In recent years, I’ve had many conversations with people from different generations. What’s striking is how much earlier—and how much more intensely—this sense of uncertainty is showing up. Many people have taken countless courses and earned every certification they could, yet still find themselves asking the same question: What does it actually mean to be ready?

These conversations have pushed me to rethink the learning paths we’ve long taken for granted. Traditionally, the sequence was clear: choose a major, spend years accumulating knowledge and skills, then enter the workforce and draw on what you’ve learned when real problems arise.

That model worked because industries evolved slowly and access to knowledge was expensive. If you didn’t prepare in advance, many doors simply remained closed.

But AI is fundamentally changing that assumption. Today, learning a new skill no longer requires years of upfront investment. As long as you have a sense of what you want to do, the relevant knowledge and tools can often be filled in later—with the help of AI. In that sense, knowledge itself is becoming inflated. Simply accumulating skills is no longer enough to create a lasting advantage.

Against this backdrop, the idea of “being fully prepared before you begin” feels increasingly outdated—and in some cases, inefficient. As we move from learn first, then apply to apply first, then learn, the real differentiator may no longer be how many skills you’ve mastered, but whether you’re clear about the problem you want to solve.

This reversal in learning order may feel counterintuitive, but it often leads to greater clarity. That doesn’t mean foundational knowledge is no longer important. Rather, it should function as a map—helping you identify good problems—rather than as the sole weapon you rely on.

Those who can identify meaningful problems early tend to see their learning efficiency grow exponentially. On the other hand, even vast amounts of knowledge can become scattered and unfocused if there’s no clear problem guiding it.

As we look ahead to 2026 and begin setting new learning goals, perhaps the better question to ask is this: What problem is worth solving in the coming year? When direction comes first, learning tends to follow naturally. And perhaps, this way of preparing for the future can make the year ahead feel more purposeful—and more exciting.

The reason is simple. AI now performs many of the skills that used to belong exclusively to trained professionals. If you spend your entire youth mastering a single, rigid skillset, by the time you finally gain expertise, there’s a good chance AI will already be doing it faster, cheaper, and at scale.

This isn’t to say expertise doesn’t matter — it does. But expertise alone is no longer your greatest competitive advantage. What will set you apart in the years ahead is flexibility: the ability to learn across domains and adapt when the world shifts under your feet. Over the next decade or two, industries we once thought were stable will be reshuffled. And that won’t stop just because you happen to be good at one thing.

I often tell students: don’t just learn knowledge — learn how to learn. It sounds abstract, but in the age of AI, this may be the most practical skill of all. AI can generate endless answers, but it cannot define the right questions. It can show you many possible paths, but it cannot decide which one you should walk.

That’s why the value of a generalist becomes even clearer. When your perspective is broader and your interests span multiple fields, you’re more capable of cross-disciplinary thinking — of combining ideas that don’t usually sit together to create something new. AI can give you all the pieces, but you need the ability to see patterns, make connections, and even challenge assumptions.

Looking back, my own career has unfolded the same way. I didn’t follow a straight professional track. I’ve been an athlete, a founder, an investor, and now I work deeply in education. These roles may seem unrelated, but precisely because I never confined myself to a single identity, I’ve been able to navigate major transitions and keep finding new directions.

So if you’re still in school, don’t rush to label yourself as “a finance person,” “an engineer,” or “a legal professional.” Instead, train yourself to pick up new domains quickly and apply your knowledge in more flexible, creative ways.

If I could leave you with one message as you step into the future, it would be this: don’t lock yourself into one specialty — build the ability to cross boundaries. Be a generalist, not a specialist.

That question immediately took me back to my teenage years — to a decisive match I was certain I would win, yet ended up losing completely.

At the time, I was ranked No. 1 nationally. Winning that match would have secured my year-end position. Everything started off perfectly — my rhythm was steady, my strategy precise, and I was fully in control. But after a few unforced errors, things began to fall apart. The shots I trusted most suddenly failed me. Anxiety crept in: What’s happening? My focus shifted from “How do I play the next point?” to “Please don’t make another mistake.”

From that moment on, I was no longer playing to win — I was playing not to lose. My opponent sensed the hesitation and turned up the pressure. I grew increasingly cautious, until eventually, I lost the match altogether.

It took me a long time to move past that defeat. Because deep down, I knew I hadn’t been beaten by my opponent — I had been beaten by the version of myself that was afraid to lose.

Years later, as I stepped into the professional world, I realized that almost everyone faces the same inner opponent. In entrepreneurship and investing alike, success often hinges less on intelligence or skill and more on mindset. When things go wrong, some people panic and lose focus, while others pause, assess the situation, and recalibrate. The difference is not in how fast they react, but in how well they reset. The ones who don’t dwell on the last point are the ones who have the energy and clarity to play the next.

I’ve seen founders whose first ventures failed, even earning them the label of “loser.” Yet they didn’t stay down. They absorbed the lessons, shifted focus to what came next, and tried again. Those are often the ones who go on to build great companies.

Watching them, I came to understand that the real turning point isn’t external — it’s internal. This isn’t just a founder’s lesson; it’s a lifelong practice. Life, like tennis, is a series of matches against yourself. Losing to your own fear isn’t shameful — it’s often when true growth begins. Real victory isn’t about never making mistakes, but about learning to let go, reset, and win again — this time, against the version of yourself that came before.

But over the years, I’ve watched countless founders, and almost none of their original ideas grew up unchanged. Some pivoted from consumer to enterprise markets, some rebuilt their products from scratch, and some only found a breakthrough path at the edge of giving up.

My first lesson: ideas are never the ultimate key to success.

An idea is more like a window—revealing a founder’s worldview and thought process. Why this market? Why now? Most importantly: what problem do they see, and how do they define it? Ideas are merely a starting point, constantly reshaped by the market. What truly matters is the founder’s insight into the world and how they ask questions—these determine the direction and quality of every adjustment. What’s worth investing in is not a “perfect answer,” but the unique way of thinking behind it.

Over the past decade, I’ve also come to realize that markets are far more powerful than I once imagined. Products can always be revised, but if the market is too small—or the timing too early—even the smartest solution may end in vain. Entrepreneurship is never a solo battle; it needs the push of a larger wave. Otherwise, it’s hard to go far. Many teams that seemed technically perfect still failed, often because the market wasn’t big enough or the rhythm was off.

Most importantly, what ultimately determines whether a company can endure is people. What brings most companies down isn’t the wrong direction—it’s founders who can’t fix mistakes or keep going when things get tough.

When faced with misjudgments, can a founder swallow their pride and admit fault? After repeated failures, can they still stand back up? Ideas can be adjusted, markets can be re-chosen—but the founder’s integrity is non-negotiable. In the end, those who succeed are not always the smartest, but those who are honest with themselves and refuse to give up.

I once believed investing was a science. After ten years, I’ve learned it is much more an act of trust. The future cannot be predicted, and data is never complete.The biggest lesson I’ve learned in this decade is to keep faith when things are uncertain, to look beyond the moment, and to see the future with a longer perspective.

Many assume that “storytelling” is a natural-born talent. But this student’s performance proved something else: what truly influences others is not innate eloquence, but a skill that can be learned and developed. I call this skill Story Crafting.

Imagine walking into a room. Your first task is not to speak, but to observe and listen—to understand what the other person truly cares about. Once you discover the angle that resonates, your story gains its entry point. Then, you layer emotion with evidence, so your message touches the heart while standing on reason. As the conversation unfolds, you guide the interaction—when the listener starts nodding or even engaging actively, you know they’ve already stepped into your story.

Finally, you must leave behind something they can carry with them: perhaps a short but powerful phrase that echoes in their mind; a vivid image that lingers in memory; or, most importantly, a concrete action that motivates them to take the next step after the meeting. A story is only complete when the listener walks away still remembering you.

When a story follows these steps, it ceases to be mere performance—it becomes a force that drives decisions and inspires change. It creates resonance in the moment, and leaves a lasting aftereffect long after the conversation ends.

In the post-AI era, information is more abundant than ever, and knowledge is at our fingertips. What’s scarce is no longer content, but trust and influence. AI can generate endless text, but it cannot reveal your values. It can mimic language, but it cannot build authentic connection. Ultimately, what determines success is whether the other person chooses to keep the conversation going—or even take action—after hearing you.

That is the true value of Story Crafting. It is not a “superpower” reserved for the gifted few, but a hard skill that anyone can hone through practice. And mastering it may well be the key to seizing your next opportunity.

At one point, she lowered her voice, as if sharing a secret.

“A lot of people quietly use AI to finish their homework,” she said. “The professors know it happens, but they still expect us to do many parts on our own.”

It was an offhand remark, yet it stayed with me.

When technology can complete a task faster—and often better—why insist on doing it by hand? Is it because learning demands the slow grind? Or because we believe something only counts if it’s done the hard way?

For her, the answer was discipline—an exercise in sharpening her own mind. But her dilemma belongs to more than just students.

When ChatGPT’s new Agent Mode can answer emails, map itineraries, prepare presentations, shop for groceries, even draft financial reports, it forces a question most of us would rather avoid: how much of what once filled our days was truly work, and how much was ritual?

AI holds up an unforgiving mirror. In its reflection, the “busywork” that propped up entire careers is suddenly stripped bare. And if the doing is no longer the point, then what is?

What remains is judgment. In a world where execution is cheap, deciding what deserves to be done becomes priceless.

Choosing the right task, knowing when to stop, and allocating scarce time and resources—these are no longer side skills. They are the core.

That shift changes our role entirely. Workplaces once depended on legions of people moving step by step through a process. Now they need those who can set the direction, choose the tempo, and decide which notes are worth playing at all. We are less the performers, more the conductors.

And conducting, at its heart, is about values. If everyone has access to the same tools, what separates one person’s output from another’s is no longer speed or polish—it’s the convictions that guide their choices.

AI will make execution faster. It will make the wrong choice faster, too.

The real test ahead is not whether we can do more, but whether we will choose, with care, what is truly worth doing.

Congratulations on starting college in 2025! I know you’re feeling both excited and a little overwhelmed right now. You might be wondering: Does studying still matter when AI can write essays, create videos, and code better than you? Will the world even need someone like you when you graduate? It’s okay to feel that way—I did too.

Here’s what I want you to know: you don’t have to have it all figured out. Instead, start by asking yourself what truly matters to you. What’s something you can’t stop thinking about? What’s something you’d love to make better? Maybe it’s fixing slow processes at school, helping friends who are struggling to find classes, or calling out something unfair. Choose something that speaks to your heart, and start from there. Even if you don’t master it all before you graduate, you’ll gain a much deeper understanding of yourself and your journey.

Don’t worry so much about picking the perfect career right now. Focus on finding problems you’re passionate about solving—that’s what will take you further than any job title ever could.

And don’t get too hung up on what you’re majoring in. Think about what you can start doing today. Remember: college can be your playground for trying new things. Organize a talk with students from different majors, build a small AI tool, help a local café create social media videos, or set up a system to help your student group run more smoothly. You don’t need to wait until graduation to start building—these days, tools and resources are everywhere, and creating something new has never been easier. Let your curiosity guide you, and take action even when you’re unsure. You’ll learn so much just by trying.

I want you to also work on building your own perspective. AI can know everything, but it can’t tell you what truly matters to you or what kind of world you dream of creating. It’s okay if you don’t know all the answers yet. Write down your thoughts, talk about your ideas, and keep asking questions. Over time, your feelings will shape into your own voice.

And above all, embrace trying, stumbling, and growing—that’s how you’ll move forward. In a world changing this quickly, mistakes are some of the best teachers you’ll ever have. The outcome doesn’t matter nearly as much as the experience you gain. You don’t need to be amazing before you start; you just need to start—and that’s how you’ll eventually become amazing.

Take your time. Stay curious. Keep exploring. Believe in yourself, and you’ll find your own way, one step at a time.

—Your Future Self

Since the most crucial ability for the next generation is no longer just “problem-solving” but “exploration,” this signals a shift. A common parenting logic in many Asian households—living life on behalf of the children, or “proxy parenting”—needs to step aside.

Over the years, I’ve met many brilliant high school and college interns. They’re intelligent and diligent, yet often lack decisiveness. When I dive deeper into conversations, I frequently hear things like: “My dad said this would help me get a job,” or “I wanted to switch majors, but my mom told me not to be impulsive,” or “I want to make films, but my parents say that’s just a hobby, not a career.”

It’s not that these young people don’t want to take responsibility for their lives—they’ve simply been trained to believe there is a “standard answer” to life, and the safest path is to follow the answers given by adults.

But the world has changed. As AI rises, more companies are caring less about which school you attended or whether you scored perfectly, and more about whether you possess key abilities: the courage to make decisions under uncertainty, the self-drive to learn independently, and the flexibility to make mistakes, reflect, and adapt.

These traits stand in stark contrast to simply being “obedient.” They’re often forged through making wrong choices, failing, and clashing with societal expectations.

Our generation—parents, educators, and even investors—must accept this truth: the future will not be led by those who excel at filling in the blanks, but by those who think independently and carve their own path.

So I’d like to say to fellow parents: let go of the bat you’re holding over your child’s hands. Be their audience, their cheerleader, the one who catches them when they fall—but don’t step in to play for them. Because this game of life is theirs alone. Even if it’s messy and full of stumbles, they must be the ones to play it through.

Letting kids make their own choices and learn through trial and error may mean a slower path, but it’s one shaped by their own learning curve—not a continuation of your own life.

AI can simulate countless skills, but it can’t replicate the human experience of sincerely exploring the world. And that is exactly the most irreplaceable value in this era.

Will I be replaced by AI?
But more importantly: Do founders still need us?

That day, Buffett didn’t talk about technology, AI, or the next big trend. Instead, he shared three words: Clarity. Judgment. Long-term thinking. None flashy. All essential. And in today’s world of automated tools and endless information, more relevant than ever.

Because let’s face it, nearly every traditional VC skill can now be replicated by machines. AI can analyze markets, generate research memos, model financials, and even offer operational suggestions. But it still can’t do the one thing this job truly demands: to see potential in a founder before they can fully articulate it themselves and choose to believe in them anyway.

Early-stage investing has always been about navigating ambiguity. It’s not about betting on who looks the best today, but on who has the drive and vision to become something meaningful tomorrow. Our role is to make that call when the product is unfinished, the data unclear, and the team still coming together.

When I invested in Hims, its founder Andrew had just come off a failed startup. He didn’t sugarcoat it, he walked me through everything that went wrong and what he learned. His new idea? A direct-to-consumer brand for men’s hair loss treatment. Most investors dismissed it. A niche product in a crowded market. But I saw something else.

In that failure, Andrew had developed a sharp instinct for consumer behavior, a refined sense for brand and storytelling. And in that pitch, I didn’t just see a product. I saw a platform in the making. A company that could reshape how men view their health and identity.

I was extremely fortunate to become Andrew’s first and only investor in his angel round.

Sure, AI could’ve dissected his pitch deck. But it couldn’t have picked up what he didn’t say aloud: the fire to prove himself, the insight shaped by past mistakes, the conviction to solve a long-standing, deeply personal problem. That emotional clarity turning pain into purpose is invisible to algorithms. But not to us.

Over the years, I’ve realized our best investments rarely came from the most polished pitches. They came from moments when we saw a spark the data couldn’t explain, and the founder trusted us enough to walk the hard road together. The journey doesn’t begin with a term sheet. It begins with two people daring to believe in a future not yet written.

So no, I’m not worried about being replaced by AI. Because the heart of this job has never been about having the best tools. It’s about being the best human. It’s about whether we’re willing to stand in uncertainty with a founder and stay there as they figure it out.

When we choose to trust someone over a spreadsheet, when we walk with a team through their darkest months instead of waiting for their breakout moment, when we ask not “Is this a smart investment?” but “Is this someone worth walking alongside?”

That’s when AI stops being a threat and becomes just another tool. That’s when our real value shows up.

As we look ahead, here are three questions we should all ask ourselves if we want to grow into the kind of investors founders truly need:

Are we sharpening our human instincts?

Not just observation, but the ability to sense drive, values, and unspoken fears. That comes from deep listening, shared time, and reflection—on what we feel, not just what we hear.

Are we training our judgment muscles?

When AI gives us more data than we can absorb, we need stronger internal compasses to choose what—and who—to back. Every investment decision reflects the kind of future we believe in.

Do we have the courage to sit in uncertainty with founders?

Our job isn’t to hand out answers. It’s to hold space while they find their own. That takes empathy. Patience. And above all—trust.

Ultimately, our ambition isn’t just to write the biggest checks.

It’s to be the person a founder calls when nothing’s working, and everything’s at stake.

That’s our real edge.

That’s the part no machine will ever replace.

If I could leave you with one truth for the world you’re inheriting, it’s this: In the age of AI, how you learn matters more than what you know.

The pace of change has never been this fast. And yet it will never be this slow again. What worked for us: degrees, credentials, seniority may not work for you. The rules have changed.

Artificial intelligence can learn what you know. But it still can’t replicate your creativity, your judgment, or your understanding of people.

Recently, the CEO of Shopify put it bluntly: “Anyone requesting more resources must first prove the job can’t be done by AI.” Palantir went even further. They declared: “College is dead.”

Instead of waiting for education systems to catch up, they’ve begun training young minds themselves, directly from high school.

These statements aren’t just bold headlines. They’re signals, telling us that the old models of education and employment are breaking down.

Knowledge and degrees alone are no longer a competitive edge. What truly matters is your ability to create value that AI can’t.

So what can’t AI do?

It can’t imagine something that’s never existed. It can’t connect dots from unrelated worlds and spark something magical. It can’t feel the world the way you do, and turn that feeling into insight.

Your job isn’t to follow a syllabus. Your job is to learn like a builder — to do what Ultralearning teaches: break skills into smaller parts, dive into the unknown without waiting for permission, solve real problems instead of just passing theoretical tests, and apply what you’ve learned as quickly as possible in the real world.

Stop asking, “What do I know?” Start asking: “What can I create that AI can’t? Because that’s the only question that will matter in the years to come.

The future belongs to the fast learners. The brave creators. The ones who know that learning is not a phase — it’s a lifelong competitive advantage.

This isn’t just advice for your career. It’s a way of being in a world that’s shifting beneath your feet.

I don’t want you to fear AI. I want you to rise above it — to become someone that even AI can’t replicate.

You are the architects of the future. Keep learning. Keep creating. Keep evolving. The world needs what only you can do.

With hope, belief, and urgency,
Someone who’s rooting for your brilliance