Minimal Regrets, Maximum Purpose

Charlie Munger lived to 99, still respected for his wisdom. His approach: identify the biggest mistakes and worst-case outcomes—then avoid them. In contrast, Steve Jobs, though arguably more impactful, likely passed with more regrets.

So far, minimal regrets. The focus now shifts from chasing success to:

• Mind & Body – Physical and mental well-being are intertwined; neglecting either is giving up on life.

• Family & Friends – Relationships define fulfillment. Investing in the next two generations is now a priority; today’s 10 kids will grow into a clan of 80+.

• Earned Success – Like happiness, success is fleeting. Managing expectations and being present prevents common regrets.

• Service – With age comes a shift from self-interest to meaningful contribution.

True fulfillment lies in devoting energy and resources to others.

These priorities align with launching the Foundation this year, focusing on innovation, entrepreneurship, and leadership development. Success addiction and hyper-competitiveness may not fade, but they can be redirected. The next decade’s earned success will come from mastering the roles of Investor & Educator—investing in hopes and dreams.

Final lesson: Find joy in the present, let go of the chase for future validation. Tomorrow will take care of itself if today is well-lived.

It used to be keeping up with the Joneses, now it’s keeping up with the Kardashians.

Envy is a dark passenger. Social media magnifies one of the most problematic human emotions, giving it an ever-present form.

Recent studies, including one from the NIH, have indicated a strong correlation between phone usage and social media with higher rates of suicidal ideation. Curated highlight reels of how everyone else is seemingly happier and living in a rosy world form a distorted mirror for the hapless person, spiraling deeper and deeper into despair.

Envy: Nothing’s Ever Enough

Take the story of Bernie Madoff, the man who out-Ponzi’d Ponzi and destroyed countless lives, including his own. Before starting his massive scam, Madoff was a pivotal figure in NASDAQ, earning over $20 million a year. Yet somehow, that wasn’t enough—compared to the ever-expanding lists of wealth and status.

Or consider Rajat Gupta, who came from the streets of Calcutta to become the first foreign-born Managing Director at McKinsey. By all accounts, Gupta achieved astounding feats in corporate America, with many zeros after his name. Yet the pursuit of one more zero became such an obsession that he risked decades of reputation and success, engaging in insider trading, which ultimately led to felony convictions.

It’s probably written into human DNA: envy can help us stay motivated and survive. But in excess, and when left unchecked, it invites misery.

The surest route to misery in life is to be driven by envy.

Mirror, mirror, on the wall…

Stop Following Your Passion—Follow Your Talents

I used to subscribe to the “follow your passion” mantra, but after decades of reflection, I’ve realized it’s misguided advice for most people. Passion is fleeting—it comes and goes, and many don’t even know what their true passion is, especially with limited life experience. Before Steve Jobs found his passion in designing iPhones and Macs, he was passionate about fruit diets, barefoot walking, calligraphy, being a contrarian, and hacking long-distance calls. His real breakthrough came when he discovered his talent for salesmanship and his ability to create a “Reality Distortion Field”—convincing others that the impossible was possible. His passion wasn’t a starting point; it emerged from assembling and applying his talents.

“The key is to figure out what you can do that others can’t or aren’t willing to do—a collection of advantages and tolerances.” Writers like Scott Galloway and Morgan Housel have argued convincingly that talent should take precedence over passion. Human existence operates on supply and demand—ignoring this reality leads to struggle. Success comes from identifying and developing talents that are in high demand but low supply. When mastered and recognized, talents can evolve into passion. Talent + focus = mastery, and mastery often leads to passion, not the other way around.

Looking back, my strengths lie in resilience, focus, and pain tolerance—likely on an average intellect curve. Cultivating both innate and learned talents is the optimal path, and if those talents align with market demand, passion naturally follows. Starting with passion as a career direction is like attempting to climb Mount Everest without training or tools—a fool’s errand for most. Occasionally, an outlier succeeds in perfectly aligning passion with career, but statistically, it’s a long shot not worth betting on.

Give and Take V.2

On track for a $150K loss tied to the migrant crisis—just one fallout of failed state policies. A tough lesson, but a necessary one.
That said, humanity will endure because kind and generous people exist. With age comes a bit of wisdom, and with that, a shift in focus: becoming a net contributor to building a better future.
This year marks the beginning of a committed philanthropic effort—supporting four students, with plans to double that number each year. The goal: 100+ scholars by 2030. One of them, Ashley from the Philippines, recently sent a note:
“Greetings, Sir Leo. I just want to say thank you for the scholarship. I really appreciate this opportunity.”
The mission is simple—give opportunity to the driven few who will make the most of it. A small percentage of people have the vision and resilience to challenge the status quo, but many flicker out without support.
This is a work in progress: making a dent in the universe by building a launchpad for new talent. Moving forward, the focus sharpens—expanding efforts in medicine, performing arts, and entrepreneurship. The goal isn’t just giving back but embedding giving into the very fabric of business growth. 

Immigrant-Centric REIT: A High-Growth Investment Strategy

Thesis: Immigrant communities tend to generate above-average economic activity. By strategically investing in these areas, a specialized REIT can achieve superior market returns. Consolidating supply lines within these communities also presents unique advantages—H-Mart, for example, has successfully leveraged this model. Aligning shareholder interests with venture projects they understand creates opportunities for outperformance.

A public REIT offers greater transparency and regulatory compliance than traditional syndications, providing investors with clearer insights and reducing risk. Sam Zell revolutionized real estate investment by enhancing liquidity through public markets and pioneering modern REIT structures. Applying similar principles, this REIT would focus on local-level development and cash-flow businesses, using real-time, ground-level data to drive investment decisions.

The REIT could form joint ventures with promising local businesses, scaling them into dominant players with strong competitive moats. For example, McDonald’s is primarily a real estate company that happens to operate a world-class retail brand. Similarly, real estate investment should follow the flow of people and capital—growth areas almost always outperform. Success lies in identifying durable trends, investing early, and exiting before saturation (see Austin as a cautionary example).

By leveraging demographic shifts, supply chain integration, and local market intelligence, an immigrant-focused REIT could unlock untapped value in high-growth communities while offering investors a structured, scalable, and transparent vehicle for real estate investment.

Post-Mortem 2025+: Ignoring Two Glaring Issues—The Economy and Immigration

The economy is in a dire state for half the country. While it remains strong for those who own assets or have skills aligned with the modern economy, the other half is in a downward spiral. Pointing to positive metrics—such as low unemployment, rising home values, and a strong stock market—only worsens the disconnect when those numbers don’t reflect the lived reality of millions.

On immigration, open-border policies proved to be a critical misstep, leading to a widespread erosion of public support—even among immigrants. A far more strategic approach would have been to clear the decades-long backlog of existing immigration applications rather than allowing uncontrolled entry.

Ultimately, these two issues alone were enough to push the majority toward seeking change. The political sweep was the inevitable consequence of leaders remaining in an echo chamber, only listening to voices that reinforced their views while ignoring mounting frustrations from the broader population.

Teen Work Makes the Dream Work

A recent survey of hiring managers on Gen Z new hires raised some concerning points. My take—backed by our internal data—is that much of it likely stems from a lack of basic exposure to work environments.

Anyone who came of age before Y2K was in a peer group where after-school or summer jobs were the norm. Half of their friends held some sort of job, gaining early exposure to managers, customers, and workplace expectations. That experience built resilience in ways today’s younger workforce may be missing.

Adam Grant’s recent op-ed highlighted a trend among college students: many now expect an A for effort and a B for showing up, regardless of actual performance. This mindset reflects a broader shift in the education system—where K-12 students aren’t adequately challenged, and in higher education, adjuncts and TAs (with little career stability) hesitate to push students too hard for fear of job risks. The result? New grads who need mental health days because of tough bosses, rude customers, or everyday personal crises.

Building resilience—anti-fragility (a topic for later)—comes from exposure to small, manageable difficulties. Just as vaccines introduce controlled doses of germs to build immunity or workouts tear muscle fibers to make them stronger, early work experience develops critical life skills.

So, should teens take fast food or cashier jobs? It depends. But here’s a rule of thumb: a kid who avoids challenges at 15 likely won’t embrace them at 25—and by 35, they may have completely given up on doing hard things. If a child refuses all challenges, it’s likely a failure of parenting.

Biologically, a parent’s primary instinct is to ensure their offspring survive and thrive—this principle holds across species. In fact, declining birth rates (another topic for later) can be understood through this framework: animals instinctively have fewer offspring under stress.

The surest path to weakness is avoiding hard things. So, why would anyone choose the harder path when an easier one is right there? Because they want to be special—and they’re willing to pay the price, decade after decade, to get there.

Philosophy on Modern Masculinity: Becoming a Man of Value

Part 1: Build Competence, Radiate Usefulness, Amass Goodwill

A man’s standing in society is largely determined by his perceived usefulness. Before anything else—status, relationships, or respect—his utility score is assessed. A man without value becomes invisible at best and actively avoided at worst, often left dependent on the kindness of others.

Competence and goodwill serve as the foundation for building meaningful relationships. When men feel obsolete, they deteriorate—mentally, physically, and socially. Fortunately, human civilization has embedded reciprocity into our consciousness. Those who contribute meaningfully in their prime can accumulate goodwill that acts as a support system in their later years.

Part 2: Parlay Goodwill into Meaningful Relationships

A fulfilling life for men is one of continuous effort—building, cultivating, and contributing. It’s encoded in our biology. To abandon this drive is to risk irrelevance, isolation, and decline. The modern 躺平 (lying flat) movement, where people disengage due to perceived futility, is a direct path to depression.

When faced with insurmountable odds, the wise move isn’t to give up but to pivot—to find a different game or arena where progress is possible. The desire for respect and significance has remained constant from ancient times to today. The path to achieving it remains unchanged:

1. Climb the competence ladder.

2. Signal value.

3. Invest in relationships that matter.

In the end, masculinity is about staying in the game—evolving, adapting, and continuing to build. Winter is always coming, but preparation makes all the difference.

Play the Long-Term Game with Long-Term People

Many conflicts arise because people treat relationships and interactions like a single-round, zero-sum game, where each party tries to optimize their own gain at the expense of the other. This leads to adversarial tactics.

However, the key to better outcomes is to think long-term and view interactions as multi-stage games where reputation and cooperation matter. In this approach, decisions are spaced out over time, and past actions influence future behavior. As players become aware of each other’s actions, they move toward more cooperative strategies.

For example, Costco has built a reputation for great customer service, even though some people abuse its return policy. However, Costco’s long-term strategy of prioritizing customer satisfaction pays off in the form of loyal, sustainable customers. They do track repeat offenders and drop members who engage in adversarial behavior.

In the investment world, Berkshire Hathaway plays long-term games. Instead of focusing on short-term gains, they focus on multi-stage deals that ensure mutual, long-term benefits for all parties. Contrast this with the behavior of investment banking or IPO dealmakers, who often optimize for one-time profits with little regard for the long-term success of the business.

By framing life as a multi-decade game, we make better choices, especially when collaborating with people who are also in it for the long haul. In a long-term game, the incentive is cooperation, mutual benefit, and reputation.

Life is short—50 years might be all we have in the optimal scenario—so choose to play the long-term game with long-term people.

Civ 2050: The Age of Infinite Leverage

The modern era is defined by stacked leverage—the compounding power of labor, capital, and knowledge tech (media/code). This exponential growth formula explains why figures like Gates, Bezos, and Musk have reshaped the world.

• Labor Leverage → Building teams and corporations.

• Capital Leverage → Raising and allocating resources for scalable ventures.

• Knowledge Tech Leverage → The infinite scalability of media and code (e.g., the printing press, radio, TV, internet, AI).

Historically, Carnegie, Vanderbilt, Rockefeller, and JP Morgan mastered labor and capital leverage to dominate the industrial age. Today’s titans wield an even more powerful tool—knowledge tech leverage—which allows for near-zero-cost distribution of ideas, products, and automation through software and AI.

The Exponential Power of Knowledge Tech

The past 200 years of human progress have far outpaced the previous 200,000 years due to rapid technological compounding. Anyone willing to dedicate a decade to mastering knowledge tech can potentially:

• Create the next YouTube (originally a video dating site).

• Write the next Harry Potter.

• Build the next Joe Rogan Experience.

• Develop a personal media empire like Oprah.

When labor, capital, and knowledge tech are combined and compounded, society advances at an accelerating rate. The same leverage that powered Columbus’ voyage is now being applied to energy, robotics, and AI, setting humanity on a trajectory toward a Star Trek-like future.

The power of leverage today far surpasses anything in history—moving from stacking stones for pyramids to building entire digital empires and beyond.