I went to business school and dropped out after 3 months. For me, it turned out to be a waste of time and money. But that doesn't mean business school is useless for everyone (which is the popular opinion in Silicon Valley these days). It's been a little over a year since I've dropped out, and I can think of 3 good reasons to attend.

  1. Career Transition

    Business School facilitates industry and/or functional career transitions. While it's typically difficult to change both industry and function (ex: energy sector analyst to sports marketing), it's even possible to achieve such a dramatic change by taking some small steps (academic year internships, etc.) over the course of two years. If changing just industry or function, the transition is relatively straightforward.

    While it technically wouldn't be impossible to make such transitions without the significant financial and temporal commitment of business school, what these programs offer is considerable de-risking of the transition. It virtually guarantees a soft landing in even the worst case scenario even if things don't work out perfectly.

    Yes, there are people who can make these transitions without another academic line item on their CVs. But not everyone has the track record, network, or drive to make it a reality.

  2. Rest

    For those coming from an excruciating career start in places like banking or consulting, business school can be a 2 year respite that won't leave a blank in the resume. Students who are sponsored by their employers won't even have to fork over the tuition that can be prohibitive to many. Even without this, they may have enough of a cushion built up and have very good financial prospects coming out of school that the financial downside can be mitigated.

    Terms like "funemployment" are thrown around casually in Silicon Valley, but not every industry or career trajectory will let people randomly take 12+ months off and come back to the workforce seamlessly. "I was working on some side projects" doesn't (a) have much credibility and (b) isn't even possible for some functions (ex: corp finance) for most careers outside of software or design.

    For many industries, not having a blank period in the CV can be worth a lot of money.

  3. Network

    The business school alumni network is a value-add that I understand in theory, but have yet to see used in the wild. However, I have been using my undergrad alumni network from time to time, and thus I can see how people without a super-nepotistic (i.e. helpful and supportive) alumni network like that of my alma mater would see a great benefit to being part of an alumni network that seeks to help each other out as a kind of a fraternity.

    Further, no matter who we are, our current network of friends and professional acquaintances tends to encompass a fairly narrow range of backgrounds. A business school class of roughly 400 students covers a very wide range of industries and functions. The ability to quickly tap the knowledge and perspective of someone in the trenches in practically any sector can be an asset.

    For example, when I needed a sanity check and first order guidance for what to do for year end tax compliance at my startup, I was able to chat with my business school friend with an big-four accounting background to confirm what next steps I needed to take.

This is likely not an exhaustive list of reasons why business school might make sense for someone. But what I learned through my own experience enrolling and dropping out is that it's critical to have something concrete that you want to gain over those 2 years that would be very difficult to obtain otherwise. I only had vague, weakly held ideas that brought me there, and I paid the price for it (literally).


disclaimer: this post is written from the perspective of a resident of San Francisco working in high tech

My friends are always shocked when I claim that Tokyo is a very affordable city to live in.

How could this be, they ask. Tokyo has, in their minds, always been one of the most expensive cities in the world to live in.

There are a handful of factors at play:

  1. Inflation and Deflation

    The idea of Tokyo as an expensive city was cemented in our minds during the 90's, when it was indeed one of the most expensive cities in the world to live in. But Japan has spent the last 20 years in a deflationary environment where asset prices have largely remained stagnant.

    Contrast that with the West where inflationary policy has lead to a steep increase in prices throughout the economy. This is most acute in San Francisco, where real estate expenses continue to skyrocket, health care costs continue to rise, and college tuition increases know no bounds.

    Yes, Tokyo is still an expensive place to live compared to most of the world. But living expenses in the pockets of the West where we live in as tech workers has dramatically increased to the point where Tokyo is now an attractive option.

  2. Food

    It's easy to eat out and get cheap, healthy, good food in Tokyo for about $10. The equivalent in the Bay Area would cost about $20.

  3. Health Insurance

    Health Insurance is heavily subsidized by the State, and its burden is substantially lighter for Japanese residents compared to the US.

  4. Tip

    There is no tipping culture in Japan, making meals automatically 15% less expensive than in the states, all else being equal.

  5. Public Transit

    The train and bus system in Tokyo is (I believe) the finest in the world. It is on time, frequent, clean, and the riders are extremely courteous (do NOT use them during rush hour though). There is no need to ever own a car living in Tokyo (unless you're a gearhead, of course)

  6. Apartments

    A 1 bedroom in a great neighborhood in Tokyo costs roughly $2500/mo. The equivalent in SF would be about $3100~$3500. There are also options that are less than $1000/mo with great public transit access to the heart of the city.

    Of course, the caveat is that rooms in Tokyo are substantially smaller than the SF counterparts. However, (a) you get used to the smaller sizes, and (b) we often don't even have the option to pay less for a smaller room in SF.

  7. Tax

    Japan has a surprisingly low tax rate for moderate income earners. At a $60k income, the base federal income tax is roughly 15%.

    US federal income tax at the same level would be roughly 20%, with an additional 10% added on for California state income tax.

  8. Currency

    This may perhaps be a temporary phenomenon, but with the exchange rate at 120 Yen to the Dollar (it was as low as 78 Yen to the dollar in 2010), our dollars go much farther than they used to just 5 years ago.

  9. Supply Demand Arbitrage

    Japan's market dynamics are unique in that the supply side must offer much more "value" to the market than anywhere else in the world. This takes the form of quality, service, cleanliness, politeness, and many other forms. While we need to pay a premium to receive such benefits in the States (where the baseline is much lower), the default "value" provided to the consumer by the supplier is much higher in Japan. As a result, on a "per dollar" basis, our money goes much farther in Japan than in the States, provided that you are a consumer who is already paying for such benefits in the States.

    This balances out in the domestic market because each person must assume both the role of the supplier and the consumer under normal circumstances. The ordinary citizen must work comparatively more as the supplier compared to other countries, but once she is on the demand side, receives much more per dollar than her global counterparts.

    This opens up an arbitrage opportunity for people who only participate on the demand side in the Japanese domestic market, and fulfill their supply side role elsewhere (ex: a remote software or design job, or accumulated savings).

As a result, Tokyo becomes a fantastic place to live, as long as you don't have to work there.


I turned 30 earlier this year. Naturally, I now know things that I wish I had known earlier in my life. Here are ten things I've learned in my twenties, from both my success and failures -- but mostly failures.

  1. The Geographic Location of Your College Matters

    This matters for two reasons: work and friends. All things being equal, you are much more likely to end up working for a company in the area than elsewhere (there are many forces that contribute to this, from the on campus recruiting to the perceived coolness of the surrounding industries that are ingrained in you over the years). Because of this, your friends are likely to stay in the general area of the school (e.g. East Coast vs West Coast). This means that even if you defy the odds and start working elsewhere, you will lose many of the good friends you made in college.

    I personally experienced this going to an East Coast, Wall Street feeder school and going back to Silicon Valley. Yet another factor to consider when considering the impossible question of which school to attend.

    Bonus tip: On campus recruiting is 10x easier than off campus recruiting after graduating. Take advantage of it! (I never did it and paid the price for it, as the financial crisis hit)

  2. Under Load on Courses during Your First Semester of College

    The first 6 or so weeks of college are when everyone is looking to meet new people and make friends. After this period, people become comfortable with spending increasing amounts of time with whatever cohort they have discovered for themselves. It's also the time where you can try out a bunch of different student clubs and see what works for you. And for many (including myself), you can use the extra time to adjust to a new city and a new stage in your lives where you will need to make decisions and set schedules by yourself.

    I overloaded on courses my first semester and paid the price both physically and mentally. I hardly slept or ate, losing 15 pounds over the first 6 weeks of college. I felt completely burnt out, and was not performing well academically. My schedule was a mess and I was living hour to hour, let alone day by day. This remains one of the three darkest times of my life.

  3. Take Difficult Courses Your First Year

    It will be torture, but you will make lifelong friends there who will there, suffering alongside you. There is a reason why Vietnam vets remain lifelong comrades. That "we're in it together" environment fosters lifelong bonds.

    For me, this was Physics 105, the Physics major track Mechanics course. Problem sessions would run weekly on Thursdays from 8pm to indefinite in the Physics building in the corner of campus. We would be there until 2am, give up for the night, go play Mario Kart 64 at one of our rooms until 4am, split up, meet up again at 11am the next day, keep working until 4:50pm, and make a mad dash to the Physics building to make it in time for the 5pm deadline. It was hellish and made me give up any hope of majoring in Physics after that course. But the guys who struggled alongside me and the brilliant ones who would lend us a hand at tackling the problems became my best friends in college and thereafter.

  4. Be a Host

    Feel like you're losing touch with friends because you're too busy? Having trouble meeting new friends? Got some money but no time? Host events!

    Board game night, video game night, poker night, chess night, movie night, Super Bowl parties, GoT viewings, you name it. Buy some beer, chips, grapes, order pizza, and encourage but don't require guests to bring something as well, from extra chess boards to deviled eggs (I have a friend who keeps bringing deviled eggs to chess night because he wants to eat them himself). You don't need to drive anywhere, friends will slowly bring their friends from other social circles, and you'll all have a great time.

  5. Investment or Hobby?

    With each purchase, know whether you're doing it as an investment or as a hobby. This applies from everything from a car, an education, to a home.

    If your car purchase is a hobby, you only have to think about how much you enjoy the car. If you need it as an investment so that it will enable you to reap financial windfalls from it (you need to get to work), then its utility and ROI should be your concern.

    If your education is a hobby and your are doing it for the love of the subject and do not need to make a living, then you can choose to study an esoteric humanities discipline and get away with it. If you need to support yourself after college, then you need to consider the return on your tuition you will gain from your studies.

    If your finances are such that your home purchase needs to increase in equity value, then you must consider your alternatives and evaluate whether purchasing a home has the best probability weighted expected return on your capital. If your home falling 20% in value makes no difference whatsoever to you, then you can buy whatever your heart pleases even if the property is very illiquid or macroeconomically likely to fall in value (e.g. Japanese real estate).

    Most purchases will fall somewhere between these two extremes, but it's a worthwhile mental exercise for your large purchases.

  6. Watch Some TV

    I urge you to watch some quality TV shows so that you can have it as an conversation topic option when meeting new people. I used to think that talking about TV was uninteresting and frankly beneath me, but I now view it in a different light.

    Conversation topics are just conduits to get a better view of another person's character. Just as we can learn about a person from what part of a Hemingway book resonated and affected them strongly, so can we with TV shows.

    For the last 10 years, I barely watched any TV. Obviously if you don't watch TV shows, you can't have a conversation about TV shows. This can be a problem when you meet people with whom you have little in common with (what do you mean you don't read trashy Sci-Fc novels!?), since TV and sports are usually the two most common and widely accepted fall back options. It's one of the easiest ways to get a conversation going, and you can glean a surprising amount of information about a person from the more meta aspects of any conversation, including TV.

  7. Spend Money on Others

    I recently realized that spending $50 on a random gift for a friend is much more satisfying than buying something for myself. This is anecdotal and I'm not exactly sure how it works, but it seems to be backed by some research as well.

    This also applies to splitting the bill on a meal. If you have a regular group for meals, try taking turns footing the bill rather than splitting it every time. Sure, someone will likely get the short end of the stick, but it'll grow the camaraderie and make it more likely that you'll get together again sooner rather than later.

  8. Overpay When Splitting the Bill

    A couple of bucks here and there is just not worth being labeled a cheapskate to your friends. The appropriate "rounding threshold" will depend on your group. It might be to the nearest 1, 5, or 10 dollars.

  9. Find "Your People"

    "But you find your tribe. Jerry Seinfeld said in an interview last year that his favorite part of the Emmy Awards was when the comedy writers went on stage to collect their prize. “You see these gnome-like cretins, just kind of all misshapen. And I go, ‘This is me. This is who I am. That’s my group.’ ” By your 40s, you don’t want to be with the cool people; you want to be with your people." New York Times

    There was a time in my early to mid 20's where I wanted to be with the "cool people". In High School, scoffed at classmates who played D&D. Looking back, it was a reaction against my own uncoolness and a reflection of my lack of self confidence.

    But I gradually realized that I was just trying to be someone who I wasn't. To the people who mattered to me, it didn't matter where I fell on the objective coolness scale. I felt more alive and invigorated and excited about everything when I re-embraced my deep rooted nerdiness. I felt at home and in my element around my fellow smart, uncool, nerdy folks.

  10. What It Means to "Make the Most Out of Your Mistakes"

    This phrase is such a cliche that I always subconsciously rolled my eyes at it. To be honest, I still roll my eyes at it. Cliches are a problem because their ubiquity prevents us from thinking deeply what the phrase is actually trying to communicate.

    I've made many many decisions that in hindsight can be classified as mistakes. Let's take my own career for example. Going to school in the East Coast was a mistake considering I knew I wanted to be in Silicon Valley high tech. Majoring in EE rather than CS was a mistake. Not committing myself to becoming the best engineer I could be (even if I was never going to be the best) was a mistake. Going to the UK made it even harder to come back. In many ways, my experience in Japan was traumatic, and I made very little money or career progress. I once negotiated way too hard with a semiconductor company and had an offer rescinded. Going to business school was a waste of time and money given who I was and what I wanted to do. My mistakes far outnumbers the optimal decisions I have made.

    Each mistake puts you in a situation that is objectively worse than where you could have been. Some doors that were available to you will now close. But unknowingly, new doors will start to creak open as you move forward in your currently suboptimal path. There will be some cool opportunities that will arise from the things you learn and the people you inadvertently meet. I wouldn't have met my team if I hadn't made all these mistakes in my life. Maybe my optimal path would have put me in a better place (maybe I'd be a Facebook millionaire!), but maybe not. There's no way to know, it's useless worrying about something I no longer have any control over, and I'm quite happy where I am today. That's probably why we say we would do the same things all over again, despite all our mistakes.

Thanks to Kevin Ko for reading drafts of this post.


I've had the (mis)fortune of having had to work with lawyers several times over the last few years, so I decided to write a short post listing out the little things that have proved valuable in working with them. This list is based entirely on personal experience and personal preferences, so take any information with a bucket full of salt.

Finding a Lawyer

There are two "good" ways to find a trustworthy, capable lawyer, assuming that the office of the lawyers that you usually use doesn't have a practice area for your legal soup de jour.

The first option is to talk to a lawyer who you have worked with in the past whose character and skills you trust, and ask for a reference. This obviously isn't foolproof, and I've had some poor experiences when my doctors have referred me to practitioners of other medical disciplines, but your batting average will likely be better than a shot in the dark or (god forbid) a stab at the Yellow Pages (do the Yellow Pages even exist anymore?).

The second option is to talk to a friend / acquaintance / business partner whose professional judgment and past use of legal advice you know and trust, and ask for a reference. Note that this shouldn't be any random friend, but someone you know to have sound sense and mileage using legal services. This should not be your dental hygienist (yes, my dental hygienist really did refer me to a lawyer. I accepted the information but went to a law office with whom my family has worked with in the past).

I'm actually not sure if asking for a referral from a friend who is a lawyer is an option that works. I have no evidence, but my instincts tell me that practicing law and knowing quality legal professionals in a different practice area are very different things. The issues are exacerbated if said friend is a relatively junior lawyer.


Some Lawyers are aggressive, and some are more "reasonable" in their approach. This is true whether you're dealing with a liability case, a tax law case, or anything else. There is always a range of strategies that can be pursued, and different lawyers will choose different parts of the specturm. Find one whose style fits your needs and / or your particular situational needs.


When you call the law office and set up a consultation, ask her what materials you should bring that day. Having all the materials in front of you will make the conversation go much smoother.

You will likely have many documents, so be sure to label each with post-it notes as tabs and have a short cover letter that lists the contents of the set of documents that you have brought.

This organizing step will (a) help you refresh yourself about the scope of the case, and (b) cut down the time you'll be billed by the firm.

Refuse Their Offers to Come out to an Office Near You

Lawyers at big firms will sometimes offer to have meetings at an office closer to where you live or work, separate from their every day office. Refuse this offer and take the time to go to their regular office. Your lawyer will bill you for his travel time, and when you are paying hundreds of dollars per hour, this can really hurt your wallet.

Be Aware that Some Lawyers Have Pet Strategies and Arrangements

Each lawyer will have "pet strategies" that they like to use and suggest to their clients. Depending on your circumstance and the lawyer's inclinations, what they most strongly suggest may not be the optimal choice for you. It would be nice if we could place infinite trust in the services we hire, but the reality is that we often have to oversee the effort and make some judgment calls ourselves. This is true when hiring contractors to do work on your house, and is true when hiring lawyers.

Of course, we laymen can't hope to understand all the intricacies of certian complex legal structures or strategies, but getting high level information on the options available to you and forming your own thoughts on what might be best for your situation will be necessary to begin having a constructive conversation with your lawyer in order to figure out what is truly optimal for you. You can't depend on anyone but yourself to represent you in fighting for your best interests, even if you are paying them.


Hopefully you're fortunate enough to never have to work with a lawyer, but keep some of these things in mind if you do. Even if you reject any or all of my suggestions (which is totally fine by me), just thinking about these issues in earest will be helpful.