What is it like to be rejected by Y Combinator?

Originally posted on Quora on Sep 19th, 2014.

I applied six times between 2005 and 2010, before getting in the seventh. Someone on Hacker News once called it winning the Oscar of Rejections. I can’t say I’m particularly proud of that distinction, as I’d rather be successful. That said, the lessons are more apparent when you fail, compared to when you succeed. I wrote about it in the form of advice for people applying to YC.

So as for what it feels like. The first couple of times, it felt like disappointment and a huge letdown. At the time, I wasn’t sure what they were even looking for, but maybe we got it. So after sending the application in, it had all the tension and melodrama of gambling: the ball is spinning around the roulette wheel waiting to land on your number.

After a while, I started to figure out what they were looking for, and subsequent rejections were not disappointing, but felt expected. When I finally got it, it was a little unsurprising. We have done more to prepare and shore up our chances much more than any other time–though it was no guarantee.

Nowadays, I feel if you’ve been rejected by anything, all you do is keep working. Sometimes, it’s a blessing in disguise. If you’re not at the right stage in your own development as an entrepreneur, even if you get in, you won’t be able to properly leverage YC to build a successful company. Other times, you’re overlooked, but don’t take it personally. Mistakes happen. Keep on working. Get to be so good they can’t ignore you.

I read somewhere about how it feels for athletes to win a championship game, rather than feeling like a fluke of high performance, like it seems in the movies, it feels rather like an execution of a habit. That’s probably what it should feel like.


Objections to Blockchains remind me of objections to Git

On the HN thread.

It’s just really hard for people to see beyond the present. Innovators in one cycle are often blind to the opportunities in the next. I see it in a couple of my successful friends that built their own companies on the web and mobile when it comes to crypto.

I’m reminded of the quote about the radio:

“The wireless music box has no imaginable commercial value. Who would pay for a message sent to no one in particular?” — Associates of David Sarnoff responding to the latter’s call for investment in the radio in 1921.

And then a couple of years later, for someone that made their stake in radio:

“While theoretically and technically television may be feasible, commercially and financially it is an impossibility, a development of which we need waste little time dreaming.” — Lee DeForest, American radio pioneer and inventor of the vacuum tube, 1926

And remember TV didn’t really come into its own until decades after 1926.

Yesterday, I was reading about past objections (circa 2007) to using Git vs CVS or SVN, and most of the objections were things that turned out to be unimportant. The objections focused on how their team doesn’t have a decentralized workflow that the Linux Kernel does, so they don’t need git. Or that the interface sucked, so they don’t need git.

Turns out everyone mostly uses git in a centralized way (via Github), to coordinate, but the decentralized design reveals secondary affordances that are really useful in practice. The decentralized design allows you to work and commit offline–great as laptops became more pervasive and more people worked on them. (You use to have to be online to commit, and can sometimes take minutes) The decentralized design also used content hashing with parent chains, which allows for inherent self-checking–no object modification can escape detection. Git’s data structure makes commits fast, which in practice makes fine-grained commits possible. And the decentralized design gives everyone a backup of the repo, so the central repo getting nuked by the intern doesn’t take down the org. Nowadays, in saying these things, I’m preaching to the choir. But back then, it was completely non-obvious.

The only people that got it right back then are the ones that dug into the technical details, and then actually tried it out. Notably, the guy at X.org.

And I think it’s a similar thing with cryptocurrencies, in the way that the fundamental different design and architecture of blockchains allows for secondary effects that are harder to see (until you’ve actually used or programmed in it) that aren’t available to you at all otherwise.

The trap most people fall into is that they compare the new X with what the old Y does very well. But they never consider that if it’s actually got a new underlying concept, it might suck at what the old Y has had time to get good at, but it allows for some other thing that we just couldn’t do at all before.


Marginal Cost vs Full Cost

Fallacy of marginal cost when making decisions only applies when a fundamental shift has occurred. If no shift has occurred, making decisions solely on the comparison of marginal cost works.

That means when it comes to leveraging personal skills and connections, you should double down on what you’re good at if something fundamental about the environment hasn’t changed, whether this environment is distribution, relationships, technology, culture. But when it has changed, you need to take a deep breath and fully retool, and allow yourself the time and the mindset of a beginner in order to make the transition. That also means you need to save the money and create the environment so that you can do so.

How to tell if something fundamental about the environment has changed? It helps when you can extract the concept of something from the concrete something. For example, lots of front end frameworks proliferated in 2013, so lots of people felt like they couldn’t keep up. So they threw up their hands and would joke only the cool kids knew something new. The only way they could judge something was if it was new. You should only learn something if the underlying concept is something new to you. Concepts are an abstraction or generalization of how something works.

That’s why learning about something’s concept will go a long way. Knowing the how’s and whys of something, and finding a generalize-able abstraction will help you recognize shifts, so you can better make decisions in a changing world.

Working on a Personal Relationship Manager

I got asked if I wanted to work on a Personal Relationship Manger. I politely declined, and wrote the reasons why:

On the technical side

if you’re going to be writing something to help do relationship management, it’d better be really constrained and focused in scope. Because we often use umbrella terms to mean different, but related things, it’s really easy to build assumptions into the software that doesn’t serve large segments of your users. For example, we built Noteleaf to cover ‘meetings’, but the workflow we had only meant to cover ‘coffee meetings between founders’. We had all sorts of people sign up for it that we weren’t built for, since they saw ‘meetings’, and thought it applied to them. As a result, we got a hodge-podge of user feedback that we couldn’t decipher at the time, because it was actually different segments of users having completely different needs and jobs to be done. That’s not to say it can’t be done in the near future. DNNs may be able to handle all the different variations of ‘meetings’, but that’s mostly just hand-waving on my part, than anything concrete.

On the business side

Most people don’t care enough about managing their personal relationships to pay for it, and hence, it’ll be really difficult to build a business on top of it. That’s why most relationship software are CRMs, as businesses care alot about knowing who their customers are and what they’ll buy. On the flip side, the closest we come to a personal relationship manager is facebook and other social networks. And even then, it’s not so much about the management (managing is work…no one want to do work), but getting news (pictures and text) about their friends. It seems like there’s a new social network about every 7 years or so. AOL IM ~1997, FB 2004, Instagram 2010/Snapchat 2011. 2018 might be ripe for another one. I’m not sure if it’s because teenagers don’t like being where the adults are or what, but that seems to happen. If you want to work on something related to personal relationship manager, I’d work on a new email (search for DotMail). People get tons of email and really hate their email client, and are excited for something that works better. You should really understand why people use email (i.e. people use it as a todo list rather than point to point messaging, or people use it to transfer files between their devices). before attempting it. However, be forewarned that email protocols are old and shitty to work with. It’s a lot of work to get something basic up and running.

How to take apart the Panasonic Toughbook CF-W2

From the archives. Good thing for the Wayback Machine.

1. 1 screw inside the CD/RW unit underneath the cover on left. Do this before you power down the unit. Otherwise you will have to force open the drive from the bottom.
2. 2 nut screws on the VGA connector on the top left side.
3. Take the plastic cover off the Wireless antenna near the Intel logo on the right side of the unit by prying the cover loose. Remove 2 screws at side of antenna.
4. Turn the notebook over.
5. 7 screws at back. Make a note of the screw positions in a piece of paper, since there are 3 long and 4 short screws.
6. 1 screw for the Memory Cover
7. 3 long screws holding the Honeycomb cover, next to the memory slot. These screws hold the keyboard.
8. 1 inside after the Honeycomb cover is removed.
9. Turn the unit over. Open the lid. Push The keyboard up from back under the battery. The top part comes up. Now lift up the keyboard. Pull the ribbon out underneath the TOUGHBOOK Sign. Unclip the ribbon from the unit very carefully.
10. 2 silver screws on inside just above the logo Intel Centrino under the keyboard
11. 6 black screws under the keyboard
12. Now close the lid and turn the unit over.
13. 4 screws holding the LCD Hinges at back (2 Screws each side).
14. Now slowly pull the back cover up.

Writing copy is like drawing a comic strip

Once, I remember reading that a cartoonist said that the important part of drawing a comic strip is not actually what’s in the panels themselves, but the space between the panels. The pictures that you draw are, in fact, just bookends and anchors to your readers’ imagination. If the reader can’t use your anchors to make the transition to the next panel through the use of their imagination, then you’ve failed as a cartoonist.

This is something we as comic strip/comic book readers tend not to notice, especially when it’s done well. It’s only glaringly obvious when you can’t follow the dialog or the action due to confusing camera angles between one panel to the next or a bad panel layout.

So it is with copy on your website, or an HN title submission. Like panels on a comic strip, copy is the anchor which you bookend your visitor’s understanding and imagination. If it’s not something that stirs their curiosity, or even better, their sense of imagination, then you’ve failed to carry them from one step to the next.

And as it is with a comic strip, you can’t be overt with the copy, nor should you lie to them. That’s when people get irked and call things link baits. When done right, people don’t even notice at all.

Knowing yourself

When I was younger, I often heard the phrase, “Know yourself”. I didn’t quite know what that meant. At the time, I thought, “Of course I know myself. I know that I like vanilla ice cream.” It wasn’t until I was older that I figured out there’s more to those two words.

What’s so important about knowing yourself? For one, at many points in your life, you’ll have to make decisions about your life and the lives of others. Should I take this job or should I work on this idea? Should I marry this girl or should I try to find another? Should I be the whistleblower or should I protect my family? Making these decisions is tough enough, as you oftentimes have incomplete information, your own biases, and peer pressure of others to mask you from thinking clearly. Knowing what you value will help make the decision process easier (though justifying it is another topic altogether).

In addition, the world has many different types of people in it that value different things. One way or another, they’re going to try to impose, coax, or try to convince you of their values to achieve their own goals. This happens with advertisements to buy a product, when someone asks you to go into business with them, or to go on that trip to Thailand. When your goals are aligned with theirs, then alright, high-fives all around and let’s execute. But when you are unsure of your own values, it’s easy make choices for yourself that are not actually aligned with your values. When you have a lack of alignment between your actions and your core values, it contributes to a lack of control in your life, which contributes to happiness.

So what should you know about yourself? I’m specifically talking about what you value, though Values is an often overloaded term. In this context, I mean it as not simply what you think is important, but the relative prioritization you’d give of one over another. If I asked you whether you value security, you might say ‘yes I do. I like knowing I’ll have a job next year’. And if I asked you whether you value progress, you might also say ‘yes, I like how technology moves forward to bring better standards of living’. But when security is pitted against progress, which would you choose? What if in order to make technological progress, old industries and markets disappear and people lose their jobs? What if it was your job on the line? Some might not find that decision so easy.

How would you go about discovering your prioritization of values? One way would be to take every combination of values and pit them against each other in an either-or contest. I did this exercise once, and it was not only tedious, but also relatively inaccurate. We have a tendency to lie to ourselves because of who we’d like to be (or who others would like us to be), rather than who we are. What we say is oftentimes not what we do.

How do we look at what we do in an honest light? One way is to put yourself in stressful situations and see how you react. We often don’t know what we’d do in a situation until we find ourselves in that actual scenario. You want to put yourself in situations where you are a bit intimidated but not in completely over your head, doing things that may be uncomfortable but will ultimately lead you to stretch yourself. Sometimes, we’re surprised by our own courage, acceptance, or kinkiness. Other times, we’re disappointed by our cowardice, lack of confidence, or our spitefulness.

When I finally connected the dots, I realized that’s why people choose to backpack around Europe or SE Asia. It’s an opportunity to put yourself in new and stressful situations where you don’t quite have all the solutions and will have to react to new situations. That’s how you find out whether you are okay flying by the seat of your pants or whether you like to have a plan; whether you’re too trusting of strangers or not quite trusting enough.

I see people miss this point all the time when they cargo-cult others’ path of self-exploration. I had a friend go to France to teach English, and she found herself doing the same things as she would have done back home–go to work, come home, eat microwave dinners in front of the TV. As can be expected, she reflected that it wasn’t much different living in France as it was living in the US. Similarly, I see people add to their bucket lists “run a marathon”, “go skydiving,” or “do a startup” simply as one more thing to check off, to serve as bragging rights to others, or mostly because they see other people doing it. [1]

Doing and experiencing things is a great start, but it’s more fruitful to learn something about yourself along the way. Those opportunities will not only inform later decisions in your life, but they will also enable you to see others with a keener eye. And that alone would be a pity to miss.

Time for the obligatory concluding quote.

He who controls others may be powerful, but he who has mastered himself is mightier still. — Lao-tzu

[1] Of course, there are some people who already know that they value experiences as a whole and go around gathering as many as they can. It’s perfectly fine if that is the case and they already know that about themselves.