594: $2 Billion NYC Real Estate Broker on the Strategy of Homeownership
The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving
Release Date: 10/15/2025
617: Inc 5000 fastest growing company on Psychology behind leadership influence and human behavior (with MichaelAaron Flicker)
The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving
Michael explains that people often struggle because “adding and adding must be more effective,” yet humans are “more confident when just one advantage is presented.” He shares that Five Guys succeeded because they “only do burgers and fries” and that “if you say you are best at one thing most of all, they’re more likely to believe that.” He emphasizes that “buyers…have a top force-ranked prioritization of the most important thing,” and focusing on the thing you are “best in the world at” is “more believable and more memorable.” On pricing, he notes that...
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616: NYU Stern’s Prof on How AI Is Rewriting the Future of Work (with Ben Zweig)
The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving
When most executives discuss AI, they focus on automation. Dr. Ben Zweig, NYU Stern professor and CEO of Revelio Labs, explains why the real disruption isn’t machines replacing people, it’s our failure to rethink how work is structured. “Labor markets are not as sophisticated as capital markets,” Ben explains. “We allocate capital efficiently, but not labor. That’s a huge weakness in how our economy operates.” In this conversation, we explore: Why every company must learn job architecture, seeing jobs not as titles, but as bundles of tasks that must constantly evolve. The...
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615: $12B Investment Firm CEO on Saving the American Dream (with Mark Matson)
The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving
In this conversation, Mark explains that “we often build our lives on things we are certain about that simply are not true.” He describes how “we don’t actually see the world… we see screens of how we think the world is.” He explains that these screens create “a double paradox” shaping what we think is safe, what we think is risky, and how we choose to act. Mark describes the difference between someone who sees a large employer as stability versus an entrepreneur who sees it as danger, saying “which screen is right? Well, it depends on which screen is going to give you more...
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614: Why Executive Leaders Feel Lonely
The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving
Adam McGraw is a Fortune 100 VP turned entrepreneur and co-founder of a leadership community. “We try and really curate it for folks that are in the VP and above through CEOs as well, founders, etc., so that they have this kind of safe white space atmosphere to really consistently plug in and build community.” “Not just transact network-wise in things that are typically narrow and niche… we really love the idea of a melting pot for leaders.” “This is kind of the new normal: constant change, constant uncertainty, constant transition.” “Being in crew keeps me grounded and...
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613: Microsoft CTO on AI, Human Agency and the Future of Work
The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving
Technology is reshaping the world at a pace few people, inside or outside the industry, expected. But every so often, you meet someone who has not only witnessed the major waves of technological change, but helped build them. In this conversation, Marcus Fontoura, Technical Fellow and Corporate Vice President at Microsoft, CTO for Azure Core, walks us through the story of AI, what leaders are getting wrong, and how to develop the one thing that will matter more than any model or algorithm: human agency. Marcus has lived through every major inflection point: early search, the rise of cloud...
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612: How to Have More Hope with Dr. Julia Garcia
The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving
In this episode, Dr. Julia Garcia explains why hope is a habit and why it is critical for us to remove what blocks hope. She describes what happens inside teams when leaders lose hope, including “the culture that creates, the burnout that leads to, the discouragement and defeat.” Julia shows how unprocessed emotions drain leaders even when they appear high-functioning. “If we emotionally feel disconnected, we’re going to start looking elsewhere or we’re going to end up in a place of hopelessness where maybe we completely shut down in our career and now we’re just a robot.” One of...
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611: Former U.S. Intelligence Officer on AI, Leadership, and Thinking Like a Spy (with Anthony Vinci)
The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving
In this conversation, Anthony Vinci explains that “AI is going to be able to do more and more of what people do.” He describes a future where “AI is going to get better and better at doing what people do,” and highlights that leaders must understand “how do you figure out what AI is good at and then implement it to do that” and “how do you manage your workforce so that they are able to partner with that AI.” He warns that leaders often “overestimate what AI can do and underestimate it at the same time,” and stresses the importance of “getting that balance right.” As he...
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610: Cas Holman on Play, Creativity, and the Future of Work
The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving
When was the last time you played, really played? For Cas Holman, founder and chief designer of Heroes Will Rise and star of Netflix’s Abstract: The Art of Design, play isn’t childish. It’s the foundation of human creativity, resilience, and connection. She worked with LEGO, Disney Imagineering, and the LEGO Foundation and on a mission to help adults rediscover what children know instinctively: that play is how we learn, adapt, and feel alive. “Play isn’t what happens after work,” Cas explains. “It’s how we manage uncertainty. It’s how we cope, experiment, and find our way...
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609: UCLA Professor and MD on How Gravity Shapes Your Health and Mind
The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving
Dr. Brennan Spiegel, Director of Health Services Research at Cedars-Sinai and Professor of Medicine and Public Health at UCLA, author of the book Pull, explains why illness is often a failure to manage gravity. He describes how our relationship with gravity defines strength, balance, digestion, mental stability, and emotional health. Take the Gravotype Quiz at to identify how your body manages gravity. Key Insights and Action Steps — Dr. Brennan Spiegel “Every single cell of your body evolved from this force of gravity. Physics came first, and biology came second.” Illness arises...
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608: Harvard Professor and former CEO of Medtronic, Bill George, on How Leaders Should Manage Challenging Times
The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving
Bill George, former CEO of Medtronic and Harvard Business School Executive Fellow, explains how leaders can stay grounded, principled, and effective in chaotic times. “It’s a world of chaos and it requires a very different kind of leader than in more stable times.” The skills that once mattered (process control, long-term plans) are now secondary to courage, self-awareness, and moral clarity. George says most executives still lead comfortably “inside the walls” but fear the external world (media, public scrutiny, and rapid change). “Today, if you’re a leader, you are a public...
info_outlineScott Harris, a New York City real estate broker with more than $2 billion in career sales and author of The Pursuit of Home, reframes buying and selling property as an emotional journey—“a place where life is happening for you”—that requires the same discipline leaders apply to strategy, systems, and people. Drawing on two decades of high-volume practice, he shows how clarity, structure, and empathy turn one of life’s biggest financial decisions into a more deliberate, rewarding process.
Key insights and practical lessons:
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Hire with intent. “Take the time to hire a real estate agent that speaks their language… so they feel seen and heard.” The right agent is not a transaction cost but a guide to psychological clarity.
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Use offers as diagnostics. “When you make an offer… your body says, ‘Oh my God, I’m so nervous. I love this place.’ That’s the truth.” Even small commitments reveal what a buyer truly values.
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Design systems around strengths. Harris explains how scaling from solo agent to top-producing team required separating client-facing judgment from operations, codifying SOPs, and hiring for execution.
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Lead through service during downturns. In crises such as COVID-19, Harris focused on community logistics and donation drives rather than retreating, actions that “added tons of value” and built long-term trust.
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Read the market, not the myth. Buyers err by “negotiating as if real estate were their industry,” while sellers overvalue personal attachment. Both sides win with rigorous market framing and honest prep.
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Match investments to capacity. Real estate, Harris reminds, “is not a get-rich-quick scheme.” Choose asset types (short-term rentals, LP stakes, or diversified funds) based on desired involvement and risk.
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Protect personal capacity. Sustained performance comes from “daily meditation, consistent exercise, and the accountability of a coach.”
For executives managing high-stakes transactions or scaling service businesses, this conversation offers a pragmatic playbook: clarify who adds value, create low-risk tests that expose real preferences, and build repeatable systems that keep human judgment at the center of growth.
📚 Get Scott’s book, The Pursuit of Home, here: https://shorturl.at/9YwXv
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