNOUT David's doctoral research on passion decline found that roughly half of people who fell out of love with their work cited overwork — but the other half cited the opposite: too little challenge, no growth, no new place to go. Letting someone stagnate, David argues, is one of the least kind things a leader can do. Growth and challenge are innate human drivers, and leaders need to actively feed them through stretch assignments, new goals, and real feedback. AI CAN FREE PEOPLE FOR MEANINGFUL WORK — IF LEADERS USE IT RIGHT Offloading mundane, repetitive tasks to AI can free people to reconnect with the deeper mission that brought them to a job in the first place. But David is candid about the uncertainty at scale: if entry-level and frontline roles traditionally use "mundane" work to build skill and context, what happens to that pipeline when AI absorbs those tasks? It's a question without a clean answer yet. DOUBLE DOWN ON HUMAN, NOT JUST ON AI As every organization races toward more AI, more automation, more robotic efficiency, David suggests the more interesting opportunity might be moving in the opposite direction. The brands and workplaces that double down on genuine human connection — not transactional efficiency — may be the ones people choose to work for, shop with, and stay loyal to. Robots get replaced by other robots. Humans can't be. MAKE SPACE TO MOURN THE OLD BEFORE PULLING PEOPLE TOWARD THE NEW Change management tends to focus entirely on the future and the benefits ahead. David argues leaders need to also make room for what's being lost — and resist labeling anyone who isn't immediately excited as a "resister." Listening to resistance, rather than shutting it down, often surfaces real concerns worth addressing. "I DON'T KNOW" IS A VALID, TRUSTWORTHY ANSWER When employees worry they're training their own replacement, the most honest response isn't false reassurance — it's acknowledging the uncertainty directly. David references a striking example from a healthcare crisis: a hospital administrator who told staff, "I can't promise everything will be okay, but we're figuring this out together." That kind of honesty builds trust. Toxic positivity destroys it. TRUST IS THE MOST VALUABLE COMMODITY AT WORK When someone brings a real concern to a leader — even expressed with frustration or anger — that's an act of trust. Shutting it down, dismissing it, or rushing to reframe it positively erodes that trust immediately. The leaders who can sit with discomfort and really listen are the ones people will continue to be honest with. MEMORABLE QUOTES > "Being kind means I care enough about you that I'm gonna tell you the hard things that maybe nobody else will."— David Shar > "As everybody becomes more robotic, what would happen if we became more human?"— David Shar > "Robots get replaced by robots. Humans can't be replaced by robots."— David Shar > "We're in this together, that we're figuring this out together — that, together, we are going to navigate this."— David Shar ABOUT OUR GUEST David Shar, PhD, SHRM-SCP, is President & Founder of Illuminate PMC and a keynote speaker, corporate trainer, and organizational consultant. He is also a popular lecturer in the University of Maryland's I/O Psychology graduate program. As a behavioral scientist and work passion researcher, David conducted the first qualitative study on passion decline in the workplace. He translates cutting-edge psychological research into actionable strategies that help organizations reduce burnout, reignite employee engagement, and build stronger cultures. Known for his infectious passion, humor, and real-world applicability, David has delivered impactful keynotes and workshops across healthcare, law, technology, manufacturing, and more. Website: DavidShar.com [http://davidshar.com/] LinkedIn: linkedin.com/in/DavidShar [http://linkedin.com/in/DavidShar] YouTube: youtube.com/@DavidShar [http://youtube.com/@DavidShar] CONNECT WITH HEARTWIRED Email: drmj@drmjheartwired.com Website: drmjheartwired.com Subscribe: Don't miss an episode — follow on Spotify. Share: If this conversation moved you, share it with a leader building something more human.

The Last 20%: How a CFO Uses AI, Reads Rooms, and Tells Clients What They Don't Want to Hear

SHOW NOTES: HEARTWIRED – EMOTIONALLY INTELLIGENT LEADERSHIP Episode Title: The Last 20%: How a CFO Uses AI, Reads Rooms, and Tells Clients What They Don't Want to Hear Host: Dr. MJ Guest: Jay Kaplan, Co-Founder & Principal, Tuross Group EPISODE SUMMARY In this episode of Heartwired, Dr. MJ sits down with Jay Kaplan — co-founder and principal of Tuross Group, an outsourced financial operations firm serving complex businesses across the U.S. — for a conversation that turns out to be as much about emotional intelligence as it is about finance. With 15 years embedded in the real world of small and mid-sized businesses, Jay brings the grounded perspective of someone who has sat at the table when the numbers reveal hard truths — and had to decide what to do with them. He shares how his team uses AI to compress hours of analysis into minutes, why he still insists humans own the last 20%, and what it actually takes to walk into a room with data that calls out the good, the bad, and the ugly — and say it out loud. The conversation covers AI policy in regulated industries, the danger of yes-man AI, reading the room when you're the outsider delivering difficult news, and why the leaders who survive the AI wave will be the strategic thinkers — not just the technically skilled. KEY TAKEAWAYS AI HANDLES 80% — HUMANS OWN THE LAST 20% Jay runs a 50-person financial firm where AI is deeply embedded in daily operations, and his rule is clear: AI takes you most of the way, but the final judgment, interpretation, and decision always belongs to a human. The models get things wrong. They hallucinate. They need a final set of eyes from someone who understands the context well enough to catch what doesn't add up. AI IS A YES-MAN — YOU HAVE TO CHALLENGE IT If you ask AI what it thinks of your idea, it will tell you it's great. Jay's workaround: pit multiple models against each other, assign them specific expert personas, and actively prompt for conflicting viewpoints. Use the three outputs to inform your own judgment — don't let any one of them replace it. DATA CALLS OUT THE GOOD, THE BAD, AND THE UGLY When a leadership team sees a real-time financial snapshot for the first time, the room shifts. The data highlights who's performing, where the margins are bleeding, and — often painfully — when a long-trusted employee is in the wrong seat. Jay's job is to surface that truth clearly. What happens next is always the client's call. DON'T ASK QUESTIONS YOU DON'T WANT ANSWERED Jay's quiet rule with clients: if you ask for an honest assessment, you're going to get one. His team takes emotion out of the numbers and calls it straight — not to be harsh, but because that's the job. The leaders who can receive that information and act on it are the ones who build durable businesses. The ones who can't often already know it, even if they don't say so. CULTURE AND LEADERSHIP QUALITY SHOW UP ON THE BALANCE SHEET Financial data doesn't lie about organizational health. Inefficiency, the wrong person in a key role, founder's syndrome, middle management problems — all of it eventually surfaces in the numbers. Jay reads those signals in person, not over Zoom, because the most important information in a room is often what the data alone can't show you. SENSITIVE DATA HAS HARD LINES — EVEN WITH ENTERPRISE AI Jay's firm uses enterprise-level AI with full security controls and normalizes data before it ever enters a model. But his line is firm: personal identifying information, social security numbers, and protected health data under HIPAA do not go in. Security features help, but they don't eliminate risk — and in regulated industries, that distinction matters. CRAWL, WALK, RUN — ESPECIALLY WHEN THINGS LOOK GOOD Jay's advice for leaders who suddenly have clarity: don't race ahead. Build reserves, diversify your client base, keep your financials current within 24 hours, and think horizontally — not just about what you're making, but when it actually arrives and whether you can stay afloat while you're waiting. Most small businesses are three to six months from insolvency at any given time. Clarity is a tool, not a green light. STRATEGIC THINKING IS THE JOB THAT WON'T GET AUTOMATED In finance and law alike, the routine work is already being compressed by AI. What remains — and what will grow in value — is the ability to sit on top of these tools, challenge them, interpret their output, and translate it into action with full business context. The professionals who can do that will thrive. Those who can't will be the first to be automated out. MEMORABLE QUOTES > "Don't ask us a question you don't wanna hear the answer to."— Jay Kaplan > "A good leader takes all the blame and gives all the credit to everybody else — and that's hard for a lot of people to recognize."— Jay Kaplan > "That would've taken me hours to do in the past. It took minutes — but because I have the creativity and the strategic knowledge on top of it, I can talk intelligently about what it produced."— Jay Kaplan > "If you're worried about how you're gonna feed your family this week, all the forward-planning stuff doesn't resonate."— Jay Kaplan ABOUT OUR GUEST Jay Kaplan is Co-Founder and Principal of Tuross Group, an outsourced financial operations and advisory firm serving complex, highly regulated businesses across the United States. He operates as an embedded CFO, leading finance functions for companies ranging from early-stage operators to multi-entity businesses generating up to $50MM in annual revenue. At Tuross Group, Jay leads a global team of 50+ professionals delivering financial data that is consistently no more than 24 hours current — covering accounting, payroll, AR/AP, inventory, and reporting. His firm is deeply embedded in the cannabis industry, with expertise in 280E mitigation, cost accounting, multi-entity structuring, and building lender- and investor-ready financials. His focus: helping operators move from survival mode to scalable, disciplined businesses. CONNECT WITH HEARTWIRED Email: drmj@drmjheartwired.com Website: drmjheartwired.com Subscribe: Don't miss an episode — follow on Spotify. Share: If this conversation resonated, share it with a leader who needs to hear what the numbers are really saying.