[alert style=”green”]Note: I was fortunate enough to go through Y Combinator to build Ridejoy and now I want to share what I’ve learned with everyone. I’m writing what I hope to be the ultimate guide to Y Combinator and I’d love your input. I’ve drafted the entire thing (it’s going to be 100% free like beer) but am looking for input before I publish – let me know your thoughts.[/alert]

Summary: YC wants to fund great startups. Great startups come from great teams. Great teams are smart, technical, get stuff done, resourceful and tight-knit.

Once I know what type of group I have, I try to figure out how good an instance of that type it is. The most important question for deciding that is

Please tell us in one or two sentences about something impressive that each founder has built or achieved.

To me this is the most important question on the application. It’s deliberately open-ended; there’s no one type of answer we’re looking for. It could be that you did really well in school, or that you wrote a highly-regarded piece of software, or that you paid your own way through college after leaving home at 16. It’s not the type of achievement that matters so much as the magnitude. Succeeding in a startup is, in the most literal sense, extraordinary, so we’re looking for people able to do extraordinary things.

From PG (http://ycombinator.com/howtoapply.html)

PG says hey look for 5 things in founders that they look for in 5 things in founders: Determination, Flexibility, Imagination, Naughtiness, Friendship. But what does this really mean? And how can you showcase these traits on your Y Combinator application?

One more quote:

For most startups at this stage, the best predictor of success is the founders. So, the most important parts of the application for me are the questions about the founders’ backgrounds and the most impressive things they’ve done.   We’re looking for evidence that the founders are smart, effective, and determined.

From Sam Altman (How to Get Into Y Combinator)

From what I understand, most companies that apply Y Combinator historically are pretty early stage. They haven’t raised much capital, they may or may not have a lot of users/revenue and they are probably under a year old. There are exceptions to this rule now that there’s the Start Fund / SV Angel $150k in funding. These days, more later stage startups are applying to, and getting accepted into YC.

My point being though, that the primary factor that determines the success of an early stage startup is the team. Your product can change, your market can change, but your team is not really going to change (unless someone leaves, which is usually bad or at least disruptive). So YC really spends a lot of time evaluating the team when reading applications.

From going through YC, talking to partners/founders and reading YC material, here’s how I think that breaks down:

1) Smart

Great teams are smart. So show YC your team is smart – meaning you are knowledgeable in the relevant fields of your industry and of starting a startup, can learn new things quickly, can process information and make smart decisions. Sam Altman calls the application’s questions about the business as “largely an intelligence test“.

I do think pedigrees matter – I’ve noticed a noticeably higher number of top 15 schools, as well as people who have worked at well known technology companies, or done Math Olympiad/won Putnams/finished college at 16 etc so don’t be afraid to flaunt those things.

But at the same time, they have also demonstrated willingness to fund younger, “unproven” folks, folks without pedigrees etc – they just have some other way of demonstrating how smart they are (ie: past projects or other notable accomplishments)

In our case, two of us went to Stanford, the other Cal and all three of us had worked at VC-backed startups.

Relevant questions on app: Background, most impressive thing you’ve done, real world hacks, what do you understand about the market that others don’t

2) Technical

You are presumably starting a company that leverages (and most likely produces) technology in some way. Teams that are knowledgeable about how technology works are “technical”.

The assumption is that there is at least one person on your team who is pretty technical (can code / build most of the core product). As time has gone on, more people without much technical backgrounds have been applying. I think it’s much harder to get in without a strong technical background but it’s not impossible. Do whatever you can to emphasize how you’re addressing this area – preferably by showing a barebones demo that you yourself built. Don’t make it seem like you are waiting for a “technical cofounder” to save the day.

It does seem like that if you’re building a “regular” web / mobile app (ie not something that requires crazy new tech), they will not really dive into your technical chops if you have a cofounder with a CS degree or real engineering experience. But if you are shaky in this area, that is not a good sign.

On a personal note, I truly understand how difficult it is to do a startup without programming experience. I have done a fair amount of “cofounder dating” and have struggled through learning bits of Ruby on Rails without much success.

I can only say that I was really really lucky to find myself with two friends and roommates who were excellent programmers and had the startup itch. It can happen, but it’s not easy. Then again, no one said starting a startup was a walk in the park.

Relevant questions on app: Background, most impressive thing, hack, projects worked on together

3) Gets stuff done

Great startup teams have high output. They create things from nothing, and overcome hurdles to achieve their objectives. You need to show the YC partners that you guys will get stuff done, and ideally have experience getting stuff done together in the past.

PG has said that a really bad sign for a startup would be they meet him at office hours, discuss a bunch of issues / questions etc, and 10 days later meet again and PG had the feeling they were discussing the same things as if basically nothing really had happened in between that time. It means the founders were not getting stuff done. Very bad.

Personal story: my cofounder Kalvin and I had started and built a nonprofit together in college way before deciding to team up for Ridejoy which was the basis for his “most impressive thing”. We also discussed our rather ridiculous startup roommate finding project that all three of us worked on.

Relevant questions on app: Most impressive thing, hack, projects worked on together,

4) Resourceful

Kind of like being smart and get things done, but also something else. Clever comes to mind. As does “naughty”. Willing to break the rules, find loopholes / tricks. You can’t always power through stuff, so YC founders want to see that you can find the back door and you’re wiling to maybe get in a little trouble to do something.

I’ve written a lot more about being relentlessly resourceful elsewhere on the blog.

Relevant quotes from PG:

“In any interesting domain, the difficulties will be novel. Which means you can’t simply plow through them, because you don’t know initially how hard they are; you don’t know whether you’re about to plow through a block of foam or granite. So you have to be resourceful. You have to keep trying new things.” – Relentlessly Resourceful

“Though the most successful founders are usually good people, they tend to have a piratical gleam in their eye. They’re not Goody Two-Shoes type good. Morally, they care about getting the big questions right, but not about observing proprieties. That’s why I’d use the word naughty rather than evil. They delight in breaking rules, but not rules that matter.” — What We Look for in Founders

5) Tight-knit

People say that having cofounders is like being married with kids minus the sex. Your cofounders and you have this intimate connection, your baby, the startup, and you are pretty much willing to share your entire lives and your efforts are devoted to raising that kid/company.

YC really wants to see founding teams who have known each other for a long time, worked together and have a good fit. One thing that hurts startups is when cofounders bicker constantly. This is highly unproductive. Even worse is when they split entirely. And this happens not infrequently, both to YC and non YC companies. This can tank the company completely.

PG lists “Fights Between Founders” as number 17 in Mistakes that Kill Startups and says that 20% of the startups YC funds has a founder leave. 1 in 5!

Do your best to show why you and your cofounders are going to make it. Why are you a match made in heaven? Will you stick it through thick and thin even when the going gets rough and you’re pissed at your cofounder and you don’t have enough sleep etc.

“Startups do to the relationship between the founders what a dog does to a sock: if it can be pulled apart, it will be.” – PG

Relevant questions: How long have you know each other, projects worked on

Personal story – I lived with my cofounders for a year before we decided to do YC. We already knew each others personality quirks. We had argued about stuff, dealt with money things, and coordinated parties / hunted for new roommates etc together. And we said all those things are in our app.

We knew what we were getting into, and we liked each other a lot. Now not every team has the good fortune of so much history and connection / synergy, but the more you can convey how tight your team is and how your tendencies complement one another, the better.

[alert style=”green”]Note: Now having read through this post, if you have any feedback on my project to create the ultimate guide to Y Combinator please let me know. I’d love to hear your thoughts.[/alert]

photo credit: ‘PixelPlacebo’ via photopin cc

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David Durante on Highbar
(One of my favorite gymnasts to watch, David Durante (2007 US National Champion & World Championship Team member) on the high bar)

I want to talk today about hero worship and why you shouldn’t do it.

Back when I was training gymnastics seriously, before college even, I was invited several times to the United States Olympic Training Center in Colorado Springs, CO as part of a week-long training camp.

There I was, along side a bunch of other impressionable teenagers, training with some of the best gymnasts in the country (and the world). I’d seen these guys on TV, when NBC would broadcast the US Championships (where I would later make my brief one-time cameo on national television) and the Olympics. I was ready to be blown away.

But after training with these guys for a week, I realized something:

My heroes weren’t really that special

They still struggled to learn new moves. Messed up and got mad at themselves. Nursed injuries. Argued with their coach. Even slacked off and fooled around sometimes.

Just like I did.

The biggest difference between us was the intensity of their training and their all encompassing dedication to the sport (living and breathing the sport at this training facility in the middle of nowhere for years and years). Of course there were some components of natural ability (a sense of air awareness or an ease with developing great strength) but other than that, my heros were pretty much like me and every other gymnast I knew.

I’ve taken that lesson to other areas in my life.

We got to meet and talk to some amazing founders in going through Y Combinator – which is awesome, but not something to get too hung up about it. I learn what I can from them and move on. There’s no need to assign them some mythical wisdom or god-like abilities that you can never reach.

Mark Zuckerberg? Brian Chesky? Drew Houston?

They’re mostly just passionate, hardworking and somewhat nerdy dudes who are very good at certain things and now find themselves leading influential Silicon Valley companies.

My current perspective is that with focused dedication, deliberate practice and good advice/strategy/coaching, you can, over time, get really really good at most skills. Maybe even into the 90th percentile. The last 10% is out of your hands – good genes, an early start, an exceptional mentor. And of course the multiplicative factor of great timing/luck. But again, not something you can control, so why worry about it?

Just focus on what really matters, bust your butt and stop worshipping your heros.

Relentlessly resourceful.

This is the essential quality of a good startup founder according to Paul Graham, cofounder of Y Combinator. When asked by Forbes what he looks for in founders, four out of the five elements relate to resourcefulness. He’s written two essays (Relentlessly Resourceful & A Word to the Resourceful) dedicated to the concept.

And yet people don’t seem to really understand what being resourceful means. The top comment on HN from his most recent post posed this question:

Yes, there are certain skills that make it easier to find information on your own. But this is also a function of the problem domain and how well you know it. If you give me a credit card and a problem statement, chances are that I can come up with a working webapp that solves the problem.

But if you give me the name of a VC and tell me to go raise money – where do I start? How do I approach him? What will burn bridges and what won’t? (emphasis added)

Some great HNers jumped in to answer that question, but I thought I’d take a crack a laying out, in full, what I believe being resourceful looks like and how someone can act with more relentless resourcefulness.

Let’s start by talking about the two types of resourcefulness: internal and external.

Internal resourcefulness is really just creativity. It’s figuring out how to fit a cube into a cylinder on Apollo 13 or resolving that nasty bug in your code. You might benefit from the advice or perspective of others, but the resources you need to solve the problem are generally within your grasp (or inside your brain).

External resourcefulness is when you need resources that are outside your control. Things like seed capital for your startup, a liquor license for your bar, a distribution channel for your new product. You will likely need to interact with other people / entities to GET the resources you need to address your problem.

This post focuses more on that external resourcefulness because I think in someways it’s more open ended and confusing and academically/technically intelligent people often struggle to be externally resourceful.


Before we begin, I think there are fundamental underlying conditions needed before someone can really be relentlessly resourceful.

Willingness to Endure Discomfort

I originally wanted to call this guts or courage but it’s much more than this. It’s being willing to talk to people you feel you have no business saying, ask for more than you feel wise and do work you might not like or feel competent in. If you can’t or are unwilling to endure rejection, embarrassment, uncertainty, fear or failure, just close the window now because it’s not happening.

Communication Skills

You don’t need to be a world-class public speaker or best-selling author to be resourceful, but you need to have some threshold ability to communicate ideas clearly and persuasively to relevant audiences. This is definitely a skill you can develop – start a blog, join toastmasters, study copywriting, learn how to sell. If people struggle to understand you or are never convinced to do something you suggest, it’s going to be really rough going.

Grit/Not Quitting

Researchers at UPenn have found that grit (perseverance and passion for long-term goals) is a better predictor for success over IQ or conscientiousness. What you should draw from this is that you should have long term goals you are really really determined to achieve. Because you will face a lot of setbacks during the journey – so don’t start unless you have the bullheaded tenacity to finish.

The Formula

Alright, now that we’ve gotten that out of the way… here are the 3 things you do to be relentlessly resourceful. Continue reading

I’ve been thinking about viral microsites (aka Single Serving Sites) for a little while and in doing research for this post, stumbled across the very thorough and well written paper by Ryan Greenberg: http://isthisyourpaperonsingleservingsites.com/

Quick definition from Ryan: a viral microsite typically has 1) a dedicated URL 2) a narrowly defined message/purpose and 3) that purpose/message is expressed through a single webpage.

Rather than give an academic treatment (which Ryan’s thesis does superbly) I want to discuss some of the characteristics of popular microsites that I’ve come across over the years (and see if I can maybe apply them!)

Clean, Focused Layout

I think the primary element of great microsites are their focus. You need to immediately grasp the purpose of the site when it loads or else you’re gone. Great sites that do this:

[alert style=”grey”]isthemanburningyet.com
A basic status site that answers the question posed in the URL. Very similar to isitichristmasyet.com and shouldiusetablesforlayout.com)[/alert]

[alert style=”grey”] nooooooooooooooo.com
When you hit the button, the anguished scream of Darth Vader comes forth from the screen. If that wasn’t obvious. [/alert]

[alert style=”grey”]pleasemaketheiphoneweatherapplicationlocationaware.com
I’m not sure if this site actually played a role in the new iOS feature, but the site creator did provide a helpful mockup back in the day.[/alert]


CAPS, Gigantic Font and Profanity

You’ll notice that a lot of the more popular sites a mix of large font, caps lock and profanity to state their messages. It sort of feels like the site is shouting at you. Yet somehow, this makes the site more appealing. There’s a feeling of naughtiness as you share the site on your social networks. Certain sites that do this:

[alert style=”grey”]barackobamaisyournewbicycle.com
One of the biggest memes to hit the internet in 2008 – it’s got a humongous typeface, spawned numerous copy cat sites and its cutesy lines that proved so popular they made a book with them. [/alert]

Continue reading

This is a post about why new years resolutions matter. But it begins on a seemingly unrelated topic: death.

Death is not an easy subject for discussion. Given how much violence we encounter in movies, television, video games and other mass media, you’d think our society would be open to more frank conversations on death. And yet try to begin a serious conversation with someone about the fact that all of us will one day no longer be alive and you’ll quickly encounter resistance:

“Let’s discuss something a little more light hearted,” or maybe, “Geez, do you have to be so morbid?”

Perhaps the only times when discussing death is not frowned upon is at funerals and intensive care units, where its presence is so strong and near that it becomes impossible to ignore.

Why should this be so? After all, if you going were on a trip, wouldn’t you talk about the final stop with the other passengers? Our lives’ ultimate destination is death – it is the inevitability we all share.

Everyone you know – your friends, family, coworkers, customers will eventually die. Like candles, they will burn through their wick and their flames will be extinguished. Some will die by accidents, others by illness, most simply by old age. But eventually, all will be taken.

[This is going somewhere, I promise.]

The practice of pledging to change behavior during a new year is an old one. Historians believe civilizations as ancient as the Babylonians in 2000 BC began reforming their lives by returning borrowed goods and paying back debts. In Roman times, citizens would make promises of good conduct to the God of Janus (where January gets its namesake). Today, somewhere between 40%-50% of Americans say they will be making a new years resolution.

Continue reading