Aswath Krishnan

Why do you like people or music instantly — and not others? You didn’t do a structured analysis. You didn’t create a pros-cons list. You just felt something click — and that was that. The same goes for cities, coffee shops, relationships, products, and even presidents. Why Brad Pitt over Chris Evans? Why Tokyo over Paris? Toyota or Mercedes? Claude or GPT? Why does one place feel like home and another feel… off? When I asked a sales lead for our B2B software what makes us win or lose a customer, I expected to hear about features, pricing, or buyer personas. But he shrugged and said, “Honestly, it mostly comes down to whether product managers or execs are on the call.” There’s a pattern here. And it isn’t logic. Most of us pretend we live like Spock, but we make decisions like jazz musicians — improvisational, intuitive, all feeling. From friends to lovers, brands to beliefs, the throughline in our choices isn’t reason. It’s resonance . It’s mostly vibes. “Vibes” is the best word w...

They used to say you're the average of the five people you spend the most time with. That was before the internet hijacked your attention span and filled your brain with digital sludge. Today, your closest companions aren’t friends, mentors, or thoughtful voices. They're algorithmically boosted, attention-seeking strangers yelling into the Internet void—clickbait journalists, TikTok dancers, Twitter thinkbois, clout-chasing grifters, promiscuous influencers, silly comedy Reelers, and conspiracy-peddling uncles in WhatsApp group chats. In short: idiots. And the worst part? They’re shaping you. Your brain—like an AI model—is plastic. Moldable. Continuously trained on whatever data you feed it. And right now, you’re feeding it junk. Doomscroll long enough and you’re not just consuming idiocy—you’re becoming it. Look at your feed. Really look. Out-of-context quotes. Shallow outrage. Celebrity gossip no one will remember in 48 hours. Fake experts selling fake solutions. Outrage bai...

If your goal is exceptional compensation, then you need to cultivate talent that's rare, in high demand, and visible and legible to hiring managers and execs. This typically involves deeply specialized or cross-discipline training, continual practice, and public demonstration of your skills through recognizable achievements, projects, or networking within your industry. But that isn't sufficient. You also need to strategically position yourself at a company and a role with the machinery, team, capital, and market to effectively translate your specific talent and energy into revenue, or at least investment; companies that believe that quality of talent can make or lose millions of dollars, so they don’t mind paying top dollar for top talent. Imagine you are a brilliant mathematician or computer scientist -- your earning potential will be far greater at a well-functioning quant trading firm like Jane Street than, say, at a local bank, Walmart, or the US government. Or to use an F...

I wrote earlier about the absurdity of reality . But paradoxically, this absurdity operates according to strict and predictable laws and mathematical formulae, like gravity, electromagnetism, or thermodynamics. Why these laws? Who or what defined them? Consider evolution: No one sat down and designed creatures, yet living beings have intricately fine-tuned features—eyes, wings, intelligence—purely because only those possessing useful traits survived to reproduce. Evolution doesn’t create; it filters. What if the universe works similarly, not designed but naturally selected? Imagine an infinite primordial landscape of universes, each born from some cosmic chaos, each bearing its own randomly tossed dice of laws.  In most of these universes, randomness reigns supreme. Gravity randomly fluctuates, electromagnetism never stabilizes, and quantum effects rip reality apart before atoms even form. In some universes, gravity was slightly stronger, collapsing space into black holes immediate...

There’s a certain pressure to have goals and wants; to do and achieve something with our lives. We make it a point of asking kids and adults what their goals are. What do you want to be when you grow up?! What are your new year resolutions?! Where do you see yourself in 5 years?!  There are benefits of having a future vision, but it comes at a price. Every want and goal can take up time and mind space, and make you defer contentment and just be-ing. So you need to be more intentional about the wants you pick up consciously, or often, subconsciously. I know at least a handful of people who have wanted to be managers, advisors, or startup founders. They like the idea of it - the title or the perception of being a leader. But they end up disliking the job. I know people, myself included, who want to have a good community and circle of friends, but hate the process of meeting new people. Most people want to look fit but dislike the routine of exercise and diet.  For all your curre...

I don’t think there are many shoulds in how to live life— because who knows, really?  But if there’s one  should , it’s this: radically live how you want to . Whatever that means to you. It sounds obvious, yet almost no one actually does it. Most haven’t even thought deeply about why and how they want to live. Let’s step back for a second. We spawned into this mysterious universe with zero instructions. No clear purpose. Just here, suddenly, like magic. And one day—just as suddenly—we’ll be gone. It’s like we all woke up stranded on some cosmic island with strange matter, life, and laws, Lost style.  It's quite mind-blowing and absurd, really. And equally bizarre that most of us go through the motions of our lives confidently and seriously, without regular confusion and fascination about the unknown nature of our reality and existence. And even for those who have dwelled on the situation and  get  it intellectually, there’s a massive gap between knowing life ...

If you are a farmer, you want a high yield from your crops. But if you are not a professional, you plant trees just because. You want the tree to take root, grow, bloom, and be healthy. You don’t have expectations about how tall the tree grows, what shape it takes, or how much fruit it yields. You don’t compare it to other trees. You just want it to be, and you take joy in its being. You care, but you don’t control. You enjoy the presence, not some performance.  Unless you are a professional child-rearer, the same philosophy applies to parenting. It’s about creating the right conditions for growth rather than dictating the outcome. When you parent with this mindset, you nurture without imposing, support without shaping, and trust the natural course of development. This feels like a more fulfilling and less stressful parenting experience. Instead of anxiously measuring milestones or comparing achievements, you can simply enjoy the unfolding of your child’s unique journey and be...

Nearly all companies ossify as they grow larger. Product, organization, and operations become more unwieldy, more complex, less agile, and less innovative, Newer and nimbler competitors slowly steal market share, and the cycle continues.  The most resilient and durable companies - say, Apple, Facebook, Google, United Healthcare, LVMH, etc. have one essential quality to outweigh the forces of ossification - powerful and inherent flywheels to get better and more competitive as they scale.  These “accumulating advantages” can come in many forms - as network effects, economies of scale, brand and marketing efficiencies, IP, data, deepening product or operational expertise, capital, regulatory capture, etc. Google’s search becomes better as more people search and more publishers follow Google’s standards; Facebook gets better with more people and content; LVMH’s brands become more popular with more customers; and United Healthcare can offer bigger networks and better pricing. ...

We are out of the ZIRP era, and Ubers and Lyfts are now back to costing the same as a taxi ride. As I’m taking more taxi rides, I’m noticing that taxi drivers drive much more recklessly than rideshare drivers and are also more distracted on their phones. Car cleanliness and politeness is also a hit or miss.  I theorize the main driver of this difference is feedback. Rideshare drivers get a feedback rating after every single ride and are de-platformed if their rating goes below a threshold (I believe 4 or even 4.5 stars). Taxi drivers have no such feedback loop.  You can similarly compare restaurants and medical providers. Restaurants are a brutally hard industry - ones that don’t get consistently good reviews from patrons and critics fail inevitably. This also improves the overall quality of restaurants that do survive. Hospitals and doctors, on the other hand, have no such feedback loop. Patients have no good place to check a provider's ratings or even know if a doctor is tre...

We were doing a major renovation last year and a lot of rearrangement in our home this year.  Both followed the same pattern - initial excitement, then a trying period of effort, doubt, and despair as things got messy, and finally light and joy at the end of the tunnel.  This is true with many things in life - career transitions, relocations, starting a family, new business, hobby, or health journey.  Getting to a higher maxima often requires you to climb down from the comfort of your current local maxima. That’s always difficult and uncertain.  But if you don’t risk it (and endure/enjoy the process), you don’t get the biscuit. 

Longevity is having its moment, thanks to the growing influence of thought leaders like Bryan Johnson, Peter Attia, and Andrew Huberman. Yet, it’s an unfortunate term, often misunderstood and criticized. For many, it seems like a futile and even vain fight against death, a sacrifice of the present day for questionable benefits in the far-off future, or dragging out life into decades riddled with frailty, dependence, and pain. It’s a PR problem for what is actually an essential and transformative idea. The real goal of this movement isn’t about living longer or defying death. It’s about staying younger and healthier, and reaping the benefits now. Our physical health peaks in our late 20s and begins to decline after 30. Staying younger means maintaining vitality, lucidity, resilience, and avoiding disease and pain every day. It’s less about stretching life to 120 and more about feeling 25—even at 30, 50, or beyond.  Living longer and staving off death are simply side effects of stayi...

We were bringing over a fragile gingerbread house, precariously placed on the floor of our car’s back row, to a Christmas party. With every stop, swerve, and bump, I felt an involuntary pang of worry. My body tensed, my thoughts raced, and I caught myself clenching, both mentally and physically. The gingerbread house arrived safely, and everyone loved it. But the ride wasn’t enjoyable for me. The concern and the clenching—it didn’t actually contribute to the house’s safe arrival. It just made the trip unpleasant. Looking back, I realized this wasn’t just about a gingerbread house. This is how most of us go through life—clenched. We’re constantly on edge, worrying about what others think, stressing over unfinished tasks and goals, craving more, fearing failure, envious, judgmental, or bracing ourselves for what might go wrong. Even when things are fine, we’re often stuck in a low-grade state of tension. A lot of this clenching is automatic and subconscious . It happens so fast, in micro...

I feel a rush of energy whenever I'm in NYC.  It hits me the moment I step out of the airport, and it's there every time I leave my hotel or brother’s apartment. NYC has majestic buildings, thriving retail, and jam-packed roads. But the main catalyst for making it feel so alive is its people — Pedestrians. Everywhere. When I first left home to attend university in Singapore, my uncle (who had lived abroad before) wisely advised me to go to crowded places if I felt lonely—and it really helped. But my hostel didn’t have crowded spaces, especially after dark. Sure, you can go to malls, restaurants, or events, but those aren’t practical everyday activities. I find Seattle and most suburbs or even cities in the US to be similar. You barely see people in the streets; just cars or an eerie (serene, if you prefer) emptiness. My mom is often surprised by how she doesn't run into a single soul, save the birds and rabbits, during her daily walks in the neighborhood.  But NYC? That...

I was debating with friends about whether GDP should be the North Star for a country. What is GDP and why it matters GDP measures the total exchange of goods and services in a country, capturing the scale of economic activity and trade. It’s an effective shorthand for material prosperity. Historically, countries with high GDPs tend to offer better living standards, infrastructure, and public services. When economies grow, people generally gain access to better healthcare, education, and opportunities. At a personal level, I align with Kanye’s philosophy: “Having money isn’t everything, but not having it is.” This captures the duality of wealth: it’s foundational for security and opportunity but insufficient as the ultimate life goal. Without it, basic survival becomes a struggle. But once those needs are met, the returns diminish, and other values, like social connections, health, or fulfillment, emerge. The Limits of GDP GDP has significant blind spots. It doesn’t measure inequality, ...

When you’re unkind to someone, you’re not just creating a fleeting moment of discomfort; you set off waves—within you, within them, and outward into the collective consciousness of those around you. Your behavior leaves an emotional residue and becomes part of your and someone else’s story and neural wiring. They carry that hurt forward—sometimes consciously, sometimes not—spreading it like an emotional contagion to others in their orbit. What starts as a harsh word can grow into a pattern, a culture, or even a generational legacy. Kindness, on the other hand, is a ripple effect we all wish to swim in. Every small act of generosity or love creates its own chain reaction. Neuroscience shows that acts of kindness release oxytocin and dopamine, not just for the giver and the receiver but for those who witness it too. These interactions shift our neural wiring toward empathy and openness. They teach us—subconsciously—that the world is safer, better, and more collaborative than it might som...

Many people lament about Elon Musk's outspoken views on government inefficiency and his plans for DOGE. They point to how government programs and regulations are helpful, and how his estimates for cost savings are overblown. They are technically right , but Elon is directionally right . It's more likely than not that the government has lots of wasteful spending and unnecessary bureaucracy. In closed systems — predictable and well-understood environments — being technically correct can lead to optimal outcomes. Precision matters when variables are limited and controllable, and the consequences are dire. Engineers designing a bridge, for example, must calculate loads and stresses with exactness to ensure safety. But most of the world is not a closed or critical system. It is an open, infinite, and inherently chaotic environment. Variables are countless, and conditions change rapidly and unpredictably. In such a world, you find answers and progress by doing stuff . Consider how su...

You won’t find many miserable people lounging on a Hawaiian beach. There’s something transformative about the meeting of sea and shore that seems to wash away the burdens of the world. Even toddlers and their usually-under-duress parents are in good spirits. So, I’m only half-joking when I say the beach life might be a good vision for a happier humanity; much better than flying cars, immortality, or space conquests.  Think about it: at the beach, everything’s just... right. You’re not caught up in a to-do list. No meetings, deadlines, or worries. The sun kisses your skin just enough to make you feel alive. The water? Hypnotic, refreshing, and fun. You nap, you read, you write, you frolic, and you just be. The beach life, both literally and as a metaphor, feels like a piece of paradise. Imagine if we could turn this once-a-year indulgence into a way of being. To those of you who instantly feel the practicality alarms going off, thinking, "But we can't live on vacation!” —you ne...

Much like life itself, most things have a beginning, middle, and end. Consider a song, a fashion trend, the rise and fall of civilizations, the quiet evolution of a relationship, or the flow of a regular day. All of them follow the natural arc of existence—the S-curve. Beginnings rarely rush. They are slow, clumsy, and uncertain. When they find a rhythm, it gives way to a glorious middle - a period of exciting growth and flourishing. Eventually, even the best days and songs, slow down and fade. While the speed and length of these phases may differ, the pattern holds true for most things. Though the ends poignantly clear the stage for fresh beginnings, you can't deny the personal impact of these S-curves. Most of us are vulnerable to the emotional and pragmatic fallouts of an exciting or lucrative thing slowly and suddenly disappearing. When a once cherished hobby or career is no longer fulfilling, a profitable product turns obsolete, or a thrilling relationship loses its spark, it ...

Whoever deciphers the universe's secrets wields tremendous influence over the future and those seeking answers and hope. For eons, religion and science have battled for this influence. Religion enjoyed a monopoly on truth and as the middleman to god and salvation until pesky science started asking too many questions and doing experiments. Persecuting and executing the rational buffoons could not hold back the compelling fruits of their methods - the medicines and steam engines worked a tad bit better than sacrifices and prayers, shaking faith in the messengers of god. Religion lost ground and now we pray at the altar of Saint Huberman.  Yet, the geeks have one Achilles heel, the unsolved and elusive question - why did the Big Bang? Naval said in a podcast, “Existence is a miracle, everything else is science.” Everything but one thing! The mystery of existence is religion’s final stronghold. Its persistently nagging nature makes it a powerful refuge, one that becomes increasingly re...

Roman politicians had a clever formula for controlling political unrest: panem et circenses—“bread and circuses.” By offering free food and entertainment, they kept the population distracted, too preoccupied to think or challenge the status quo. Sadly, this same tactic is alive today, but on a much grander scale. Both adults and children have fallen into a cycle of constant distraction, filling every spare moment with mindless phone scrolling or TV watching. We consume sloppy, superficial content and are stuck in an incessant stimulus-response loop that leaves no room for fertile boredom, mind wandering, deep exploration and work—the very conditions that lead to connection with self, original thought, deeper understanding and unique insights, inner peace, meaningful action, and exceptional outcomes. Even life’s essentials—sleep, exercise, hobbies, chores, and relationships—have been displaced by screens.  We have become half-present zombies, with foggy brains and attention spans re...

Many boo-ed and ridiculed Zuckerberg when he pivoted the company to VR and pummelled billions of dollars into it. The lukewarm reception of Oculus and Quest added fuel to their naysaying.  But that didn't stop Zuck. Today, after years of persistence, criticism, and perceived failures, Meta launched a product and form factor that is showing this vision has legs to be as ubiquitous as smartphones, and perhaps even more useful.  If you take a step back, the vision is easy to get behind - of course, it'd be much better to augment reality with digital artifacts instead of staring into 5-inch phones. Of course! And the company that invents it would herald a significant platform shift and can benefit immensely, as Apple has from smartphones. The challenges are mainly capital for R&D and technical feasibility, which Meta has realized through many iterations.  It is better to follow difficult but obviously true and impactful visions, than easy but low conviction and reward pro...

If you crossed paths with me last week, you likely encountered one version of me—the one that was probably distracted, dull, low energy, a bit irritable, and maybe even short with you. But if you run into me today, you’ll meet a different version: calm, lighthearted, lucid, kind, and full of energy. There are plenty of versions of me in between, but it’s no secret which one I prefer. And out of both kindness and self-interest, I’d much rather the people I care about—my family, friends, colleagues, and anyone I interact with—meet this better version of me more often. The question is: how do I show up as the best version of myself more often, and less as the stressed, impatient one? Last week, the "first me" took over due to a mix of circumstances. A nagging back pain threw off my exercise routine, which led to a domino effect—poor diet choices, restless sleep, and way too much screen time. To make things worse, a work trip added more disruptions to my routine and left little s...

Today was the first time I walked up a neighborhood hill I had driven through several times.  When I drive, I mostly notice the road, other cars, a few big buildings, and the intersections. When I walked, I experienced a whole other world - the plants and trees, homes, yards, and people. My inner world of thoughts and sensations was also different. It also struck me that the same paths also hit differently when I bike or depending on the time of the day, season, and mood.  In the TV show, Lessons in Chemistry, a character says he has read Great Expectations several times and each time feels different; not because the book has changed, but because he has. Another author has written about how we can live our entire lives within a 10-mile radius and still have more to experience.  It isn't just where you go that matters - how you travel and who you are matters too. You can go fast, far, and wide, or you can go slow and take it all in.

In 1954, Roger Bannister did what was long thought to be impossible—he ran a mile in under four minutes. It wasn’t just a personal triumph; it was a breakthrough for the entire running community. Incredibly, another runner broke the same barrier that same year, and before long, the once impossible feat became almost routine. It was as if Bannister had opened the floodgates, and suddenly everyone was rushing through. I felt something similar during my time on my university debate team. For years, we struggled to make it to the semifinals or finals of major competitions like the Asian or Australasian championships. We believed it was beyond our reach. Then, one year, our captain—a determined, confident, and ambitious leader—took the team to victory. Suddenly, NTU became a regular contender in the later stages of these tournaments. A barrier had been broken, and everything changed. More recently, I had a simpler, yet similar experience. I was trying to replace a laptop battery, but I coul...

I love a good metaphor, and someone shared the perfect video metaphor to capture an entrepreneur's journey:  A fish escapes a tank, makes a treacherous journey on land, and finally ends up in open water.  What caught me most by surprise when I tried being an entrepreneur for the first time was the fish-in-land feeling. I have heard colorful descriptions from entrepreneurs about how this is like chewing glass or jumping off a cliff and making a plane on the way down. But nothing prepares you for that level of discomfort, fear, and uncertainty than actually doing it .  Nearly everyone just stays in the tank. Most of those who do escape don’t survive the journey. For the few that take the risk and make it, a  nice river (or ocean) , significantly better than a tank, awaits. 

People often misunderstand the Buddhist concept of "detachment," mistaking it for a withdrawal from life. But the Buddha rejected apathy and asceticism in favor of a middle path—a way to engage with life without being enslaved by it. True detachment isn’t about rejecting the world; it’s about freeing yourself from cravings and aversions. These mental constructs—the endless clinging to desires or pushing away of discomfort—are what bind us, not the world itself. By letting go of the need to control outcomes, we liberate ourselves to experience life fully. For example, love becomes richer when unburdened by demands. You can cherish someone without needing them to act a certain way or even love you back. Similarly, pursuing a passion can be joyful when detached from the fear of failure or the need for recognition. Even fleeting experiences like fame or wealth can be appreciated without grasping desperately as they fade. At the core of true detachment lies a profound belief: the ...

Everything we enjoy today was born out of someone's aspiration. We have the comforts, safety, and convenience of a modern home because hundreds of generations aspired for a better home. We enjoy an abundance and variety of food, magical infrastructure, air travel, computers and internet, music and art, and so much more because some people aspired for a better life. Aspiration is the root of all progress, even if not all aspirations or manifestations are good for individuals or society. Of course, just aspiration is not sufficient. It takes an enormous amount of grit, vision, capability. cooperation, and leadership to turn those aspirations into reality. I love Stripe founder, John Collison's quote: "As you become an adult, you realize that things around you weren't just always there; people made them happen. But only recently have I started to internalize how much tenacity *everything* requires. That hotel, that park, that railway. The world is a museum of passion proj...

My heart sinks whenever a product spec or a startup pitch refers to a generic "user" or a category like "student" because it's a telltale sign that the PM or founder doesn't know whom they are building for and therefore, what the real problem and context is, if there is one at all. And that means the venture is almost certain to fail. I made the same mistake when I built a product for "people who need therapy". Eventually, I distilled it down to "people with subclinical mental health issues who can't afford therapy", then to "college students who need help", and finally to "college counseling centers who were struggling to support their students". Only then, I was able to identify specific people I could interview, learn their problems more deeply, ideate on solutions, and identify some conferences where I could recruit early customers. Many PMs and founders worry that by defining a user very specifically ("pa...

An old proverb says, "You die twice - the first time when you draw your final breath, and the second time when someone says your name for the last time." My maternal grandfather passed away at a relatively young age. I was only a small child then, so I don't remember him much. But stories of his wisdom, incredible passion for food and music, deep love and generosity toward his family and friends, and kindness to strangers are told and retold decades after he passed. So he's still living his second life, as a legend. Of course, it doesn't matter to you what happens after you are dead. And it's never a good idea to be beholden to what others think of you. But it can still inspire you to live how you want. Notes:  1. A corollary to this is you can revive a physically dead person by remembering and mentioning them. 

As a leader and manager, you have responsibilities to fulfill, outcomes to achieve, and personal boundaries to protect.   You can try to do that with obnoxious aggression. But it’s unkind and unpleasant, and people around you will leave you or never rise to their potential. You may be able to go fast, but you won’t go far.  If you swing the other way and be a nice pushover, you will not achieve your goals and be taken advantage of. The tolerance for mediocrity, lack of progress, and bottled-up frustration will eventually catch up to the people who work with you, your customers, your performance, and your business.  There's a better way - be firm on standards, but be fair, kind, and respectful. You can't fake this. You must authentically and deeply care for the mission, business, quality of work, and yourself, and for the well-being and success of the people you work with.  Appreciate and reward great work. Give everyone a fine reputation to live up to. Be straig...

In our recent renovation project, the contractor brought in a new tile guy they hadn’t worked with before. Unfortunately, the guy turned out to be a complete amateur and botched the job. This misstep was avoidable with some straightforward practices: Vetting thoroughly. Check their track record, skills, and references. A quick but deliberate evaluation can save a lot of headaches later. Clarifying expectations upfront. Make sure they understand the scope and standards of the work. A simple conversation about their approach can reveal a lot. Testing with small projects first. Start with low-stakes tasks to gauge their ability before handing them the keys to something bigger. Providing active oversight. Supervise early and often, especially at the beginning. Offer feedback and course corrections as they go. Here’s the key principle: When you delegate, you’re not off the hook. You’re still responsible for the outcome. If they underperform and you didn’t manage them effectively, the ri...

I started writing my first book in mid-Feb 2023. By the end of February, I had my first chapter and the book outline. In the next 2 weeks, I had 4 chapters, or 50% of the book. And a month later, in April, I completed all 8 chapters. By early May, I had it reviewed by a copywriter and by early June, I had a title and draft cover. A fantastic start and progress - I was *nearly* done with my first book in ~4 months! But the last 10% was the hardest. I ran into a few pesky formatting issues with Kindle that I couldn’t figure out.  I wasn’t happy with the book cover and had a dispute with the illustrator. I started a part-time contracting project, in addition to my startup. I was also hosting my parents for the summer. I was exhausted at the end of the day and week.  I made no progress in July, August, and September. I started convincing myself that it wasn’t a worthy or aligned project. I almost gave up and moved on.  Luckily, my friend Preet, who regularly checked in on my...

Many people in America crave walkable neighborhoods instead of suburban sprawl; where they can walk to their daily chores, food & entertainment, and parks. It’s so much more livelier, healthier, and connected. Not to mention, better for the environment.  But walkability also requires density, so that there are enough people within walking distance around you and around businesses.  You can’t have both large, affordable single family homes and walkability. 

My entire career has been in software, and I have taken it for granted. Only when I recently started considering brick-and-mortar businesses, I truly appreciated the magnificence of software businesses.  If you know how to code, you can create and sell software from your bedroom, with little investment or risk. You don’t have to sign leases, buy expensive tools or materials, or hire many people. It's so much easier and quicker to go from idea to MVP.  Software also has tremendous leverage. Once written, it can serve millions of customers with little marginal cost and high margins. Aside from dealing with the occasional fires, you are free to direct your time and resources to innovate (or chill). Compare that to running a restaurant where you (or an employee) have to bake a pizza for every single customer, over and over again.  And the reach of software is limitless! You can live in an idyllic village in India, like the CEO of Zoho, and sell your software to the Fortune 50...

"Sparks of inspiration" is an astute metaphor. A spark can turn into a glorious fire, but only if it immediately gets in contact with some kindling, which can burn and produce enough heat for bigger logs to light up.  Think of how many times you have had compelling ideas, but didn't act on them. Most of our sparks of inspiration just die, without kindling and logs. Eventually, we even stop paying attention to the sparks and the sparks just stop. Why bother?  What a tragedy it is to not follow our inspiration and to not engage our uniquely extraordinary capacity for creation!  I have my share of unrequited inspiration, but I like how a recent spark turned into a fire.  Last week, I had an idea to build a newsletter that automatically summarizes top Hacker News posts and comments. A spark!  If I had tried to develop a full program to do it with my rusty programming skills, it'd have been too overwhelming and a slog, and the spark would have died. Before throwing i...

I shut down a startup within a year and closed a position on a stock within a day. In retrospect, I folded earlier than I should have.  Many high-reward business and life opportunities start as bleak, lonely, and hard but pay off over the long run.  You don't have to play these games. You can fare well with low/mid-risk-reward opportunities. But if you do decide to play these games, you might as well play to win. Don't half-ass them!  The only way to win is if you commit for a long time. You can only commit if you have (a) deep belief, passion, and rationale in the thesis, outcomes, project, and yourself, (b) staying power to sustain losses and bad case scenarios, and (c) emotional resilience to weather failures and naysayers In my recent, prematurely ended ventures, I was missing more than one of these factors. 

There's no surfing without waves.  Surfers need skills to balance, maneuver, and ride the waves as they break towards the shore. But it's as important for them to have waves! And to know where and when the waves will be swelling.  Business is no different.  We all know how Bill Gates and Steve Jobs surfed the microprocessor wave to create humongous businesses around personal computers, operating systems, and applications. That caused the internet wave, which shifted consumer behaviors online and led to the creation Google, Amazon, Facebook, Netflix, Youtube, and many popular web businesses. Then came the smartphone wave, which led to the rise of the likes of Uber, Instagram, and Robinhood. The fourth-degree and third decade ripples of the humble microprocessor led to an explosion of creator tools and businesses like Canva. All this explosion of digitized knowledge, data, and compute has resulted in the latest AI wave.  The largest opportunities emerge from shifts in ...

Someone on my team was facing a crisis and needed my help. I had room in my calendar, so I could spend a few hours to help them out.  Slack in my calendar also means that I can explore curiosities and opportunities that could turn into something meaningful and significant. I can have leisurely strolls, or brunches that turn into day-long adventures.  We are in a world obsessed with productivity and efficiency. Being busy with a packed calendar seems like the best way to succeed at work and in life. But high efficiency often means low resilience and innovation, because of low capacity to fight fires or uncover new possibilities. And not to mention, the risk of debilitating burnout.  Gaps in your days and weeks because they are essential - to survive and to provide fertile ground for growth. Create and guard them. 

You can make fully rational decisions in a small, closed, predictable universe.  But most situations aren't that. There are too many variables, unknowns, and unpredictability. The source and purpose of life itself are on shaky grounds, causing any rationality on top of it to be baseless outside a defined scope. Evolution through randomness, not logic, is the nature of our reality.  Most big and hard decisions are based on some rationality but largely by instinct or circumstances. When a decision succeeds, there's post hoc rationalization and further success. When it fails, as most do, they disappear and are forgotten. This gives an illusion of a rational and deterministic universe.  The best you can do is reason and decide on the high-order bits and then go with your gut for the rest. Make bets proportional to your risk tolerance and resources, make multiple bets, bias toward action, and course-correct along the way. As John Von Neumann said, "Truth…is much too complicate...

We are remodeling our bathroom and I have to ensure that the work is done right and within a reasonable time and cost. But I have zero experience in construction! So how can I do this well?! This is the predicament of product managers and leaders as well - they are responsible for product outcomes and quality, without having the functional expertise in engineering, design, or GTM. Here’s what helped me with remodeling and product management - 1. You can be the curator and editor, even if you aren't the artist. You can bring an eye and taste for great work and craft; not just the end deliverables, but also how the sausage is made. You develop this through curiosity and interest, and by working with amazing people who can show you what's possible. 2. Make the goals, vision, and milestones crystal clear for everyone involved, and be an effective communication bridge. This will help the team avoid wastage and frustration because of miscommunication and misunderstanding.  3. Help yo...