Move 37 and the Shape of What’s Next

There’s something about forced stillness that creates space for the unexpected.

Molly was a few weeks into recovery from her second ankle surgery—the one where she “won the ankle injury lottery in the worst way possible.” Her boot-clad ankle propped up next to me on the couch, she wasn’t going anywhere. Neither was I. So we did what any reasonable father-daughter duo does when escape isn’t an option: we binged two documentaries about artificial intelligence.

First, AlphaGo—the 2017 film about DeepMind’s AI beating the world champion at Go. Then The Thinking Game—the 2024 documentary that follows DeepMind’s broader quest toward artificial general intelligence, filmed over five years by the same team.

What I didn’t expect was that this double feature would turn into one of the best conversations we’ve ever had.

Molly is a Computational Biology major. I’m a lifelong computer science nerd. Our worlds were about to collide in the best possible way. (Fun aside: one of her friends from MIT—his dad appears in one of the documentaries. We got a good laugh out of that.)

Why Go Matters (And Why No One Thought This Would Happen)

If you’re not familiar with Go, here’s the short version: it’s a 2,500-year-old board game that makes chess look like tic-tac-toe.

Chess has roughly 10^47 possible game states. Go has 10^170. For perspective, there are approximately 10^80 atoms in the observable universe. Go has more possible positions than there are atoms—by a factor of 10^90. Let that sink in.

This isn’t just trivia. It means you can’t brute-force Go. You can’t calculate every possibility the way Deep Blue did against Kasparov in 1997, evaluating 200 million positions per second. That approach simply doesn’t work here. The game is too vast. Too deep.

For decades, the best Go programs were… embarrassing. They played at the level of a decent amateur, routinely getting crushed by club players. Experts confidently predicted that AI beating a professional Go player was 10-20 years away. Some said it might never happen.

In 2016, DeepMind did it anyway.

How AlphaGo Actually Works

Neural Networks: Teaching Intuition

AlphaGo wasn’t programmed with rules about how to play Go. Nobody sat down and wrote “if your opponent plays here, respond there.” That approach had been tried for decades. It didn’t work.

Instead, AlphaGo was trained.

First, it studied millions of games played by human masters. The neural network learned to “see” the board—not as a grid of black and white stones, but as patterns. Shapes. Flows. The kind of intuition that takes a human player decades to develop, encoded in the weights of a neural network.

This is the key insight that changed everything: intuition can be learned. It’s not magic. It’s not some mystical human quality that machines can never possess. It’s pattern recognition at scale.

Reinforcement Learning: Playing Itself

But learning from humans only gets you so far. Humans, after all, are limited.

So after learning from human games, AlphaGo started playing against itself. Millions of games. Billions of moves. Twenty-four hours a day, at speeds no human could match.

This is reinforcement learning—trial and error at superhuman velocity. And here’s the kicker: through self-play, AlphaGo discovered strategies that no human had ever seen. Not because they were wrong. Because we never thought to try them.

The machine had started to see things we couldn’t.

Monte Carlo Tree Search: Guided Exploration

AlphaGo doesn’t evaluate every possible move—that’s mathematically impossible, remember? Instead, it uses its neural network intuition to guide its search.

Think of it like this:

  • Policy Network: “What move looks promising?” (Intuition)
  • Value Network: “Who’s winning from this position?” (Evaluation)
  • Monte Carlo Tree Search: “Let me simulate a bunch of games from here to check.” (Verification)

It’s intuition combined with calculation. The machine equivalent of a grandmaster “feeling” that a move is right, then verifying it with deep analysis.

Human experts have both systems too—the gut and the grind. AlphaGo unified them into something more powerful than either alone.

Move 37: The Moment Everything Changed

Game 2 of the match against Lee Sedol. If you haven’t seen the documentary, go watch it. If you have, you know exactly what I’m about to describe.

Lee Sedol is one of the greatest Go players in history. Eighteen world championships. A player of profound intuition and legendary fighting spirit. He sat across from AlphaGo expecting a battle. He got something else entirely.

Move 37.

AlphaGo places a stone on the fifth line—a move that looks, to the trained human eye, wrong. Commentators are confused. Experts call it a mistake. Lee Sedol leaves the room, visibly shaken. The move violates centuries of accumulated Go wisdom.

And then it wins the game.

Move 37 wasn’t in any textbook. It wasn’t copied from any human game in AlphaGo’s training data. The machine had discovered something new about a game humans have played for 2,500 years.

What does it feel like to watch a machine be creative? I still don’t have a great answer. But I know it changes how you think about intelligence—artificial and otherwise.

From Go to Protein Folding: Where Our Worlds Cross

This is where The Thinking Game picks up the story.

Here’s the thing about DeepMind: they weren’t just trying to win at board games. Go was a proving ground. A demonstration. The real target was always bigger.

Enter AlphaFold. And enter my daughter’s world.

The Protein Folding Problem

Proteins are the workhorses of biology. They do almost everything—carry oxygen in your blood, fight infections, make your muscles contract, replicate your DNA. And every protein is built from a chain of amino acids that folds into a specific three-dimensional shape.

Here’s the critical insight: the shape is the function. A protein’s 3D structure determines what it does. Get the shape wrong, and the protein doesn’t work. Misfolded proteins cause diseases like Alzheimer’s, Parkinson’s, and cystic fibrosis.

The problem? We know the amino acid sequences for over 200 million proteins. But determining the 3D structure experimentally—using X-ray crystallography, cryo-electron microscopy, or nuclear magnetic resonance—is brutally slow and expensive. In 60 years of global scientific effort, we had solved about 170,000 structures.

Predicting how a protein folds from its sequence alone? That was the “50-year grand challenge” of biology. The Mount Everest of molecular science.

CASP: The Olympics of Protein Prediction

Every two years, computational biologists compete in CASP—the Critical Assessment of Structure Prediction. It’s basically the Olympics of protein folding. Teams submit predictions for protein structures that have been experimentally determined but not yet published. Then they get graded.

For years, scores hovered around 40 out of 100 for the hardest targets. Progress was incremental. Slow. Scientists would publish papers celebrating a 2-point improvement.

Then AlphaFold 2 showed up in 2020.

The “Holy Shit” Moment

There’s no other way to describe it.

AlphaFold 2 scored above 90 on two-thirds of the targets. Some predictions were so accurate they were essentially indistinguishable from experimental results. The competition wasn’t close. It wasn’t even a competition anymore.

The judges called it “astounding.” One researcher said it was “like landing on the moon.” Another said protein structure prediction had been “solved.”

I looked at Molly. This is her field. Transformed overnight.

How AlphaFold Works

Like AlphaGo, AlphaFold uses neural networks. But the architecture is different—it’s built on attention mechanisms, similar to the transformers that power GPT and other large language models.

The key insight is co-evolution.

Here’s the intuition: if two amino acids that are far apart in the sequence consistently mutate together across many different species, they’re probably close together in the 3D structure. Evolution leaves fingerprints. AlphaFold learned to read them.

The system analyzes millions of protein sequences, looking for these co-evolutionary patterns. Then it uses that information—combined with geometric reasoning and iterative refinement—to predict the spatial relationship between every pair of amino acids.

It’s pattern recognition. The same fundamental idea as AlphaGo—but applied to the language of life itself.

AlphaFold 3 and the Nobel Prize

In 2024, DeepMind released AlphaFold 3. It doesn’t just predict individual protein structures—it predicts how proteins interact with DNA, RNA, and small molecules. The implications for drug discovery, gene therapy, and understanding disease are enormous.

Oh, and Demis Hassabis and John Jumper won the Nobel Prize in Chemistry for their work on AlphaFold. No big deal. Just the highest honor in science for a system that started with a board game.

What It Meant to Watch This Together

Here’s what I didn’t tell Molly while we watched: I was so damn excited for her.

She’s walking into a world where the tools to understand life at the molecular level are suddenly, radically more powerful. The intersection of computer science and biology isn’t a niche curiosity anymore—it’s the frontier. And she’s not watching it from the sidelines. She’s studying it. She’s going to use it.

I’ve spent my career in tech, watching waves come and go. I’ve seen hype cycles inflate and collapse. But this one feels different. Her timing is impeccable.

We didn’t plan this documentary double feature as a “teaching moment.” It was just couch time—her ankle in a boot, me with the remote, nowhere to be. But somewhere between Move 37 in AlphaGo and the protein folding breakthrough in The Thinking Game, something clicked.

Her world and my world aren’t separate anymore. They’re the same world.

And she’s going to take it places I can’t even imagine.

The Thread

These two documentaries tell one continuous story—a thread that runs from a board game in Seoul to a protein database that covers all of life.

It’s not about computers being smarter than humans. It’s about building tools that let us see what we couldn’t see before.

AlphaGo showed us a move no human had imagined in 2,500 years of play. AlphaFold showed us the shapes of 200 million proteins that would have taken centuries to solve experimentally.

What’s next? I don’t know.

But I have a feeling Molly is going to help figure it out.

And I’ll be cheering from the couch—boot or no boot.

Bold Moves: The Antidote to the Status Quo

I still remember the feeling—the mix of excitement and terror—as I packed the last box into a U-Haul after college. Two buddies of mine drove with me across the United States driving a U-Haul and my 1999 Toyota 4-Runner (that I still own and drive today). The destination was San Francisco, California, the goal was the Silicon Valley dream. Along the way, we attempted to visit as many Major League Baseball ballparks we could get to. Our favorite was Wrigley Park in Chicago. As a Computer Science major, I was drawn to the epicenter of the digital gold rush. It was 1999, and the headlines were intoxicating: companies like GeoCities and theGlobe.com were having record-breaking IPOs despite having no profits. The air was thick with stories of 20-somethings becoming overnight millionaires, and the promise of a ‘new economy’ fueled by giants like Yahoo! and countless other dot-coms felt limitless. It truly felt like the center of the universe, the only place to be. But in reality, it was less a carefully planned career step and more a blind leap of faith. I didn’t need to do it. I had job offers in Washington DC and New York City for lucrative programming jobs. Wow, my life would have been different if I didn’t do this. Looking back, I can see how that single, impulsive move set the tone for my entire life. It was my first real lesson in a principle I now live by: the life you get is a reflection of the bold decisions you’re willing to make.

The Seduction of the Status Quo (and the Gravity of Safety)

Life has a funny way of pulling us toward the center. Both personally and professionally, there’s a natural gravity toward safety, predictability, and the well-trodden path. It’s the comfort of the known, the security of the status quo.

The problem is, safety is an illusion. The real risk isn’t in taking a leap; it’s in standing still. The cost of avoiding bold moves is stagnation. It’s a slow fade into irrelevance as the world moves on without you. The comfortable path inevitably leads to a place of regret, wondering “what if?”

My Bold Moves: Personal Stories That Shaped Me

That U-Haul to San Francisco was just the first of many bets I’ve made on myself. Each one felt like defying gravity at the time.

  • Starting a company right after our second child was born: On paper, it was the worst possible time. The responsible move would have been to find a stable job with a predictable paycheck. But the pull of building something from the ground up was stronger than the fear of instability. That company became one of the most formative experiences of my life.
  • Leaving stable corporate jobs for startups: I’ve done this a few times in my life. It meant leaving the safety of a clear career path for the chaotic, high-stakes world of a startup. Each time, it was a bet on impact and accelerated learning over the comfort of certainty, and each time it paid off.
  • Moving my family to Park City during COVID: The world was shutting down, and we decided to uproot everything. We left the familiar for the mountains, seeking a different quality of life. It was a bet on a lifestyle, and it paid off in ways we couldn’t have imagined.

Each of these moves was a conscious push against the gravity of safety. And each one returned dividends in growth, learning, and fulfillment that far outweighed the perceived risks.

What Bold Moves Create (in Business & Life)

This principle isn’t just personal; it’s the engine of progress in business. History is littered with examples of companies that won or lost based on their appetite for boldness.

Think of Apple launching the iPhone, a bet-the-company move that cannibalized their successful iPod business. Or Netflix going all-in on streaming when their DVD-by-mail service was at its peak. Or Amazon Web Services, a wild idea that had nothing to do with e-commerce but now powers a significant portion of the internet.

Conversely, think of the corporate graveyards filled with companies that clung to the status quo. Kodak invented the digital camera but buried it to protect its film business. Blockbuster laughed Netflix out of the room. BlackBerry was convinced its physical keyboard was invincible. They all played it safe, and they all lost. Boldness is what scales outcomes, both for individuals and for empires.

Bold Moves Don’t Always Mean Giant Leaps

But boldness doesn’t have to be a U-Haul across the country or a nine-figure business bet. Sometimes, the boldest moves are the small ones that accumulate over time.

It’s speaking up in a meeting when everyone else is silent. It’s making the cold call you’ve been dreading. It’s making the difficult decision to part ways with a team member who was perfect for the company’s past but has outgrown its future. It’s saying “no” to a good opportunity to protect your time for a great one. These small acts of courage build the muscle for bigger leaps. They create a compounding effect, where each small, bold move creates the foundation for the next.

The Fear Factor: Why Boldness Feels So Hard

Let’s be honest: bold moves are terrifying. The fear is real. It’s the fear of failure, the fear of judgment, the fear of leaving the stability we’ve worked so hard to build. With every big decision I made, fear was a constant companion. When starting a company with a young family, the fear of not being able to provide was immense.

But I learned that fear isn’t a stop sign. It’s a compass. It points you toward the areas where you have the most to grow. Leaning into that fear, acknowledging it, and moving forward anyway is what unlocks progress.

The Payoff: Why Boldness Wins

The beautiful thing about bold moves is that they create momentum, even when they appear to “fail.” We spend too much time measuring success in dollars or fearing what others might think when they see something fall short. But a failed startup teaches you more than a decade in a safe corporate job. A move that doesn’t work out still expands your perspective and builds resilience. There is no such thing as a failed bold move, only learning opportunities that propel you forward. Each step, successful or not, compounds over time, building a life and career defined by growth, not stagnation.

Bold Moves Are Required in Startups and Transformations

This mindset is non-negotiable in the worlds I operate in. In a startup, playing it safe is a death sentence. The only way to break through the noise and overcome the inertia of established players is to make bold bets.

The same is true for corporate transformations. Companies don’t pivot from legacy models to future-proof businesses by making incremental tweaks. It requires fundamental, bold shifts. History is a testament to this: Sears clung to its catalog model while Amazon built the future of retail, Nokia dismissed the iPhone to protect its existing phone business, and Yahoo had the chance to buy Google but played it safe. In my work, I’ve seen what happens when companies embrace this, but the truth is, I don’t see it enough. The winning companies are the ones making bold moves in their product strategy, aggressively adopting AI to reinvent “non-tech” industries, and challenging every assumption about how their business should run. Without this commitment to boldness, any company is destined for the corporate graveyard alongside Kodak and Blockbuster.

Making Bold Moves a Habit

Boldness isn’t a personality trait; it’s a practice.

  • Mindset: Start reframing risk not as a threat, but as an investment in your future growth.
  • Strategy: Use a barbell approach. Protect your core (pay the bills, maintain key relationships), but make bold, asymmetric bets on the edges.
  • Practice: Constantly ask yourself, “Am I living and working in a way that is bold enough to generate bold outcomes?”

Your Challenge

That U-Haul journey to a California wasn’t just a trip; it was a decision to choose the unknown over the known. Life’s gravity will always pull you toward safety, and the only way to break free is through conscious, bold moves—big and small.

So, what’s your U-Haul moment? What bold move are you avoiding right now?

Grit is a True Superpower

A Personal Story

My daughter, a collegiate soccer player, recently called me with some tough news. After months of grueling recovery from surgery on a torn tendon in her left ankle, her doctor suspected the same issue in her right. She had, “won the ankle injury lottery in the worst way possible.”

The frustration in her voice was palpable. The momentum she had fought so hard to rebuild was gone. The path forward, once a straight line back to the field, was now clouded with uncertainty. It was one of those moments every parent dreads—seeing your child face a setback that feels profoundly unfair. But it also became a powerful life lesson, the kind you can’t learn from a textbook. It got me thinking about the one quality that truly defines us in these moments: grit.

What is Grit, Really?

We throw the word “grit” around a lot, often mistaking it for simple toughness. But it’s more than that. Angela Duckworth, in her groundbreaking research, defined it as the combination of passion and perseverance toward long-term goals. It’s not just about enduring hardship; it’s about having a clarity of purpose that fuels that endurance.

From my perspective as a leader, this is the critical distinction. Grit isn’t just about having the talent to succeed or the luck to avoid failure. Plenty of people have those. Grit is the sustained, focused effort applied over time, driven by a deep sense of meaning. It’s the conscious decision to keep going when it would be far easier to stop, not because you’re stubborn, but because you believe in where you’re going. In a world where giving up is all too convenient—and often encouraged as the path more traveled—choosing to persevere is a radical act.

I saw this firsthand growing up as the son of immigrants. For my parents who immigrated from the Philippines, grit wasn’t a concept to be studied; it was a daily necessity. They arrived with no safety net and no backup plan. Pushing forward wasn’t a choice; it was the only option. Their perseverance was forged in the simple, non-negotiable reality of survival, teaching me that the deepest forms of grit often come from a place of profound necessity. There is no doing hard in life without grit.

Grit in Leadership and Business

Organizations face their own version of a torn tendon. A product launch fails. A key customer churns. A quarter ends in the red. These are the moments that test a company’s character. But the real test often comes when things are going well. This is the core of the innovator’s dilemma: the gravitational pull toward what is already successful, which prevents companies from discovering their next, necessary engine of growth. It takes organizational grit to fight that inertia and venture into the unknown. Look at Netflix. They could have remained the king of DVDs-by-mail, but they had the grit to cannibalize their own successful business to lead the streaming revolution. Then they did it again, risking billions to become a creator of original content. Each pivot was a bet against their own proven success, driven by a gritty vision for the future.

In my career as a CTO, I’ve seen this play out time and again. The teams that survive and ultimately thrive aren’t always the most brilliant, but the most persistent. Whether it was navigating massive industry transformations, driving digital adoption, or preparing for the disruption of AI, the journey was never a straight line. There was always resistance and the temptation to revert to the old playbook. The successful teams were the ones who could absorb the blows, learn from them, and maintain their conviction. They had the grit to stick with the vision through the messy, uncomfortable, and often frustrating process of making it a reality.

Grit as a Cultural Superpower

When grit is embedded in an organization’s DNA, it becomes a cultural superpower: resilience. A culture of grit normalizes setbacks. It reframes them not as catastrophes, but as learning opportunities. It creates an environment where people feel safe to fail, as long as they fail forward.

To get past a dip, you have to empower everyone to be a problem-solver. There’s no room for bureaucratic project managers who simply pass messages along. You need a team culture built on customer empathy, deep subject matter expertise, and first-principles thinking. When people are equipped and trusted to solve problems, they don’t just manage the work—they own the outcome. This is the engine of a gritty organization.

This is what separates the sprinters from the long-distance runners in the corporate world. A team that panics at the first sign of trouble will burn out. But a team that views challenges as part of the process builds a sustainable advantage. Their resilience compounds over time, allowing them to outlast competitors and navigate market shifts that would cripple more fragile organizations.

Where Grit is Forged

Grit isn’t an abstract virtue; it’s a muscle built in the face of real adversity. There are a few arenas where it is tested in its purest form. The first is in a health crisis. As I wrote about previously, watching a friend battle cancer is a profound lesson in perspective. For someone facing a devastating diagnosis, there is no option but to push forward through pain and uncertainty. It is the ultimate test of will, where perseverance is not for a promotion or a product launch, but for life itself.

The second is in the trenches of a startup. I’ve seen it countless times: a company is about to run out of money. The metrics are flat, investors are hesitant, and payroll is looming. This is the moment that separates enduring companies from footnotes in history. When Airbnb’s founders were deep in debt, they famously designed and sold cereal boxes named “Obama O’s” and “Cap’n McCain’s” to keep the company alive. That wasn’t a glamorous strategic pivot; it was pure, unadulterated grit.

The third is during a large-scale transformation. The truth is, most transformations fail. The inertia of “the way we’ve always done things” is a powerful force. Pushing through requires weathering setbacks like deep-seated employee resistance, the failure of a new technology platform, or a key project that goes off the rails. Sticking with the vision when everything and everyone is telling you to revert to the comfortable norm is the very definition of organizational grit.

These are just a few examples. Where have you seen true grit? In a family member, a colleague, a historical figure, or maybe even in the mirror? Recognizing it in others is the first step to cultivating it in ourselves.

The Sickness of Entitlement

If grit is the superpower, then entitlement is the kryptonite. It is a true sickness in any organization or individual. Entitlement is the belief that you are owed success, that the path should be easy, and that struggle is an injustice. It’s the counter-emotion to grit. Where grit sees a challenge as an opportunity to prove oneself, entitlement sees it as an unfair burden. It replaces the drive to earn with the expectation to be given. This is why one of the most important things you can do for your kids is show them what hard work and grit look like. They see what you do far more than they hear what you say. When they see you push through, they learn that they can, too.

The Gift of Setbacks

It’s a paradox, but the very challenges we try to avoid are the ones that forge the strength we need. NVIDIA CEO Jensen Huang told a group of Stanford Business School students, “I wish upon you ample doses of pain and suffering.” It sounds harsh, but his point was profound: greatness and character aren’t formed when things are easy. They are formed by people who have suffered and persevered.

Easy paths don’t build grit; they don’t have to. Setbacks are crucibles. They strip away the non-essential and reveal what people and organizations are truly made of. They are the antidote to entitlement. My daughter is learning this right now. This painful, frustrating journey is forcing her to dig deeper than ever before. She is discovering a reserve of strength and determination she might never have known she had. In the same way, leaders and teams only discover the depth of their own grit when faced with real adversity. These moments, as difficult as they are, are a gift.

The Power to Get You Through

As my daughter begins her long road back—again—I’m reminded that her resilience is the real victory. The strength she is building today will serve her long after her soccer career is over. I told her these are stories she will share to her teams when they need to get through tough times. She just doesn’t know it yet.

The same is true for all of us. I encourage you to cultivate grit in yourself and in your teams. It will be the one true differentiator when industries shift, strategies fail, and the path forward is anything but clear.

Innovation, talent, and strategy can take you far. But grit is the superpower that gets you through.

Perspective is a Gift

The words hung in the crisp Park City air, feeling more real and significant than the mountain peaks surrounding us. “I’m cancer-free.”

My friend said it with a mix of exhaustion, disbelief, and pure, unvarnished joy. We were sitting at an outdoor table, the casual clinking of glasses and plates around us a stark contrast to the gravity of his announcement. In that instant, the light seemed brighter. The food tasted better. And every single item on my mental to-do list—the emails I needed to answer, the project deadline I was worried about, the minor frustrations of the morning—evaporated.

They didn’t just fade; they were revealed for what they were: noise.

In the face of my friend’s monumental news, my own world was instantly, and gratefully, reframed. That’s the power of perspective.

What Perspective Really Means

We talk about “gaining perspective” as if it’s some abstract wisdom you acquire with age. But it’s not. It’s a visceral, lived shift in how you see the world and your place in it. It’s the sudden, clarifying force that reorganizes your priorities without your permission.

Perspective is the invisible filter that separates what truly matters from what merely feels urgent. The overflowing inbox, the buggy code, the traffic on the way to school pickup—these things feel consuming in the moment. It’s a concept ancient Stoic philosophers embraced: we don’t control external events, only our response to them. When held up against the backdrop of life’s true milestones—health, love, family, and survival—our daily frustrations shrink to their proper size.

In Family and Life

This lesson shows up constantly at home. With my wife, Sarah, and our kids, Molly, Brooklyn, and even our late dog Phoenix, life is a beautiful, chaotic dance of college visits, late-night phone calls, and the inevitable friction of siblings navigating new chapters from afar. It’s easy to get caught up in the small stuff—the spilled milk, the forgotten homework, the argument over screen time. It’s easy to let frustration win.

But perspective is the quiet voice that asks: Is this the moment that matters? Will this argument be remembered tomorrow? Or is the real work to build a home filled with grace, forgiveness, and the knowledge that we are each other’s safe harbor?

My own health journey with my stroke a few years ago was another one of those clarifying, non-negotiable moments. It was a forced reset. Before it, my worries were scattered across a dozen different professional and personal anxieties. After it, they consolidated into one: the profound gratitude for being able to walk, to talk, and to be present with my family. The frustration of a slow-moving project is nothing compared to the painstaking work of relearning a simple motor skill. That is a lesson you don’t forget.

In Business and Leadership

This isn’t just a “life” lesson; it’s a critical leadership tool. In my role as a CTO, my world is filled with sprints, fires, and strategic roadmaps. The pressure to move faster, ship more, and solve complex technical problems is constant. It’s incredibly easy to get lost in the weeds and develop what I call “false urgency”—where every task is treated as a crisis.

But true leadership requires perspective. It’s the ability to remain calm in the chaos, to zoom out from the immediate fire and see the whole forest. It’s what allows you to distinguish between a genuine emergency and a manufactured one.

With perspective, you stop asking, “How can we fix this problem right now?” and start asking, “What’s the most important thing for our team to accomplish this year?” At a senior level, you might only make a few critical decisions a day, but those decisions have a massive ripple effect. Perspective helps you lead with empathy, recognizing that the people you work with are navigating their own lives, their own battles. It guides you to make better long-term decisions, because you’re not just building a product; you’re building a resilient team and a sustainable culture.

In this sense, perspective isn’t just a defensive tool for staying calm; it’s an offensive weapon. In the war of business, where competitors are consumed by short-term fires, a leader with perspective can see the entire battlefield. Instead of charging head-first into the mountain, you find a way around it.

A perfect modern example is the Nintendo Wii. In the mid-2000s, Sony and Microsoft were fighting a costly war over who could build the most powerful console for hardcore gamers. That was the mountain. Nintendo, using perspective, didn’t try to climb it. They went around it. They reframed the problem from “How do we make games more realistic?” to “How do we make games more fun for everyone?” With a simple motion controller, they created a new, uncontested market and outsold their more powerful competitors for years.

Historically, one of the greatest examples is Napoleon’s Ulm Campaign in 1805. An Austrian army was waiting for him in Germany, guarding the direct passes of the Black Forest, ready for a head-on fight. Instead of attacking them where they were strongest, Napoleon sent a small cavalry force to create a diversion while he marched the bulk of his army in a massive, rapid flanking maneuver. By the time the Austrians realized what was happening, Napoleon’s army was behind them, cutting off their supply lines. Their strong defensive position had become a trap. Without a major battle, Napoleon won by making the battle his enemy had prepared for completely irrelevant.

Both Nintendo and Napoleon won, not because they fought the hardest, but because they fought the smartest. They used perspective to sidestep trivial conflicts, conserve energy for the battles that truly mattered, and spot opportunities that others, lost in the fog of false urgency, completely missed.

The Beautiful Byproduct: Gratitude

When your perspective shifts, something amazing happens: gratitude flows in naturally. You don’t have to hunt for it or write it down in a journal (though you can). It simply shows up.

You become grateful for the difficult client, because they are sharpening your skills. You become grateful for the challenging project, because it’s an opportunity for your team to grow. You see obstacles not as roadblocks, but as the raw material for progress. You become thankful for the ordinary, because you’ve been reminded just how fragile it is.

Choosing to See

A serene view of layered mountains under a pastel sky at dusk, showcasing a gradient of blue and soft orange hues.

As I walked away from that lunch, the glow of my friend’s good news stayed with me. It was a powerful reminder that perspective isn’t something we should wait for a crisis to deliver. It’s a gift we can give ourselves, every single day.

It’s a choice.

It’s the choice to pause, take a breath, and look up from the screen. It’s the decision to value presence over productivity, and empathy over efficiency.

So today, I invite you to do the same. Take a moment. Look around at your life, your family, your work. Find one small, ordinary thing and see it for the extraordinary gift it is.

Let’s not wait for life-altering news to see what truly matters. Let’s choose to see it now.

Finding Perspective.

Both my parents worked throughout my childhood.  They were out of the house by 7am and usually didn’t come home until 10pm at night. I developed my work ethic by watching them.  My mom would get called to the emergency room at all hours of the day.  I spent a lot of time hanging out with the emergency room nurses waiting for my mom to take care of something.  I was basically raised by a woman I called “Lola” but she was not actually my grandmother but rather a nanny from the Philippines. My first language was Tagalog because that what “Lola” spoke.  She was 4′ 6″ tall but could probably wrestle battle an ox in her prime. I loved her dearly like I do my parents.

Now, here is a tightly held secret.  Ok, not really.  My nickname as a child was “Joel”.  My dad and I have the same first name so somewhere along the lines they started calling me “Joel”.  I have no idea where the name came from and neither do my parents.  Upon moving to California after college, I decided to just stick with my legal name “Renato” after a work colleague suggested it.  The east coast knows me as “Joel” and the west coast knows me as “Renato”.  At my wedding, half the attendees were there for “Renato & Sarah’s Wedding” and the other half was there for “Joel & Sarah’s Wedding”. To this day, I respond to both names!

Well, my Lola spoke very little English even as I grew up into my teens.  My friends would come over asking for me and my Lola would provide short answers and close the door.  For example,

  • “Joel School” — I was at school
  • “Joel Work” — I was working in my parents office
  • “Joel Gym” — I was working out
  • “Joel Eat” — I was out grabbing food
  • “Joel Girl” — I was out with my girlfriend at the time she didn’t like. 

Fast forward, I went with my friends to the Grateful Dead concerts at the Meadowlands in New Jersey.  A buddy of mine came to the door and my Lola responded “Joel Dead” and slammed the door.  Well, needless to say my buddy freaked out and this was before cell phones.  I’m sure I must have been dead to him for most of that day until I got back from the show. 

Alas, Joel is not actually dead but the story does remind us about the importance of perspectives.  Lola just wanted to provide information on where I was.  My buddy just wanted to know where I was.  Joel just wanted to listen to some jamming music.  Referring to myself in the 3rd person felt appropriate right there.

Gaining perspective is a crucial element in both life and business.  It allows us to see situations from different angles, leading to more informed and balanced decision making. Perspective isn’t something we’re born with; it’s developed over time through experiences, challenges, and by actively seeking to understand viewpoints that differ from our own. Whether it’s through travel, reading, or engaging in meaningful conversations with people from diverse backgrounds, each of these activities enriches our understanding of the world. In business, having a broad perspective can lead to innovative solutions and help navigate complex challenges with a clearer vision.

All that being said, having a strategic perspective is incredibly challenging because it requires the ability to step back from immediate concerns and view the broader landscape, often in a highly complex and rapidly changing environment. This means looking beyond day-to-day operations to consider long-term goals, potential risks, and emerging opportunities. However, the difficulty lies in balancing this long-term vision with the urgent demands of the present. We are often so focused on immediate tasks and short-term results that it becomes difficult to shift our mindset to a more strategic level. Additionally, the uncertainty of the future and the vast amount of information that must be processed and interpreted to make strategic decisions can be overwhelming. As a result, maintaining a strategic perspective requires discipline, focus, and the ability to anticipate and adapt to change—a skill set that is not easily mastered but is essential for sustained success.

Now, lets apply some perspective to my life in the form of a time line backwards and forward from 2024.  I started 29 years ago at my high school and moved forward 29 years into the future. This is what I came up with.

1995 (29 years ago)

Graduated from Fairfield College Preparatory School

1997 (27 years ago)

First coding job at Lockheed Martin LMS in Tarrytown, NY

1999 (25 years ago)

Graduated from the University of Richmond 

2003 (21 years ago)

Sarah and I get married in California

2006 (18 years ago)

Molly was born 

2010 (14 years ago)

Brooklyn was born 

2023 (1 year ago)

2028 (+4 years)

Brooklyn Graduates High School, Molly Graduates College

Raising Amazing Daughters. Proud Dad.

2032 (+8 years)

Brooklyn Graduates College

2033 (+9 years)

Sarah and Renato married 30 years

2039 (+15 years)

Average retirement age and social security eligibility

2043 (+19 years)

Sarah and Renato married 40 years 

2044 (+20 years)

Average life expectancy of Filipino male (67 years old)

2051 (+27 years)

Average life expectancy of American male (74.8 years old)

2053 (+29 years)

Sarah and Renato married 50 years

The timeline provides a unique perspective on my life.

  • Life is short and moves fast.
  • My wife Sarah is my most consistent passenger with me on this ride.
  • I have more years behind me than ahead of me.
  • Family and friends are things that hold the test of time.
  • Physical belongings fad away into the background. 

Perspective helps with finding joy because in the bigger picture, so many things we worry about are irrelevant and we have so many more things to be grateful for.  Don’t waste a minute. Live life to the fullest. Find your joy. Make a dent in the universe.

Thanks for reading.  I hope you enjoyed!

-rjm

Work after 25 years.

25 years ago this summer three buddies of mine made our way across Europe. We all graduated college and were doing the customary post-graduation Eurail European adventure. We started in Italy and worked counter clockwise across the European continent ending the trip in Spain. The stories are endless.

  • We drove too fast in a promotional Hertz rental car that was all yellow and covered in logos. 
  • We climbed the Swiss alps. 
  • We consumed so much beer in Munich that I somehow was able to sing Lithuanian folk songs through the streets at 3am.
  • We got wildly lost in the red light district of Amsterdam. 
  • We recreated scenes from the Sound of Music in Vienna. 
  • We drank sangria all night and ran with the bulls in Pamplona, Spain the next morning with no sleep. I’m pretty sure we slept on a street bench that night.  
  • And the stories go on and on. 

When it was all done, I loaded up a U-Haul with two buddies and we drove from Connecticut to the center of technology, Silicon Valley.  Silicon Valley was where I needed to be.  I had a Computer Science degree in hand and dreams to change the world.  Fast forward to today — I’ve been driving technology products and teams for 25 years now and have been fortunate to take all sorts of awesome products to market in many different scenarios — start ups, venture backed, public companies, private equity backed, consumer, enterprise, education, government, financial.  From no name brands to big brands, I just worked my ass off and continue to work my ass off.  I like it that much. 

25 years of hard work hard work requires some reflection. As I’ve said in previous blog posts, sometimes this reflection is for me as much it is for anyone else. My blog posts are like public journal entries. Below are some higher level questions that I was reflecting upon —  

What have I learned? 

Here are is a list of axioms I’ve picked up along the way in no particular order.

  • Play chess, not checkers.
  • First principle thinking is paramount.
  • Keep challenging your assumptions. 
  • Get your team as close to the customer as possible.
  • It’s all about the people and your teams.
  • Micromanagement only gets you so far.
  • Try to lead, not manage.
  • Be genuine. 
  • Be respectful. 
  • Work hard. 
  • Stay hungry.
  • Listen more.  Talk less. 
  • Setbacks are opportunities.
  • Ego kills.
  • Keep your standards high.  Don’t settle. 
  • Stop the whining.   
  • Have urgency but be patient. 
  • Smile and laugh more.

What adjustments have I had to make after 25 years of working?

Experience can be a blessing and a curse.  Yes, there exists 25 years of experience to draw from but that doesn’t mean I know everything.  Ego can get in the way of learning new things.  “I’ve done this enough, I know what I’m doing” becomes the new slogan.  Its important to not get caught in that mindset. The reality is “I don’t know everything, I’ve not seen all situations.” Keep an open mind.

Additionally, the more experience you have the more career optionality you have which makes it too easy to bail out of one situation and into another rather than doing something differently.  I have to apply first principles thinking to myself in these scenarios.  I don’t always have all the answers.  My assumptions that I’ve held for years likely have changed.  Feedback is good. 

What is my perspective on the next 15 years of work? 

I think I’d like to take this train 15 more years. 40 years of work feels like a nice round number.  I’m happy with the success/exits under my best but I enjoy work too much to retire. If I keep picking them right, there probably feels like two more big rides.  That seems reasonable.  Currently, the technology future excites. We are pushing into another huge technology wave with artificial intelligence (AI).  AI is every geeks dream. Frankenstein. Hal.  Rosie. Jarvis. Roy Batty. Wall-E. R2D2. C3PO  We’ve been day dreaming of a world with AI beings for years.  We are  going to see an another profound technology shift over the next 5-15+ years and its going to go faster than we think.

What would I be looking for if I were evaluating new opportunities?

My work motivators in my twenties are surely different than my motivators in my fourties. As a kid, I wanted to be featured in a TechCrunch blog post and bags of money. I wanted to prove to my parents that I could make it as a technologist and not a medical doctor. Time passes by and I am looking for different things. I am definitely less motivated by money.

Now, I care deeply about …

  • the people I work with.
  • the impact I can make.
  • the opportunity being big and bold.

What would you tell yourself from 1999? 

  • Keep building. 
  • Take more risks.  
  • Stop listening to other people.
  • Stop overthinking things.
  • Find the road less traveled.
  • Make time for your friends and family. 

I like to say “trust the universe”.  Things seem to work out. I’m grateful for my career path and all the wonderful people I’ve been able to work with along the way.  I’m not sure I would have done it any other way.  Here’s to another 15 years of building innovative products!  

Thank you for reading.  I appreciate you. 

-rjm

My Blog.

My first blog post on Renato.mascardo.com/blog was on March 9, 2007.  16 years ago.  The post was titled “Hello World!” to which I just wrote

Hello World!

That was followed by two insightful blog posts titled —

Absolute drivel.  Haha.  I started my blog 16 years ago as just an experiment and it has evolved into an expression of my life and creativity. My interest in writing posts has come and gone through the years.  You’ll see big gaps in my writing or sometimes I would just post a YouTube video.  Earlier posts were trying to be “TechCrunch like” and then later evolved into more thoughtful writing about my family, our move to Utah and my stroke.  My blog has become more for me than anyone else —  a public facing journal and expression of creativity. 

As a child, my focus was on math and science.  I joke that I barely passed the “Test of English as a Foreign Language” (TOEFL) and English was sort of my second language behind Tagalog.  (Or, if you saw me as a kid you might think my first language was “eating”). Writing did not come naturally to me but I do find enjoyment in the expression of my thought through writing.  I’m sure any English major would laugh at the run on sentences and random drivel being throw around like spaghetti on a wall.   (I think I subconsciously married an English major as a ying to my yang.). But, as I have gotten older I’ve cared less about what others have thought.  Or put another way, I find it liberating to limit how much I care about what other people think especially when it comes to being creative. 

The photos on my blog at 98% taken by me.  I’ve always enjoyed taking pictures.  My father passed that passion down to me and I think I passed it down to my daughter.  I still own an old Nikon D90 camera with several lenses but have since moved to taking pictures on my phone.  The Apple iPhone camera is simply amazing.  My dad handed down a bunch of Leika gear to my daughter.  She has developed her own passion for photography and has one some photography competitions.  We share the joy of being in a dark room with some Pink Floyd playing and being alone with your thoughts.  

Being creative is a unique and elusive thing for me. Growing up Filipino, we became doctors or lawyers. As a technologist, I’m at the fringes of an acceptable career. I’m pretty sure my parents think I’m a “Chief Train Officer”. My parents encouraged I learn piano like any good Asian child but no way did I ever consider a role as a traditional creative. But, I always highly appreciated the ability to come up with unique ideas, perspectives and approaches. As a child, I picked up playing the guitar.  My first guitar was an inexpensive black Fender Squire Stratocaster in honor of Eric Clapton.  I would sit for hours working on scales and imagining different patterns and riffs. 

So, lets take take a step back and reframe why I write this blog.  I enjoy telling stories.  I enjoy expressing myself.  I enjoy sharing knowledge.  And I enjoy sharing what’s on my mind.  Family, work, technology, life, whatever.  I’ll write about it. 

Thank you for reading.  I appreciate you. 

-rjm

There is Life Outside the Bay Area: Two Years Later (Part #5)

Hello Friends & Family,

Holy macaroni!  Sarah, the girls and I are enjoying our two year anniversary in Park City, Utah this week!  Oh, what an adventure it  has been.  I’ve documented many of our move observations through my blog —

This will be the final installment of this series of blog posts — the two year check in.  I guess I could do a five year check in but that feels like a long way away.  I’m going to try something different this time around and make this an “ask me anything” type of format. I’ve collected the various questions folks have asked Sarah and I throughout.

Just as a recap, in August 2020 — Sarah, the girls and I decide to uproot ourselves out of Danville, California (Bay Area) to Park City, Utah in the middle of COVID.  I had originally moved to the Bay Area in 1999 with the first dot com boom.  20+ years in California with a brief stink in Seattle, Washington for two years. Sarah moved to California back in the 1980’s so many more years living in the Golden State.  Change and action can be hard so this was a big decision for us.  It’s amazing how fast life goes looking back but can feel slow when you’re in it.  I thought I would be in the Bay Area for a couple of years and then I would move back to the east coast.  

All great changes are preceded by choas.

Deepak Chopra

This week two years ago was absolute chaos. The house was sold and half packed. Realtors were coming in and out of the home getting the staging furniture out and the final fixes in place. The buyers were gigantic pains in the ass so we were dealing with 100 different details. And, a leak sprung in the kitchen that took us a week to figure out that that HVAC guy had screwed up the condensation lines.

Moving is the absolute worst. I had PTSD looking through the old photos.

Sarah and the girls left via car earlier in the week ahead of me so that I could deal with clearing out our old home and the movers. We had sold or thrown out half our stuff but we still had a ton of things to move. Sarah later told me that the car ride was full of tears from the Bay Area to Sacramento. We had to have a family meeting later that evening to discuss, “are we doing the right thing?”. There I sat outside Sarah’s sisters home with a beer in my hand going through the seven stages of grief in about 2 minutes.

  • Shock and denial — “What was going on? How did we get far into the journey and suddenly have second thoughts? It is not possible that this is happening!”
  • Pain and guilt — “Did I do this to my family? How could I have let this happen?”
  • Anger and bargaining — “Ok, we can fix this. Maybe there is a clause for me to get out of selling our house?”
  • Depression — “Oh, this makes me very sad.”
  • The upward turn — “No big deal. We’ll figure this out.”
  • Reconstruction and working through — “This change is the right change. We just need to get through this first week.”
  • Acceptance and hope — “Ah yes, we will get through this first week and it will be great.”

Well, we made it through that moment and I guess the rest is history. It was one of the best decisions we’ve made as a family unit together. And I think we’re stronger for having gone through it together. Folks have asked us so many questions along the way so here are just a few of them.

Q: Who brought up the idea of moving first? 

A: Sarah.  She started talking about leaving California probably back in 2015, maybe further back.  I was the hold out because I cared deeply about staying in the Silicon Valley community.  I had identified with Silicon Valley since I moved to the Bay Area in 1999. 

Q: How much did COVID play a role in your decision to move?

A: Some.  COVID definitely opened my mind to something different.  I think for Sarah it just added fuel to her interest of leaving California that started a long time ago.  Plus, the technology sector went 100% remote after COVID and for the most part continues to be remote.  It helped that Park City, Utah is the most accessible mountain town in the United States.  We’re < 30 minutes from the Salt Lake City Airport so jumping on a plane to get somewhere is very easy. 

Q: After two years, how are things going?

A: We love it here and love our decision to move.  No regrets.  Park City is one cool little mountain town. 

Q: How have the kids enjoyed Park city?

A: I think Molly and Brooklyn have thrived here.  New school. New friends. New sports clubs.  New activities.  Lots of new things and they have responded.  I don’t think moves are for every kid but I think ours have really enjoyed the change. 

Q: How have the winters been?

A: No harder than the winters in New York/Connecticut but the last two years have been mild winters so it’s tough to say yet.  There are some differences though. The snow is light, fluffy and dry.  I could use a leaf blower to clean my steps.  And as soon as the snow stops, the sun comes out.  The dry humidity and altitude makes the winters unique.   

Q: What have been your biggest surprises — either good or bad?

A: I’ve got a few —

  • The people are amazing.
  • The scenery and nature is out of this world. 
  • It is magical living 10-15 minutes from world class skiing, hiking, mountain biking, etc.
  • The snow is more amazing than i thought.
  • It is equally as magical being less than 30 minutes from Salt Lake City and the Salt Lake City Airport. 
  • Everything is just more accessible here as compared to California or New York/Connecticut.
  • University of Utah is a hidden gem. 
  • Sundays are actually days off in this state.  Kids sports are discouraged.  Lots of things are closed. 
  • The taxes are materially less as compared to California or New York/Connecticut.
  • The restaurants / food in Salt Lake City and Park City are not great.  Specially, the Asian food scene is absent.
  • The booze laws in Utah are messed up and overly complicated. 
  • The soda shops are unique.  They combine Mountain Dew and Pepsi then add pixie stick flavoring in a 64 oz cup.  What the heck? 
  • There are less people and working class here which makes standard services or contractors harder to get.
  • Backyards in Park City don’t have fences. 

Q: What would you have done differently?

A: I should have listened to Sarah  and considered a move sooner than we actually moved.  It really has been great for us.

Q: Factoring everyone – personalities, ages – how hard was it to start over? How long did it take to feel settled?

A: I didn’t find it too hard starting over but I’m a unique soul.  Starting new challenges is fun for me.  I’d say it took 6-12 months to really feel settled.  There we were lots of moving parts. 

Q: How has the work transition been?

A: There really wasn’t a transition.  We just picked up in a different state.  But, that might have been a problem in itself.  We just fork lifted our lifestyle into a different state.  It took until the second year to make some real lifestyle changes. 

Q: What was the hardest part of the transition?

A: Leaving our friends and family. 

Q: Would you do it again?

A: Absolutely! 

It is not the strongest of the species that survive, nor the most intelligent, but the one most responsive to change.

Charles Darwin

So, what is the moral of the story? Change is good. Embrace adventure. Choose to do something different. Get comfortable being uncomfortable.

Thank you for reading and listening in on the journey.  Please don’t hesitate to reach out or leave a comment.  Sarah, the girls and I hope to see you in Park City, Utah sometime soon. 

Life Reevaluation: Breaking Through The Local Maximum

Hello friends and family,

I love the mathematical term “Local Maximum”. 

“A local maximum, also called a relative maximum, is a maximum within some neighborhood that need not be (but may be) a global maximum.” 

https://mathworld.wolfram.com/LocalMaximum.html

If you apply this to life, your overall goal may be to achieving a broader goal like getting so good at a sport to compete in the Olympics but you may feel trapped in a plateau in your skills development along the way.  Worst case, you are overconfident and fooling yourself to think that you are the best at something when you are actually not.  There has to be recognition that you have reached a plateau usually caused by feedback or an event.  Then you need to figure out how to get out of it.  These break through moments tend to be very hard and very big.  The harder the problem, the more likely you give up along the way.  So much drive, passion and hard work is required. Most are satisfied with getting to some “local maximum” and not getting to the “global maximum”.  This phenomenon exists in so many things in life. 

  • Learning new skills. 
  • Solving hard problems.
  • Start ups moving from one phase of growth to the next.  
  • Established companies moving from one focus to another.
  • Transitioning from one phase of your life to the next.  
  • Encountering a “life crisis”

In my case, it feels like I encountered a “life crisis” that that broadened my perspective and has me asking “what is beyond this local maximum I’m in right now?”   The American Psychological Association defines a life crisis as —

“a period of distress and major adjustment associated with a significant life experience, such as divorce or death of a family member. In studies relating health to life crises, individuals experiencing recent major stress-producing experiences are more likely than others to show significant alterations in mental and physical health status.”

https://dictionary.apa.org/life-crisis

Am I having an actual “life crisis”?  I don’t think so. I’m generally very happy and grateful for everything that I have been provided in life.  But, I have had a “significant life event” with my stroke.  I have discovered that life is fragile and am asking myself if I am taking advantage of everything I can.   Not in a bad way but just thinking that this ride eventually ends.  When it does, what will I look back upon?  I am fond of the ending of Walter Isaacson’s book Steve Jobs where Steve Jobs is reflecting upon what happens after death.

I would call it more a “life reevaluation”.  Something one might encounter during a quarter or midlife crisis.  So, I invite you to come along with me on this journey and maybe something I write about will strike a chord with you.  One caveat, this is my journey and mostly my own self reflections.  I’m just thinking out loud.         

Below is a list of questions that checks in on my alignment. I have no idea if this is my complete list but these are the ones I’ve been reflecting on recently. 

  • Am I being a good boss, coworker, friend, family member, husband and dad? 
  • Am I working on something I am passionate about? 
  • Am I making a dent in the universe? 
  • Am I over-indexing on what I think society thinks I need to be doing? 
  • Am I being kind to others? 
  • Am I helping other people? 
  • Am I being open minded?
  • Do I listen deeply to others? 
  • Am I being respected and do I respect others? 
  • Am I working on something creative?
  • Am I being positive and surrounding myself with positive people?
  • Am I learning and growing every day?   
  • Am I being challenged? 
  • Am I surrounded by people that challenge me?
  • Am I enjoying my craft?
  • Am I being genuine?
  • Am I enjoying the moment? 
  • Am I being thankful?
  • Am I happy? 

Do any of these resonate with you? 

I find it enjoyable to reflect on these things periodically.  It’s easy to be “comfortable” with where you’re at or where society thinks you should be doing.  We are capable of doing so much more.  Helping many more people.  Making the world a better place.  As I tell my kids, you can do anything with the right amount of passion and hard work. 

Hope you enjoyed this post.  Comment below or send me a note!  Thank you for reading!

-rjm