I am nothing

On a scale of one to ten, how good of a cog are you? How well do you function in your assigned role? How much of a man or woman are you? How do you rate yourself as a son or daughter, father or mother, wife or husband, heterosexual or homosexual, liberal or conservative, black or white, winner or loser, shark or sheep, introvert or extrovert, Christian, Muslim, atheist? How smart are you? How rational? How emotional? Do people like you? Are you getting ahead, or falling behind?

How do you know? Are you keeping an eye on the others in your category, comparing to see how you measure up to your peers? Is it more important for a man to be tall, or to have good hair?

This is, of course, the path of insanity, and not the good kind of insanity.

What will you do if you're too tough to be a good woman, too sensitive to be a good man, too selfish to be a good husband, too lazy to be a good employee, too shy to be a good friend, too caring to be rational, too fat to be pretty, too effeminate to be straight, too introverted to be a good leader, too smart to be kind, too young to be taken seriously, too old to make a difference, or too far behind to even get in the race?

These are all false standards and false dichotomies, but they are so common and so ingrained that we sometimes believe in them without even realizing it. And this leads to a mountain of insecurities, because nobody measures up to these crazy standards (and nobody should). But even if we don't believe in these things, it still matters what other people think, right? What will the neighbors think? Or how about our co-workers, or the people at church? And so everyone works to hide their insecurities, and they look around at their peers for comparison, and maybe they feel bad because everyone else seems to have it easy, to have it all figured out. The truth is, nobody can see the truth anymore. They are all working to hide the truth, because the truth is that they are afraid of who or what they really are. So they all put on a show, and they pretend to be a good whatever. Or maybe they rebel, and make a point of being a bad whatever, but then they are still under the control of that false standard, and they are still not being themselves.

That is all so exhausting. 

I am nothing. It's simple. If I were smart, I might be afraid of looking stupid. If I were successful, I might be afraid of failure. If I were a man, I might be afraid of being weak. If I were a Christian, I might be afraid of losing faith. If I were an atheist, I might be afraid of believing. If I were rational, I might be afraid of my emotions. If I were introverted, I might be afraid of meeting new people. If I were respectable, I might be afraid of looking foolish. If I were an expert, I might be afraid of being wrong.

But I am nothing, and so I am finally free to be myself.

This isn't license to stagnate. Change is inevitable. Change is part of who we are, but if we aren't changing for the better, then we are just slowly decaying. 

By returning to zero expectations, by accepting that I am nothing, it is easier to see the truth. Fear, jealousy, insecurity, unfairness, embarrassment -- these feelings cloud our ability to see what is. The truth is often threatening, and once our defenses are up, it's difficult to be completely honest with anyone, even ourselves. But when I am nothing, when I have no image or identity or ego to protect, I can begin to see and accept things as they really are. That is the beginning of positive change, because we can not change what we do not accept and do not understand. But with understanding, we can finally see the difference between fixing problems, and hiding them, the difference between genuine improvement, and faking it. We discover that many of our weaknesses are actually strengths once we learn how to use them, and that our greatest gifts are often buried beneath our greatest insecurities.

Letting go of your identity can be difficult and takes time, possibly forever, but as with any change, moving in the right direction is all that really matters (which is why you shouldn't compare yourself with others -- you didn't start in the same place or with the same challenges). Fortunately, we have a variety of emotions that can help us: pride, anger, fear, jealousy, insecurity, unfairness, embarrassment, bitterness, etc. These are sometimes portrayed as bad emotions, but there's no such thing as a bad emotion, just bad responses to emotions. (For example, torturing children is a very harmful response to fears about your own sexuality) If we instead use these emotions as a cue to remember, "I am nothing", let go of our identity, and examine why we are feeling the emotion (typically because something has threatened our identity) then these emotions are actually beneficial. They point us towards the buried truth.

True self improvement requires becoming a better version of our selves, not a lesser version of someone else. But without self acceptance and understanding, how can we even know what that looks like or whether we're headed in the right direction? It would be like putting the final touches on the Mona Lisa while picturing some celebrity you saw on the cover of People magazine -- the result would be a mess. Until we let go of our mental images of who we are or who we should be, our vision remains clouded by expectation. But when we let go of everything, open ourselves to any truth, and see the world without fear or judgement, then we are finally able to begin the process of peeling off the shell of false identity that prevents our true self from growing and shining in to the world. And it starts with nothing.

The two paths to success

The recent WSJ article on the supposedly Chinese style of parenting has generated a lot of interesting discussion. The most amusing commentary comes from The Last Psychiatrist, who also points out that Amy Chua, the "Chinese" mother, was actually born in America. There were also claims that the WSJ misrepresented her views, which may or may not be true, but is ultimately irrelevant since it's the ideas that are being debated.

Here's the part of the article that interests me:

What Chinese parents understand is that nothing is fun until you're good at it. To get good at anything you have to work, and children on their own never want to work, which is why it is crucial to override their preferences. This often requires fortitude on the part of the parents because the child will resist; things are always hardest at the beginning, which is where Western parents tend to give up. But if done properly, the Chinese strategy produces a virtuous circle. Tenacious practice, practice, practice is crucial for excellence; rote repetition is underrated in America. Once a child starts to excel at something -- whether it's math, piano, pitching or ballet -- he or she gets praise, admiration and satisfaction. This builds confidence and makes the once not-fun activity fun. This in turn makes it easier for the parent to get the child to work even more.

She has two main points here: 1) Learning is not fun and 2) It's important to make kids dependent on praise and admiration.

One of the problems I've faced throughout life is that I'm kind of lazy, or maybe I lack will power or discipline or something. Either way, it's very difficult for me to do anything that I don't feel like doing. If I try to force it, my energy disappears, and I hate life. Furthermore, not only were my parents not Chinese, but they had five kids, so there wasn't time for Amy Chua's style of parenting. I kind of had to figure it out on my own.

My strategy can be reduced to two rules: 1) Find a way to make it fun and 2) If that fails, find a way to do something else.

For example, I didn't really like school, and I especially hated homework, so I turned it into a game to see how little time and effort I could possibly waste on it while still getting "good enough" grades. I barely made it into the top 10% of my public high school class, so I probably wouldn't be accepted into whatever college Amy Chua has picked out for her kids, but I find that I really don't care. Instead, I went to a "good enough" college, slept through most of my classes, then got a "good enough" job after graduation. Meanwhile, I taught myself how to program and build all kinds of things, which to me was much more fun than school.

I'm not going to claim that my approach is superior to Amy Chua's, or that it will work for everyone, but I do think it provides an interesting contrast.

Amy Chua's approach is based on extrinsic motivation. Children must do exactly what they are told to do, and they must not be happy unless an external authority gives them praise and admiration. They must learn that their own internal motivations and judgement are worthless and not to be trusted. They are successful when an external authority, such as an Ivy League school, tells them that they are successful.

The extrinsic path to success is to focus on being the person you are told to be, and put all of your energy and drive into fitting that mold.

The approach I stumbled into is based on intrinsic motivation. To the greatest extent possible, do whatever is most fun, interesting, and personally rewarding (and not evil). External constraints, such as the need to go to school or make money are simply obstacles to be hacked. Be skeptical of external authorities, as they are often manipulating you for their own benefit, or for the benefit of the institutions they represent (often unknowingly, as they were already captured by the same systems which are attempted to ensnare you). Your identity comes from within -- external recognition such as degrees and awards are only of tactical importance -- don't allow them to define who you are.

The intrinsic path to success is to focus on being the person that you are, and put all of your energy and drive into being the best possible version of yourself.

Of course this leads to the question, "What is success?" Someone who spent his life working 80 hour weeks, living in hotels, and fighting his way up the corporate ladder to become VP of toilet paper marketing would probably consider himself more successful than a sandwich shop owner who spends his nights and weekends playing with his kids and working on hobby projects, but maybe the sandwich shop owner would be happier and healthier. Ultimately, it is up to each person to decide what success means to them, but I think it's important that everyone be mindful of the decision they are making. 

It's often said that people become entrepreneurs because they can't handle a regular job. Perhaps these people are simply too "defective" to fit into any mold, or maybe they lack the extrinsic motivation necessary to care about bosses, performance reviews, and other things which are so important for success in the corporate environment. However, what they do have is the creativity and natural sense of direction necessary to run their own business. I doubt that this is a coincidence.

As explained in this TED talk by Dan Pink, extrinsic motivation is a great way to get people to do boring and repetitive tasks, but it actually harms performance on more creative tasks. Creativity is a surprisingly fragile thing. It comes from deep inside, and external concerns (most especially, "What will people think?") seem to scare it away. But that's a topic for another time.

Of course, intrinsic vs extrinsic motivation isn't a completely black and white distinction, and we probably can't survive entirely on one or the other (I aim for 90% intrinsic). I also doubt it's possible to simply "switch" from extrinsic to intrinsic motivation. It's a skill like anything else. It takes time to find your internal voice, learn when to trust it, and stop fearing outside opinion (closely related: ego-fear).

Amy Chua's book was about parenting. Her style is based on extrinsic motivation. How do we raise successful, intrinsically motivated children? I'm sure someone will leave book recommendations in the comments -- Alfie Kohn comes to mind. However, I suspect that one of the most important factors is how we live our own lives. If we demonstrate that work and creativity can actually be fun and enjoyable, that at least sets an example. If we first solve the puzzle for ourselves, we have a better chance of helping others to find their answer.

Angel investing, my first three years

I started investing in startups with the assumption that I don't know what I'm doing (which is always true), but that the only way to actually learn anything is through experience. Therefore, my goal was to invest in a variety of startups, learn from the experience, help some startups, and hopefully not lose too much money while doing so. I don't have any single criterion for investing. Sometimes, the idea seems good, sometimes the people seem good, and other times I'm just curious to see what will happen. No matter what though, I want to be helpful and learn something interesting from the experience.

I've definitely learned a lot, but the recent Heroku acquisition (for a reported $212 million) made me wonder if I've also reached the point of "not losing too much money", so I did the math. From 2006 (when I started investing) through 2008, I invested about $1.21 million in 32 different companies. About half of those companies were either acquired or are dead/mostly-dead. The other half are still alive and seem to be doing well. The current acquisitions total about $1.34 million, only about a 10% gain, which isn't great, but at least I'm not losing too much. Fortunately, the "still alive" category includes a number of very promising investments, such as Meraki, Weebly, and Wufoo, so I expect the final return will be much better than 10% (which is all gravy anyway, since my primary goal was to learn more and be helpful).

Of the current acquisitions, only two have yielded a greater than 10x return: Heroku and Mint. Unfortunately they were also two of the smaller investments, proving that I don't know what I'm doing, or at least showing that I need to make a point of investing more money into the best companies (Mint was oversubscribed, but I don't remember why I didn't put more into Heroku -- edit: apparently it was also oversubscribed).

It's worth noting that the highest return was from a Y Combinator company (Heroku, winter 2008). I've been investing in the YC companies almost from the start (Wufoo was winter 2006), and they keep getting better. YC is attracting the best founders, and Heroku is just the tip of the iceberg. The more great YC companies there are, the more reasons there are for other smart founders to join YC, and I find myself asking non-YC companies why they aren't yet in YC. This trend definitely contributed to my decision to join YC as a partner.

There were also a couple of medium-sized acquisitions (AppJet/Etherpad and 280North) and several smaller but still nice (2x-3x) exits such as Auctomatic, Parakey, and Zenter. Sometimes people complain about these deals, but as much as I'd like to get a nice 10,000x exit, I'm certainly not going to complain when someone doubles my money!

A few companies (such as ScanScout) were acquired by other private companies, so I include those in the "still alive and doing well" category, since it was not an exit from the investor perspective (no liquidity). Only two companies are officially dead, but there are at least four "zombies" that still exist, but in a minimal form and are almost certainly worthless.

The two bits of advice that I always give to people looking to get started with angel investing are: 1) Assume you'll lose your money and 2) Plan on investing in a large number of companies. (my third bit of advice is to attend YC demo day) I think my experience so far validates this advice. It's important that investors have the right motivations (helping out startups and learning how to be a better investor) and the right expectations. Anyone doing it with the idea that they can simply find the next Google, invest a bunch of money, and then get super-rich is going to be very disappointed. That said, finding the next Google and buying a 1% stake is my current billion dollar plan :)