WholeCEO With Lisa G Podcast

We have more data than ever before. So why are leaders less certain than ever? In this episode of WholeCEO with Lisa G., executive coach Lisa Goldenthal explores one of the biggest leadership challenges of the AI era: the Judgment Gap. Discover why unlimited information doesn't automatically lead to better decisions, why organizations miss warning signs hidden in their own data, and what separates...

What if everything you've been taught about investing is missing the most important distinction? In this episode of WholeCEO with Lisa G. , Lisa sits down with investor and entrepreneur Joseph Argiro to unpack the hidden dynamics shaping today's private investment markets—and why many investors don't realize the risks until it's too late. They explore the critical difference between exposure and o...

You think you're building a company that's ready for investment or acquisition. Your revenue is growing. Customers are happy. The future looks promising. But what if the very things you're overlooking are quietly destroying your valuation?   In this episode of WholeCEO with Lisa G. , Lisa sits down with operator and transformation expert Mark Sims to reveal the hidden factors that separate compani...

Your top performer isn't planning to quit tomorrow. They may have already left in their mind. The most dangerous employee turnover doesn't come with complaints, dramatic exits, or warning emails. It starts with silence. Fewer ideas. Less curiosity. Just enough effort to get by. In this episode of WholeCEO, Lisa Goldenthal reveals why high performers don't quit loudly—they go quiet first. As AI res...

Most AI initiatives fail. Not because of the model. Because organizations skip the boring, essential engineering work that makes software survive contact with reality. Jake Dubin has spent 25 years building production systems, starting with neural networks that solved CAPTCHA back in 1999. He is the founder of Transcendent Software and is building CoffeeBreak, an AI platform focused on reliable hu...

What if the most important person advising your company was never on the org chart? Dennis Cagan invented the trademarked Shadow CEO® role in 1983 and has spent four decades being exactly that person for some of the most successful companies in America. With 74 boards, multiple CEO stints, including one public Unicorn, and a keynote at the very first COMDEX show in 1979, Dennis has seen every vers...

Why are so many companies investing heavily in AI yet struggling to see meaningful results? In this episode, Lisa Goldenthal reveals a hard truth: most AI initiatives do not fail because of the technology. They fail because AI exposes the hidden inefficiencies, outdated approval systems, and legacy processes that have been slowing organizations down for years. Lisa explores why AI often uncovers d...

Why do smart, well-funded companies still end up slow, stuck, and unable to execute? In this episode, Lisa Goldenthal breaks down the hidden forces that stall AI initiatives and quietly drain momentum from top-performing teams. From "permission addiction" to approval overload, she explains why organizations don't fail because of bad strategy—but because decisions move too slowly and talent stops s...

What if the very thing that helped you succeed is now holding you back? In this episode of the WholeCEO Podcast, Lisa G. sits down with entrepreneur, investor, and startup builder Safeer Qureshi to challenge one of the most common assumptions in business: that being smart is the key to success. Safeer explains why intelligence can sometimes become a founder's biggest obstacle, leading to overthink...

Most organizations think AI failures are technology failures. They're not. Companies are investing millions into AI tools, training programs, dashboards, and automation initiatives—yet many leaders are still experiencing the same bottlenecks, communication breakdowns, slow decision-making, and exhausted teams. In this episode, Lisa Goldenthal explores why AI initiatives fail even when the technolo...

Most people think building a $450 million real estate portfolio means sacrificing everything else. Family. Health. The things that actually matter. Gino Barbaro proved that wrong. 1,900 multifamily units. $450 million in assets under management. Six kids. One remarkable marriage. And a legacy he is genuinely proud of. In this episode of WholeCEO, we talk about how he built all of it — without choo...

What if the biggest obstacle to AI success inside your organization is not the technology at all?   This week on WholeCEO With Lisa G, I am joined by AI strategy advisor, author, and founder Phillip Corey Roark. With more than 25 years of experience in enterprise technology and business transformation, Phillip has built the frameworks and playbooks that help executive teams do what most AI rollout...

Most leaders think their biggest problem is delegation. But what if delegation was never the real issue? In this powerful episode, Lisa GoldenthaL breaks down why so many founders, CEOs, and senior leaders stay trapped in operational chaos even after following every leadership and productivity framework they were taught. You will discover why tasks keep boomeranging back to you, why your team stil...

What if the most important leadership skill in the age of AI has nothing to do with technology? In this episode of WholeCEO with Lisa G. , host Lisa G. sits down with globally recognized advisor Charlene Li—who has worked with 49 of the Fortune 100, spoken at the World Economic Forum, TED, and South by Southwest—to unpack what it really takes to win in an AI-driven world. Her latest book, Winning...

Most leaders think the problem is delegation. It isn't. The real issue is leadership design — and whether your business is built to scale beyond you or collapse around you. In this episode, Lisa Goldenthal breaks down a provocative idea inspired by Warren Buffett: the most powerful question isn't about money — it's about structure, control, and leverage. Because in most companies, the CEO is eithe...

MIT reports that 95% of AI projects are failing—not underperforming, not delayed, but outright failing. So, what's really going wrong? In this episode, Lisa Goldenthal cuts through the hype and exposes a hard truth: the problem isn't your technology—it's your leadership. If your organization has an "AI strategy" but isn't seeing real results, this conversation will feel uncomfortably familiar. We...

Chronic inflammation, environmental toxins, and the wrong medications are silently destroying CEO performance — and almost nobody is talking about it. Dr. Joe Nieusma is a Senior Toxicologist with 37 years of experience helping leaders reclaim their energy, clarity, and longevity from the inside out. In this episode, he reveals exactly what is eroding your performance — and the highest impact chan...

Your meetings aren't broken. They're designed to reward the wrong behavior. In this episode, Lisa Goldenthal puts a bold leadership experiment to the test: removing slide decks entirely—just like Bezos. What followed? Three people quit. Not the quiet ones—the polished performers. This conversation goes straight to the fault line inside most executive teams: Are your meetings driving real thinking…...

Your team isn't resisting change the way you think they are. In this episode of WholeCEO with Lisa G, Dr. Irena O'Brien breaks down the neuroscience behind why people fail to follow through—even when they know exactly what to do. If you've ever felt frustrated by a team that "gets it" but doesn't execute, this conversation will challenge everything you assume about motivation, accountability, and...

What if the biggest threat to your company isn't the market—but you? In this episode, Lisa Goldenthal unpacks the leadership mistake behind Steve Jobs's departure from Apple—and why it's still quietly limiting modern businesses today. If your team stalls without you, decisions keep climbing back to your desk, or growth feels heavier than it should, this conversation will hit close. At the center i...

What if the real measure of leadership isn't how indispensable you are—but how unnecessary you've made yourself? In this episode, Lisa Goldenthal challenges one of the most deeply ingrained beliefs in leadership: that being involved equals being effective. Through sharp insights and uncomfortable truths, she introduces the 48-Hour Dependency Test —a simple but revealing way to see whether your bus...

Stop posting into the void and start turning LinkedIn into a real revenue engine. In this powerful episode of the WholeCEO Podcast, Lisa G. sits down with LinkedIn expert and CEO Joe Apfelbaum to break down what actually works on LinkedIn today—and how to grow your business without losing authenticity or burning out. If you've been creating content but not seeing results, this conversation will sh...

What if being "indispensable" is the very thing holding your business back? In this episode, Lisa Goldenthal delivers a powerful wake-up call for CEOs and founders: if your business can't run without you, it's not an asset—it's a high-pressure job. Triggered by a real moment—dropping a wine barrel on her foot and immediately worrying about work—Lisa unpacks the deeper issue behind CEO dependency,...

What if the very thing that built your business… is now limiting its value? In this powerful episode, Lisa Goldenthal breaks down the hidden cost of CEO-driven growth and why grit—once your greatest strength—can become your biggest liability. If your business depends on your constant involvement to function, you don't own an asset—you own a high-pressure job. And that's exactly what investors see....

In an era defined by algorithms, automation, and "frictionless" transactions, how does a leader maintain a pulse on the human experience? In this episode, Lisa G. sits down with Mark Andrew Steiner , the visionary behind GigSalad, to discuss the delicate art of building a massive digital marketplace without sacrificing the human element. Mark shares his journey of scaling a business while protecti...