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In this episode, Gevorg Shahbazyan shares a story shaped by rejection, resilience, and relentless ambition. Despite earning a master’s degree, speaking multiple languages, and completing internships in Washington D.C., he was rejected by nearly 60 employers before pivoting into real estate. One of the most defining moments in his journey came after closing a major deal early in his career - instead of maximizing his own commission, he voluntarily offered his broker a larger share than expected. That act of fairness earned deep trust and mentorship, accelerating his growth dramatically. Rather than becoming comfortable once the commissions started flowing, Gevorg dreamt bigger, teaching himself development from scratch and eventually building Starlife Group into one of the world’s top 100 development companies with over 2,000 units and 5 million square feet under development.

The conversation also explored his philosophy around risk, leadership, and lifelong learning. Gevorg spoke about constantly choosing growth over comfort - from walking construction sites to learn development firsthand to later joining Harvard’s AMDP and OPM programs to continue evolving as a leader. He emphasized the importance of optionality in business, strong capitalization, surrounding yourself with exceptional people, and never becoming complacent. More than anything, his story reflected the belief that persistence matters most: when life feels like walking through fire, the only way out is to keep moving forward.

Here are the Top 10 Takeaways from the conversation:

1. Rejection doesn’t define your ceiling - Gevorg was rejected by nearly 60 employers before finding his path in entrepreneurship.
2. Long-term trust matters more than short-term gain - offering his broker a larger commission share created a mentorship that changed his life.
3. Mentorship compresses time - the right mentor can teach you in years what may otherwise take decades to learn.
4. Don’t become comfortable too early - even after earning significant commissions, he pushed himself toward bigger goals.
5. Curiosity compounds - Gevorg taught himself development by studying projects, reading extensively, and walking construction sites.
6. Success is about optionality - every real estate project he takes on has multiple exit strategies to reduce risk.
7. Strong businesses are built conservatively - he emphasized high equity positions and disciplined financing over excessive leverage.
8. Exceptional talent is worth paying for - he believes great people create disproportionate value inside an organization.
9. Lifelong learning is a competitive advantage - despite major success, he continues investing in programs like Harvard AMDP and OPM.
10. Persistence is everything - his advice to his younger self: “Never give up. If you’re walking through fire, keep walking.”

Books:

• The 38 Letters from J.D. Rockefeller to His Son 
• The Art of War 
• The Prince 
• Why Nations Fail

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This conversation with Caio Zapata was particularly refreshing because it blended entrepreneurship with deep introspection and philosophy. Beyond discussing business growth and leadership, Caio spoke thoughtfully about freedom, gratitude, adventure, and personal growth. His reflections on purpose being tied to independence, and his belief that happiness is often the outcome of pursuing adventure, stood out as especially meaningful perspectives.

Caio shared his journey from growing up in a fourth-generation Mexican family business to becoming the solo founder of Enestas, an infrastructure and logistics company focused on fuels and raw materials. In 2016, he made the difficult decision to leave the security of the family business and commit fully to building Enestas from scratch. He spoke candidly about the loneliness of being a solo founder, the uncertainty and failures encountered early on, and the discipline required to scale a business sustainably.

A particularly compelling aspect of the conversation was Caio’s approach to self-education. Despite coming from an engineering background, he deliberately studied marketing, sales, compensation, finance, leadership, and organizational behavior through books and continuous learning. His philosophy was clear: entrepreneurs cannot effectively lead areas they do not understand at a foundational level.

Caio also reflected on how his definition of success has evolved over time. Earlier in life, success may have been associated more with achievement or growth, but today he views it primarily as independence: the ability to control one’s time, choose meaningful work, and pursue life intentionally. 

Here are the Top 10 Takeaways from the conversation:

1. Success means independence: Success was defined not as wealth alone, but as freedom, owning one’s time and choosing one’s path.
2. Adventure creates happiness: Human beings are built for adventure and challenge, and happiness often emerges as the result of meaningful pursuit.
3. Gratitude brings presence: One of the strongest reflections was the importance of appreciating the present moment rather than constantly chasing the next milestone.
4. Passion can be developed through work: Passion for LNG was not immediate, but developed through immersion, learning, and experience.
5. Trust is foundational in business: In infrastructure and fuels, reliability and trust are critical because customers depend on uninterrupted operations.
6. Continuous self-education is essential: Leadership growth came through intentionally learning every major business discipline.
7. Solo entrepreneurship is rewarding but lonely: Building alone offers freedom, but also comes with emotional isolation and decision-making pressure.
8. Growth without discipline can destroy companies: Rapid expansion without budgeting and operational discipline can become dangerous for a business.
9. Hire people who challenge you honestly: One of the most valuable leadership lessons was the importance of surrounding oneself with truth-tellers rather than people who simply agree.
10. OPM reinforced strategic thinking through “adjacencies”: A major takeaway from Harvard Business School’s OPM program was learning how to expand intelligently into related business opportunities.

Books:

• 12 Rules for Life 
• The Art of Spending Money 
• Work Rules! 
• The 1-Page Marketing Plan

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In this episode, Marc Goldberg and Christine Carville share their journey from individual entrepreneurial paths to co-founding Resilience Lab and now leading at Cerebral. Christine’s career evolved from early entrepreneurship into clinical psychology, while Marc brought deep experience in software and systems thinking. Together, they saw an opportunity to fix a fragmented mental health system by scaling clinician training and introducing a data-driven standard of care.

They built Resilience Lab on the belief that mental health outcomes could be improved through measurement-informed care and AI, well before AI became mainstream. Their model focused on training early-career clinicians at scale (700+ trained) and using data to enhance treatment, despite regulatory hurdles and cultural resistance within the field. Following the acquisition by Cerebral, they are now scaling this vision further, supporting 500+ clinicians and reaching networks covering 100M+ lives.

The conversation also explores their unique experience as a married couple building a company and attending HBS OPM together. They reflect on how the program added structure, rigor, and global perspective to their leadership. The episode closes with insights on resilience, continuous learning, and the importance of simply showing up, even when most efforts fail.

 Here are the Top 10 Takeaways from the conversation:

1. Entrepreneurship Can Start from Necessity: Christine’s first company came from needing a job - action often precedes clarity.
2. Reinvention Is a Superpower: Her pivot into clinical psychology shows it’s never too late to build domain expertise.
3. Big Opportunities Hide in Broken Systems: Marc targeted healthcare because it’s massive, inefficient, and lacks standardization.
4. Mental Health Is Human, but Can Be Systematized: While therapy is deeply personal, training + data can scale quality.
5. They Bet on Data Before AI Was Popular: Their early conviction: better data leads to better care.
6. Owning the Tech Stack Matters: Building their own systems enabled innovation and control over outcomes.
7. Regulation Is a Double-Edged Sword: It protects patients but slows innovation and scalability.
8. Working as a Couple Requires Clear Roles: They invested in coaching early to define lanes and avoid conflict.
9. HBS OPM Accelerates Leadership Growth: It gave Christine frameworks and Marc a rare space to learn and reflect.
10. Success = Showing Up Consistently: Marc’s philosophy: most attempts fail, but persistence compounds into results.

Books:

• Unleashed
• Move Fast & Fix Things
• Scaling People

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Isa Lorenzo’s story is anchored in three powerful ideas: stay endlessly curious, view failure as timing rather than defeat, and continually rediscover your purpose. She believes curiosity has been the driving force of her life, pushing her to explore new paths, while failure. like her Singapore gallery experience, was not an endpoint but a learning phase that opened new opportunities. Her journey reflects a constant return to purpose, asking not just what she does, but why she does it.

Her career began in medicine, shaped by family expectations and academic strength at the University of the Philippines College of Medicine. But during clinical training, she realized patient care did not fulfill her, and a personal tragedy, the loss of her father, became a turning point. With his encouragement to pursue her passion, she completed her degree, became board-certified, and then made the bold decision to retire from medicine.

She moved to New York to immerse herself in the art world, studying at Parsons and working in galleries before founding Silverlens in Manila in 2004. Over the past two decades, she has built a globally recognized gallery representing Filipino, Southeast Asian, and Asian diaspora artists, with locations now in Manila and New York. Her work is deeply relationship-driven, focused on placing artists into global conversations and institutional collections.

Her experience at HBS OPM further shaped her thinking, particularly around hiring exceptional talent, clarifying purpose, and exploring new business models beyond traditional art sales. Ultimately, Isa’s journey is one of courage, structure, and reinvention - proof that taking risks, staying curious, and embracing uncertainty can lead to meaningful impact.

Here are the Top 10 Takeaways from the conversation:

1. Curiosity is the central driver of Isa’s life. She actively seeks answers and new paths.
2. Failure is not final; it often reflects timing and can create new opportunities.
3. Purpose evolves, regularly revisiting “why” is essential to long-term fulfillment.
4. She pursued medicine due to expectations but discovered it wasn’t her true calling.
5. A pivotal moment came when her father encouraged her to follow her passion.
6. She finished medical school for security, then retired immediately after becoming board-certified.
7. Her medical training still shapes her structured, disciplined approach to business.
8. Silverlens focuses on long-term relationships and global placement of artists, not just transactions.
9. HBS OPM taught her to hire overqualified talent and think more strategically about business.
10. Her advice: enjoy life more, take risks, and remember that success often comes from simply trying.

 Books: How to Hide an Empire

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A defining moment in Elie Nour’s journey came from attending the Berkshire Hathaway Annual Shareholders Meeting, where he met Warren Buffett and Bill Gates. That experience shaped two core beliefs: humility at the highest levels of wealth and the principle that “cash is king.” These lessons proved critical during the 2008 financial crisis, helping him avoid major losses while positioning him to invest in high-quality assets at discounted prices.

Elie shares his journey from immigrating from Lebanon to Canada, studying at McGill, and building a career in wealth management before launching his own firm in 2013 to gain flexibility and better serve clients. His philosophy centers on capital preservation, disciplined investing, and building the right tax and estate structures before pursuing returns.

He challenges the misconception that wealthy individuals take more risks, explaining instead that they are highly selective, focused on calculated decisions, and committed to long-term wealth preservation across generations

He highlights how technology and AI have transformed investing, allowing analysis of tens of thousands of companies and thousands of data points while stressing that human judgment remains essential. A strong advocate of continuous learning, he credits reading, surrounding himself with capable people, and programs like Harvard Business School’s OPM for helping him scale further.

The conversation closes with a key reflection: mistakes are the most powerful teachers, and embracing them early accelerates both personal and professional growth.

Here are the Top 10 Takeaways from the conversation:

1. “Cash is king” is more than a phrase, it’s a strategy.  Liquidity creates the ability to survive downturns and capitalize on rare opportunities.
2. The wealthy focus on not losing, not just winning. Capital preservation is always the first priority, with growth coming second.
3. Risk is deliberate and deeply understood. Investments are only made after thorough analysis or with the help of trusted experts.
4. Wealth requires structure, not just returns. Tax planning, estate design, and legal frameworks are essential to long-term outcomes.
5. Scale increases the cost of mistakes. At high levels of wealth, even small errors can have outsized consequences.
6. Data-driven investing is the new standard. Screening ~70,000 companies and thousands of data points enables sharper decisions.
7. AI boosts efficiency, but humans make the call. Technology accelerates analysis, but judgment, experience, and discipline remain irreplaceable.
8. Entrepreneurship demands adaptability. Building independently allows flexibility and innovation beyond traditional institutions.
9. Great teams outperform individuals. Success comes from surrounding yourself with capable people and trusting their expertise.
10. Mistakes are the ultimate learning advantage. Early failures teach more than success and are critical for long-term growth.

Books: The Intelligent Investor

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Caroline Elkins is a Pulitzer Prize–winning author and one of the world’s leading historians on empire, power, and institutions.

We explored a central question: How should leaders think when the world order is changing?

A few themes stood out.

We’re not in a temporary moment of instability, we’re in the middle of a structural shift. The global system that business leaders have relied on for decades - predictable, rules-based, and increasingly globalized is evolving into something far more complex and fragmented.

Through her lens of history, Caroline emphasizes that history doesn’t repeat itself, but it rhymes. Today’s world echoes moments like the interwar period when power was shifting, leadership was uncertain, and global coordination weakened. But unlike the past, this transition is unfolding alongside massive technological disruption, from AI to semiconductor supply chains, making outcomes far less predictable.

The conversation also touched on the rise of China, the long-term potential of India, and the relative decline of the U.S. The future is increasingly multipolar, with no single country fully shaping the global order.

One of the most striking insights: globalization isn’t ending, it’s being reconfigured. Supply chains, alliances, and trade flows are changing shape, not disappearing. Nowhere is this more evident than in semiconductors, where national security, industrial policy, and global dependence intersect.

For leaders, the implication is clear: This is not a time to optimize for efficiency alone. It’s a time to build resilience, think in scenarios, and prepare for second- and third-order effects, especially as geopolitical tensions reshape energy, markets, and supply chains.

Perhaps the biggest mindset shift: The world isn’t necessarily becoming worse, it’s becoming different.
And those who adapt early will be best positioned to navigate what comes next.

Here are the Top 10 Takeaways from the conversation:

1. This is a structural shift, not a cycle. Global power and economic systems are being fundamentally reconfigured.
2. History “rhymes” most during transitions. Today resembles the interwar period of uncertain leadership and shifting power.
3. The U.S. is in relative decline. Not collapse, but losing uncontested dominance across innovation and geopolitics.
4. The future is multipolar. China’s rise and India’s emergence are reshaping global balance.
5. Globalization is evolving, not ending. Expect regional blocs, new alliances, and reconfigured trade flows.
6. Technology is reshaping power dynamics. AI, semiconductors, and digital infrastructure are central to economic and national security.
7. Semiconductor supply chains are strategic battlegrounds. Dependence on regions like Taiwan highlights vulnerabilities and is driving major policy shifts globally.
8. State vs. market models are back in focus. Governments are playing a larger role in driving innovation and industrial policy.
9. Conflict has deep ripple effects. Wars create long-term disruptions across energy, inflation, and global supply chains.
10. Resilience > efficiency. Scenario planning, risk mapping, and long-term thinking are now essential for leaders.

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How many of us can genuinely reinvent our skill set as our business demands it? From Wall Street finance to hands-on real estate investing, and now to building AI-powered technology, Sherry Li has done exactly that. But what makes her evolution truly remarkable isn't just the range of skills she's acquired, it's that each chapter was driven by following the problem deeper, not chasing the next shiny opportunity.

It started with finance. Her 10 years on Wall Street gave her the capital allocation and investment lens to identify real estate as a compelling opportunity. Then came C-STAR, where she got her hands dirty actually owning and managing over 400 single-family rental units across four funds and discovered firsthand that property management was broken. Repairs dragged. Timelines slipped. Costs ballooned. She didn't just observe the pain; she lived it. And so she built PaiBox, an AI-powered home repair automation platform, as a natural answer to a problem she understood at every layer. Then, rather than chasing AI as a trend, she pulled agentic intelligence into PaiBox because it was precisely the right tool for the workflow automation challenge she had already spent years defining.

Each stage unlocking a deeper understanding of the same core challenge, with Sherry building into that understanding rather than moving sideways for growth's sake.

Here are the Top 10 Takeaways from the conversation:

1. Pain is the best product inspiration. PaiBox was born directly from Sherry's own frustrations managing repairs, rehabs, delays, and cost overruns across her portfolio, a classic "build what you need" founding story.
2. Corporate experience is a launchpad, not a trap. Sherry spent 10 years on Wall Street intentionally, accumulating the financial, macro, and strategic skills she knew she'd need before going out on her own.
3. Field experience humbles and sharpens you. Moving from spreadsheets to talking to tenants about leaky pipes gave her a grounded understanding of real-world problems that pure financial modeling never could.
4. Don't lose money first. Her core advice to her younger self: you don't need spectacular returns out of the gate, but losing capital early destroys trust and kills future fundraising. 
5. Scale before you hire. Building a team too early is a trap. She waited until she had enough properties in a market (50–100 units) to justify a full-time hire, using third parties in the interim.
6. AI should enable trust, not replace it. Her philosophy with PaiBox is clear: automation handles coordination and transparency, but human relationships, especially with tenants, are what drive a 99% collection rate.
7. Culture is an operational asset. She deliberately built an internal culture around results, integrity, transparency, and enabling teammates rather than competing with them and credits this for her team's performance.
8. Be pulled by curiosity, not pushed by pressure. When asked how she moves fluidly across finance, real estate, and AI, she said she doesn't jump between fields, she's drawn to what's worth exploring.
9. Networks compound. The most valuable part of HBS's OPM program for her wasn't the curriculum alone. It was the global peer network, the diverse perspectives, and the exposure to how others think and operate.
10. Integration beats balance. She doesn't separate music, work, and life. She sees them as a cohesion that enriches everything. Her identity as a pianist and entrepreneur aren't in tension; they fuel each other.

 Books: AI Superpowers

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Working with Linda Miklas, my executive coach during the OPM program at Harvard Business School, was one of the most formative experiences in how I think about leadership.

In this conversation, we go beyond frameworks and into the lived reality of leadership under pressure. Linda brings over 30 years of experience coaching senior executives, founders, and CEOs through moments of transition when stakes are high, roles are expanding, and internal clarity often lags behind external expectations.

What stands out in her perspective is not complexity, but simplicity applied at depth: leadership challenges are rarely about intelligence or intent. They are about clarity, communication, execution, and self-awareness. Through stories and patterns drawn from thousands of coaching conversations, she explains how leaders evolve as they scale, and why their greatest strengths often become their most subtle constraints.

We also explore the quieter side of leadership that is rarely discussed openly: the loneliness of decision-making, the constant recalibration of pace and passion, and the internal doubt that even highly successful leaders carry into new environments. Ultimately, the conversation returns to a central idea: leadership is not defined in moments of ease, but in how you show up when things are uncertain, unexpected, or uncomfortable.

Here are the Top 10 Takeaways from the conversation:

• Executive coaching provides a rare, judgment-free space for leaders to think, reflect, and gain clarity under pressure.
• The most valuable coaching moments often come from simply articulating thoughts out loud and hearing them clearly for the first time.
• Speed and passion are double-edged strengths, they create momentum but can distort judgment when uncalibrated.
• Leadership effectiveness consistently depends on three pillars: clarity, communication, and execution.
• One of the most common blind spots is when leaders assume alignment instead of explicitly communicating direction and expectations.
• As leaders scale, the capabilities that once made them successful must evolve to match new levels of complexity.
• The strongest leaders are defined less by confidence and more by curiosity and self-awareness in unfamiliar situations.
• Leadership can feel deeply isolating, making trusted reflective relationships essential for sustained performance.
• Even highly accomplished leaders experience moments of doubt when stepping into new or high-stakes roles.
• True leadership character is revealed in unexpected moments - crisis, failure, or sudden success when instinct replaces preparation.

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Judy Liu begins with an unexpected insight: her thinking today is deeply influenced by Buddhist philosophy and introspection, which help her navigate leadership, ego, and the different roles she plays across life. From that foundation, she shares how she built her career at the intersection of technology, luxury, and China, spotting early shifts during the rise of mobile internet and platforms like WeChat. 

She walks through founding CuriosityChina, adapting its business model to market realities, and scaling it to serve 100+ global luxury brands before its acquisition by Farfetch. At Farfetch, she grew the Asia Pacific business to over $1B by focusing on deep localization, strong customer insight, and disciplined unit economics, especially controlling cost of sale. Throughout the conversation, Judy emphasizes boldness, curiosity, and continuous self-reflection as the foundations of building enduring businesses and meaningful lives.

Here are the Top 10 Takeaways from the conversation:

1. Build your advantage by working at the intersection of multiple disciplines rather than staying in one lane.
2. Pay close attention to early shifts in technology and consumer behavior, and act on them before they become obvious.
3. Stay flexible and be willing to change your business model when reality doesn’t match your original plan.
4. Deeply understand both your product and your customer to create a meaningful competitive edge.
5. In fast-changing environments, speed and adaptability matter more than perfect planning.
6. When making big decisions, prioritize long-term alignment and values over short-term gains.
7. In negotiations, having a strong alternative gives you clarity, confidence, and leverage.
8. Always ground your strategy in clear unit economics and simple business fundamentals.
9. To win in new markets, adapt your product to local needs rather than copying what worked elsewhere.
10. Sustainable growth comes from balancing expansion with disciplined cost control.

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When you compete on a global stage for Entrepreneur of the Year and lose to Narayana Murthy, you don’t just come back with a trophy or a ranking - you come back with perspective.

That experience shaped how Pàdraig O Céidigh thinks about entrepreneurship, success, and life. What struck him most was not business scale or wealth, but Murthy’s humility, spirituality, discipline, and belief in helping other people grow. It raised a bigger question: What actually makes a great entrepreneur   and more importantly, what makes a great life?

This conversation is less about building companies and more about building a life of purpose, awareness, resilience, and good decisions.

Pàdraig shares how he grew up in a working-class family where two values shaped everything he later became: hard work and integrity. Over time he became an accountant, lawyer, airline founder, entrepreneur of the year, senator, professor, and author - but he emphasizes that titles and success are not the most important things. The real lessons came from failure, setbacks, stress, betrayal, and difficult decisions.

One of his strongest beliefs is that the biggest waste of time in life is feeling sorry for yourself. Entrepreneurs fall off the horse many times - the difference is that they get back on again.

One idea that deeply influenced him came from Harvard Business School, where a professor asked a question he never forgot:
 “What is the world with you versus the world without you?”
He believes this is not just a business strategy question - it is a life question. Each person should try to leave the world better than they found it.

The conversation then moves into wisdom and decision-making. After running an airline for 26 years with hundreds of flights per week and no accidents, he realized something important: the quality of your life is largely the quality of your decisions. This realization eventually led him to write The Purposeful Decision Maker.

Another major theme is the difference between success and happiness. Many successful people are not happy, and many happy people are not successful by society’s definition. Happiness, he argues, comes from gratitude, contentment, awareness, and not comparing yourself to others.

He also shares one of the hardest lessons of his life: business problems rarely broke him — people he trusted who betrayed him caused the most stress and nearly cost him his life. If he could advise his younger self, he would learn earlier how to recognize difficult people and avoid them.

Overall, this conversation is really about awareness, resilience, decision-making, success vs happiness, and living a purposeful life - not just building businesses, but building a meaningful life.

Here are the Top 10 Takeaways from the conversation:

1. Losing to great people teaches you more than winning. 
2. Hard work and integrity are long-term advantages. 
3. Failure is inevitable - self-pity is optional. 
4. The most important education is understanding yourself. 
5. Ask yourself: What is the world with me versus the world without me? 
6. Decision-making is one of the most important skills in life. 
7. Success and happiness are not the same thing. 
8. Gratitude and contentment matter more than comparison. 
9. People problems are often harder than business problems. 
10. Awareness is the foundation of wisdom. 

 Books:

• Give and Take 
• Snakes in Suits